North Star Podcast on Smash Notes

North Star Podcast podcast.

December 28, 2019

A deep dive into the stories, habits, ideas, strategies and methods that drive fulfilled people and create enormous success for them. The guests are diverse, but they share profound similarities. They’re guided by purpose, live with intense joy, learn passionately, and see the world with a unique lens. Each episode lets us soak in their hard-earned wisdom and apply it to our lives. Guests include Neil deGrasse Tyson, Seth Godin, and Tyler Cowen.

Recently updated notes

My guest today is Will Mannon, the student manager for my online writing school called Write of Passage. Will oversees all aspects of the student experience with the exception of curriculum design. He’s at the frontier of thinking about live online learning, from how assignments should be delivered to how live sessions should be structured.

This conversation is a deep-dive into our work together. We start by talking about the difference between Type 1 and Type 2 online courses. Then, we move towards psychological topics like how to hold students accountable to helping them navigate the fear of publishing online. Please enjoy this window into Write of Passage and the future of online learning. 



Show Notes

1:50- David and Will’s focus on customer happiness. Type one and type two online courses. What online educators can learn from the Navy Seals.

13:45- How fear is a part of transformational experiences. What held Will back from starting writing. What music can teach us about great writing.

19:27- Why we fear achieving our vision. Write of Passage guilt. How Write of Passage prioritizes helping people make friends. 

27:23- Striking the balance between creating community and letting it grow naturally. How interest groups allow students to create their own communities. The structure of Will’s job as course manager.

35:58- Forte Lab’s yearly planning process. The three phases of Will’s course management. How Will and David are thinking about data collection.

49:14- How Will and David met. How Will’s course feedback led to working with David. Why classical education theory doesn’t really apply to online education.

59:11- Why Will and David create “type 2” courses. Why David learns from his students. How Write of Passages integrates feedback.

1:07:20- What feedback David listens to. The future of Write of Passage. Why David tries to solve very specific problems using software.

1:12:10- How the Internet makes attention a commodity. Why WOP can thrive with zero cold traffic marketing. How the Internet will help make creators money in the future.

Key points in this episode

My guest today is Sara Dietschy, a YouTuber with more than 620,000 YouTube subscribers. This is the fourth interview I’ve recorded with her. It’s her second appearance on the North Star Podcast, and I’ve been interviewed twice on her podcast called That Creative Life. 

Sara makes a couple of videos every week focused on creativity, technology, and entrepreneurship. Most of her revenue comes from paid partnerships, and she’s teamed up with brands like Intel, AT&T, Visa, Squarespace, and BestBuy, and Adobe. 

This episode begins with a discussion of what it means to be a YouTuber, so Sara shares lessons about hiring and monetizing a channel. Then, she talks about her creative process with ideas like her “one for them, one for me” model of creating content. We also talk about the future of influencer culture, homeschooling, the Despacito music video, and what we’ve learned about delegation.


Links to Sara:

Sara’s Youtube Channel

Sara’s Website


Other Links:

Linus Tech Tips

Paul Graham’s Maker Schedule, Manager Schedule

David’s Obsession Tweet

Eric Weinstein- What Should We Be Worried About

Epidemic Sound


Key points in this episode

I have two guests this week: Austin Rief and Alex Lieberman, the founders of Morning Brew. Their business-focused daily email newsletter now has more than 2 million readers. These two gentlemen started the company in college while studying at the University of Michigan. It began as a simple idea — to make business news more interesting for young people. While helping his college classmates prepare for job interviews, Alex noticed they failed to connect with traditional business news. They wanted something better to keep them informed, so he created a daily newsletter that later became Morning Brew. 

I will never forget the first time we met. We were introduced by a mutual friend and agreed to coffee at the Beekman Hotel in New York City. We spoke for two-hours about the future of media, then raced to Morning Brew headquarters where we immediately wrote an article called The Pivot to Owned Commerce. One year later, Austin and I recorded a podcast about the secrets of email marketing and the story of Morning Brew. 

In this episode, we spoke about the benefits of showing how you run your company, what a Cross-Fit-for-Writing community could look like, and Morning Brew’s secret sauce for hiring writers. Please enjoy my conversation with Austin Rief and Alex Lieberman. 


Morning Brew

Business Casual Podcast

Austin's Twitter

Alex's Linkedin

Key points in this episode

My guest today is Tiago Forte. He runs an online course called Building a Second Brain, which I took in August of 2017. I went from being overwhelmed by information to being in control of it. My writer’s block disappeared and my productivity skyrocketed. Tiago changed the way I thought about work and my relationship with information. Fast forward to today, and Tiago and I are business partners. He helped me create my online writing course, Write of Passage and together, we’re building the infrastructure required to scale an online education business. Tiago is one of my closest friends and the person who shaped my career more than anybody else. In what’s becoming a tradition, Tiago and I used this podcast to reflect on our work together. First, we talked about what we’ve learned about email marketing. Then, we moved onto ideas like leadership, working in small packets, and personal growth. Please enjoy this window into our work and friendship.





Great Assistant

No code 


The Decadent Society 

David Allen- Getting Things Done 

Venkatesh Rao 


Tyler Cowen- Emergent Ventures 



1:54 Being a Citizen of the Internet. The role that ConvertKit provides for Tiago’s team. How thinking systematically changes how we work for the better.

14:05 The difference between training and teaching through SOP’s. Why David and Tiago hired expensive personal assistants. Why David and Tiago have the goal of only doing something once before finding an automation solution. 

27:07 What David and Tiago have learned about running online courses. How online teaching has changed since Tiago and David began their school. What role entertainment and community have in the structure of their courses.

35:05 The dangers of only formulating for ease. The psychology of pricing. The benefits of small, self-motivated teams when you work remotely.

45:05 How “reusable packets” are the backbone of David and Tiago’s work. The “lego block” technique of creating content. How Tiago orients using objects, not humans as linchpins in his business. How David writes first and researches second. 

56:33 How the “beginner’s mind” aids David and Tiago write well. How David takes 5 observations a day to create deep and insightful content. 

1:04:00 Why books are a mark of legitimacy. The illogicality of fashion. Why publishers want a sure bet.

01:11:40 The next chapter of online education. How scarcity can make time important again. Tiago’s theory about how you to be your full self online now. How instinct works online.

1:23:40 The hero’s journey of sharing your authentic self online. How Tyler Cowen’s mentorship changed David’s life. How Venkatesh Rao changed Tiago’s life.

1:33:22 The shift from interchangeable courses to interesting and specific courses. Why Forte labs is creator-focused, not curriculum-focused. Why building a business is an act of discovery at Forte Labs.

1:42:16 Why David and Tiago are looking for people who have vision combined with passion. Why innovation is directly related to intuition. How to learn faster.

1:53:43 How growth is paying attention to what you are not capable of doing. The skill of knowing the difference between a challenging situation and a fundamentally incompatible one. How the internet can help people create their own definition of success.

Key points in this episode

My guest today is Michael Mayer, the co-founder and CEO of Bottomless.

This episode explores business from a variety of angles. Michael talks about how he thinks about marketing at bottomless, and the accumulating advantages that drive the company. He also talks about what he learned at YCombinator, why startups that move fast have such an advantage, and how to think about execution in a fast-growing company. Five years ago, Michael was a dish washer. Then he worked at Nike before receiving funding from YCombinator and starting Bottomless. Please enjoy my conversation with Michael Mayer.




Lateral Thinking with Withered Technology

Y Combinator

Paul Graham

Satoshi Nakamoto’s Bitcoin Whitepaper

Sam Altman-

Wyden and Kennedy

David Ogilvy



Key points in this episode

My guest today is Matt Cooper, the CEO of Skillshare — a subscription-based online learning platform where people can take classes on-demand. The main categories are creative arts, design, entrepreneurship, lifestyle, and technology. Before joining Skillshare, Matt was the CEO of Visually, an online marketing place for creative work. And before that, he was the VP of Operations for oDesk, the world’s largest marketplace for online work now known as UpWork. 

Matt and I spoke about the future of education, online and offline. We discussed different business models for online creators, such as Skillshare’s subscription model and the a-la-carte model that I use with Write of Passage. We also talk about what it takes to be successful running an online course, from creating a curriculum to entertaining your students to building an online audience. Please enjoy my conversation with Matt Cooper.


1:55- Skillshare’s model of education. The accessibility of a subscription model. How Skillshare uses behavior to build their algorithms.

11:11- Skillshare's success and failures moving into business education. The benefits of using Skillshare for teachers. Skillshare's revenue model and why they are leaning towards shorter lessons.

15:08-How teachers should tailor their courses for online learning. The production style and schedule of a Skillshare Original class. Why the best teachers are not always the best experts. 

22:17 How teachers should consider personality when creating their online materials. Matt's career creating businesses that help freelancers- from unemployment to Skillshare. Why the human element drives Matt's business sense.

30:04- What Matt loves about the open marketplace model. Supply and demand in open market learning. International pricing as an opportunity to build markets. How bundling may be the future of growing certain international markets.

40:28- Matt's experience with education and why there are so many companies based in Plano, TX. Why Skillshare is the new community college. What Matt would do if he was the president of an Ivy League School. Matt's vision for a more efficient model of higher education. 

51:30- The value and the cost of a liberal arts education.

59:46- How remote work can both change the quality of life of employees and give companies access to talent they aren't competing with locals for. Why David and Matt bike in New York. Tik tok and the future of production. 

1:07:40- Why completion rate is not the most important metric for Skillshare. The challenge of determining user intent. Who is doing the best on search and browse. How Skillshare manages feedback and the social aspects of learning.

Key points in this episode

My guest today is Hollywood actress, producer and director Jennifer Morrison. She’s known for her roles as Dr. Allison Cameron in the medical-drama series House and Emma Swan in an adventure-fantasy series called Once Upon a Time. She also appeared in movies like Star Trek and TV shows like This is Us and How I Met Your Mother. 

We got connected through a workshop I hosted called “How to Crush it on Twitter,” which is exactly the kind of wonderful serendipity I talk about when I talk about why you should share your ideas online. We begin this conversation talking about Jennifer’s time playing clarinet in a marching band. Then, we spoke about how she finds inspiration for stories, chooses what to work on, and how she takes on the role of a character. But the best part comes at the end when we talk about imagination and a movie called “Field of Dreams." Please enjoy my conversation with Jennifer Morrison. 



1:36- How Jennifer Morrison began playing clarinet and what separates a world-class marching band from a mediocre one. How Jennifer uses a coach to hone her craft. How Jennifer keeps focus in the high-distraction environment of a live shoot.

13:25- Why Jennifer’s bottom line for judging an acting performance is “do I believe you” and “do I care about you?” How directing has changed Jennifer’s acting. How trust, research, and imagination are Jennifer’s keys to great performance.

25:25- Why Jennifer asks, “what is the ecosystem I am about to join” before signing on a project. How conflict can drive creativity. Posturing versus collaborative problem-solving in Hollywood. 

35:15- The cogs of the Hollywood “machine,” and the huge financial bet a studio makes when they hire a new actor. Jennifer’s take on the downsides of celebrity, and the baffling art of being “known for being known.”

48:30- Why coming home after being present with thousands of people is one of the most dangerous moments for an actor. How Jennifer reestablishes her own identity after working. How digital streaming and the internet are like quantum physics.

58:35- How Jennifer and David navigate growing and evolving as individuals while having a backlog of performances and writing available to the public. How Jennifer deals with uncertainty and criticism while still moving forward as an actor.

1:08:12- How reestablishing trust in the world will come from individuals reconnecting to their own truth rather than from the media. Why Jennifer only works on projects that she feels strongly driven to. 

2:13:27- How Jennifer thinks the current COVID-19 crisis might influence international film making and consumption. 

2:18:25- Why Jennifer thinks that Field of Dreams is a perfect movie.

Key points in this episode

Today’s guest is Alex Danco, one of my favorite writers in the world. Back when I was in college and before I started writing, Alex was one of the first people who made me say “Wow I want to write like this for a living.” For years, he worked on the Discover team at Social Capital where he wrote a weekly newsletter called Snippets. Now, he’s joining the Shopify Capital team, where he’s building the future of financing merchants and entrepreneurs with everything they do. This episode begins with a conversation about a book called Technological Revolutions and Financial Capital. It’s a favorite of investors like Fred Wilson and Marc Andreessen and Alex breaks it all down for us. Then, we talk about cities and the growth of suburbs in North America. And finally, we talk about the mechanics of writing online.



2:10- How Alex found Carlotta Perez and her book Technological Revolutions and Financial Capital through the work of Bill Janeway. Why, if you are creating an unknown truly new product, you cannot know the value of your equity. How the venture capital community uses tested milestones to show potential value to investors.

10:20- An overview of the two main ways that risky business ventures were funded before VC. How financial capital and production capital exist fundamentally in tension with each other. Carlotta Perez’s theory on the life cycle of financial bubbles.

17:15- Is entrepreneurship across the US growing or shrinking today? Why the current VC and tech industry is a great example of "we shape our tools and then they shape us." Why founders are increasingly interested in funding that prioritizes optionality.

27:00- Why venture capital values opposite indicators of success than the general economy. Why so much education for innovators is focused on venture capitalism. Why Alex believes that financial Twitter will help fill the role of intellectual stimulation for people managing boring businesses. 

34:30- Why Alex writes 5,000 words a week. How writing in public can help in ways that just thinking does not. 

39:10- How to find "the villain" in your writing. How Alex believes urbanization and intellectual migration to cities will change in the US in the future. Jane Jacobs and the idea of complete communities versus gentrification.

48:18- Why complete communities are now found in the suburbs. The growing pains of Toronto. Why so many world-class musicians have come out of Toronto. How do highways create local culture?

59:10- What the organic, long-lived nature of cities means for how they change. How autonomous vehicles will change cities. How the pricing power and efficiency of large companies distorts the true cost of shipping, healthcare, and education.

1:08:10- How audio changes our brains. How the feed-forward system works in our sensory perception and motor function. Alex explains Claude Shannon's information theory and Marshal McLuhan quote "the medium is the message."

1:21:42- Why audio is the most information-heavy medium. Why great writing is not written the way that the author speaks. How Alex interprets the classic Nixon/Kennedy debate story. 

1:27:22- What the rise of podcasts means for media consumption and mental processing in the US. Why Donald Trump thrives in an audio environment. 

1:32:07- How Alex uses summarizing to improve his writing. How publishing every week informs Alex's content. Why the background information in your writing is some of the most important material in your post.

1:37:14 How Alex crafted his piece Social Status in Silicon Valley. How to create new ideas and work using an anchor in what you know.

Key points in this episode

My guest today is Ryan Singer, the head of Project Strategy at Basecamp. Ryan recently published a book called Shape Up where he describes his process for planning, designing, and executing projects at Basecamp.

In this interview, instead of talking about Shape Up and the principles in the book directly, we danced around those topics and applied them to ideas like consciousness, architecture, and product management. We talked about the interaction between design and consciousness and how Ryan’s love of architecture lead him to Christopher Alexander. We talk about relationships between top-down and bottom-up perspectives on the world and how you can synthesize the two. Our conversation begins by applying Shape Up to the writing process. At times this conversation is practical and at times it gets spiritual.



2:02- How Ryan used the core principles of Shape Up to structure, focus, and ultimately write his book, using workshops to refine how you present your ideas and the necessity of using time constraints and process clarification to move through the different processes of writing.

8:29- Ryan’s transition from being a designer to a designing programmer and the successful elements of teamwork that Ryan has identified over his 16 years at Basecamp.

15:13- How impact and team satisfaction drives productivity and focus for Ryan’s team and how the 6-week schedule at Basecamp facilitates this satisfaction. The balance you can find by asking, “How far can you push in one push?”

19:57- How enthusiasm paired with timeboxing helps a team feel energetic but still healthy, the nuance of using a firm 6-week time boundary for a project, and how hard walls with a soft middle are key to the Shape Up method. 

26:44- How a team can be committed to the end goal without being attached to how to get there, why Ryan uses the deeply matured truth of architecture to inform his work in the newer field of interaction design and his appreciation of Christopher Alexander’s design principles.

35:18- How only a deep understanding of a problem can inform the comparison methods for the potential solutions, the multiscale principle as relates to Modernist buildings and design, and the playout of human scale and architecture in Minecraft and tourist destinations. Ryan asks the question, “how do we specify the large scale and allow the people living there to design the small scale?”

49:44- Why Ryan chose “Felt Presence” as the name of his website, how consciousness and the mind inform Ryan’s design work, how Bob Moesta’s work to understand why people reach for a Snickers bar informed a redesign of the candy.

55:52- How understanding the underlying causes of a situation can help you design a useful solution.

Key points in this episode

My guest today is software engineer, designer, and researcher Andy Matuschak. He’s focused on Tools for Thought — which is a fancy way of saying that he works on technologies that expand what people can think and do. Before working as a researcher, he helped build iOS at Apple, focusing on foundations like multitouch, animation, and inter-app coordination. Then, he worked at Khan Academy where he led and co-founded the Research & Development group. In this conversation, we talk about the structure of online education, how to take notes, strategies for developing new ideas over time, secrets of creative partnerships, and what it means to do creative work. This conversation begins with a discussion of my online writing course, Write of Passage. I hope you enjoy this conversation.

Key points in this episode

My guest today is Chris Zarou, the CEO of Visionary Music Group and the behind-the-scenes mastermind behind the success of Logic and Jon Bellion. I’ve been a fan of both his artists since my early days of college, so I’ve watched them both blow up with my own eyes. The episode begins with Chris’ time playing Division 1 soccer before transitioning to artist management. From there, he talks about how he met Logic and what he’s learned from Jon Bellion about the creative process. And finally, we dive into all facets of the Hip-Hop industry from his method of finding new artists, to the economics of concerts and music festivals. I hope you enjoy this episode.

Key points in this episode

My guest today is Robert Cottrell, the founder of The Browser, which has become my go-to source for articles. Here’s how it works. Every day, he recommends five articles and includes a short summary for each one. They’re wild and random — but that’s what makes his work so exciting. For example, today’s issue has an articles about how bees argue, the battle of ideas in China, how Americans should think about nuclear weapons, the circus arts, and the future of machine-created art. In this episode, we talk about why journalism is one of the most under-valued crafts in the world, what we should know about Latvia, and the cutting edge of language translation software. Please enjoy my conversation with Robert Cottrell. 

Key points in this episode

My guest today is Andy McCune, an entrepreneur and creative who co-founded Unfold, a mobile design tool kit for storytellers that was acquired by Squarespace.

He also runs an Instagram account called Earth (@earth on Instagram) with 1.1 million followers. Andy is one of the very most talented people I know. And he has a more intuitive, make-it-and-test-it way of working than most of the people on this podcast. I’ve built a friendship with him as he’s flown under the radar for years. I remember talking to Andy about Unfold back when it was just a small side project, and it’s been a joy to watch Andy grow and scale the business.

Please enjoy my conversation with Andy McCune.

Key points in this episode

My guest today is Samo Burja, the founder of Bismarck Analysis, a firm that analyzes institutions, governments, and companies for high net worth individuals. Samo is known for an idea called Great Founder Theory, and his research focuses on the causes of societal decay and flourishing. 
This is my second time having Samo on the podcast. In this episode, we spoke about high vs. low trust societies, the difference between writing styles in New York and San Francisco, the economics of building an online audience, and how the Internet is raising the value of being a good photographer. But first, we begin talking about how-to videos on YouTube, and their influence on culture. I hope you enjoy this episode.  

Key points in this episode

My guest today is Tiago Forte, who runs an online course called Building a Second Brain.
This episode is different than most of my podcasts. It’s less of an interview and more of a conversation.
Tiago and I have collaborated closely for the past year. In February, we worked together to film and produce my online writing course called Write of Passage. And throughout the year, we’ve teamed up to improve every aspect of the student experience.
We recorded this episode from Arizona where we were hosting our Creative Process Workshop, which offers a radical new approach to writing in the Information Age, just like Write of Passage. 
In this conversation, we reflect on the time we’ve spent working together, explore the key trends in online education, and talk about what we’ve learned by teaching more than 1,000 students combined.
Please enjoy my conversation with Tiago Forte.  

Key points in this episode

My guest today is Ryan Holiday.

He’s a writer, media strategist, and the author of ten books. He dropped out of college at 19 years old to apprentice under Ryan Greene, author of Mastery and The 48 Laws of Power. He worked at American Apparel and founded an agency called Brass Check.

We begin this episode talking about two stories from Ryan’s book, Stillness is the Key. One is about Michael Jordan and the other is about Winston Churchill. Then we transition into new topics. We talk about the philosophy of stoicism, the benefits and drawbacks of anger, and what Ryan has learned from Peter Thiel.

Please enjoy my conversation with Ryan Holiday.

Key points in this episode

My guest today is Cameron Porter, an investor and former professional soccer player. 

We begin the conversation talking about AliCorp, an investment firm in New York where Cameron is responsible for new company research and development and due diligence on seed investment. Then we move to Cameron’s experience playing professional soccer in Montreal and Kansas City, and leading the NCAA in goal scoring during his senior year at Princeton.

Since Cameron is a true generalist, we explore neural networks and brainstorm ways to increase technological progress beyond the smartphone. We end the podcast with a deep and unbounded discussion about community and loneliness. In it, we explore the societal and personal impact of social media, social clubs, and the decline of religion in the West.

Please enjoy my conversation with Cameron Porter.

Key points in this episode

Emmett pioneered the Direct-to-Consumer aesthetic. The bright colors, the flat design, and the sans serif fonts are a direct result of his work. At Gin Lane, he worked with brands like Bonobos, SweetGreen, Harry’s, Smile Direct Club, and Recess. Now, he’s switching gears. Emmett and his team launched Pattern, a family of brands with products and guidance that inspire people to live a more present life.
Emmett isn’t a Luddite, but he’s skeptical of the effects of modern technology and our obsession with efficiency.  
I admire Emmett’s ability to match the intuitive and the intellectual, the quantitative and the qualitative. He loves to read but doesn’t get bogged down by the dogma and precedent. He loves to be creative but isn’t trapped by the myth of the messy artist whose life is in shambles. He’s a sharp critic, a careful observer, and a prolific designer. And in this episode, Emmett reveals his true colors. But I’ll warn you, there are some curse words in this episode due to the passion of the conversation. Enjoy my conversation with Emmett Shine. 

Key points in this episode

In December, I went to a live taping of the Tim Ferriss Podcast at the famous 92nd Street Y in New York City. There was a surprise guest at the event named Adam Robinson, and after hearing him speak, I tapped my friend on the shoulder and told him I’d find a way to get him on the podcast. 

Adam Robinson cracked the SAT before co-founding the Princeton Review. He also wrote the only test preparation book to ever become a New York Times bestseller. He attended The Wharton School at the University of Pennsylvania as an undergrad before studying law at Oxford University in England. 

He’s a rated chess master with a Life Title and as a teenager was personally mentored by Bobby Fischer—considered by many experts to be the greatest chess player of all time—as he prepared for the world championship. 

Today, he applies his unique philosophy and methodology as an independent global investment advisor to the heads of some of the world's largest hedge funds. 

After this conversation, I can confidently say that nobody thinks like Adam Robinson.

Key points in this episode

My guest today is Renée DiResta, who spends her time investigating the spread of malign narratives across social networks. She has advised Congress, the State Department, and policymakers in understanding and responding to the problem of misinformation. In this episode, we talk about the history of misinformation and propaganda. We go back to the roots of media theory and explore the ideas of people like Edward Bernays, Walter Lippmann, and Marshall McLuhan. I found Renée through an excellent essay called The Digital Maginot Line, which we discuss at the end of today’s podcast. I hope you enjoy this episode.

Key points in this episode

My guest today is Tren Griffin, a Senior Director at Microsoft and the man behind an excellent blog called 25IQTren is one of the most prolific writers I know. He’s written books about negotiation, entrepreneurship, and Charlie Munger. He published an article every week for almost six years, and because of all that hard work, he’s now posted more than 1.3 million words online. We start the conversation by talking about his writing process. Then, we talk about distribution in the cellular business, Software-as-a-Service business models, and lessons from his legendary entrepreneur Craig McCaw. After an afternoon with Tren, I feel like he gets more excited about ideas than anybody I’ve ever met. Tren loves life, loves people, and in this conversation, you’ll see just how much he loves ideas.


Find Tren online:

Other links:


1:46 How did Tren get started with writing, why he is so disciplined about the writing process, and  

9:44 What Tren told data scientists during his talk on complex adaptive systems, how to calibrate yourself to business cycles, and trusting the process

21:21 Acquiring judgment through seeing smart people make decisions and what Tren learned from Craig McCaw

33:25 The genesis of the software in the box business model, what the future of the book is going to look like, and the importance of curated marketplaces

41:02 The influence of the Santa Fe Institute, why distribution is so hard, and the key elements of defensibility of companies

54:03 Patrick Collison on raising the intellectual bar at Stripe, what Tren has learned from Richard Zeckhauser, and the importance of first party stories

1:05:02 Demand side economies of sale and what Tren has learn from Charlie Munger, Ed Thorpe, and Lil Wayne

1:17:48 How Tren got into hip hop, Nassim Taleb, and John Malone

1:29:53 What Tren has learned from Bill Gurley

Key points in this episode

My guest today is Mason Hartman. For years, I’ve admired Mason's perspectives on the culture, childhood, and the education system. I teach an online writing course called Write of Passage. So education –  and especially writing education – is a subject that's close to my heart. We recorded this episode in Los Angeles, where Mason works at a school for gifted children and does most of her research. In this episode, we chat about all things education early childhood development, the road to college, and why childhood has become a full time job. Then we close the episode with lessons from two of Mason's favorite people, David Deutsch and Patrick Collison. I hope you enjoy this episode.



Find Mason online:

Other links:


1:17 How to move away from the Overton window, why David’s most creative podcast guests grew up in rural environments, and why it’s important to let kids take a few bruises in a relatively safe environment

5:15 The Coddling of the American Mind, how to design schools that don’t coddle kids, and why teenage sleep deprivation leads to more accidents than drunk driving

14:05 Why standardized testing are antithetical to the underlying skills they are trying to measure, how to evaluate people when real stakes are involved, and Mason’s thoughts on the recent college admissions scandal

21:26 The binding thread that ties together Mason’s intellectual interests, how gifted kids identify each other’s strengths, and why is obsession so important to develop mastery 

30:36 How obsession can equate to imagination and resilience, Masons’ thoughts on the professionalization of young kids, and the standardized expectations for kindergartners

39:44 Unbounded and bounded learning environments, how to use remixing as a way to deal with blank page syndrome, and what Mason thinks about homeschooling

52:44 What Mason thinks are the best ways to raising other’s expectations of themselves, how middle class kids are forced to pursue uncreative paths, and how exclusive colleges exploit low acceptance rates

1:01:37 The commodification of kids, the balance between rationality and intuition, and how to raise the status of obsession

1:11:47 Why you shouldn’t work on projects that you can get a grant for, how risk taking leads to progress, and what Mason learned from David Deutsch

1:23:31 Why is Mason inspired by Patrick Collison, how to ask a poignant and precise question, and why the most curious people are good at listening


Key points in this episode

My guest today is Jeff Morris Jr., the Director of Revenue at Tinder. We begin this episode talking about the future of education. Jeff recently completed an MBA at UCLA and wrote his thesis on the future of Lambda School, the San Francisco based education startup. We talked about the transition from marketing funnels to marketing loops and how Tinder is growing its average revenue per user. We also explore Hollywood's transition from movies to television, and the letter Jeff received from legendary UCLA college basketball coach John Wooden. We also explore some career strategies for sparking serendipity. I hope you enjoy our conversation.


Where to find Jeff online:

Other links:

Show Notes:

1:18 What Jeff learned from working with Lambda school on their Outcomes team, why the incentive structure for traditional colleges is broken, and why Jeff got an MBA despite believing in the future of education looking like Lambda school?

7:43 How Jeff had to scale himself up by becoming a lot more quantitative as the Director of Revenue at Twitter, how marketing at startups has changed from funnels to loops, and the cultural power of the Tinder swipe.

12:54 How average revenue per use has come up at Tinder over the last two years, how to build a successful social product that is low in the Maslow’s hierarchy of needs, and how Tinder balances perceived coolness and utility.

18:11 The historic geographical limitations of dating, the evergreen trends in dating, and what has Jeff learned about compatibility between people through his time at Tinder

23:17 How Jeff thinks about inequality in the Tinder ecosystem, how movies and TV have set up a false idea of how people meet, and what Jeff learned about romance from film school.

30:08 The switch from Hollywood to TV for film school graduates, why TV is uniquely suited to the subscription model, and why David thinks that exporting cool is LA’s core competency

44:34 Retraining in the Lambda school era, high growth jobs that are easy to retrain for, and dynamics of proving competence and expertise

52:26 Why Jeff sent a letter to John Wooden and other celebrities, what he learned about outbound emails, and how to find the ‘underpriced assets’ when it comes to talent

1:00:55 How Jeff got a job at Zaarly ahead of hundreds of other candidates, how that experience expanded his worldview, and what you can do to set yourself apart in the job search process

1:04:47 David and Jeff give the listeners a challenge, what Jeff learned from Brian Norgard about products, and how Jeff thinks about disruption

1:17:17 The verticalization of LinkedIn and other incumbents, and why Jeff thinks being on Twitter is the reason for his high growth career


Key points in this episode

My guest today is Steve Cheney, the cofounder of Estimote. Before founding Estimote, Steve was the head of business and platform at GroupMe, which was acquired by Skype. I’ve been reading Steve's writing for more than half a decade, but this year, he picked up the pace of his publishing and now I’m hooked. This episode begins with the discussion of startup dynamics. We talked about fundraising, capital efficiency, and why Steve believes that every dollar from a customer is five times more valuable than a one dollar from an investor. Then we explore the world of frontier technologies. We talked about augmented reality, self driving cars, and image recognition software. Then at the end of the episode, Steve talks about why he's been so successful writing online. Steve talks about his journey of sharing his ideas, how he started writing for Techcrunch, and why writing online is the best way to get discovered right now. This was without question, my favorite part of the episode because it ties right into my work. I teach an online course called Write of Passage where students learn to accelerate their career by writing online and by building an audience. i hope you enjoy my conversation with Steve Cheney.




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1:53 What startups get wrong about capital efficiency, trap door decisions, and how fundraising cycles for startups work 

11:35 Why Steve changed his perspective on capital efficiency, why is every dollar from a customer is five times more valuable than a one dollar from an investor, and the importance of employee retention in startups

20:09 The importance of avoiding competition for talent, why Steve’s Electrical Engineering background was very good training for startups, and the future of image recognition

33:16 Tesla and why image recognition is the next act of the internet, why frontier technologies are driven by cost curves, and the latest improvements in eyesight 

43:53 The physical limits to wireless and how they are being pushed, what the future of authenticity will look like, and the defining experiences in Steve’s childhood

57:37 Steve’s core beliefs, how he has changed his views on them, and what Steve believes are his core skills

1:01:57 Why you want to work at a product-driven organization, creating something in a new area of technology, and zero sum games

1:09:40 Why Steve got back to writing online, how writing helps him learn, why writing online is the best way to get discovered

1:12:46 The switch from public to private conversations when you write online, how to crank out blog posts and get your ideas on the page, why inspiration is perishable and the importance of taking notes on things that inspire you

1:19:12 How to not get discouraged by an initial slow pace of writing, the importance of reading a lot to be a good writer, and how to become good at curation



Key points in this episode

My guest today is Matt Mullenweg, the founder and CEO of Automattic. Automattic is known for Wordpress, which powers a third of the internet. Matt and I talk about the democratization of the web, the early days of Wordpress, and how he makes sense of the incredible scale of the company. We dive into the benefits of writing online, talk about inbound vs. outbound opportunities and the open web. Then we discuss why Automattic bought Longreads, the content triangle, and the Caro books. Finally, we talk about his love for sci-fi, why writing is the ultimate long-now activity, and what’s next for Wordpress. I hope you enjoy this episode.




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1:56 Democratizing the web, building an operating system for the open web, how Matt thinks about everything in terms of communication, and the tradeoff between powerful and intuitive

9:33 How Matt makes sense of the incredible scale of Wordpress, commodification in the age of social media, and building communities

18:57 The difference between inbound and outbound opportunities, how to reverse engineer your goals, and what Matt thinks about Ben Thompson’s Stratechery

26:26 The democratization of the means of distribution, what Matt was writing about at age 19, and the acceleration of evolution through the internet

35:23 Why Matt and Automattic bought Longreads, Robert Caro’s The Years of LBJ, and the feeling of not having anything important to say when you’re starting out

43:54 What Matt thinks about the content triangle, the good and bad ways of collaborating, and why iteration is the way to improve your writing

49:50 How a healthy comment section is like a good dinner party, why default settings are important, why Matt likes reading sci-fi, and why writing is the ultimate long-now activity


Key points in this episode

My guest today is Jason Zweig, a personal finance columnist for The Wall Street Journal. He's also the author of the revised edition of Benjamin Graham's The Intelligent Investor, which Warren Buffett has described as "by far the best book about investing ever written." We begin the episode by discussing the evening Jason spent with Charlie Munger at his home in Southern California. Then we talked about Jason's collaboration with Daniel Kahneman, the Nobel Prize winning behavioral economist. We discuss Jason's time growing up on a small farm in upstate New York, and why Jason's Wall Street Journal columns are intended to save investors from themselves. Then we had a conversation talking about the power of small details and communication, and why writing demands fresh language. And nearly every single part of this conversation applies to my online writing course called Write of Passage, where I teach students to launch a personal website, build their writing habits, and attract an online audience.




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  • Charlie Munger, Unplugged by Jason Zweig (Paywall)

  • The Intelligent Investor by Benjamin Graham

  • Thinking, Fast and Slow by Daniel Kahneman

  • Look Homeward Angel by Thomas Wolf

  • The Years of LBJ by Robert Caro


1:38 What Jason learned from his six-hour long conversation with Charlie Munger, delivering the same information in different and entertaining ways, why you should bet on regression to the mean instead of being procyclical when it comes investing.

8:00 What are the similarities between Charlie Munger and Daniel Kahneman, why you have to be ready to kill your darlings when it comes to writing, and what does Jason’s information diet looks like.

24:10 How Jason thinks about the idea of “saving investors from themselves”, the role of entertainment in Jason’s writings, why clichés are a symptom of lazy thinking, and inflection points in Jason’s career

42:10 How growing up in rural New York fueled Jason’s intellectual curiosity, how Jason would approach building a writing career if he was just starting out, and why you should treat words like 45 pound dumbbells.

55:44 Pivotal moments that influenced Jason’s writing process, the importance of being able to take criticism well, and how Jason uses collective intelligence to improve his thinking

1:08:17 The dangers of learning too narrow a lesson, how Jason was as a young college student, and why overconfidence might a positive influence for young writers


Key points in this episode

My guest today is Austin Rief, the Co-founder and Chief Operating Officer of Morning Brew, a daily email newsletter with the latest news from Wall Street to Silicon Valley. Austin started the company when back when he was a student at the University of Michigan. And now Morning Brew has more than 1 million subscribers. This conversation is about all things email from growth through attention to strategy. We talked about Morning Brew’s early growth strategies, its ever growing referral program, and the power of exclusive content for loyal subscribers. And then we talked about my own Monday Musings newsletter and my online course called Write of Passage and how people like you and me can harness the power of email. When it comes to media and commerce, Austin is one of my very favorite people to talk to. I hope you enjoy this episode.




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1:50 How Austin thinks about building virality into the product, how to optimize paid marketing for your consumer brand, and having a unique pitch to your advertisers

10:16 The framework of “need vs. feed” in advertising, the origin story of Morning Brew, building memorable experiences, and how not having the weight of being successful can be good

21:33 Doing things that don’t scale, Morning Brew’s referral program and partnerships with other newsletters, and A/B testing

28:00 Building Morning Brew for other industries, using the psychology of readers to design the product, and aligning misplacing and underpricing of marketing channels with your specific product

39:52 Thinking about the tradeoff between depth of content and legibility, why you should make your product for a very specific person, and the under exploration of non-personal influencers

50:21 What are Austin’s axioms of growth, having multiple revenue streams to build a moat, the switch for Austin’s focus from growth to retention, and why your own customers are your build marketing channel 

1:00:57 Why Austin loves sweetgreen, focusing on authentic experiences, the importance of a personal newsletter, and the future of the newsletter space 


Key points in this episode

My guest today is Jason Fried, the Co-Founder and President of Basecamp, a Chicago based company that builds web based productivity tools. Jason is famous for his contrarian approach to work and his blog Signal vs. Noise. On this episode, we talked about both of them. We recorded this conversation at Basecamp's headquarters in Chicago. In this conversation, we discussed Jason's new book, It Doesn't Have To Be Crazy at Work. We also discuss Jason's philosophy of work and dive deep into how Jason was able to maintain control of Basecamp and build a business that mirrored his beliefs. We talk about the history of Chicago architecture, why Jason values time in nature so much, and how designers should balance the trade offs between elegance and utility.


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1:30 What was the “ah-ha” moment when Jason realized that the way we work is broken, the measures at Basecamp that he cares about, and how the entire business is structured around how they work

5:15 Keeping things intentionally small, why “hustle porn” is overrated, how management pushes people towards made-up, unnecessary expectations

11:03 How Jason thinks about moments vs hours mode of working, how to build a profitable business from day one, creative vs hard work

16:03 How good habits can form the backbone of a good workplace, how Jason structures his days, how projects are structured at Basecamp

23:50 How the end goal determines how you work, how Basecamp is able to sponsor $5000 vacations every year for all its employees, how scratching your own itch can lead to a really good business, the origin story of Basecamp

33:45 Basecamp’s “content” strategy and why Jason doesn’t call it that, why failure is overrated in the software industry, why focusing on the fundamentals is the key to sustainable business 

41:10 Growing your business like an oak tree, Jason’s favorite buildings in Chicago, how the Great Chicago Fire shaped the cities architectural landscape

53:10 Why aesthetics are not important, optimizing for the right things, Brian Eno, and why being able to articulate how you’re thinking is a powerful tool

1:04:10 Equinox and how high friction can lead to better experiences, how Jason thinks about pricing, and why softwares don’t need to give away a large part of their product

1:11:35 Why Basecamp doesn’t have any salespeople, why Basecamp is what Jason chooses to spend his time on, and what was the moment when he realized that Basecamp could be his life’s work


Key points in this episode

My guest today is Jason Stein, a general partner at Steins, an investment management business and holding company that provides capital and strategic partnership to consumer brands, media and technology companies. Jason also founded Laundry Service, an advertising agency that sold to Wasserman Media Group in 2015. And full disclosure, I worked for Jason at Cycle Media, the sister company of Laundry Service, and that's where we met. In this episode, we talked about the direct to consumer commerce wave, sports advertising and also the future of marketing. And this conversation begins with a story of how Jason use Twitter to recruit me back when I was a senior in college. I hope you enjoy this episode.


Find Jason online:



1:07 How Jason uses Twitter and why he thinks advertising begins with creating a great product, and how social media can be leveraged for product development

5:27 Why Jason thinks Mark Zuckerberg and Jack Dorsey are working on the right problems, how writing can help you become an “influencer”, and the addictive incentives of social media

9:08 Why long form content is not dead, why David thinks “Always be paranoid” is the most important thing he learned from Jason, and why Facebook and Twitter are facing the problems they are today

16:19 Jason’s mindset while building Laundry Service, the importance of a personal end goals, the difficulty of building a services business, and why you should always “Make it about the work.”

25:27 Why Jason is a bit jealous of David, how Steins is different from VC firms, and why is Front Office Sports so important?

35:28 The viral spread of TikTok, why Jason loves it, and how algorithmic feeds become important as a social network scales up

38:17 Why “nothing is binary”, the DTC wave, and why DTC brands are still reliant on wholesale and traditional retail channels

47:08 Why does sports advertising suck, misaligned incentives, and why it’s different to own a brand than be a brand agency

Key points in this episode

My guest today is Erika Nardini, the CEO of Barstool Sports. Barstool was started by Dave Portnoy in 2004. And Erica first learned about the company when she was living in Boston and she immediately became a fan. Now if you don't know about Barstool Sports, they are one of a kind. They cover sports and pop culture through a uniquely Barstool lens and they produce blogs, videos, and podcasts. They are part-media company, part-subscription service, part e-commerce company, and Barstool is responsible for many of the memes I grew up with. They are all over the place. For example, Barstool has an amateur boxing league with pay per view events called Rough and Rowdy. And some of their other shows include Chicks in the Office, Pardon My Take, Spittin Chiclets, and Schnitt Talk. In this conversation we explore every aspect of Barstool – from personalities like Big Cat, Uncle Chaps and El Presidente. We talked about the future of advertising, how Barstool things about its future, and how memes on social media become e-commerce products. Then we talked about Barstool's hiring philosophy, and how being an internet native impacts ad reads and content strategy. I hope you enjoy this episode.


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1:47 How Erika thinks about Barstool as a company and the future of media companies

5:41 The different personalities at Barstool and what Erika thinks makes them unique and authentic, the meaning of “being from the internet”, why Pizza Reviews are a premium format

14:03 Erika’s view of relationships that personalities have with their fans on the Internet, how that’s evolved over time, and all things Jon Bellion

18:09 Why the music industry has had such a tough time getting disrupted from within

20:52 The future of sports, what Erika thinks about sports rights in different leagues, and the idea of company orientation deciding end product experience

29:03 How sponsored content can be used effectively by brands, creative freedom for influencers, and how Erika found Barstool

33:16 David finding out about Barstool memes like “Saturdays are for the boys”, how that turns into an e-commerce product, and the balance between creative freedom and monetization

36:57 How Erika thinks about hiring at Barstool and the Barstool “it” factor

40:06 How is Barstool using data to influence decision-making, how people move through the Barstool brand, how internships turn into jobs for self-starters

47:17 Ecommerce at Barstool, switch from industries to media companies, which sports league would Erika bet for a 10-year time frame?

51:10 How have video games impacted Barstool, golf personalities, people stealing the Barstool way of doing things and why ultimately that doesn’t help them

1:00:10 Why did Erika choose to spend her career in the intersection of content and technology and monetization?

Key points in this episode

My guest today is Nick Kokonas, the Co-founder of The Alinea Group of restaurants. His restaurant Alinea has been named the best restaurant in America and also the best restaurant in the World. Nick is also the Co-founder and CEO of Tock incorporated, a reservations and CRM system for restaurants with clients in more than 20 countries. In this episode, we dive deep into the restaurant industry. Nick and I begin by discussing how he applies behavioral economics to his bars and restaurants. Then we talk about the design of Next bar, the Aviary, and how he's thinking about the upcoming redesign. We explore many aspects of the restaurant industry. From menu design, to branding, to reservations, to designing experiences. We talked about why golf is the greatest sport in the world, how to increase throughput at a bar or restaurant, and the virtues of dynamic pricing. We also compare and contrast high end restaurants around the world from New York to Argentina.


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1:49 How Nick came to meet Noble Prize winning Economist Richard Thaler, how he applies behavioral economics to the restaurant business, and how small behavioral cues can lead to big changes in results

7:05 Why does Nick care about metrics like revenue per minute per seat instead of average check size, the importance of throughout, and the new Flex AI tool offered by Tock

11:22 Why has the restaurant industry not adopted dynamic pricing?

14:34 Is fine-dining around the world becoming all the same due to Instagram? How has shifts in information created a new kind of chef who mixes art and science at a very early age?

21:44 How does Nick look at food costs and why are truffles so expensive?

25:50 How does the Alinea group manage the trade-off between hospitality and efficiency, and the thought-process behind the new re-design.

31:06 How Chicago’s West Loop become such a hotspot for good restaurants, parallels with New York’s Meatpacking district of Chelsea, and the importance of real estate in the restaurant business

35:31 Importance of giving false choices in parenting and in restaurants

39:02 The origin story of Tock and how it delivers a superior experience for restaurants and customers

51:10 Why Nick becomes every business plan with the experience of going to the place, what’s wrong with most business plans for restaurants, and behind-the-scenes drama at high-end restaurants

58:17 Why are Half Mezcal Margaritas Nick’s favorite drink?

1:00:30 Why Nick enjoys playing golf, David’s story about sneaking into Cypress Point, and how Bryson deChambeau is changing golf

1:07:30 What does Nick think about effective business writing, the importance of editing, being ok with saying “I don’t know” and Trump’s ability to distill ideas into simple rhetoric.

1:13:00 Why did Nick called everyone into work on Chicago’s Polar Vortex day and willingness to do things that others don’t.

1:17:30 How is Nick prepping for the macro environment slowdown given that restaurants are one of the least recession proof industry?

1:18:57 Why people don’t like to make decisions, and why Nick will never work with anyone who can’t make decisions – even if they are the wrong ones.

1:20:36 Nick’s requirements for hospital hotel and why he likes the Crosby Street Hotel in NYC.

1:23:49 How Nick and Grant studied the dew point of water to avoid condensation at the tables in Alinea.


Key points in this episode

My guest this week is Andrew D'Souza, the Co-founder and CEO of Clearbanc, a fundraising alternative to traditional venture capital. The company is based in Toronto and helps businesses fuel their marketing spend – because right now 40% of venture capital invested in companies goes directly to funding Facebook and Google ads. Equity is an expensive way for founders to fund repeatable growth and Clearbanc exists to solve that problem. Here's how it works – Clearbanc gives startups anywhere between $5,000-$10 million and in exchange Clearbanc typically receives a 5% to 10% revenue share of that company's earnings until the funding is paid back plus a 6% fee. Now here's the secret, Clearbanc picks merchants by developing technology that scans the merchants' Stripe payments and Facebook ads and that way they can assess the financial health and momentum of the company. In 2018, Clearbanc poured more than 100 million dollars into 500 companies.


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1:55 How Systems Engineering helped Andrew helped think about the intersections of different disciplines like Neurobiology, Psychology, Marketing, and Macroeconomics

5:36 Why authenticity is key to building great marketing campaigns and why your job as the CEO is to create the necessary conditions for success

10:12 The origin story of Clearbanc and how 40% of all venture capital goes to Facebook, Google, and Amazon

20:05 How companies build a culture that allow people to fail and how Clearbanc started by funding Uber drivers which keeps them true to their origin story

25:14 How Andrew squares the dichotomy between funding growth through social media and the idea of a disproportionate portion of VC going to Facebook ads

29:42 Airbnb and the future of how cities will evolve around self-driving cars and subscription songs

35:00 Why Andrew thinks that the advent of self-driving cars is more a policy problem than a technological one

40:48 The independence of Canadian provinces and how Quebec has managed to preserve the European culture against huge pressures

47:31 How meeting YC partners showed Andrew that VCs are just one way to build your company

50:43 How Andrew builds and cultivates relationships while building Clearbanc

55:10 What Andrew thought about traveling to Israel and thinking about Jesus as a founder of a movement

58:29 How Andrew returned to his initial passion for selling a product that he believes in through hiring people in positions which were their passion

Key points in this episode


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2:11 Amazon's Organizational Structure 4:09 Steve's Google Platform Rant 12:42 AWS & The Government 22:53 Disruption as rearrangement 30:47 Thesis-driven Discovery Team @ Social Capital 38:52 The role of transportation in shaping cities 45:47 Suburban vs Urban life 53:13 Sidewalk Labs in Toronto 1:00:11 Chief Resilience Officers in Cities 1:03:03 Alex & his interest in Biology 1:11:28 The Organization Man 1:18:58 What has Alex learned from Chamath Palihapitiya 1:22:05 Alex's writing advice 1:25:02 Ways to Think About Water


Key points in this episode

My guest today is Web Smith, the founder of 2PM, Inc. a curated, subscription-based media company with quick commentary on brands, data, and eCommerce. He invests in and advises for digitally native vertical brands, and spends most of his time in the intersection of digital media and eCommerce. Within the eCommerce industry, Web’s done many tours of duty: he was the cofounding CMO of Mizzen & Main. Before that, he handled marketing at Rogue. Most recently, he was the Director of eCommerce at Gear Patrol.

We begin the episode talking about what Web learned working for Rogue Fitness. We discuss misconceptions around eCommerce. We talk about the purpose of advertising and how brands should think about spreading their messages. Then, we dive into the intersection of content and commerce, and explore brands like Supreme who turn off as many people as they attract. We talk about the future of retail, and explore the developing prospects for Dollar General, Wal-Mart, and J-Crew. Finally, we end with a conversation about Web’s journey from a hungry Houston kid to a multi-time founder. Web’s grit shines through in this conversation. I left the conversation in awe of Web’s humility and ambition. Please enjoy my conversation with Web Smith.





Show Notes


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1:12 - How Web began with the e-commerce industry with Rogue, some of the misconceptions he first had with the industry, and a few of his experiences of a blue-collar mentality within e-commerce.

7:20 - Product becoming less of a differentiating factor within e-commerce companies, Web’s thoughts on this, as well as his thoughts on companies doing things in-house versus outsourcing.

11:46 - A few other things that Web looks for within an e-commerce company and some factors that stand out to him.

14:22 - The direct to consumer industrial complex and Web discussing how the real winners of this era are the people that are supporting these brand efforts. Also, a bit on what Web is building within 2 PM and the strategies he’s using.

19:32 - What Web’s original vision for 2 PM was and where the company is currently going. Also, some thoughts on if you’re not doing a paid route, then word of mouth being very important. The most important factor within the Supreme brand discussed, as well.

26:29 - Web’s thoughts on the collaborations that Supreme and Virgil Abloh have done. (Paying $300 for a Supreme branded brick)

29:08 - What Web has learned from CrossFit, his thoughts on it, and a few of his experiences within that community. Also, thoughts on brands relating to being a religion.

36:20 - What is it with the structure of the industries like food, beverage, or cosmetics that makes them not go public. Afterward, discussion on the convergence of media and e-commerce.

49:24 - The rise of dollar stores rising up around the country and Web’s thoughts on this. Also, why the same benefits of these dollar stores (high convenience, close to your home, and low prices) can’t be improved through e-commerce vectors.

54:22 - What stands out about Walmart and what they’re doing within the industry to Web. One of his experiences with Walmart here, as well.

58:46 - Columbus, Ohio being one of the major retail capitals of the world and some thoughts on the things going on within the retail space there.

1:01:41 - What Web has learned from Casey Neistat. His huge amounts of discipline and strict schedules. Where he came from and where he’s going.

1:06:22 - As the cost for testing and launching products go down, more and more companies are coming out with more and different products than what they’re known for. How Casey has also done this.

1:08:31 - The lessons and ambitions Web got from growing up and some discussion on his earlier days and experiences with poverty. How this has translated into him raising his kids.

1:13:13 - Why Web has chosen 2 PM as a way to share his knowledge and to give his gift to the world. Also, what Web deals with within the intersection between e-commerce and media.

1:16:40 - What Web has learned about the craft of writing and how he’s gotten better at it. Why it’s important to always write, especially when you don’t want to do it.

1:19:00 - How Web thinks about talking to people, creating ideas, learning, reading and then making those ideas and that information real and then sharing those with the world. How Web approaches learning through conversation and how he goes about it.


“I don’t think you can be all things for all people. If you’re not pissing someone off, you’re doing something wrong.”



Key points in this episode

My guest today is Tal Shachar, the Chief Digital Offer of Immortals, a global eSports organization in Los Angeles where he leads consumer-facing operations. At Immortals, Tal is working to build the most engaged and inclusive community in eSports. Before joining Immortals, Tal lead strategy and growth for BuzzFeed studios, focusing on growing audience and monetizing Buzzfeed’s intellectual property across channels. Before that, Tal worked for an independent media holding company called the Chernin group, and worked with companies like Barstool Sports, the Action Network, and Headspace. And finally, Tal writes for Media REDEF, where he analyzes the media and technology industries. I can confidently say Tal’s articles are some of the best articles ever written on the media business. We devote this entire episode to the future of media. We talk about Netflix, Disney, Amazon, HBO and the changing definitions of scale in the media business. We explore the present and future of niche media and discuss the emergence of food culture on the internet. Then, we talk about some of Tal’s craziest ideas like the differences between Tiles and Feeds, why Hollywood is like an API for Silicon Valley, an how fast feedback loops between digital and physical reality are changing the world.


Show Notes


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0:35 - The constraints in the past regarding the limited choice people had. Comparing this to now where we have numerous ways to choose various things and how we want them. How this relates to communities emerging - “With limitless distribution and limitless choice, we can find exactly what appeals to us, including other people.”

5:35 - The distinction between a push-discovery and a pull-discovery (having something pushed onto you versus choosing and being drawn to something). Some examples of these. Also, detailing passive and active forms of content consumption.

8:11 - How advertising and subscription business models tie into push versus pull theory (most television being 50/50 split). The passive and active aspects of media, as well. Going into Netflix’s strategy and scaling, and discussing why it doesn’t have advertising or sports. How being at scale has changed and what this means.

20:20 - What some of the bottlenecks are regarding sports media and television. Also, what sports television may look like in the future.

23:10 - Tiles versus feeds. How passive and active consumption ties into both of these (for example, Facebook feeds much more suited for passive consumption). Tile-based consumption being more suited to active consumption.

27:15 - How Disney, Amazon, and HBO use much more different strategies compared to Netflix and why they do this. Going in-depth into their specific strategies.

31:50 - How Tal’s prediction with content leading straight to purchase and how this has largely come to be true. Also, how parts of this prediction have been wrong. Discussion on and examples of focusing at the top of the funnel, and then focusing solely at the bottom of the funnel. A bit on how online shopping may evolve to begin having a similar experience that in-store shopping might have.

40:49 - Who has a structural advantage in the world and some examples of these advantages. How the type of product will be better suited for online distribution versus a more physical distribution. A future increase in the number of direct consumer brands.

44:31 - How the goal is not to pay the least amount but to pay the most for your content. How we’ve gone wrong in terms of how we think about this. Paying for the best content, to then monetize it at the highest rate, and then return to paying for the content again is really what’s going to matter. For passive content, the model is different.

47:19 - How Tal sees Hollywood changing in terms of risk and reward. How Netflix ties into this and detailing that. Discussing the nature of music and the monetary aspect of top-tier content.

54:00 - Discussing media-consumption and how the demand may not be increasing but the supply is always increasing. The opportunity-cost arising. What begins to shift when there is no longer any attention left to give to media. The possible integration of companies using facial expression data from cameras to create even more accessible and efficient data.

58:45 - The idea of Hollywood as an API for Silicon Valley. Some discussion on this idea and how companies use Hollywood as an API.

1:03:34 - If we go back to the 1960s, how music mainly ran the culture at the time. Now, how travel is a shelling point for culture, for people to meet, and in many other sectors. Some examples of this with food, as well.

1:06:54 - What Tal learned from Peter Chernin and some unique skills that Peter has.

1:08:29 - Why Tal has watched almost every romantic comedy. Some discussion on what makes them unique and on what they can teach us with storytelling.

1:10:55 - John Malone and what he does really well. Why Tal admires him and why John might have the unique perspective that he does.

1:13:08 - What does LeBron James coming to Los Angeles say about Los Angeles, LeBron, and for the increasing importance of entertainment.

1:15:05 - What stands out to Tal regarding Ze Frank and Jonah Peretti.

1:16:15 - How the internet has increased our ability to share information more easily and effectively. Some discussion on how Buzzfeed has capitalized on that shift and the competition that comes with sharing content.

1:19:35 - How Tal thinks about the trade-off Seth Godin-style daily blog, couple hundred words, versus pouring your heart and soul into an article. Frequency and consistency discussed, as well. (articles mentioned listed above)

1:21:54 - Tal’s perspective on Evan Spiegel and some thoughts on Snapchat. What Snapchat does well and has struggled with. A bit of discussion on what’s to come in the future regarding social media.

1:27:50 - How communication has changed over time from speech to pictures and words. Thoughts on this and previous forms of entertainment compared to now.

1:32:10 - Some of the two-way feedback loops we’re currently seeing. Distribution-based content impacting the real-world, then coming back around to impacting the distribution of that content again. Also, discussing the increasing number of people that are finding trends and capitalizing on them. A bit on the uncertainty caused by these ever-increasing tight feedback loops.

1:38:31 - Why Tal is so excited about media and why he devotes his life to it. How powerful media can be for enriching our daily lives, meeting people, understanding people, and with learning.

“There’s no other industry that sits at the nexus of culture in society like media does.”



Key points in this episode

My guest today is Keith Rabois, the Managing Director at Khosla Ventures. At Khosla, Keith focuses on the consumer internet, education, enterprise, financial services, and digital health.    Keith has had a front-seat to Silicon Valley history. He’s had five bosses in his career: Peter Thiel, Max Levchin, Reid Hoffman, Jack Dorsey, and Vinod Khosla.    In this episode, we talk about the lessons of sports from the San Francisco 49ers to the Oakland A’s. Keith shares a story from his first week at PayPal, where he went on a run with Peter Thiel, which sparked his hiring philosophy. Then, we talk about the future of education, how to find undiscovered talent in society, the power of accumulating advantages, and how to raise the level of ambition in society. Keith has built more billion dollar companies than just about anybody on Planet Earth, and all that wisdom shines through in our conversation.    






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1:32 - Outlining the book, The Score Takes Care of Itself and its significance for entrepreneurs. “Rather than focusing on the score, focus on the process and the rest takes care of itself.” Also detailing Bill Walsh, the underlying infrastructure that he built, and the philosophy that successful companies like Square and Apple have used.


4:41 - Leadership lessons that can be learned from sports and the insights that Keith learned from Peter Thiel in the past on evaluating people and on building great companies. Pairing yourself with people that cover your blind spots and weaknesses.  


9:20 - Emulating companies like Apple, Amazon, and Tesla rather than companies like Google or Facebook. The problem with people choosing the easier path in building companies and detailing building things from the ground up rather than inheriting other companies infrastructures.


12:28 - Thoughts on people who are naive about markets doing better than those who have more experience and know the markets. Hiring people who have expertise to jump the learning curve that comes with starting successful companies.


15:43 - Ways to accelerate learning and jump learning curves. Reading (primarily books and printed materials), find experts and constantly inquire, and using experts to find the right path to take. How Keith began venturing into real estate and him detailing his journey with it.


21:28 - Keith on using Twitter and his experience with finding a specific thread on China, then meeting the author of the thread. Examples of writing insightful things online and the potential in doing so. Finding people and breaking through to clutter with original content.


26:07 - Detailing accumulating advantages with companies and the effects of them. A few examples of what accumulating advantages may be within companies. A bit on accumulating advantage at the individual level, as well.


32:08 - What Keith has learned from being a bit of a Silicon Valley historian and why conference room names are predominantly Silicon Valley names. Also, a bit on why you would want to understand the history of Silicon Valley and the history of successful companies. Reading less short-form content and long-form content. Being a voracious reader.


36:35 - A musical example of being aware of things in the past and learning from tradition. Mixing original sparks with tradition. Learning more so you can better interpret information. For example, artists seeing ten-times more in a museum than an average person would.


42:47 - Keith describing the process of speech-writing and comparing it with coding. Also detailing what makes certain speeches stand out from others. William Safire’s book on great speeches, Lend Me Your Ears: Great Speeches in History.


45:30 - Creating ambition and the fluctuation of ambition over time. Discussing ambition more, spending time with the five most ambitious people you know, and believing that things are possible. Keith’s experience with ambition while growing up and his experiences with moving into tech. Specializing in your strengths and surrounding yourself with complimentary people.


52:28 - Becoming the only person in the world that does what you do and detailing this concept. Where he learned the concept and how Keith describes this for himself.


56:22 - What Keith has learned about organization and productivity that scales down to an individual level. Allocation of time and under-valuing your time. Detailing how the number one predictor of success is knowing how to efficiently allocate your time and how to get the most output out of that time.


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Gillian Morris is the founder and CEO of Hitlist, an app that alerts you when there are cheap flights for your dream trips. Fast Company named Hitlist one of the Best Apps of 2017 and the app has been featured as a 'Best New App' by the app store in 83 countries.   We begin this episode with a discussion of Gillian’s time as a journalist in Turkey and the time she spent in war zones in Syria and Afghanistan.   We talk about Gillian’s experience swimming across Guantanamo, why Tinder is the world’s best travel app, and how to make travel meaningful. Finally, we end the podcast with a discussion of community living and alternative parenting strategies.   


Guest: Gillian Morris Twitter:@gillianim




Show Topics 1:24 Gillian opens with her passion for travel and how journalism opened the doors to all kinds of adventures and experiences traveling.


5:45 How living in different places and cultures opens and shapes ones perspectives and worldview.


9:00 Gillian shares the misconceptions of the western world regarding some of the Middle Eastern countries she has visited.


12:30 The differences of living in a peace prone vs conflict zone and how it affects the overall quality of life and standard of living.


19:55 Gillian shares her vision for being a catalyst in getting more people to travel as a way to broaden their perspective. How more traveling for the average American could have a profound impact on their sense of the world and themselves.

23:30 Misconceptions about travel and myth that it is extremely expensive.


32:01 David and Gillian discuss communication barriers and opportunities when dealing with new cultures or in new places.


39:35 Gillian on how flights and travelling rules are constantly changing and evolving. Flying and traveling can’t be generalized, but there a processes one can do to make it easier and more accessible.


42:05 David and Gillian discuss the trend of countries relaxing the barriers of entry for tourism and the ensuing results.


50:48 How Hitlist uses intelligence to profile a personalized experience on the app that would be most appealing and tailored to each person. 


51:50 David opens of the dilemma of the two sides of privacy and freedom when it comes to subscribers privacy.



52:38 Gillian on how privacy is handled within Hitlist.


57:40 Gillian on learning an instrument and some of the key factors that make it more understandable when learning.


1:04:06 The power of small group environments and the effect of an environment on the development of its individuals.


1:08:40 Looking historically at the issues within society and the traditional family structures vs modern communities.


1:11:40 Parenting and accessibility; creating additional accessibility and affordability when it comes to child rearing for those who are interested, but maybe unequipped or afraid.


1:14:25 Gillian shares a story of her time swimming across Guantanamo.

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My guest today is Michael Shellenberger, the Founder and President of Environmental Progress. Michael is one of the world’s leading pro-nuclear environmentalists. He’s been an environmental and social justice advocate for over 25 years. In the 1990s, he helped force Nike to improve factory conditions in Asia and in the 2000s, Michael advocated for the expansion of federal investment in renewables and energy efficiency.   In this episode, Michael and I talk about the virtues of nuclear energy and tackle the big misconceptions surrounding it. We explore how media narratives have shaped nuclear energy perception, the virtues and drawbacks of wind and solar energy technologies, why 17% of teachers in California can’t afford a home, the problems with anonymous lawsuits, and the fascinating impact of Proposition 13 on housing in Silicon Valley. 






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1:34 - Michael’s experiences in Nicaragua and Guatemala in 1988 and the effects of culture shock on his sense of gratitude and wealth. David’s own experiences with culture shock here, as well.5:15 - Discussing activism and scholarly work. Michael’s first degree (peace and global studies), his early traveling experiences, him working at a left-wing activist group, and then a few of the campaigns he’s done. Then, how he formed a coalition to push government investment in renewables and clean energies.


8:17 - Some of the technical issues with renewable energies. Also, discussing nuclear energy and fossil fuels. Detailing the story of environmental progress and the power of uranium (a can of it will produce enough energy for your life).


12:12 - The common perspective on nuclear energy and waste (weapons, Chernobyl, Fukushima, and other negative connotations). Michael clearing up some of these common misconceptions. Also, some facts on why solar and wind power aren’t as effective and efficient as most people think.


23:26 - How nuclear power gained its negative view over time. The idea that the more countries with nuclear weapons, the safer the world is. Detailing the nuclear left and the nuclear right perspectives.


31:52 - The range of unexpected things that may happen with nuclear weapons and a few close calls in the past. How the more experience with these devices, the more manageable people are with them.


34:30 - How Michael views changing people’s perspectives with rhetoric. Instead of telling someone what or how to think, rather tell them your experiences.


38:40 -  Michael’s perspective on using the media to share his ideas. How people want to follow people, instead of companies. The more personal aspects of social media.


42:29 - How changes with the media influence other things, such as politics. Discussing the benefits that come with being aligned with a particular party. A few of Michael’s favorite role models.


48:09 - How 17% of teachers in California cannot afford to live there and some details on this. The high levels of inequality there and common viewpoints from the homeowners there.


53:24 - Examples of changing human consciousness with images rather than rhetoric and some thoughts on this. Discussing the rate of improvement and development of the world over the years.


59:20 - The change in optimism for the future now compared to the high level that it was in the 1930s. Speaking on a few anxieties that we may have for the future. Also, a bit on unemployment and the replacement of jobs by technology.


1:08:20 - Michael’s idea of extending the time spent in education by a year, removing homework, and extending the school day. Also, improving the social aspect of education and improving the amount of physical activity in schools. A few extra ideas for improving education here, as well.


1:14:59 - What proposition 13 is and how it’s impacting numerous things in negative ways.


1:19:39 - A few things we can learn from Michael. How he filters information to get a higher level of truth than he would otherwise. The adjacent possible and how learning on your own can be much better than how it would be in a traditional setting. Also, a bit on what Michael’s goal is (nature and prosperity for all).


1:26:22 - What Michael does to make sure he’s producing at a consistent pace and producing quality work.


1:29:00 - Michael’s favorite story regarding nature and what inspired him to do so much with the environment and nature. Some powerful closing thoughts from Michael here, as well.



Key points in this episode

Introduction: My guest today is Samo Burja, the founder of Bismarck Analysis, a firm that analyzes institutions, governments, and companies for high net worth individuals. There’s never been an immortal human society and Samo is on a quest to find out why. Known for his Great Founder Theory, Samo’s research focuses on the causes of societal decay and flourishing.    In this episode, we talk about Samo's Great Founder Theory through the lens of Apple, Amazon and the myths that drive Silicon Valley. Then, we move to a discussion of geopolitical strategy where we talk about China, the Suez Canal, the Panama Canal, and the importance of Eurasia from a geopolitical perspective, before we jump around between ideas like intellectual dark matter, knowledge transfer, and the story of Singapore. I hope you enjoy this episode.      


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2:15 - Silicon Valley being a great way to understand the great founder theory and discussion on great founders of our time. Discussion on companies later and the skills necessary for a successful company.

9:30 - Samo on Jeff Bezos’ and learning from Amazon’s ability to communicate effectively. Discussion on the bar-raiser concept within Amazon that negates the typical long-term decline of employee quality.

14:18 - Speaking on retaining people within a company and how Amazon does this effectively. Also, how a lot of the ideas around talent and institutions in Silicon Valley have come from Peter Thiel. How him and his book, Zero to One, factors into these ideas.

19:46 - Samo’s experience living under communism for a few years in Slovenia, a bit on his background, and discussion on communism itself.

25:38 - The different ways of judging and trusting institutions and the world in general. Some examples of this and the best ways to go about trusting something, as well. Living in an attention-based economy.

38:08 - How to go about building truth-based institutions within an attention-based economy and some thoughts on this. Discussion on the tradeoffs of stability and dynamism.

45:28 - Thoughts on how to build the right incentives to promote regeneration and continual growth within a society. Speaking on NASA, it’s creation, and its powerful vision in the past. A bit on the origins of the FBI, as well

56:37 - The design of an institution and the natural course of them. Thoughts on handling and improving the problem of succession.

1:02:55 - The role of death in institutions and how iconic deaths may influence major events and preserve institutions.

1:07:06 - Samo’s belief on who controls Eurasia, controls the world. America’s incentive to have some tension in Europe. Discussion on the relation between a countries economy, its naval force, and its geographical location.

1:12:15 - The Sovereign Individual thesis versus the large nation-states and some discussion on this. Thoughts on tracking every computer and a user's actions. The empowerment of people by technology. A bit on nationalism and tying it to smaller communities.

1:18:13 - Lee Kwan Yew and the radical transformation of Singapore, a bit of history and importance on the Suez Canal and the Panama Canal, and discussion on Samo’s term, intellectual dark matter.

1:29:55 - How we might be able to teach tacit knowledge, the advantage of video with this, and some examples of learning tacit knowledge. How education should be and how Samo learns and consumes information.

1:37:20 - What Samo would have said to himself and done differently ten years ago in terms of learning through conversation and from people more effectively. The significance of gaining perspectives from multiple cultures.

1:38:36 - How Samo can help us travel more effectively in terms of heuristics to think through and with learning more tacit knowledge.

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My guest toady is Patri Friedman, a political theorist whose on a mission to increase competition in government. In 2008, Patri founded the Seasteading Institute with a mission create sovereign ocean colonies and "establish permanent, autonomous ocean communities to enable experimentation and innovation with diverse social, political, and legal systems.” We spend tons of time talking about Seasteading and competitive governance in the episode. 

We also talk about the incredible foresight of Marshall McLuhan, the impact of modern technology on government, the future of the nation-state, the rise of city-states, and the rise of digital addictions in the internet age. I hope you enjoy this episode. This episode is everything the North Star Podcast is supposed to be: wild, wacky, weird, and wonderful. Patri has so many new and thought-provoking ideas. I hope you enjoy this episode.

Key points in this episode

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My guest today is James Clear, a writer focused on how we can create better habits, make better decisions, and live better lives. He recently published a new book called Atomic Habits and after reading it, I just had to interview him.

In this episode, we explore the nooks and crannies of habit formation. We discuss habits through a series of conversations about James’ favorite activities: baseball, travel, weightlifting, marketing, and writing. A former ESPN academic All-American college baseball player, James has an uncanny knack for taking important ideas and making them simple and easy to implement. There’s so much actionable wisdom in this episode, so find a pen, grab a piece of paper, and press play. I hope you enjoy this episode.


James Clear’s Website

James Clear’s Twitter

Atomic Habits by James Clear

Show Topics

1:45 David shares his thoughts on “The Power Broker” and what makes it such an informative and impressive book.

5:50 James describes his reading habits and reading structure; specifically diving into where and what mediums he finds to be the most information rich and accessible. 

9:20 – James discusses the dilemma of prioritizing “classic” books that have stood the test of time, compared to the new ideas that are innovative and have built on previous knowledge; but have not yet been tested by time.

10:35- David and James begin to delve into habits, specifically in regards to fitness and the personal responsibility that’s required.

13:45 – Sports habits; how the lessons of sports ,when applied well, can have major impacts on our habits and success in life. 

18:00 - David and James continue to examine various sports and the habits and lessons they have learned from them. 

27:59 - All behaviors produce multiple outcomes across time.” – James goes in depth explaining this fascinating insight about the broad influence our actions can have on our immediate and distant futures.    

34:30 David descries how he structures some of the rules he has set for himself in order to make a positive effect on his goals. 35:30 – James expands on how David’s habits and structure help develop freedom and spontaneity.

38:50 – Examples from Lebron James and Brett Favre serve as case studies that explore some of the incredible feats of awareness and “one step ahead” kind of thinking that result from years of habit development.

41:44  - James shares his thoughts on compounding habits and the potential long-term gratification. 

44:55 - The importance of starting small when it comes to habit forming, rather than becoming fed up with failure when overreaching. 

45:55 – David questions James on  “How do habits effect or influence ones identity.”

50:53 – Tips and advice on building habits by starting small and working your way up.

53:46 – “A habit must be established before it can be improved.” James explains the importance of establishing a habit and building on it.  

56:15 – How our environment and surrounding influence us and open up new opportunities. 

1:00:30 – James shares his thoughts and advice on keeping up habits when on the road or traveling. 

1:04:00 – James shares how his love for photography was kindled and developed.

1:07:10 – David and James continue to discuss the art and unique interpretations of photography

1:11:45 – James shares some of his writing habits and strategies used as he built up his website and articles.  

1:22:10 – James goes down the rabbit hole with a question that has been on his mind: “Does conscious arise from language” 


1:45 – The Power Broker by Robert A. Caro

8:30 - The Lessons of History

9:18 - Origin of Species by Charles Darwin

21:20 - The Art of Learning by Josh Waitszkin

38:07 - Cleaning the Glass

Hey again, it’s David here one more time. 

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My guest today is Steve Schlafman, a venture capitalist, leadership coach and partner at Primary VC. This episode is a wide-ranging, emotional journey through the nooks and crannies of investing, introspection, and sobriety.

Steve is a man of many passions. In the business world, he’s invested in breakthrough companies like Zipline, Brightwheel, Bark & Co., Managed by Q, Bowery Farming, Citizen, Care/Of, Boom Aerospace, TheSkimm and View The Space. Our exploration of investing was driven by five themes: leadership, market demand, customer focus, emotion, and human impact.

Outside of the office, Steve lives a sober life free of alcohol and other substances. He’s a passionate cyclist and rides more than 2,500 miles every year. This episode is particularly profound. Steve and I down down, deep into the depths of human emotion — from struggle, to pain, to addiction, to wonder and joy. I hope you enjoy this episode.

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3:30 – Steve explains his role and his program learning what’s called “transformational coaching” and how he became attracted to the idea of coaching.

6:30 – The value of coaching and common misconceptions of how a coaching can push and direct people. As Steve puts it, as a coach, “you shouldn’t be trying to fix, but instead, [trying] to understand. You’re not coaching the issue, you’re coaching the client.”

9:50 – The mindset of a good coach.

10:30 – David raises the questions of what makes a good coach versus a great coach.

11:04 “Self management” as a coaching mechanism.

13:45 – Steve reflects on coach Belichick and what he admires about him as a coach.

15:45 – Steve continues to dive into some of the abilities beyond coaching that Belichick exemplifies, namely the ability to asses and project players potential before even becoming their coach as well as his ruthlessness and situational awareness.

19:25 – The “human centric investment philosophy” Steve pursues. 

22:48 – Steve dissects genuine leadership and how it’s relevant to success as a coach and individual.  

26:45 – Where does that “drive” that successful people share in common come from? 

29:20 – Steve explains “Market Demand” via a story about opiate addiction and recovery. 

30:10 – David and Steve dig a deeper into the opioid crisis and how they have seen it affect those around them 

35:15 – Digital desensitization; how our modern relationships to tech and social media have been affecting our empathy and view of what’s going on in the world around us.

38:14 – What makes a brand a brand and the following and loyalty that having a good brand generates.

42:00  -Steve gives some examples of how great things happen organically, and not always when planned. 

47:50 – David reflects on the form of expression and communication GIFs introduced when communicating digitally.

52:40- Having children is on a downward trend. David and Steve discuss some of the factors surround this new trend. 

55:45 – Steve shares some of his observations from his recent trip to Sweden and the perceived quality of life by its residents.

01:02 – Steve shares some of the reasons he fell in love with cycling and what makes the sport so unique and non mundane to him. 

01:08- Steve talks sobriety and what it means to him.  He details the positive and transformative effects it has had on his life.  

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My guest today is Daniel Gross, a partner at Y Combinator, the world’s best startup studio. Daniel focuses on artificial intelligence at Y Combinator and recently founded AI Grant, a distributed AI Research Lab. 

Daniel was born in Jerusalem, Israel and was accepted into the Y Combinator Program in 2010. At the time, Daniel was the youngest founder ever accepted. In 2013, Cue was acquired by Apple. At 22, Daniel was leading several search and AI efforts across the company spanning iOS, OS X and Apple Watch. 

In 2017, Daniel joined Y-Combinator as a Partner. He launched YC AI, Y-Combinator’s first vertical dedicated to investing in AI companies. In 2018, Daniel founded Pioneer. Pioneer is a search engine for the millions of “Lost Einstein’s” — extraordinarily creative people around the world who have the talent, but lack opportunity. Once identified, Pioneer and makes small investments to support whatever project they’re working on.

In this episode, Daniel talks about the experience of coming to America and starting a company with Y Combinator. He talks about the power of seeing life like a video game with levels, and fast, continuous feedback. Daniel also shares lessons from John D. Rockefeller on business, decision making, and company building. Finally, Daniel talks about Israel and shares his insights on why the country is so innovative.


5:40- Daniel talks about some of things he became fascinated with early on in life.

8:20 How Daniel took an early interest in coding through video games and reverse engineering.

8:50 The “gamifacation” strategy Daniel uses to set goals and motivate himself.

9:20 “Everything in life is some form of a video game”  Daniel explains how life can be similar to a video game in terms of seeing stages of life as levels, and setting goals and strategies to progress one from level to the next.

11:22 Daniel delves into what motivates people and specifically how our need for approval is not necessarily something to be ashamed of.

14:00 Daniel talks about YC’s earlier years and his first encounter with Steve Jobs.

16:00 Daniel describes his initial vision to create a “personal” search engine capable of sorting through your own personal data.

17:10 Daniel explains a variety of features and functions that AI and his coding have on iOS and OS devices 

18:15 How will we interact with artificial intelligence in the future?

21:00 The pitfalls of trying to superimpose the current futuristic thinking rather than expecting the unexpected. 

22:56 New tech often seems like a toy or novelty at first, up until it becomes mainstream.  

23:27- Daniels offers his perspective on the bottlenecks we have on scientific progress and the current lack of diversity in terms of ideas. 

26:00 Entry barriers most start ups have to face and overcome when entering AI development.

27:32 Daniel speaks about Assembly A.I., a start up that YC worked with.

29:30 Daniel explains the benefits of reevaluating a strategy when stuck on a challenging “level.”

34:45 David suggests the first steps to perusing progress is surrounding yourself with great people or ideas.

35:09 Reverse engineering your vision, into a plan. How to set “levels” as goals when playing the game of life.  

37:39 How vital of a role our environment plays in our development and pursuit of  of progress.

38:15 Optimizing for a city versus a small group and the importance of one’s surroundings when pursuing a goal or idea.

39:38 Social/professional groups and their validity while shifting to a digital format. How strong are our online relationships when it comes to motivating us?

43:06 What makes Israel so different and innovative?

45:20 Daniel describes the first and second Intifada in Israel and the resulting send of community that was cultivated during the shared suffering. 

47:46 “Scarcity creates greatness” How Israel innovates out of necessity rather than experimentally. 

51:30 The “harsh” culture of Israel and its contribution to the deterrence of pursuing potentially good or risky ideas. 

53:45 How optimism can be both a positive outlook for growth, but can also lead to false or unrealistic expectations  

57:00 Daniel on how we can learn from history when looking at it from a cyclical point of view.

1:00.24 – How ‘stupid little ideas” can turn out to be some of the most innovative endeavors when pursued.

1:01.38 “Fitness as a ticket of admission to the world” and how it enables us to better experience more aspects of life.


Key points in this episode

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My guest today is Arianna Simpson, the Managing Director at a cryptocurrency hedge fund called Autonomous Partners.

Arianna’s background is fascinating. She grew up in Italy and spent time in Zimbabwe, where she got a first-hand perspective on hyper-inflation and what it does to people. That’s where we began this conversation. Then, we moved on to learning. Arianna is a voracious reader. At one point in her life, she was reading 300 books per year. 

We also talk about her love for Burning Man and how to find new ideas on the internet. We explore how and why San Francisco has the culture that it does, and explore Arianna’s investing philosophy. 

Please enjoy my conversation with Arianna Simpson.

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Arianna Simpson


Arianna Simpson’s Twitter

Arianna Simpson’s Website

David Perell’s Website

North Star Media

North Star Podcast

“Tall Poppy Syndrome”

Show Topics

2:18- Arianna discusses her childhood in Italy and her frustrations with bureaucracy.

3:00 Arianna discusses her philosophy of optimism and reveals why she’s excited about the future.

4:11 Arianna compares Italian culture with American culture. She discusses how growing up in Italy shaped her worldview.

7:50 David explains the concept of “tall poppy syndrome” and discusses his trip to Australia.

9:00 Arianna shares lessons and learnings from her time in Zimbabwe, and tells a story about running elephants.

10:30 The wild and vastly different realities of life in Zimbabwe compared to the US.

12:00 Arianna describes how cryptocurrencies became relevant in Zimbabwe despite its lack of infrastructure.

12:30 David and Arianna dive into the relationship between culture and money.

14:30 Money touches everything; beyond capitalism it touches our culture, how we eat, our security, and just about everything

16:30 The appeals of crypto in regards to transparency and cutting out the middle man. 

18:45 Arianna gives some examples of financial catastrophes, such as the collapse of Long-Term Capital Management.

20:19 What makes crypto different?

21:30 Human psychology and how it drives peoples long term financial decisions 

23:05 Arianna explains a “multi-year horizon” as a good starting point for long term financial planning

24:30 Investing is not that hard in terms of intellectual complicity, it’s the emotional side and risk management aspect that present the real challenge.  

24:50 How Venezuela may be one of the best real world examples of the security and necessity for crypto. 

27:30 What should governments think about when they think about cryptocurrencies.

30:10 The history of money and why understanding it may be more helpful than we realize. 

31:38 if crypto is not backed by anything, what makes it any better than monopoly or make believe money?

33:02 David ask Arianna to breakdown and explain what the learning processing looks like when learning about crypto online. 

35:20 How Arianna spends and managers her time studying both and history and projections of crypto 

39:29 David and Arianna dive into books and learning from reading and how it fits in as a way of life. 

47:20 How cross-pollination of ideas can lead to surprising creative discovers 

48:45 What makes San Francisco special?

50:49 Arianna explains a concept she calls “the suspension of disbelief” and shows why it applies to San Francisco.

54:00 Arianna shares some of the special factors that make Burning Man such a great experience for her.  

57:31 Arianna shares how she likes to rebel against her own fears by challenge them and facing them.

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My guest today is Derek Thompson, a Senior Editor at The Atlantic who writes about media, culture and economics in America today. 

I first discovered Derek’s writing while researching the state of Hollywood for an essay I was working on last year. Derek cultural observation has stuck with me ever since. Derek wrote that Hollywood audiences are ignoring movies that aren’t a sequel, adaptation, or reboot. This statistic stuck with me: In 1996, none of the top 10 movies were sequels. Twenty years later, in 2016, more than half of the top 10 movies were sequels, adaptations or reboots.

In this episode, Derek talks about his background in acting and his love for Hamlet. Together, we nerd out on the magic of theater and the surprisingly large differences between what happens in the theater and what happens at the movies. Then, we explore taste and culture. We talk about Stewart Brand’s “Pace Layers” theory of architecture, Japanese Emperors, what fashion can teach us about the world, and the history of impressionism. We investigate how blockbuster success isn’t a matter of chance, but a fascinating intersection of power, network science, art, and sheer brilliance. 

Here's my conversation with Derek Thompson.


Derek’s Twitter Account

Derek’s Articles

Derek’s Podcast

Derek’s Book — Hit Makers

Show Notes

3:45 Derek expresses his appreciation of theater 

5:51 Derek explains why Hamlet is one of the greatest plays in history

7:08 What made Shakespeare so great?

9:30 Derek discuss the features of Shakespeare’s writing that make it so timeless 

9:53 What makes a perfect movie? 

11:00 Derek discusses some of the best movies and plays written over the last several decades 

12:15 The key differences and difficulties of getting theater to a screenplay

15:00 The cannon of art has a different meaning now. The real question is “what is the best?”

17:23: “We often conflate familiarity with fact.” Derek speaks about familiarity and its influence on our perceptions of facts and quality.

17:50 How our modern perception of cannon has changed as we have begun to question and challenge its history and validity

19:30 Our sense of “good taste” and how it’s defined in the contemporary age

20:19 “Cultural Capital” and “Cultural Omniscience”

22:47 The shift of culture from valuing scarcity to valuing familiarity

23:45 Modern celebrity and the rise of “manufactured intimacy”

25:50 Formality, and how its quickly losing its reverence and relevance in modern culture. Why is the world becoming more formal?

28:00 Derek takes a closer look at how informality has affected modern culture, specifically in the case of presidential speeches

31:45 The blurring line between work and home

32:20 How taste is trained or influenced

37:59 “M.A.Y.A- Most advanced, yet acceptable” 

38:56 The sweet spot of familiar and surprising

42:02 Derek picks a point in history he would go back to if he had the chance

50:00 The over-looked and under-rated importance of art history

55:39 Derek delves into the concept of nature vs nurture and the influential and guiding elements of personal development

57:47 Derek talks about his favorite authors.

59:35- How should writers explain complicated ideas?

1:12.04 - Non fiction and journalism compared to the ironic honesty and realism of fictitious writing.

1:07.57 Derek’s take away thoughts on the craft of writing and shares his strategies for learning and information consumption.


5:53 Hit Makers: How to Succeed in an Age of Distraction

21:30 Jon Bellion, The Making of Luxury

25:18: A Matter of Taste: How Names, Fashions, and Culture Change

37:03: Raymond Lowey

44:06 Louis XIV

47:28: Beowulf

57:50 Philip Roth

58:39 Jonathan Franzen

58:45 Donna Tartt 

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Key points in this episode

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My guest today is Austen Allred, the founder of Lambda School — a revolutionary new school. Here’s how it works: Lambda School trains people to be software engineers at no up-front cost. Instead of paying tuition, students agree to pay a percentage of their income after they're employed, and only if they're making more than $50k per year. If you don't find a job, or don't reach that level of income, you'll never pay a cent.

So, how does tuition work? 

There are no up-front costs for Lambda School; they only get paid when students do. Once you’re earning at least $50k per year they'll pay back 17% of your income for the first two years, and total tuition is capped at $30,000. 

In an age where continuous learning is essential and student debt has skyrocketed, I’m struck by this model. Information is everywhere but learning is still difficult. Online, it can be hard to push through the difficult moments that get you over the hump or find others to share the journey with. 

Austen has some exciting solutions and we devote this entire conversation to the present, past and future of education.

David Perell and Austen Allred

Time Stamps

2:50 - Understanding the trade offs of the job market when making education choices

7:33- How Lambda compares to other universities or colleges

13:01 - Austen describes some of the problems with online education

14:43 Participation differences between pre recorded lectures and interactive lectures

15:50 Austen describes living out of his car during his beginnings in Silicon Valley

21:40 Lambda’s end goal and pursuit of sustainability for both the school and its students 

22:49 Shifting peoples perceptions on education and the future

24:10 How the current public education system fails to teach people “how” to learn.

27:05 Why hasn’t education changed much over the past 50 years, and how can we change it?

30:50 Austen explains his perspective on the pitfalls and shortcomings of the current high education system and student loans

34:10 Student loan payments and the adverse effects on the borrower

36:05 How apprenticeships fit into the modern education system and how the affect both job readiness for the apprentice, as well as the impact on a mentor.

43:00 The growing divide among society and conflicting schools of thought among sub regions of the USA.

48:30 Austen shares some Lambda School success stories.

Click here to learn more about my company, North Star Media.

You can support the North Star Podcast by leaving a review on iTunes. Or you can share the podcast on Twitter or Facebook.

To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell.

Key points in this episode

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My guest today is Devon Zuegel, a writer of code and writer of words who spends her time unlocking human potential through incentive design and tools for thought and cities. In this conversation, we jump from coordination problems to urban planning to travel to architecture. We compare cities like Singapore and San Francisco and talk about the power of urban density and architecture to make us happier and healthier. Then, we talk about writing, specifically the three tiers of common knowledge, how to find good ideas, and the concept that Devon calls playing chess with yourself.

One thing sticks out from this podcast and other conversations with Devon. Above all else, Devon lives in obsessive pursuit of high leverage ways to spend her time and energy. In the past, that’s led her to computer science and in the future, I suspect it will lead her to cities and infrastructure. Why cities? Devon offers an excellent answer. Cities are big enough to have real importance in the world and small enough to be nimble and somewhat understandable and there are a lot of cities. You can actually hope to make some comparisons in a way that you can’t really do with countries. 

Please enjoy my conversation with Devon Zuegel.



Algorithms To Live By: The Computer Science of Human Decisions


Devon’s articles related to this episode: 

Advice on Writing

Why Flaking Is So Widespread in San Francisco

A Day In Singapore: Urban Identity

2:03 Devon on coordination problems and the problems they’ve caused, such as climate change and housing issues, and how clever solutions to these problems are the reason humans have progressed so much in the past hundreds of years

6:19 Human cognition and thought as it is augmented by media, cities and blockchains and the benefits of this augmentation

8:10 The most classic tool for thought and why it’s such a catalyst for healthy and productive cognition, long term and short term memory function and increased IQ

16:41 Devon’s writing process and why she defines it as playing chess with herself

17:45 How Devon has been able to get her writing to flow and the three categories of topics available to write about, common knowledge, obscure knowledge and the intersection in the middle

20:17 Devon’s theory of on why people in San Francisco are so flaky in comparison to sister cities like Chicago, Los Angeles and New York City

28:16 How Devon chooses what rabbit holes she wants to go down prior to writing an article and how to make most topics interesting by creating a model around the idea

32:25 What makes Singapore so interesting to Devon, in regards to history, culture, GDP growth, etc. and her major observations after visiting the country

47:20 The moment Devon became aware of the effect of architecture and how it can make employees less involved with their colleagues by not promoting micro-interactions

50:53 The five metrics that a house should be described with, that are never used, when being promoted on websites like Airbnb, Zillow, Craigslist, etc. 

57:00 Devon chooses the three metrics that she’d pick when it comes to the city she lives in and the home she’s living in for maximum interaction, convenience and mental economy

1:03:16 Algorithms To Live By and why Devon sees it as the best self help book she’s ever read, despite it not being a self help book

1:05:37 Devon’s opinion on Georgism and how people talk about economics as a spectrum from capitalism to socialism or communism and the third category of economic goods that it doesn’t touch upon

1:07:30 Devon’s changing opinions and her epistemic status placed on each of her blog posts written with a strong opinion

1:10:03 Devon’s philosophy of travel and why she views it as scale free regardless of how many or little places you visit

1:11:51 Devon’s philosophy of productivity and how she writes down dozens of notes and uses long form emails to repurpose her ideas into publishable articles

Subscribe to my “Monday Musings” newsletter to keep up with the podcast. Quotes

“I am very interested in coordination problems. I think that they explain a lot of the problems that we see in the world, everything from climate change to nuclear disarming to issues in cities to making it so that people can actually live where they are the most productive to housing policy. I could go on and on. The solution to coordination problems is incentive design, and clever solutions that are some of the reason humans have been able to progress to the extent they have throughout the past few hundred years.”

“The most classic tool for thought, and one that I think we tend to take for granted, is writing. Most people think of writing as a way to communicate ideas that they’ve had in their head to other people. Obviously, it does serve that purpose and people sell books for a reason. But, I think it goes way beyond that.”

“In the last year, I have found that writing has gotten a lot easier for me. There’s probably a lot of reasons for this but I think the core is that I realized there are three categories of topics you can write about. There’s the stuff that everybody knows that is trivial to write about because it’s easy. On the other end, there’s stuff that nobody knows yet or nobody around you knows yet, so it takes a lot of time to figure it out and it takes a lot of research. Now, there’s this middle area between common knowledge and really obscure knowledge of stuff that you have a unique perspective on because of where you happen to be in life and you understand it so intuitively that you can just talk, think and write about it fluidly. But, a lot of people don’t know it yet. That’s the sweet spot.”

“For me, it’s very important that I can walk places. Walking is a way to interact with your community in these small ways, every single day. The way people get comfortable in a place and in a social group is not through one really intense interaction, but through a bunch of smaller ones where you see things from different angles. You experience, what does my neighborhood looks like on a sunny day, on a cloudy day, or when I’m tired. These tiny, trivial things help you understand, much better, how things function. You get to know the vibe so much better and you meet people you wouldn’t meet if you were in an Uber.”

“Algorithms To Live By is the best self help book I’ve ever read and it’s not intended to be a self help book, it’s intended to be an algorithmic look at certain problems that people see day to day. But, it helps me frame certain problems that I personally run into in terms of the algorithmic complexity. I realized the stress that I was feeling about certain things I was worrying about, were actually totally rational.”

Subscribe to my “Monday Musings” newsletter to keep up with the podcast. TRANSCRIPT


I am very interested in coordination problems. I think that they explain a lot of the problems that we see in the world. Everything from climate change to nuclear disarmament to issues in cities and making it so that people can actually live in where they're the most productive, in housing policy. Well, I could go on and on and on with the list. So the solution to cooperation problems is incentive design. And I think clever solutions to incentive design are some of the reasons why humans have been able to progress to the extent that they have throughout the last few hundred years. So a primary example is contract law, it makes it possible for people to trust one another. Other examples are the development of risk and the concept of commodifying the risk.


I was having a conversation yesterday in another podcast and the guest was saying that in 1471, what happened was people were able to pool maritime risk. And what happened was it let big expansive ship voyages happen because you could pull risks together. And so if you invested in a ship and say that ship broke down, then you wouldn't lose all your money. And by pooling risk and by coming up with new financing and coordination solutions, you could do things that weren't previously possible. I thought that was really interesting.


Totally. That's a great example. Actually. Old maritime risk looks a lot like venture capital today wherein venture a lot of things fail. A lot of things fail spectacularly. But if you can spread out that risk across a whole pool of investments, it only takes a few to like really, carry the whole fund. In the case of maritime investments, a lot of the ships broke down, they had problems. But if one ship came back with a whole load of goods that could repay all of the rest of the costs. However, most, most investors back then couldn't take that risk because most of them would have failed. They might've lost all their money before they hit that one big one. And so by the development of that maritime risk, they were able to get past that sort of short-term problem and to get into the run longer returns.

I think that's a really good metaphor for all sorts of problems that we run into wherein the short term it's rational to do a thing that is not as interesting, that it's not as lucrative, but it's also not as risky. But if we're able to coordinate as a society, as a company or whatever level you want to talk about. So one more concrete example to bring it down from like highfalutin, venture capital and maritime risk, you could just look at cooperation problems as simple as when you're dating someone for the first time, there's that standard wait three days until you text them back after you met them because you want to come off as cool. You don't want to come off as desperate, right? But if you really like each other, like all this is going to signal is that you don't like them very much.

And that may be rational for you because you don't want to come off as desperate. But if you're both doing that, you end up with an outcome where it seems like you don't like each other very much and it takes a really long time to actually realize that you do. Ideally, you would have some neutral trustable third party who could be a person A, person B, out Alice and Bob like you both like each other. You told me that you liked each other, just go for it. You know, have fun. And I think a lot of healthy relationships that I've seen have actually started in this way because of some small quirk at the very beginning. It can be super useful, but a lot of the pain that I see my friends going through when they date is literally just the result of playing games because rationally, you're supposed to. It's basically a prisoner's dilemma. And so if you can have someone who forces you into the correct quadrant where everyone is better off, that's much better.


So then let's jump into sort of human cognition and human thought. Maybe begin with media. What interests you? Sort of when I think of where this conversation is going to go today. So much of it is about augmentation, right? Like cities augmenting the potential for humans interact and making that so much easier. And blockchain augmenting human coordination is making that easier. And then here with thought and having tools, augmenting human thoughts and letting us go places that we probably wouldn't be able to go if we were stuck in the mountains on our own.


I think the underlying reason I'm interested in incentive design is because it allows us to unlock human potential and allows people to do much cooler stuff that makes them happier, healthier, makes life more worth living. I see ways to augment our cognition as serving that same purpose though from a different angle. The umbrella term that people sometimes give this is tools for thoughts and we have basically the same brains that we and our ancestors had thousands of years ago, but we're able to do so much more. Part of that is because we've developed incentive design. The other reason is because we've developed tools for giving our cognition more leverage. And I use the term leverage actually very specifically. You can only get so strong no matter how much you lift. How once you go to the gym, like you're still not going to be an order of magnitude stronger.

You're definitely not going to be two orders of magnitude stronger. However, if you design an engine, if you just even add a lever that gives you that leverage, you can do so much more with your muscles. I see that that translates directly to your brain. The most classic tool for thought and one that I think we tend to take for granted is writing. Most people think of writing as a way to just communicate ideas that they've had in their head to other people. It obviously does serve that purpose. People sell books for a reason, but I think it goes way beyond that. So one thing that writing does for you is it expands your working and your long-term memory. With the long-term memory, it's pretty obvious. You take notes, maybe you don't remember all the details, but you can look them up later.


To your point, even today I was writing something this morning and I wrote something that I wrote about a year ago and I have no recollection of writing it and I read it and I was like, wow, that's actually pretty smart and it really helped me, but I think to your point, there's a permanent element of writing and being able to sort of work through sentences and craft them, makes it so that you can achieve thoughts because of the repetition and the sort of tweaking and editing of writing that you can't do if you're just speaking like we are right now.


100 percent. And I've also had that experience more times than I can count of like coming across something I've written and being like, oh, this is interesting, I wrote that. That came out of my brain. And as long as you have enough of a pointer to that idea that you can find it when it's necessary, or it gets surfaced by accident because you happen to open up an old notebook. That's extremely powerful. It makes you much better at remembering. I think even more importantly, a writing helps you with your short term memory, your working memory. There have been a lot of studies showing that a working memory is one of the highest things correlated with IQ and the ability to solve problems.

And I think the reason for this is because if you have good working memory, you can hold a lot of state in your head and you can sort of fiddle with that state. You can hold contradictory but potentially correct ideas and outcomes in your head while you work through the problem. And then they collapse into one at the end.


Describe state real quick for someone who doesn't have the computer vocabulary that you do.


So state is what is the current status of the world right now. Let's say you're working through a personal problem and with your family or something, and you want to go through step by step and sort of understand the implications of what different people have done. You're getting the story from different friends, like maybe you're helping reconcile like your aunt and your uncle or something like that, having marital problems and you want to understand how they got to that point and how, given where they are right now at that point, like how different changes result in better or worse outcomes. Understanding the current state of the situation and then like fiddling with it and being able to hold all of those sort of partial computations in your head are really important to be able to compare them and to be able to move forward and find a solution.


So you're saying that writing and sort of computers at large now help us hold more state so then we can move on to higher-order tasks that perhaps aren't memory, that our brains are really well suited for.


Exactly. And they're more interesting. And working memory can kind of provide abstractions. I think the best metaphor for working memory or external working memory is like scratch paper, that there's a reason why math teachers always tell you, feel free to use as much scratch paper as you want. That's not just because they hate trees and they want to waste all paper. It's because being able to externalize that process is really, really helpful. Offload is the perfect word.


So back to writing.


I think it actually goes even much further than memory. With writing, it is fundamentally the process of externalizing an idea which allows you to play with it in ways that I don't think are so easy when it's in your head. I'm certainly not capable of it. Writing things down can reduce the amount of ego that you have as you fiddled with an idea. Maybe I'm just crazy, but when I wrote them down and almost pretend like the person who wrote that wasn't me, it was like, that's past Devon or someone else entirely. I can detach myself from it much more in a way where, when I am a thinking through something just in my head and lying in bed wondering. I'm not going to be as rigorous about it. Now that's not strictly worse. There are other things like everyone has great thoughts in the shower for instance. It's very common. But it doesn't serve all purposes, especially if you're trying to vet and find the nooks and crannies of an idea. When you write it down, when an idea has inconsistencies or gaping holes, they are clear and right in the face when it's written down in a way that is just so easy to gloss over when they're in your head.


And also when you're speaking, you can sort of gloss over some of the inconsistencies with emotion, right? If I speak really deeper and confident with what I'm saying, actually there's an element of trust there. It was really funny. So we had a meetup in Queens a couple of weeks ago and my buddy goes on Snapchat stories and he goes really confidently, coming to the meetup and he goes "Did you know that the reason it's called Queens is because Queen Elizabeth came to New York in 1754?" and you're sitting there being like "Man, you know, why are you being so smart here?" And then he finishes the thing and he goes "Well, I just made that up, but you believe me because I said it so confidently." So what writing does is it strips out the emotion out of a form of communication and it allows logic to take over emotion.


Right. And it allows you, it gives you something like almost physical to move around and change. I'm a really big believer that constraints are actually a good thing in your thinking because if you're completely working in a vacuum, you have nothing to push off of. You have no feedback cycles. Whereas if you can just get a draft onto the page, you can fiddle around with it so much more. And I find that writing that draft in the first place, that's usually the hardest part, but once I have something to work off of, it gets much, much easier. It helps you find implications that you didn't realize there were, which again, I don't fully understand like the cognitive science behind why this is. But by putting it on the page, you start seeing these almost trails in your head of like, given this, given I said this, what are the implications there?

And you can actually follow those trails and like come back to them after you've written them down and realize, oh, this thing does have an implication I hadn't considered. One of my favorite things to do when I'm writing is just looking up synonyms for words. And the reason is not just to make myself sound smarter. Though, that's always a plus. But much more importantly is that by looking up synonyms, you can think about which words don't make sense here. Even though they are technically synonyms. And why they don't make sense and analyzing that is extremely useful. It's sort of a generator function for coming up with new ideas. Similarly, I think choosing the right word is also really important. Words come with such heavy connotation that picking the right one can be the difference between concepts really striking home and like feeling kind of flat.

So I highly recommend people using sources when they write, all over the place. I actually use sources when I write code as well, for variable names and class names and things like that, because it helps you. Computer science and programming is basically the art of abstractions and abstractions is another way of saying names mostly. And coming up with really good names for things is a really critical piece of being able to write good software. So I think the source, I go to probably 300 times a day. I have never actually counted, but it's a lot of times. I've always idea called playing chess with yourself.


Walk me through that.


So I think writing, especially the writing process, before you've published, as kind of like playing chess or yourself. There's that Pixar short, it's called like Geri’s Chest Game or something like that. And it zooms in on this guy sitting on a park bench playing chess and his partner isn't around.

And you're like, oh, I guess maybe they went to the restroom, maybe they're coming back and then all of a sudden the camera zooms in and he's like on the other side, playing with the white pieces now. And then he flips back and forth and you realize he's just having a ton of fun and playing against himself. And he's really excited against himself. This is a hard thing to do inside of your own head, but it's actually a lot easier when you've externalized something because once you have that writing on the page, you can treat that as sort of another person almost. And play around with it in a way that is just much harder when you're by yourself.


Totally. And then the other thing is I think you have sort of an uncanny knack for generating unusual ideas and I don't say this to discredit you, but I think that you've built some systems to make that a hell of a lot easier. Walk me through different tiers of common knowledge. So I got an email last week from a guy who said, I love your writing, but the biggest thing preventing me from writing is that I always think that everybody else knows the things that I know and that's the biggest thing. Stopping. And I responded and I said, well, that's not necessarily the case, but I wasn't able to formulate something that I think that you've been able to grasp in terms of different ways of thinking about what is common knowledge? If you could describe that. And then how does that translate to writing and drafting an idea?


Yeah, that's a great question. So in the last year, I've found that writing has gotten a lot easier for me. There's probably a lot of reasons for this, but I think the core one is that I realized there's sort of three categories of topics that you can write about. There's the stuff that everyone knows that's like trivial to write about it because it's easy. The sky is blue. Okay, good. That's awesome. No one wants to read that. Very common knowledge. On the other end, there's stuff that no one knows yet or no one around you knows yet. And so it takes a really long time to figure it out, requires a lot of research. I can point to some examples of things I've written where I'm very proud of this writing that I've done, but it was a slog all the way through.

Some of the stuff that I wrote about, the federal housing administration last year, just required poring through hundreds of documents from old FHA manuals and things that I don't know if people have looked at in a while and I found some novel stuff, but it also was a ton of work. Now there's this middle area between common knowledge and like really obscure knowledge of stuff that you have a unique perspective on because of where you happen to be in life and you understand it so intuitively that you can just talk and think about it fluidly. But actually a lot of people don't know it yet and I think that that is the sweet spot for generating a lot of streams.


How would you know when that's true?


That's a hard question. For a long time, I just thought that this the way I think is the way that everyone thinks. And so I was like, no one really wants to read about like my theory on flaking in San Francisco. Everyone in SF knows that already.


But what's your theory on flaking?


I haven't lived really in any other city, but my impression from talking with friends is that the rate of flaking is extremely high, with friends, with romantic partners, et cetera, relative to sort of sister cities like New York or Chicago or LA. I think part of the reason is that people in my social circles in San Francisco really understand opportunity cost well. There's a very casual culture here where it seems like an acceptable flake. And we also are like, even more so than other millennial types, are very technologically savvy.

So if 10 minutes before your coffee date you're like, oh, sorry, I got caught up in something. Can we reschedule next week? It feels trivial because it's just a text. You're not going to literally stand them up because they just won't show up. But the problem with this is that it's another cooperation problem where we ended up in this equilibrium where it feels acceptable for everyone to flake all the time and just not show up to their commitments. But then like everyone's worse off because your scheduling is more complicated. You never really know. If things are going to happen when you think they're going to happen, you kind of don't want to be seen as like the pathetic one who doesn't cancel the plan. So you almost are incentivized to flake because if someone flakes on you enough times, you're like, well, I don't want to look like an idiot.

I don't want to be taken advantage of here. So, next time we make plans I'm going to double book and see which one feels more interesting that day. And I think that leads to a real breakdown of trust and like happiness and satisfaction with relationships. Since I realized this, I've personally made a stance where I'm like, I will not flake on something unless I have an exceptionally good reason. And my friends I've noticed have also started to like follow up with me where I've put a stake in the ground. It helps that I wrote a blog post about it. I put a stake in the ground of like, I don't want this to be okay anymore because it's like making everyone's life worse.


What about San Francisco makes flaking uniquely common here?


I think there's a mentality of casualness where if you walk around the city, no one's ever dressed up. I mean, literally today I am wearing yoga pants and a tee shirt, and people want to look mostly clean cut, but they'll wear athletic gear almost all the time. I think that is indicative of a broader social casualness. Certain social norms are not as strong and in fact, the social norm is to not have strong social norms. And if you want to come off as like cool and casual. If someone is placed on you and you say something and you're like, hey dude, you flaked on me last time too. That's sort of like a point against you. You're seen as uptight or something. Maybe LA is also more similar to this, but I think like in New York, I feel like there's more of a seriousness in the way people interact where it's like your people get dressed up when they go out.

Like when I go to New York, I always feel super underdressed. I think that carries over to a lot of parts of the culture. Where you don't break dates unless you have a good reason. Whereas I can look back on my calendar before I had all of these thoughts and honestly I was either breaking or having commitments broken on me like 50 to 70 percent of the time. And I don't think I'm unique in this because I've had conversations with a lot of people on my team.

So I want to go back to writing, but I just want to summarize why I think that falls into the second category of common knowledge. So the first category is things that everybody knows like the sky is blue. The third category is things like the history of FHA housing, which probably requires a lot of research and nobody knows those things. But the second category is things that everyone sort of has a common framework for discussing like flaking. But because you are in a social circle that has a high opportunity cost in San Francisco, you have unique insight into that problem. And when we have a common knowledge, a common way of speaking about something and you have unique insight into that same sort of thing, that is when you should go pursue an idea and share it with the world.


Totally. I think that's a really good framing of it. I especially like the term common knowledge. Because I don't think anything I said in the post was surprising to anyone, but I think finally sitting down and putting the pieces together as to why all of this stuff comes together, I think is the difference. And just taking the time to sort of reflect on like various dynamics in your own life I think can be a really powerful generative tool.


I gotta ask, as you think about your writing, you think about your learning sort of your process for living, so to speak. It's cool because I like people like this. Your process for living is also a process for sharing, right? It's almost like a co-dynamic between the two where you live, you share, you share, you live, and I think that they, they sort of co-evolve and develop. Who were the people who have really inspired you to become like that and who were the mentors, digital or physical that have really inspired you?


There have been a lot. And this actually ties really nicely into the framework of like common knowledge to obscure knowledge. I think I used to think that a writing had to be this big formal process where you sit down with an argument or a spectrum and you try to decide where on that spectrum of arguments you lie and then you dive deep into the literature and you study it, and then you pop out weeks later and you've like displayed to the world this thing, this masterpiece you've been working on. A lot of writing does follow that. A lot of great writing. And I don't think people should stop doing that by any means, but I think there's this other type of writing that is treat your ideas less as a final project product and more as a process.

Someone who I think does this very well, I don't know him personally, is Ben Thompson at Stratechery. He writes about the same stuff day after day, but each time he writes about it, he turns it a little bit in his mind. He comes at it from a slightly different angle and over the course of years he has built this canon of like what aggregation theory and he has this whole vocabulary that he's built up and you can see when you go back to his earlier writing, the idea is not fully developed at all, but the writing itself was the thing that developed the ideas. And I think that that is a huge mindset shift that I've had where I used to think first you have the ideas and then you write them down, but actually, you should have some seed of an idea. But then when you start writing, that's what actually brings it out and like causes it to flourish and grow. Another person who's played a really big role in helping me realize the value of this is Tyler Cowen (my podcast episode with Tyler). His blog, Marginal Revolution is just like one of my favorite things on the internet. It's the most ridiculous set of things. It's the intersection of all stuff and he doesn't take it that seriously.


Right. And the juxtaposition of ideas that you find there puts your brain in crazy places because he'll share, NBA basketball, his recent trip to Ethiopia, and then markets and everything in some weird market that you've never heard of. And I think that really cool ideas and really cool ways of thinking come not necessarily when you discover a new idea, but when you juxtapose ideas that you're vaguely familiar with and then your brain just goes in weird places through that.


Yeah, by having this huge diversity of sources and ideas, it allows for a type of lateral thinking that I think is really missing in the world. And something I particularly love about Tyler's work is that he both does and doesn't take it seriously at all. So by does, I mean he does, he spends all of his time doing this and he cares about deeply. So he's serious in that sense, but he also treats it as this big game where he's just like, you know, I'm just having fun, I'm pursuing the things I find interesting and I will go down the rabbit holes that seem interesting and ultimately they will become useful.


So talk about that. So that is a really important part of the learning journey, especially on the internet. so if you take before the internet, right? Like, think of the process of going into the library to research a project in college, right? You go to the librarian and you say take me to history and then it's between like book number 800-899 on the little codes and sort of you spend time in history. But you said something there that I don't think you realize that you said, but it is what it means to learn on the internet. It's sort of having hunches and ideas that certain rabbit holes are going to be interesting and having the audacity to go down those rabbit holes. But how do you gauge what rabbit holes do you want to go down?


So I think it doesn't matter. I actually think that almost everything can be interesting if you try to build a model for it. Now so things aren't interesting if you try to just rote memorize stuff and I think that that's going to be true with basically every topic actually. However, if you try to understand why things happen and build a causal model in your head, everything's interesting. When I was much younger I felt like, ugh, I like playing sports but I don't really enjoy watching sports. And I think this is a pretty typical like nerd opinion to have. But I realized that if you actually watch a game and you tried to understand sort of where the threads are, like if you pull this thread here, what happens to the fabric over there, have this ongoing game. It's extremely fascinating. Same with a mortgage history. Like if the FHA had done this like tiny little thing differently, like what would have been the rippling effects downstream and why do you think that's true? What are the other explanations for that same behavior? So I don't think the specific rabbit hole really matters that much as long as you are actively forcing yourself to build a model.


It's interesting because I was just watching the NBA finals and with the Warriors. So Stephen Curry, the reason where he is so good, is because after he passes the ball, he runs to the corner and tries to catch it and you just watch it and it's like, it's amazing to watch. But just, it's funny because. And then I would also watch switches on screens and what not. These are things that sound advanced, but they're super simple. And just by having two or three things that I could sort of hook to, then it opened the door for the rest of it. And it was funny because to go back to Tyler when, whenever I try to learn something the best advice that I've gotten from Tyler Cowen is the idea of entry points. Find something that you like, something that it's intuitive, a metaphor that you like, start there. And then as you begin any sort of learning journey, start with an entry point that you're familiar with and use that as your balances, your crutch to go explore new territory.


I strongly agree with that. So in high school, I thought of myself as much more of a liberal artsy type of person. I was always pretty good at math and science and so on. I didn't struggle but it just didn't click until I was 16, 17. My boyfriend and I at the time rebuilt a 67 Mustang that he owned and we did an engine swap. We replace the rear end, we did a lot of work on this car. And suddenly all of the engineering and engineering related skills that I've picked up over time became fascinating. I was like, I want to understand how all this works. I picked up something like thermodynamics books and like this, this car was the entryway to all sorts of things and now this is a particularly useful one because if we did it wrong we would die while we were driving it. So like we had pretty good motivation to figure stuff out. But I think finding some sort of entryway into that is critical. And I mean working on the car has literally changed my career in the sense that I don't think I would have gone into mechanical engineering and then computer science if it hadn't been for that thing. I mean the guy helps too, but the car was like really this concrete thing I could imagine in my head and then want to understand the pieces that made up the whole thing.


Totally. Well, I want to switch gears and talk to you about the thing that I'm most excited to talk to you about today, which is really cities and with the intersection of architecture and incentives. Maybe we can start with Singapore and I'm going to ask that selfishly because I'm really interested in Singapore. I think there's a lot to learn from Singapore, but you were also just there and you've written a lot about Singapore. What is so interesting to you about Singapore?


Oh man. What is not interesting about Singapore? So Singapore I think is one of the most interesting countries in history. And that's saying something, given that it's only been around for I think 50 or 60 years. It is a city-state. It's only about 5 million people. It is ethnically extremely diverse. There are ethnic Chinese, ethnic Malays, ethnic Indians, and many, many other groups there as well. And it's one of the safest places in the world and it has a booming economy and it has been for a long time, seen as like a center of stability in a region that has not always been stable. So all of those things are incredible about Singapore and that would be crazy for any city or any country, but especially considering where they came from, where they had, I don't remember the exact number, but they had GDP, I think equivalent to like Vietnam in the sixties, and now they have significantly higher GDP than almost any country in the world. One of the highest. Now GDP doesn't measure everything, but it correlates with a lot of important things. The reason I think if I had to pick one reason why I'm fascinated by Singapore, it's because it has one of the weirdest types of governance ever.


Describe the governance.


The governance is increasingly less so now, but it's quite to totalitarian. It's not very Democratic at all.


It's funny because my first thought is whoa, that's not good. But it seems like you're hinting at something else.


I also think it's not good. And if the whole world were run the way Singapore is run, I don't think that would be a good thing for the world. In part because of the specific things that Singapore does, like it still has like physical punishment and so on for not very big crimes. But then also beyond physical and capital punishment. It also just like having one system for the whole world is not a great thing. It's extremely fragile. Things can go wrong in ways that ripple across the entire world. Now that sounds extreme, but I bring that up because I think Singapore is interesting because it is the opposite. Not only does it not, not only is the whole world not governed the way Singapore is. Singapore is tiny. So even if you really strongly dislike what Singapore is trying to do, what it's experimenting with, it's relatively easy to leave.

Now I want to add the strong caveat that like leaving the country you were born in is never an easy decision. And I am not like underplaying that. But it is relatively much easier than leaving a massive country that is not deeply interconnected with the world. And so the thing I find exciting about this country is that it provides this room for experimentation at a relatively low cost. If the entire United States were to take on an experiment, say universal basic income or something else entirely, and if it were to go wrong, it would just, it would be a disaster. It could cripple the country and it would affect roughly 20 million people, something like that. And like you also wouldn't even really be able to know if what the causal mechanism was if UBI was the thing that screwed up or something else entirely.

Whereas if you can run a bunch of smaller experiments, which this is the idea of federalism, then you can actually compare the results. People can leave if they really don't want to be part of this experiment. And I think this is really important. People don't like the concept of being experimented on and I get it, but if we don't experiment with new models, we're never going to improve. And so I think the question shouldn't be, should we experimental or should we not experiment. It's like, yes we should, but we should find the ways to have the greatest diversity of experiments while also minimizing the cost.


Right. Like a lot of what China's doing is sort of A, B testing cities, but the downside risk is impacting millions and millions of people. And I think to your point about minimizing the downside, you know, you could argue that they've gone too far.


Yeah. I think there's a Slate Star Codex blog post that has a great word for this. It calls it archipelago communitarianism. The concept is like we could have a bunch of cities or very small countries, that had radically different systems and the only promise that they make to each other is that they won't stop the people from leaving those places if they really want to. Maybe there are a few other rules too. I'm not gonna remember the entire details of the blog post, read it a few years ago, but I love this idea of having like little islands of extremity to really push an idea to its limit. And if it, if everyone leaves them, that means that that's not what people wanted.


Well, that's sort of where the whole voice exit loyalty idea of crypto is coming from. Traditionally in terms of countries, you could voice and you could sort of vote and you could say we want to change the way that things are run by speaking up and there's an exit where you can leave. But traditionally with citizenship, you haven't really been able to leave your country. Even if you're abroad, you still have to pay taxes as an American citizen. And so you're forced to be stuck between voice and loyalty. Whereas now we're switching to where you can still voice your opinion, but if you don't like it, you can exit. And there's a lot of freedom that I think comes with that.


Yeah. I think it's not just that you can still voice your opinions and also you can leave, it's that you can voice your opinions often better if you have a very small community. A single person has much more sway over the outcome. So it seems very likely to me that it's much easier for a person in a very small community to be able to make a change in that community to begin with and like shape it in their own image than it would be for a massive country like the US or Brazil or something like that. So by bringing it down to a smaller scale, you both get added exit rates, but you also get a greater voice.


Totally. So you were just in Singapore. What stuck out about being in Singapore to you? Let's go to two places. What is the biggest thing that surprised you when you were there? And what is the biggest thing that you've been thinking about since you came back from Singapore?


I knew that Singapore had great Infrastructure. I knew that its citizens were well educated, that a lot of its systems just worked. But I didn't realize how much this is embedded in the psyche of the place. It's not just that like, stuff works well and some people forget about it and like go ahead and do their own thing. It's like the most central place of the city right next to Maxwell's Hawker Center, which is like a big destination in the core of the city. There's this place called the URA, the urban research association. I don't remember the exact acronym. Basically, it's this like big gallery on urbanism and like what it means to be an effective city with good governance and what it will take for this to continue and get better over time.

I went into this gallery exhibit because I can't keep away if you say that it's like an urban museum. I'm like, okay. It's Devon catnip. I couldn't help but to go in. And I was there at 3:00 PM on a Tuesday and it was full of students, the sense that I got is that like every Singaporean student probably goes there like once a year. I don't even think that we have a gallery like that in San Francisco. And certainly not in the center of the city and kids definitely don't go there all the time.

There was this overall sense of understanding of why things work so well, how things won't necessarily keep working well in the future unless we do something about it and like a sense of responsibility that people in the community have to like be a presence voice, which seems very contradictory with some sort of a more totalitarian style of ruling. But Singapore may be the only place in the world where there's a brain drain into the government and not out of it. That is very consistent with what I saw. It's very deeply respected to be a good technocrat. Someone who understands how systems work and like truly wants to make them better.


They pay well, what else?


They pay very well. There's really high prestige going in. I haven't really thought about this too hard.


Okay. Then we'll switch gears. So you said something really interesting about cities before we were recording the podcast that I thought that you phrased perfectly and that you're especially drawn to cities because they're in this middle of scale, right? Where they're big enough to have an importance on the world stage, right? Like a city like New York, San Francisco, Singapore, they're a big deal. But then there are small enough to be nimble and still sort of understandable like it's hard to sort of wrap your head around what it means to be American because they're just so much going on here, but then also sort of what you were talking about earlier in terms of experimenting. There's a lot of them so you can sort of abstract lessons from each one. And so it's this perfect size, perfect density, perfect volume that makes cities really interesting to study. Right?


Totally. I think that the nimbleness is really important. There is some digital ID that Singapore is rolling out for all of its citizens pretty soon and they're going to just do it. They have 5 million people, which is a lot of people to roll something out to, but it's big enough for this ID to really matter, but it's small enough where they're like, we can just do this, we can just, we can just make it happen. And I think that's thrilling that you can experiment with something of that size. At the same time, you have this really tight feedback loop. If your trash isn't picked up tomorrow, you're gonna notice within a week you're going to probably start writing letters and like your trash better get picked up. I think at the national level, the feedback loops are much longer and it's just harder to know if people are governing you well at all. And that's a recipe for disaster. It leads to much more misalignment of incentives.


Definitely. Tight feedback is key to learning.


It's key to everything. Like if you don't have a tight feedback loop, you're just not really going to improve I think, and you're actually very likely to do things that aren't purely for signaling that you care as opposed to actually doing the right thing.


Go off on that because that's an idea I haven't explored.


Yeah. Officials in the US tend to do grandstand a lot, at the federal level. And the reason for this is because they don't even really know if they're having the impact they want to have or that their constituents want them to have. The only real information that people get on both sides is like what someone said, even after the facts, even a decade later, it can be very difficult to draw any meaningful causality stemming from a particular leader. I think that's true in any organization ever. Even as small as a single person organization. You can't do randomized controlled trials on like everything or almost anything. But the problem just grows in scale to a huge extent as you get bigger. I think if you can keep it to a smaller size, it's like, well, you either did your job or you didn't. And the problems are much more manageable, the relationships are less opaque. It's just a much more transparent system overall.


Totally. So, I mean, for me what's been really interesting is in New York studying art decor, one thing that I love about architecture is I've been thinking about this idea a lot, where a lot of history is sort of subject to the narrative fallacy where it's written by the winners and the really good book on this is The People's History of the United States by Howard Zinn. He admits that it's biased, but he tries to tell American history from the perspective of the losers. And if you have a generic understanding of American history, you're going to get so many ideas pumped into your head that are totally different. So what's really cool about architecture is, if you look at something like the Chrysler building and at the very top of it and in the lobby and sort of the birds hanging off the side, you know, 60 feet below the top of the building, you can see this like technological enthusiasm, this almost sense of like a utopian spirit that technology in the twenties and the roaring twenties was going to come and save the world. And through the architecture of New York, you can really understand the city in a way that understanding history might not allow you to do.


Yeah. And I think it's especially interesting to see how buildings change over time in reaction to that original time when it was created and how they shift. I think the moment when I really became aware of the importance of architecture was in my very first job, we started out in this very small office that was cozy and like my desk was far away from the restroom and the kitchen. So when I wanted to take a break, I'd have to walk past everyone and I'd have like a little conversation and I felt very positive about all my coworkers and I feel like we had a really good rapport. About halfway through my time there, we moved into a totally different building. It was supposed to be fancier, it was nicer by everything you could put on paper.

But the shape of the rooms was super messed up. Basically, everyone was very close. It was more like a doughnut where like all of the good stuff was in the center and good stuff, meaning, like the kitchen. And so you didn't have to walk past anyone to go see it, which was kind of nice if you're focusing on a problem or you want some alone time, there are pluses to that, but you don't end up having these interactions. And as a result, I almost immediately started feeling like the only people I knew in the company were my team and a lot of the work that I was supposed to be doing was cross-functional. So this made me significantly worse in my job just immediately. Now, of course, this doesn't stop you from having coffee with a coworker and the sales team or something or organizing something with the product team or you know, inviting them to sit at your table at lunch. But these micro-interactions are really critical for building that rapport, for making, keeping people on context. I almost felt like I was a remote worker, and I don't mean to insult remote work. I think that there are huge pluses to that, but it's really undercut the benefits of being in the office as soon as we moved into this new place.


It's funny because I feel like so much of architecture now, we place such an emphasis on the outside of a building what most people see. But I don't know that we have the same sort of rich discussions about the experience of actually being somewhere. And I guess the example that comes to me is natural light. Like I value natural light in indoors just to such a high degree. It's like the number one thing that I care about in a building, but so often we look at the outside of buildings, so we say, oh that's beautiful. It looks great in a photo, but the experience of being inside of it, I don't actually know that the incentives are aligned for architects to think about that.


I agree. I mean if you have ever spent time looking for an apartment on Craigslist or a place on Airbnb, actually everything and I'll explain that later. But on craigslist it's like it tells you the square footage, it tells you how many rooms, how many bathrooms there are, which are obviously important details, but it does very little to describe features like natural light and things that make you actually happy, how livable it is. I think part of the problem for this is that it's a much harder thing to commoditize, which means that like it's harder to measure. It's harder to compare two things, there's not a strict measure that you can really use. But it really matters. It really matters a lot. The experience of being in a place is totally different from the way people will often describe a room, at least in describing a room in comparable terms. I think maybe it seems possible. Maybe someone just needs to build a vocabulary for it.


Okay. Let's play a little game. So if you had to take five metrics for deciding a house on Zillow, right? We have rooms square foot, but if you had five metrics that don't exist right now, what would it be? You do some, I do some.


Okay. I kinda like this, I'm thinking of it sort of like the, you know, the big five personality. It's kind of like that.


So you get three, I get two.


Let's see, I'd say flexibility. Like how much can you change the space to fit your own needs? Is it like very tightly custom designed? The purest example of this would be like the cabinets are built into the walls so you can't move the cabinets. Versus like a lot of ability to move stuff around.


Mine is the density of power outlets. Most houses don't have nearly enough.


Oh my god. The computer science building at Stanford has almost no power outlets, which is insane because you go there for the office hours and you know, everyone's there for hours and hours and hours and everyone's computer starts dying around hour three and there's one power outlet and the whole building. Yeah, that needs to change.


Here's another one. Where I really like houses where the rooms are super private and the open spaces are super public. So you have the kitchen, the living room, the dining room, all sort of in the same room because at the houses that I grew up in, the kitchen was always separate from the dining room. And so whenever we would cook as hosts, It was always sort of awkward because you sort of had to choose. Whereas you get this awesome communal vibe, but I think it really helps with family dynamics if all that is sort of in the same room and it has really good natural light and there's a nice ambiance in there because then people can cluster there. But then you balance that with like the privacy of the rooms.


I'll expand that one to like the ability to pass through. So in the house I live in right now, it's very hard to get to the backyard.


Yeah, describe this house because it's actually really cool. It's a commune with 10 people, but like really intelligent people here.


We call it an intentional community because commune has a lot of economic implications that probably don't apply. So I'm one of 10 people who live in this house. We're actually expanding to an upper floor and it'll be 16 soon. And we're just a group of people who we all care a lot about, having really easy relationships and what that means is I think a lot of the most meaningful and happiness-inducing experiences and interactions that you'll often have will be these little micro-interactions. It's very similar to what I was talking about with my old office. Where if it's really expensive to meet up with someone and hang out with them, it takes money, time, and energy. You have to have to call them, which seems like not a big deal. But here's an intention that's necessary therefore it to happen. You're only going to become close with people where you have an explicit reason to do so. Like sort of a motive almost. Whereas if you're just in the same place, this is why people love college so much. If you're just in the same place with a lot of people who are energetic, motivated, ambitious, like these amazing things will happen where you'll just bump into each other throughout your day and like amazing things will happen without intention and I think that's amazingly valuable and really easy to undervalue.


You make a really good point because that's almost in a place where that's not the case. Having relationships where you meet somebody right away is almost the mark of a good friendship. It was Saturday night, 11:00 PM a couple of weeks ago. My friend calls me and he goes, what are you doing right now? And it was the first time that happened to me in New York, but it was this like moment in our friendship where in order to do that. Like that happened all the time in college. Like that's college 101. Oh, what are you doing right now? But for it to happen in New York? First of all, was like shocking to me and second of all it was like this mark of our friendship where to get there with somebody takes so much more work because of the way that New York is built and that happens daily in this house here, which I think is really cool.


It's amazing. I mean, it's amazing you say that that's the case in New York because New York is probably one of the best places in the entire US for this. Like in the opposite sense of what you're talking about. Now imagine if you guys lived in Irvine, California or a far-flung suburb of Salt Lake City or something comes up for you to meet up with this person. Like right now it's just, you jump on the subway, you're there in a few minutes. Not that big of a deal. In those places, you have to like get in your car. Maybe you have to get your snow boots on. You can't get drunk and go home, which is also a good way to bond with people. Also, when you arrive, it will likely just be the two of you, probably no one else was invited, whereas like in a city, maybe you meet up at a bar where there's like a bunch of other random people around you who ended up being really interesting.

Actually one of my closest friends. I met like at an event at the MoMa, and just because we like bumped into each other at a mixer afterward. That wouldn't have happened if we weren't in the city. You don't have things like the MoMa in far-out suburbs. And so this is like another example of not just architecture but the general built environment, having dramatic effects on the way you actually interact with the world.


So let's play another game. If you were to take, I gave you three, we're just going to do metrics again, three metrics or three data points that you could pick and you're going to choose where you live, the house that you lived, a location, what city, what the house looks like, what would the three that you picked be?


That's a good one. One would be, how long does it take for you to walk from where you live to like your top 10 favorite locations in the city? I think if the answer is a long time and especially if the answer is like you can't even walk there, that's not a good sign for me. Now I don't mean this to be normative for everybody. Other people do have other preferences. Some people want to like go on a big ranch in Idaho and like never see another human. Again, totally not my type but good for them. I'm not saying it's the case, but for me it's very important that I can walk places.

I think the reason for this is because walking is a way to interact with your community in these small ways every single day where I think the way people get comfortable in a place in a social group is not through just like one really intense interaction, but through a bunch of smaller ones where you sort of see things from different angles you experienced, you know, what does my neighborhood looked like on a rainy day, what does my neighborhood look like when it's a cloudy day, what does it look like when I'm kind of tired? And these sound like tiny, trivial differences. But you can understand much better how things function. Maybe usually on a sunny day people will like to sit outside at Maxfield's coffee down the street, but on a different one, people sort of tuck inside and it has this closer vibe. You get to know the vibe just much better and you end up meeting people that you probably wouldn't meet if you were in an uber going from point A to point B all the time. So walking is one.

Another one would be if for random and sort of once in a while type things like I had to get a necklace fixed the other day, how easy is it for this to be a part of your daily routine? So is it like you have to drive like way out of your way and find some really specialty store to do it? Or like what I did, I was able to walk two blocks away. There's a little jeweler who was able to fix it in three minutes and I walked back and that was like not even my whole lunch break. That was just a little pause in the middle of my day. I grabbed coffee on the way and I came back and up until that point, I had no idea that jeweler was there and we had a nice conversation. But it was just right there. And I love that my whole community can be inside of this little circle. Number three.


I'll give you my three real quick. So my first one would be natural light, as I've said many times before. That's super important to me. The second one, yours is walking, for me, it's like not having to use a car. So I actually sort of like taking public transportation so I just don't like driving and I don't really like being in cars. So those are the two. The third one would be I like being able to walk, especially to food. Like at my old apartment I was super close with everyone who worked at the bagel shop and I'm pretty close with all the ladies who work at maya taqueria, my local taqueria. And the last one would just be a high density of super intellectually hungry people, which for me is why I've chosen to live in New York.


Oh, I see. So we can expand this beyond built environment. I would definitely make that my third one as well. This is why I'm in San Francisco, New York maybe is a good choice too, but there is just always someone I can talk to about whatever crazy idea I have going in through my head or is going through their head any given day. I find not everybody here necessarily wants to discuss these ideas, but by using twitter you can actually find these people and like create this strong core where I've basically tricked my brain. The thinking that like everyone around me is just this crazy monster of ideas, continually coming up with new things.

There's so much intersection of like different types of people doing work in the city. Everything from like researchers to engineers to entrepreneurs to artists. And unfortunately, fewer these days, as a city gets more expensive. And they're all just mixed together in this pretty small city where you can always find them. But then I think the important component is you also have to have some tools that sort of overlay this to help find them. Just walking around the city. Like I was talking about before, won't surface all of these people and you also are less likely to get outside of your current network if you just stick in your small neighborhood.


Let's do a quick fire round. So I'm going to ask you like five, six questions and try to keep your answers to like 30 seconds or less. Why do you love Stewart Brand so much?


He is a polymath. A lot of people take crusades on things. They pick one idea and they just drive it for years and years. Stewart takes hundreds of ideas and makes them all good and is still able to keep a really strong sense of identity despite not having like one thing that he ties himself.


So I have a theory that personality will end up being almost like the last mode and that sort of so much of what's happening in society right now is like brands are sort of disappearing where many people have less likely to have a favorite brand. But I think that the internet has made it really easy to connect with people. And Stewart Brand is always sort of been a pioneer of technology and I think that people can move around and explore different things through their personality in ways that institutions can't. And I think that that's really helped somebody like Stewart Brand. I don't actually think that focusing on the same thing is like a vector that really matters when it comes to consistency with a person.


I think that's true. And I think Stewart and Tyler are two fantastic examples of this being 100 percent possible. I think that most people don't realize that and they think that they have to pick one thing and so that you see that reflected in a lot of people's careers or at least they like abstract away the more nuanced. I think everyone has slightly more scattered set of things that they think a lot about, but they have to tell this one consistent story to the rest of the world. And I think that we're starting to finally see that. Like you don't have to do that. You can do a lot of things.


Totally. Fire round. Algorithms to Live By. Why do you love that book so much?


It's the best self-help book I've ever read and it's not intended to be a self-help book. It is intended to be an algorithmic look at certain problems that people see in day to day, but it helps me frame certain problems that I personally run into in terms of like literally the algorithmic complexity. And I realized that the stress that I was feeling about certain things I worried about was like actually totally rational.


Real quick, one example from the book that sort of sticks with you?


I think one of my favorite examples is when they talk about the scheduling problems, scheduling my calendar is something that you stress me out a lot because there's so many things you could do and so little time and sequencing matters. There are so many layers of constraints that you can put on it in infinite level really. And basically, what they reminded me, they analogized it to scheduling and computers like processes. They were like, this is not a solved problem in the sense of like we don't have an efficient solution to this. We use heuristics. So don't worry, this is what I took out of it. It's like, don't worry like your life also is not going to be perfectly scheduled and just pick something.


Something I know nothing about. Georgism.


Georgism. Oh, I don't know if I can do a lightning round on that. So I'll just touch on one thing. I think people usually talk about economics as a spectrum from like capitalism to socialism or communism. And I think what this really misses out is that there's sort of a third category of economic goods. So people usually think of capital and labor as like things and people basically. But there's this third category of resources, things that no one created. They aren't people, they are things, but they are different kinds of things. So land, air, water resources, et cetera. And something that capitalism and socialism treat. They've treated all of those resources as something under capital and that is incorrect because if you tax things that people have created, it will reduce the amount that they create those things because they are just incentivized to do so.

However, if you tax land, If you tax resources, those effects don't occur. The same amount of land and resources will continue to exist.


Why isn't it more popular?


My guess is that it's just a question of path dependence in history. There was a period in the late 1800's, right after Henry George wrote his famous Progress and Poverty, at which this book was the number two best seller after the bible for like a decade. So it was extremely popular at one point. But I think if my guess is that he just wasn't really good at evangelizing the idea. And history took its course, but I don't know if I have a great explanation beyond that.


Well, we can rekindle it. strong opinions, weakly held?


I have a lot of very strong opinions, but I also am infamous or perhaps famous for changing them in high school, I was extremely libertarian. I now am deeply sympathetic to most libertarian ideas, but I have since done a 180 in terms of why I hold the object level views that I do. Something I emphasize a lot is a sharing those deltas with people, because otherwise you may end up still making the same actual decisions in life or supporting the same policies, but if your underlying reasons why have changed, people's models should still be updated. And so the section on my blog where I include lists of opinions that I once held, how they've changed, why they've changed.


It back to the idea of viewing learning as a process, not a problem.


Exactly. And another component of that is I put an epistemic status at the top of everything I write.


What does that mean?


Well, what it means is that I'm lazy actually. So an epistemic status is basically describing how confident you are in a claim, how sure you are that it's true. Usually, I don't, I'm never 100 percent true of anything. I'm much more often, it's like 60 percent or something where I'm confident enough to say it. But I want you to know that there is ambiguity here. People have complimented me on this and I didn't really understand why because they're like, oh, you're so modest. There's so much humility here. But actually the reason is there's a lot of stuff I want to be able to say, but I don't want people to think that I don't. Which I mean I do want to stand behind my ideas, I'm not cowardice thing, but it's like there's, I wrote a post on Singapore where I basically said this is a really good model.

Some of the stuff we discussed earlier and I do stand by all of the facts that I stated there, but my confidence in like the ultimate claim that their model is a good one is not 100 percent sure. Like there's a chance that I'm missing something. Maybe I like calculated magnitudes of things wrong and so I want to like make it clear to people that my mind could be changed on this topic and it also helps other people in terms of understanding how much of an authority are you on this.


I think that would help as well too. Now more on your philosophy of travel.


My philosophy of travel, I see travel as scale-free or a fractal where I think you could go to as many or as few different places and still learn just as much. So I've recently been opting much more for the go to many places.

I've been traveling a lot this year, but part of me thinks I should just stay, spend all of my time in San Francisco and just explore every single neighborhood, every single nook and cranny in this place. Because I mean, again, a friend that I just recently met, he works on the same block and he's been working on this block for years and we had never crossed paths. And he's now a person that I talk to a lot. He has a lot of really interesting ideas. The company that you worked for is interesting. And it just goes to show that like there's so much life on this one block that I live on. And yet, like I hadn't fully explored this one block. And so sometimes I feel guilty where I'm like, it's much more expensive to fly to Bangalore than it is to just like walk outside my door and go to the coffee shop and have a conversation with a person.


You could get a latte every single day with that money and you wouldn't feel guilty.


You wouldn't feel guilty at all. And so this is sort of where obviously you're going to see a huge amount of difference if you go to like Jakarta versus San Francisco, but I think you actually get as much though, at a different magnitude of difference, if you really look for them in those places.


You publish a lot of content. This is the last question. You publish a lot of content and you do it regularly and it's high quality. What is your philosophy of productivity and output?


My philosophy of productivity. I'd say just writing everything down as I think of it. I use Evernote for the most part, if I'm biking, which I am a lot of the time. I will make a little audio note which I'll then later transcribe. And it's not because all my ideas are good, but because they are often, once I've written them down, I will often see themes emerge over weeks or months that then turn into a more concrete thing. And it also gives me a lot of stuff to work off of overtime where like I write dozens of notes every single day. I also read a lot of emails, a week-long pen pal emails of stuff that is not very filtered a and not super well written. But after I've written it I'll see, oh, I've had sort of similar conversations with like five different people.

Maybe there's something to this, like the fact that I keep touching on this concept means that like I should dig in more and then with all of these notes and all of these emails that I've written up until that point, I then also have all this content that I can like take in work off of. So it's often trivial to write published posts because I have stuff like seventy, eighty percent of the way there. I just have to like put it together, understand what the pieces are, you know, use my thesaurus, find some more synonyms and put it out there.


Well, Devon, thank you so much for your time today. Thanks for coming on the podcast.


Thank you. This was a blast.

You can support the North Star Podcast by leaving a review on iTunes. Or you can share the podcast on Twitter or Facebook.

To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell. And if you enjoyed this episode, you’ll like the episode with Albert Wenger, a partner at Union Square Ventures. In this conversation we talk about Albert’s fourth coming book, World After Capital, and how technological progress has shifted scarcity for humanity. When we were foragers it was food that was scarce, during the Aquarian age it was a fight for land. Following the industrial revolution, capital became scarce. With digital technologies, scarcities are shifting once more. We need to figure out how to live in a world after capital, where the only scarcity is our attention. 

Key points in this episode

Listen Here: iTunes | Overcast | PlayerFM Keep up with the North Star Podcast.

My guest today is Michael Nielsen a scientist, writer and computer programmer who works as a research fellow at Y Combinator Research. Michael has written on various topics from quantum teleportation, geometric complexity and the future of science. Michael is the most original thinker I have discovered in a long time when it comes to artificial intelligence, augmenting human intelligence, reinventing explanation and using new media to enable new ways of thinking.

Michael has pushed my mind towards new and unexpected places. This conversation gets a little wonky at times, but as you know, the best conversations are difficult. They are challenging because they venture into new, unexplored territory and that's exactly what we did here today. 

Michael and I explored the history of tools and jump back to the invention of language, the defining feature of human collaboration and communication. We explore the future of data visualization and talk about the history of the spreadsheet as a tool for human thought. 

“Before writing and mathematics, you have the invention of language which is the most significant event in some ways. That’s probably the defining feature of the human species as compared to other species.”

LINKS Find Michael Online

Michael’s Website

Michael’s Twitter

Michael’s Free Ebook: Neural Networks and Deep Learning

Reinventing Discovery: The New Era of Networked Science

Quantum Computation and Quantum Information

Mentioned In the Show

2:12 Michael’s Essay Extreme Thinking

21:48 Photoshop

21:49 Microsoft Word

24:02 The David Bowie Exhibit

28:08 Google AI’s Deep Dream Images

29:26 Alpha Go

30:26 Brian Eno’s Infamous Airport Music

33:41 Listen to Speed of Life by Dirty South

Books Mentioned

46:06 Zen and The Art of Motorcycle Maintenance by Robert M. Pirsig

54:12 Cat’s Cradle by Kurt Vonnegut

People Mentioned

13:27 Rembrandt Van Rijn’s Artwork

15:01 Monet’s Gallery

15:02 Pierre Auguste Renoir’s Impressionist Art

15:05 Picasso’s Paintings

15:18 Paul Cezanne’s Post-Impressionist Art

25:40 David Brooke’s NYT Column

35:19 Franco of Cologne

56:58 Alan Kay’s Ted Talk on the future of education

57:04 Doug Engelbart

58:35 Karl Schroeder

01:02:06 Elon Musk’s Mars-bound company, SpaceX

01:04:25 Alex Tabarrok

Show Topics

4:01 Michael’s North Star, which drives the direction of his research

5:32 Michael talks about how he sets his long-term goals and how he’s propelled by ideas he’s excited to see in the world.

7:13 The invention of language. Michael discusses human biology and how it’s easier to learn a language than writing or mathematics. 

9:28 Michael talks about humanity’s ability to bootstrap itself. Examples include maps, planes, and photography 

17:33 Limitations in media due to consolidation and the small number of communication platforms available to us 

18:30 How self-driving cars and smartphones highlight the strange intersection where artificial intelligence meets human interaction and the possibilities that exist as technology improves

21:45 Why does Photoshop improve your editing skills, while Microsoft Word doesn’t improve your writing skills?

27:07 Michael’s opinion on how Artificial Intelligence can help people be more creative

“Really good AI systems are going to depend upon building and currently depend on building very good models of different parts of the world, to the extent that we can then build tools to actually look in and see what those models are telling us about the world.” 

30:22 The intersection of algorithms and creativity. Are algorithms the musicians of the future?

36:51 The emerging ability to create interactive visual representations of spreadsheets that are used in media, internally in companies, elections and more.

“I’m interested in the shift from having media be predominantly static to dynamic, which the New York Times is a perfect example of. They can tell stories on that they can’t tell in the newspaper that gets delivered to your doorstep.”

45:42 The strategies Michael uses to successfully trail blaze uncharted territory and how they emulate building a sculpture 

 53:30 Michael’s learning and information consumption process, inspired by the idea that you are what you pretend to be

56:44 The foundation of Michael’s worldview. The people and ideas that have shaped and inspired Michael. 

01:02:26 Michael’s hypothesis for the 21st century project involving blockchain and cryptocurrencies and their ability to make implementing marketplaces easier than ever before

“The key point is that some of these cryptocurrencies actually, potentially, make it very easy to implement marketplaces. It’s plausible to me that the 21st century [project] turns out to be about [marketplaces]. It’s about inventing new types of markets, which really means inventing new types of collective action.”

Host David Perell and Guest Michael Nielsen


Hello and welcome to the North Star. I'm your host, David Perell, the founder of North Star Media, and this is the North Star podcast. This show is a deep dive into the stories, habits, ideas, strategies, and rituals that guide fulfilled people and create enormous success for them, and while the guests are diverse, they share profound similarities. They're guided by purpose, live with intense joy, learn passionately, and see the world with a unique lens. With each episode, we get to jump into their minds, soak up their hard-earned wisdom and apply it to our lives.

My guest today is Michael Nielson, a scientist, writer, and computer programmer, who works as a research fellow at Y Combinator Research. Michael's written on various topics from quantum teleportation to geometric complexity to the future of science, and now Michael is the most original thinker I've discovered in a long time. When it comes to artificial intelligence to augmenting human intelligence, reinventing explanation, or using new media to enable new ways of thinking, Michael has pushed my mind towards new and unexpected places.

Now, this conversation gets a little wonky at times, but as you know, the best conversations are difficult. They're challenging because they venture into new, unexplored territory and that's exactly what we did here today. Michael and I explored the history of tools. This is an extension of human thought and we jump back to the invention of language, the defining feature of human collaboration and communication. We explore the future of data visualization and talk about the history of this spreadsheet as a tool for human thought. Here's my conversation with Michael Nielson.


Michael Nielson, welcome to the North Star Podcast.


Thank you, David.


So tell me a little bit about yourself and what you do.


So day to day, I'm a researcher at Y Combinator Research. I'm basically a reformed theoretical physicist. My original background is doing quantum computing work. And then I've moved around a bit over the years. I've worked on open science, I've worked on artificial intelligence and most of my current work is around tools for thought.


So you wrote an essay which I really enjoyed called Extreme Thinking. And in it, you said that one of the single most important principle of learning is having a strong sense of purpose and a strong sense of meaning. So let's be in there. What is that for you?


Okay. You've done your background. Haven't thought about that essay in years. God knows how long ago I wrote it. Having a strong sense of purpose. What did I actually mean? Let me kind of reboot my own thinking. It's, it's kind of the banal point of view. How much you want something really matters. There's this lovely interview with the physicist Richard Feynman, where he's asked about this Indian mathematical prodigy Ramanujan. A movie was made about Ramanujan’s mathematical prowess a couple of years ago. He was kind of this great genius. And a Feynman was asked what made Ramanujan so good. And the interview was expecting him to say something about how bright this guy was or whatever. And Feynman said instead, that it was desire. It was just that love of mathematics was at the heart of it. And he couldn't stop thinking about it and he was thinking about it. He was doing in many ways, I guess the hard things. It's very difficult to do the hard things that actually block you unless you have such a strong desire that you're willing to go through those things. Of course, I think you see that in all people who get really good at something, whether it be sort of a, just a skill like playing the violin or something, which is much more complicated.


So what is it for you? What is that sort of, I hate to say I want to just throw that out here, that North Star, so to speak, of what drives you in your research?


Research is funny. You go through these sort of down periods in which you don't necessarily have something driving you on. That used to really bother me early in my career. That was sort of a need to always be moving. But now I think that it's actually important to allow yourself to do that. That's actually how you find the problems, which really get, get you excited. If you don't sort of take those pauses, then you're not gonna find something that's really worth working on. I haven't actually answered your question. I think I know I've jumped to that other point because that's one thing that really matters to me and it was something that was hard to learn.


So one thing that I've been thinking a lot about recently is you sort of see it in companies. You see it in countries like Singapore, companies like Amazon and then something like the Long Now Foundation with like the 10,000-year clock. And I'm wondering to you in terms of learning, there's always sort of a tension between short-term learning and long-term learning. Like short-term learning so often is maybe trying to learn something that feels a little bit richer. So for me, that's reading, whereas maybe for a long-term learning project there are things I'd like to learn like Python. I'd like to learn some other things like that. And I'm wondering, do you set long-term learning goals for yourself or how would you think about that trade off?


I try to sit long-time learning goals to myself, in many ways against my better judgment. It's funny like you're very disconnected from you a year from now or five years from now, or 10 years from now. I can't remember, but Eisenhower or Bonaparte or somebody like that said that the planning is invaluable or planning plans are overrated, but planning is invaluable. And I think that's true. And this is the right sort of attitude to take towards these long-term lending goals. Sure. It's a great idea to decide that you're going out. Actually, I wouldn't say it was a great idea to say that you're going to learn python, I might say. However, there was a great idea to learn python if you had some project that you desperately wanted to do that it required you to learn python, then it's worth doing, otherwise stay away from python. I certainly favor, coupling learning stuff to projects that you're excited to actually see in the world. But also, then you may give stuff up, you don't become a master of python and instead you spend whatever, a hundred hours or so learning about it for this project that takes you a few hundred hours, and if you want to do a successor project which involves it, more of it. Great, you'll become better. And if you don't, well you move onto something else.


Right. Well now I want to dive into the thing that I'm most excited to talk to you about today and that's tools that extend human thought. And so let's start with the history of that. We'll go back sort of the history of tools and there's had great Walter Ong quote about how there are no new thoughts without new technologies. And maybe we can start there with maybe the invention of writing, the invention of mathematics and then work through that and work to where you see the future of human thought going with new technologies.


Actually, I mean before writing and mathematics, you have the invention of language, which is almost certainly the most significant single event in some ways. The history of the planet suddenly, you know, that's probably the defining feature of the human species as compared to other species. Um, I say invention, but it's not even really invention. There's certainly a lot of evidence to suggest that language is in some important sense built into our biology. Not the details of language. Um, but this second language acquisition device, it seems like every human is relatively very set to receive language. The actual details depend on the culture we grow up on. Obviously, you don't grow up speaking French if you were born in San Francisco and unless you were in a French-speaking household, some very interesting process of evolution going on there where you have something which is fundamentally a technology in some sense languages, humans, a human invention.

It's something that's constructed. It's culturally carried. Um, it, there's all these connections between different words. There's almost sort of a graph of connections between the words if you like, or all sorts of interesting associations. So in that sense, it's a technology, something that's been constructed, but it's also something which has been over time built into our biology. Now if you look at later technologies of thought things like say mathematics, those are much, much later. That hasn't been the same sort of period of time. Those don't seem to be built into our biology in quite the same way. There's actually some hints of that we have some intrinsic sense of number and there's some sort of interesting experiments that suggest that we were built to do certain rudimentary kinds of mathematical reasoning but there's no, you know, section of the brain which specializes sort of from birth in solving quadratic equations, much less doing algebraic geometry or whatever, you know, super advanced.

So it becomes this cultural thing over the last few thousand years, this kind of amazing process whereby we've started to bootstrap ourselves. If you think about something like say the invention of maps, which really has changed the way people relate to the environment. Initially, they were very rudimentary things. Um, and people just kept having new ideas for making maps more and more powerful as tools for thought. Okay. I can give you an example. You know, a very simple thing, if you've ever been to say the underground in London or most other subway systems around the world. It was actually the underground when this first happened, if you look at the map of the underground, I mean it's a very complicated map, but you can get pretty good at reasoning about how to get from one place to another. And if you look at maps prior to, I think it was 1936, in fact, the maps were much more complicated.

And the reason was that mapmakers up to that point had the idea that where the stations were shown on the map had to correspond to the geography of London. Exactly. And then somebody involved in producing the underground map had just a brilliant insight that actually people don't care. They care about the connections between the stations and they want to know about the lines and they want some rough idea of the geography, but they're quite happy for it to be very rough indeed and he was able to dramatically simplify that map by simply doing away with any notion of exact geography.


Well, it's funny because I noticed the exact same thing in New York and so often you have insights when you see two things coming together. So I was on the subway coming home one day and I was looking at the map and I always thought that Manhattan was way smaller than Brooklyn, but on the subway map, Manhattan is actually the same size as Brooklyn. And in Manhattan where the majority of the subway action is, it takes up a disproportionate share of the New York City subway map. And then I went home to go read Power Broker, which is a book about Robert Moses building the highways and they had to scale map. And what I saw was that Brooklyn was way, way bigger than Manhattan. And from predominantly looking at subway maps. Actually, my topological geographical understanding of New York was flawed and I think exactly to your point.


It's interesting. When you think about what's going on there and what it is, is some person or a small group of people is thinking very hard about how to represent their understanding of the city and then the building, tools, sort of a technological tool of thought that actually then saves millions or in the case of a New York subway or the London underground, hundreds of millions or billions of people, mostly just seconds, sometimes, probably minutes. Like those maps would be substantially more complicated sort of every single day. So it's only a small difference. I mean, and it's just one invention, right? But, you know, our culture is of course accumulated thousands or millions of these inventions.


One of my other favorite ones from being a kid was I would always go on airplanes and I'd look at the route map and it would always show that the airplanes would fly over the North Pole, but on two-dimensional space that was never clear to me. And I remember being with my dad one night, we bought a globe and we took a rubber band and we stretched why it was actually shorter to fly over the North Pole, say if you're going from New York to India. And that was one of the first times in my life that I actually didn't realize it at the time, but understood exactly what I think you're trying to get at there. How about photography? Because that's another one that I think is really striking, vivid from the horse to slow motion to time lapses.


Photography I think is interesting in this vein in two separate ways. One is actually what it did to painting, which is of course painters have been getting more and more interested in being more and more realistic. And honestly, by the beginning of the 19th century, I think painting was pretty boring. Yeah, if you go back to say the 16th and 17th centuries, you have people who are already just astoundingly good at depicting things in a realistic fashion. To my mind, Rembrandt is probably still the best portrait painter in some sense to ever live.


And is that because he was the best at painting something that looked real?


I think he did something better than that. He did this very clever thing, you know, you will see a photograph or a picture of somebody and you'll say, oh, that really looks like them. And I think actually most of the time we, our minds almost construct this kind of composite image that we think of as what David looks like or what our mother looks like or whatever. But actually moment to moment, they mostly don't look like that. They mostly, you know, their faces a little bit more drawn or it's, you know, the skin color is a little bit different. And my guess, my theory of Rembrandt, is that he may have actually been very, very good at figuring out almost what that image was and actually capturing that. So, yeah, I mean this is purely hypothetical. I have no real reason to believe it, but I think it's why I responded so strongly to his paintings.


And then what happened? So after Rembrandt, what changed?


So like I said, you mean you keep going for a sort of another 200 years, people just keep getting more and more realistic in some sense. You have all the great landscape painters and then you have this catastrophe where photography comes along and all of a sudden you're being able to paint in a more and more realistic fashion. It doesn't seem like such a hot thing to be doing anymore. And if for some painters, I think this was a bit of a disaster, a bit of dose. I said of this modern wave, you start to see through people like Monet and Renoir. But then I think Picasso, for me anyway, was really the pivotal figure in realizing that actually what art could become, is the invention of completely new ways of seeing. And he starts to play inspired by Cezanne and others in really interesting ways with the construction of figures and such. Showing things from multiple angles in one painting and different points of view. And he just plays with hundreds of ideas along these lines, through all of his painting and how we see and what we see in how we actually construct reality in their heads from the images that we see.

And he did so much of that. It really became something that I think a lot of artists, I'm not an artist or a sophisticated art theory person, but it became something that other people realized was actually an extraordinarily interesting thing to be doing. And much of the most interesting modern art is really a descendant of that understanding that it's a useful thing to be doing. A really interesting thing to be doing rather than becoming more and more realistic is actually finding more and more interesting ways of seeing and being able to represent the world.


So I think that the quote is attributed to Marshall McLuhan, but I have heard that Winston Churchill said it. And first, we shape our tools and then our tools shape us. And that seems to be sort of the foundation of a lot of the things that you're saying.


Yeah, that's absolutely right. I mean, on the other side, you also have, to your original question about photography. Photographers have gradually started to realize that they could shape how they saw nature. Ansel Adams and people like this, you know. Just what an eye. And understanding his tools so verbally he's not just capturing what you see. He's constructing stuff in really, really interesting ways.


And how about moving forward in terms of your work, thinking about where we are now to thinking about the future of technology. For example, one thing that frustrates me a bit as a podcast host is, you know, we just had this conversation about art and it's the limits of the audio medium to not be able to show the paintings of Rembrandt and Cezanne that we just alluded to. So as you think about jumping off of that, as you think about where we are now in terms of media to moving forward, what are some of the challenges that you see and the issues that you're grappling with?


One thing for sure, which I think inhibits a lot of exploration. We're trapped in a relatively small number of platforms. The web is this amazing thing as our phones, iOS and whatnot, but they're also pretty limited and that bothers me a little bit. Basically when you sort of narrow down to just a few platforms which have captured almost all of the attention, that's quite limiting. People also, they tend not to make their own hardware. They don't do these kinds of these kinds of things. If that were to change, I think that would certainly be exciting. Something that I think is very, very interesting over the next few years, artificial intelligence has gotten to the point now where we can do a pretty good job in understanding what's actually going on inside a room. Like we can set up sufficient cameras.

If you think about something like self-driving cars, essentially what they're doing is they're building up a complete model of the environment and if that model is not pretty darned good, then you can't do self-driving cars, you need to know where the pedestrians are and where the signs are and all these kinds of things and if there's an obstruction and that technology when brought into, you know, the whole of the rest of the world means that you're pretty good at passing out. You know what's inside the room. Oh, there's a chair over there, there's a dog which is moving in that direction, there's a person, there’s a baby and sort of understanding all those actions and ideally starting to understand all the gestures which people are making as well. So we're in this very strange state right at the moment.

Where the way we talk to computers is we have these tiny little rectangles and we talk to them through basically a square inch or so of sort of skin, which is our eyes. And then we, you know, we tap away with our fingers and the whole of the rest of our body and our existence is completely uncoupled from that. We've effectively reduced ourselves to our fingers and our eyes. We a couple to it only through the whatever, 100 square inches, couple hundred square inches of our screens or less if you're on a phone and everything else in the environment is gone. But we're actually at a point where we're nearly able to do an understanding of all of that sufficiently well that actually other modes of interaction will become possible. I don't think we're quite there yet, but we're pretty close.

And you start to think about, something like one of my favorite sport is tennis. You think about what a tennis player can do with their body or you think about what a dancer can do with their body. It's just extraordinary. And all of that mode of being human and sort of understanding we can build up antibodies is completely shut out from the computing experience at the moment. And I think over the next sort of five to ten years that will start to reenter and then in the decades hence, it will just seem strange that it was ever shut out.


So help me understand this. So when you mean by start to reenter, do mean that we'll be able to control computers with other parts of our bodies or that we'll be spending less time maybe typing on keyboards. Help me flesh this out.


I just mean that at the moment. As you speak to David, you are waving your arms around and all sorts of interesting ways and there is no computer system which is aware of it, what your computer system is aware of. You're doing this recording. That's it. And even that, it doesn't understand in any sort of significant way. Once you've gained the ability to understand the environment. Lots of interesting things become possible. The obvious example, which everybody immediately understands is that self driving cars become possible. There's this sort of enormous capacity. But I think it's certainly reasonably likely that much more than that will become possible over the next 10 to 20 years. As your computer system becomes completely aware of your environment or as aware as you're willing to allow it to be.


You made a really interesting analogy in one of your essays about the difference between Photoshop and Microsoft Word. That was really fascinating to me because I know both programs pretty well. But to know Microsoft word doesn't necessarily mean that I'm a better writer. It actually doesn't mean that at all. But to know Photoshop well probably makes me pretty good at image manipulation. I'm sure there's more there, but if you could walk me through your thought process as you were thinking through that. I think that's really interesting.


So it's really about a difference in the type of tools which are built into the program. So in Photoshop, which I should say, I don't know that well, I know Word pretty well. I've certainly spent a lot more time in it than I have ever spent in Photoshop. But in Photoshop, you do have these very interesting tools which have been built in, which really condense an enormous amount of understanding of ideas like layers or an idea, different brushes, these kinds of ideas. There's just a tremendous amount of understanding which has been built in there. When I watch friends who are really good with these kinds of programs, what they can do with layers is just amazing. They understand all these kind of clever screening techniques. It seems like such a simple idea and yet they're able to do these things that let you do astonishing things just with sort of three or four apparently very simple operations.

So in that sense, there are some very deep ideas about image manipulation, which had been built directly into Photoshop. By contrast, there's not really very many deep ideas about writing built into Microsoft Word. If you talk to writers about how they go about their actual craft and you say, well, you know, what heuristics do use to write stories and whatnot. Most of the ideas which they use aren't, you know, they don't correspond directly to any set of tools inside Word. Probably the one exception is ideas, like outlining. There are some tools which have been built into word and that's maybe an example where in fact Word does help the writer a little bit, but I don't think to nearly the same extent as Photoshop seems to.


I went to an awesome exhibit for David Bowie and one of the things that David but we did when he was writing songs was he had this word manipulator which would just throw him like 20, 30 words and the point wasn't that he would use those words. The point was that by getting words, his mind would then go to different places and so often when you're in my experience and clearly his, when you're trying to create something, it helps to just be thrown raw material at you rather than the perennial, oh my goodness, I'm looking at a white screen with like this clicking thing that is just terrifying, Word doesn't help you in that way.


So an example of something which does operate a little bit in that way, it was a Ph.D. thesis was somebody wrote at MIT about what was called the Remembrance Agent. And what it would do, it was a plugin essentially for a text editor that it would, look at what you are currently writing and it would search through your hard disk for documents that seemed like they might actually be relevant. Just kind of prompt you with what you're writing. Seems like it might be related to this or this or this or this or this. And to be perfectly honest, it didn't actually work all that well. I think mostly because the underlying machine learning algorithms it used weren't very clever. It's defunct now as far as I know. I tried to get it to run on my machine or a year or two ago and I couldn't get it running. It was still an interesting thing to do. It had exactly this same kind of the belly sort of experience. Even if they weren't terribly relevant. You kind of couldn't understand why on earth you are being shown it. It's still jogged your mind in an interesting way.


Yeah. I get a lot of help out of that. Actually, I’ll put this example. So David Brooks, you know the columnist for the New York Times. When he writes, what he does is he gets all of his notes and he just puts his notes on the floor and he literally crawls all around and tries to piece the notes together and so he's not even writing. He's just organizing ideas and it must really help him as it helps me to just have raw material and just organize it all in the same place.


There's a great British humorist, PG Boathouse, he supposedly wrote on I think it was the three by five-inch cards. He'd write a paragraph on each one, but he had supposedly a very complicated system in his office, well not complicated at all, but it must have looked amazing where he would basically paste the cards to the wall and as the quality of each paragraph rose, he would move the paragraph up the wall and I think the idea was something like once it got to the end, it was a lion or something, every paragraph in the book had to get above that line and at that point it was ready to go.


So I've been thinking a lot about sort of so often in normal media we take AI sort of on one side and art on another side. But I think that so many of the really interesting things that will emerge out of this as the collaboration between the two. And you've written a bit about art and AI, so how can maybe art or artificial intelligence help people be more creative in this way?


I think we still don't know the answer to the question, unfortunately. The hoped-for answer the answer that might turn out to be true. Real AI systems are going to build up very good models of different parts of the world, maybe better than any human has of those parts of the world. It might be the case, I don't know. It might be the case that something like the Google translate system, maybe in some sense that system already knows some facts about translation that would be pretty difficult to track down in any individual human mind and sort of so much about translation in some significant ways. I'm just speculating here. But if you can start to interrogate that understanding, it becomes a really useful sort of a prosthetic for human beings.

If you've seen any of these amazing, well I guess probably the classics, the deep dream images that came out of Google brain a couple of years ago. Basically, you take ordinary images and you're sort of running them backwards through a neural net somehow. You're sort of seeing something about how the neural net sees that image. You get these very beautiful images as a result. There's something strange going on and sort of revealing about your own way of seeing the world. And at the same time, it's based on some structure which this neural net has discovered inside these images which is not ordinarily directly accessible to you. It's showing you that structure. So sort of I think the right way to think about this is that really good AI systems are going to depend upon building and do currently depend on building very good models of different parts of the world and to the extent that we can then build tools to actually look in and see what those models are telling us about the world, we can learn interesting new things which are useful for us.

I think the conventional way, certainly the science fiction way to think about AI is that we're going to give it commands and it's going to do stuff. How you shut the whatever it is, the door or so on and so forth, and there was certainly will be a certain amount of that. Or with AlphaGo what is the best move to take now, but actually in some sense, with something like AlphaGo, it's probably more interesting to be able to look into it and see what it's understanding is of the board position than it is to ask what's the best move to be taken. A colleague showed me a go program, a prototype, what it would do. It was a very simple kind of a thing, but it would help train beginners.

I think it was Go, but by essentially colorizing different parts of the board according to whether they were good or bad moves to be taking in its estimation. If you're a sophisticated player, it probably wasn't terribly helpful, but if you're just a beginner, there's an interesting kind of a conditioning going on there. At least potentially a which lets you start to see. You get a feeling for immediate feedback from. And all that's happening there is that you're seeing a little bit into one of these machine learning algorithms and that's maybe helping you see the world in a slightly different way.


As I was preparing for this podcast, you've liked a lot to Brian Eno and his work. So I spent as much time reading Brian Eno, which I'm super happy that I went down those rabbit holes. But one of the things that he said that was really interesting, so he's one of the fathers of ambient music and he said that a lot of art and especially music, there will sort of be algorithms where you sort of create an algorithm that to the listener might even sound better than what a human would produce. And he said two things that were interesting. The first one is that you create an algorithm and then a bunch of different musical forms could flower out of that algorithm. And then also said that often the art that algorithms create is more appealing to the viewer. But it takes some time to get there. And had the creator just followed their intuition. They probably would have never gotten there.


It certainly seems like it might be true. And that's the whole sort of interesting thing with that kind of computer-generated music is to, I think the creators of it often don't know where they're gonna end up. To be honest, I think my favorite music is all still by human composers. I do enjoy performances by people who live code. There's something really spectacular about that. So there are people who, they will set up the computer and hook it up to speakers and they will hook the text editor up to a projector and they'll have essentially usually a modified form of the programming language list a or people use a few different systems I guess. And they will write a program which producers music onstage and they'll just do it in real time and you know, it starts out sounding terrible of course.

And that lasts for about 20 seconds and by about sort of 30 or 40 seconds in, already it's approaching the limits of complex, interesting music and I think even if you don't really have a clue what they're doing as they program, there's still something really hypnotic and interesting about watching them actually go through this process of creating music sort of both before your eyes and before your ears. It's a really interesting creative experience and sometimes quite beautiful. I think I suspect that if I just heard one of those pieces separately, I probably wouldn't do so much for me, but actually having a done in real time and sort of seeing the process of creation, it really changes the experience and makes it very, very interesting. And sometimes, I mean, sometimes it's just beautiful. That's the good moment, right? When clearly the person doing it has something beautiful happen. You feel something beautiful happen and everybody else around you feel something beautiful and spontaneous. It's just happened. That's quite a remarkable experience. Something really interesting is happening with the computer. It's not something that was anticipated by the creator. It arose out of an interaction between them and their machine. And it is actually beautiful.


Absolutely. Sort of on a similar vein, there's a song called Speed of Life by Dirty South. So I really liked electronic music, but what he does is he constructs a symphony, but he goes one layer at a time. It's about eight and a half minute song and he just goes layer after layer, after layer, after layer. And what's really cool about listening to it is you appreciate the depth of a piece of music that you would never be able to appreciate if you didn't have that. And also by being able to listen to it over and over again. Because before we had recording, you would only hear a certain piece of music live and one time. And so there are new forms that are bursting out of now because we listen to songs so often.


It's interesting to think, there's a sort of a history to that as well. If you go back, essentially modern systems for recording music, if you go back much more than a thousand years. And we didn't really have them. There's a multi-thousand-year history of recorded music. But a lot of the early technology was lost and it wasn't until sort of I think the eighth, ninth century that people started to do it again. But we didn't get all the way to button sheet music overnight. There was a whole lot of different inventions. For instance, the early representations didn't show absolute pitch. They didn't show the duration of the note. Those were ideas that had to be invented. So in I think it was 1026, somebody introduced the idea of actually showing a scale where you can have absolute pitch.

And then a century or two after that, Franco of Cologne had the idea of representing duration. And so they said like tiny little things, but then you start to think about, well, what does that mean for the ability to compose music? It means now that actually, you can start to compose pieces, which for many, many, many different instruments. So you start to get the ability to have orchestral music. So you go from being able to basically you have to kind of instruct small groups of players that's the best you can hope to do and get them to practice together and whatever. So maybe you can do something like a piece for a relatively small number of people, but it's very hard to do something for an 80 piece orchestra. Right? So all of a sudden that kind of amazing orchestral music I think becomes possible. And then, you know, we're sort of in version 2.0 of that now where of course you can lay a thousand tracks on top of one another if you want. You get ideas like micropolyphony. And these things where you look at the score and it's just incredible, there are 10,000 notes in 10 seconds.


Well, to your point I was at a tea house in Berkeley on Monday right by UC Berkeley's campus and the people next to me, they were debating the musical notes that they were looking at but not listening to the music and it was evident that they both had such a clear ability to listen to music without even listening to it, that they could write the notes together and have this discussion and it was somebody who doesn't know so much about music. It was really impressive.


That sounds like a very interesting conversation.


I think it was. So one thing that I'm interested in and that sort of have this dream of, is I have a lot of friends in New York who do data visualization and sort of two things parallel. I have this vision of like remember the Harry Potter book where the newspaper comes alive and it becomes like a rich dynamic medium. So I have that compared with some immersive world that you can walk through and be able to like touch and move around data and I actually think there's some cool opportunities there and whatnot. But in terms of thinking about the future of being able to visualize numbers and the way that things change and whatnot.


I think it's a really complicated question like it actually needs to be broken down. So one thing, for example, I think it's one of the most interesting things you can do with computers. Lots of people never really get much experience playing with models and yet it's possible to do this. Now, basically, you can start to build very simple models. The example that a lot of people do get that they didn't use to get, is spreadsheets. So, you can sort of create a spreadsheet that is a simple model of your company or some organization or a country or of whatever. And the interesting thing about the spreadsheet is really that you can play with it. And it sort of, it's reactive in this interesting way. Anybody who spends as much time with spreadsheets is they start to build up hypotheses, oh, what would happen if I changed this number over here?

How would it affect my bottom line? How would it affect the GDP of the country? How would it affect this? How would it affect that? And you know, as you kind of use it, you start to introduce, you start to make your model more complicated. If you're modeling some kind of a factory yet maybe you start to say, well, what would be the effect if a carbon tax was introduced? So you introduce some new column into the spreadsheet or maybe several extra columns into the spreadsheet and you start to ask questions, well, what would the structure of the carbon tax be? What would help you know, all these sorts of what if questions. And you start very incrementally to build up models. So this experience, of course, so many people take for granted. It was not an experience that almost anybody in the world had say 20 or 30 years ago.

Well, spreadsheets data about 1980 or so, but this is certainly an experience that was extremely rare prior to 1980 and it's become a relatively common, but it hasn't made its way out into mass media. We don't as part of our everyday lives or the great majority of people don't have this experience of just exploring models. And I think it's one of the most interesting things which particularly the New York Times and to some extent some of the other newsrooms have done is they've started in a small way to build these models into the news reading experience. So, in particular, the data visualization team at the New York Times, people like Amanda Cox and others have done this really interesting thing where you start to get some of these models. You might have seen, for example, in the last few elections. They've built this very interesting model showing basically if you can sort of make choices about how different states will vote.

So if such and such votes for Trump, what are Hillary's chances of winning the election. And you may have seen they have this sort of amazing interactive visualization of it where you can just go through and you can sort of look at the key swing states, what happens if Pennsylvania votes for so and so what happens if Florida does? And that's an example where they've built an enormous amount of sort of pulling information into this model and then you can play with it to build up some sort of understanding. And I mean, it's a very simple example. I certainly think that you know, normatively, we're not there yet. We don't actually have a shared understanding. There's very little shared language even around these models. You think about something like a map. A map is an incredibly sophisticated object, which however we will start learning from a very young age.

And so we're actually really good at parsing them. We know if somebody shows us a map, how to engage, how to interpret it, how to use it. And if somebody just came from another planet, actually they need to learn all those things. How do you represent a road? How do you represent a shop on a map? How do you represent this or that, why do we know that up is north like that's a convention. All those kinds of things actually need to be learned and we learned them when we were small. With these kinds of things which the Times and other media outlets are trying to do, we lack all of that collective knowledge and so they're having to start from scratch and I think that over a couple of generations actually, they'll start to evolve a lot of conventions and people will start to take it for granted. But in a lot of contexts actually you're not just going to be given a narrative, you know, just going to be told sort of how some columnist thinks the world is.

Instead, you'll actually expect to be given some kind of a model which you can play with. You can start to ask questions and sort of run your own hypotheses in much the same way as somebody who runs a business might actually set up a spreadsheet to model their business and ask interesting questions. It's not perfect. The model is certainly that the map is not the territory as they say, but it is nonetheless a different way of engaging rather than just having some expert tell you, oh, the world is this way.


I'm interested in sort of the shift from having media be predominantly static to dynamic, which the New York Times is a perfect example. They can tell stories on that they can't tell in the newspaper that gets delivered to your doorstep. But what's really cool about spreadsheets that you're talking about is like when I use Excel, being able to go from numbers, so then different graphs and have the exact same data set, but some ways of visualizing that data totally clicked for me and sometimes nothing happens.


Sure. Yeah. And we're still in the early days of that too. There's so much sort of about literacy there. And I think so much about literacy is really about opportunity. People have been complaining essentially forever that the kids of today are not literate enough. But of course, once you actually provide people with the opportunity and a good reason to want to do something, then they can become very literate very quickly. I think basically going back to the rise of social media sort of 10 or 15 years ago, so Facebook around whatever, 2006, 2007 twitter a little bit later, and then all the other platforms which have come along since. They reward being a good writer. So all of a sudden a whole lot of people who normally wouldn't have necessarily been good writers are significantly more likely to become good writers.

It depends on the platform. Certainly, Facebook is a relatively visual medium. Twitter probably helps. I think twitter and text messaging probably are actually good. Certainly, you're rewarded for being able to condense an awful lot into a small period. People complain that it's not good English, whatever that is. But I think I'm more interested in whether something is a virtuosic English than I am and whether or not it's grammatically correct. People are astonishingly good at that, but the same thing needs to start to happen with these kinds of models and with data visualizations and things like that. At the moment, you know, you have this priestly caste that makes a few of them and that's an interesting thing to be able to do, but it's not really part of the everyday experience of most people.

It's an interesting question whether or not that's gonna change as it going to in the province of some small group of people, or will it actually become something that people just expect to be able to do? Spreadsheets are super interesting in that regard. They actually did. I think if you've talked to somebody in 1960 and said that by 2018, tens of millions of people around the world would be building sophisticated mathematical models as just part of their everyday life. It would've seemed absolutely ludicrous. But actually, that kind of model of literacy has become relatively common. I don't know whether we'll get to 8 billion people though. I think we probably will.


So when I was in high school I went to, what I like to say is the weirdest school in the weirdest city in America. I went to the weirdest high school in San Francisco and rather than teaching us math, they had us get in groups of three and four and they had us discover everything on our own. So we would have these things called problem sets and we would do about one a week and the teacher would come around and sort of help us every now and then. But the goal was really to get three or four people to think through every single problem. And they called it discovery-based learning, which you've also talked about too. So my question to you is we're really used to learning when the map is clear and it's clear what to do and you can sort of follow a set path, but you actually do the opposite. The map is unclear and you're actually trailblazing and charting new territory. What strategies do you have to sort of sense where to move?


There's sort of a precursor question which is how do you maintain your morale and the Robert Pirsig book, Zen and the Art of Motorcycle Maintenance. He proposes a university subject, gumptionology 101. Gumption is almost the most important quality that we have. The ability to keep going when things don't seem very good. And mostly that's about having ways of being playful and ways of essentially not running out of ideas. Some of that is about a very interesting tension between having, being ambitious in what you'd like to achieve, but also being very willing to sort of celebrate the tiniest, tiniest, tiniest successes. Suddenly a lot of creative people I know I think really struggle with that. They might be very good at celebrating tiny successes but not have that significant ambitions, but they might be extremely ambitious, but because they're so ambitious, if an idea doesn't look Nobel prize worthy, they're not particularly interested in it. You know, they struggle with just kind of the goofing around and they often feel pretty bad because of course most days you're not at your best, you don't actually have the greatest idea.

So there's some interesting tension to manage there. There's really two different types of work. One is where you have a pretty good goal, you know what success looks like, right? But you may also be doing something that's more like problem discovery where you don't even know where you're going. Typically if you're going to compose a piece of music. Well, I'm not a composer, but certainly, my understanding from, from friends who are, is that they don't necessarily start out with a very clear idea of where they're going. Some composers do, but a lot, it's a process of discovery. Actually, a publisher once told me somebody who has published a lot of well-known books that she described one of her authors as a writing for discovery.

Like he didn't know what his book was going to be about, he had a bunch of kind of vague ideas and the whole point of writing the book was to actually figure out what it was that he wanted to say, what problem was he really interested in. So we'd start with some very, very good ideas and they kind of get gradually refined. And it was very interesting. I really liked his books and it was interesting to see that. They looked like they'd been very carefully planned and he really knew what he was doing and she told me that no, he'd sort of come in and chat with her and be like, well, I'm sort of interested over here. And he'd have phrases and sort of ideas. But he didn't actually have a clear plan and then he'd get through this process of several years of gradually figuring out what it was that he wanted to say.

And often the most significant themes wouldn't actually emerge until relatively late in that whole process. I asked another actually quite a well-known writer, I just bumped into when he was, he was reporting a story for a major magazine and I think he'd been working, he'd been reporting for two weeks, I think at that point. So just out interviewing people and whatever. And I said, how's it going? And he said, Oh yeah, pretty good. I said, what's your story about? He said, I don't know yet, which I thought was very interesting. He had a subject, he was following a person around. But he didn't actually know what his story was.


So the analogy that I have in my head as you're talking about this, it's like sculpture, right? Where you start maybe with a big thing of granite or whatnot, and slowly but surely you're carving the stone or whatnot and you're trying to come up with a form. But so often maybe it's the little details at the end that are so far removed from that piece of stone at the very beginning that make a sculpture exceptional.


Indeed. And you wonder what's going on. I haven't done sculpture. I've done a lot of writing and writing often feels so sometimes I know what I want to say. Those are the easy pieces to write, but more often it's writing for discovery and there you need to be very happy celebrating tiny improvements. I mean just fixing a word needs to be an event you actually enjoy, if not, the process will be an absolute nightmare. But then there's this sort of instinct where you realize, oh, that's a phrase that A: I should really refine and B: it might actually be the key to making this whole thing work and that seems to be a very instinctive kind of a process. Something that you, if you write enough, you start to get some sense of what actually works for you in those ways.

The recognition is really hard. It's very tempting to just discount yourself. Like to not notice when you have a good phrase or something like that and sort of contrary wise sometimes to hang onto your darlings too long. You have the idea that you think it's about and it's actually wrong.


Why do you write and why do you choose the medium of writing to think through things sometimes? I know that you choose other ones as well.


Writing has this beautiful quality that you can improve your thoughts. That's really helpful. A friend of mine who makes very popular YouTube videos about mathematics has said to me that he doesn't really feel like people are learning much mathematics from them. Instead, it's almost a form of advertising like they get some sense of what it is. They know that it's very beautiful. They get excited.

All those things are very important and matter a lot to him, but he believes that only a tiny, tiny number of people are actually really understanding much detail at all. There's actually a small group who have apparently do kind of. They have a way of processing video that lets them understand.


Also, I think you probably have to, with something like math, I've been trying to learn economics online and with something like math or economics that's a bit complex and difficult, you have to go back and re-watch and re-watch, but I think that there's a human tendency to want to watch more and more and more and it's hard to learn that way. You actually have to watch things again.


Absolutely. Totally. And you know, I have a friend who when he listens to podcasts, if he doesn't understand something, he, he rewinds it 30 seconds.

But most people just don't have that discipline. Of course, you want to keep going. So I think the written word for most people is a little bit easier if they want to do that kind of detailed understanding. It's more random access to start with. It's easier to kind of skip around and to concentrate and say, well, I didn't really get that sentence. I'm going to think about it a little bit more, or yeah, I can see what's going to happen in those two or three paragraphs. I'll just very quickly skip through them. It's more built for that kind of detailed understanding, so you're getting really two very different experiences. In the case of the video, very often really what you're getting is principally an emotional experience with some bits and pieces of understanding tacked on with the written word. Often a lot of that emotion is stripped out, which makes can make it much harder to motivate yourself. You need that sort of emotional connection to the material, but it is actually, I think a great deal easier to understand sort of the details of it. There's a real kind of choice to be to be made. There's also the fact that people just seem to respond better to videos. If you want a large audience, you're probably better off making YouTube videos than you are publishing essays.


My last question to you, as somebody who admires your pace and speed of learning and what's been really fun about preparing for this podcast and come across your work is I really do feel like I've accessed a new perspective on the world which is really cool and I get excited probably most excited when I come across thinkers who don't think like anyone who I've come across before, so I'm asking to you first of all, how do you think about your learning process and what you consume and second of all, who have been the people and the ideas that have really formed the foundation of your thought?


A Kurt Vonnegut quote from his book, I think it's Cat's Cradle. He says, we become what we pretend to be, so you must be careful what we pretend to be and I think there's something closely analogously true, which is that we become what we pay attention to, so we should be careful what we pay attention to and that means being fairly careful how you curate your information diet. There's a lot of things. There's a lot of mistakes I've made. Paying attention to angry people is not very good. I think ideas like the filter bubble, for example, are actually bad ideas. And for the most part, it sounds virtuous to say, oh, I'm going to pay attention to people who disagree with me politically and whatever. Well, okay, there's a certain amount of truth to that. It's a good idea probably to pay attention to the very best arguments from the very best exponents of the other different political views.

So sure, seek those people out, but you don't need to seek out the random person who has a different political view from you. And that's how most people actually interpret that kind of injunction. They, they're not looking for the very best alternate points of view. So that's something you need to be careful about. There's a whole lot of things like that I enjoy. So for example, I think one person, it's interesting on twitter to look, he's, he's no longer active but he's still following people is Marc Andreessen and I think he follows, it's like 18,000 people or something and it's really interesting just to look through the list of followers because it's all over the map and much of it I wouldn't find interesting at all, but you'll find the strangest corners people in sort of remote villages in India and people doing really interesting things in South Africa. Okay. So he's a venture capitalist but they're not connected to venture capital at all. So many of them, they're just doing interesting things all over the world and I wouldn't advocate doing the same thing. You kind of need to cultivate your own tastes and your own interests. But there's something very interesting about that sort of capitalist city of interests and curiosity about the world, which I think is probably very good for almost anybody to cultivate. I haven't really answered your question.


I do want to ask who were the people or the ideas or the areas of the world that have really shaped and inspired your thinking because I'm asking selfishly because I want to go down those rabbit holes.


Alright. A couple of people, Alan Kay and Doug Engelbart, who are two of the people who really developed the idea of what a computer might be. In the 1950's and 60's, people mostly thought computers were machines for solving mathematical problems, predicting the weather next week, computing artillery tables, doing these kinds of things. And they understood that actually there could be devices which humans would use for themselves to solve their own problems. That would be sort of almost personal prosthetics for the mind. They'd be new media. We could use to think with and a lot of their best ideas I think out there, there's still this kind of vision for the future. And if you look particularly at some of Alan Kay's talks, there's still a lot of interesting ideas there.


That the perspective is worth 80 IQ points. That's still true.


For example, the best way to predict the future is to invent it, right? He's actually, he's got a real gift for coming up with piddly little things, but there's also quite deep ideas. They're not two-year projects or five-year projects, they're thousand year projects or an entire civilization. And we're just getting started on them. I think that's true. Actually. It's in general, maybe that's an interesting variation question, which is, you know, what are the thousand year projects? A friend of mine, Cal Schroeder, who's a science fiction writer, has this term, The Project, which he uses to organize some of his thinking about science fictional civilizations. So The Project is whatever a civilization is currently doing, which possibly no member of the civilization is even aware of.

So you might ask the question, what was the project for our planet in the 20th century? I think one plausible answer might be, for example, it was actually eliminating infectious diseases. You think about things like polio and smallpox and so many of these diseases were huge things at the start of the 20th century and they become much, much smaller by the end of the 20th century. Obviously AIDS is this terrible disease, but in fact, by historical comparison, even something like the Spanish flu, it's actually relatively small. I think it's several hundred million people it may have killed. Maybe that was actually the project for human civilization in the 20th century.

I think it's interesting to think about those kinds of questions and sort of the, you know, where are the people who are sort of most connected to those? So I certainly think Doug Engelbart and Alan Kay.


Talk about Doug Engelbart, I know nothing about him.


So Engelbart is the person who I think more than anybody invented modern computing. He did this famous demo in 1968, 1969. It's often called the mother of all demos, in front of an audience of a thousand people I believe. Quite a while since I've watched it and it demonstrates a windowing system and what looks like a modern word processor, but it's not just a word processor. They're actually hooked up remotely to a person in another location and they're actually collaborating in real time. And it's the first public showing I believe of the mouse and of all these different sorts of ideas.

And you look at other images of computers at the time and they're these giant machines with tapes and whatever. And here's this vision that looks a lot more like sort of Microsoft Windows and a than anything else. And it's got all these things like real-time collaboration between people in different locations that we really didn't have at scale until relatively recently. And he lays out a huge fraction of these ideas in 1962 in a paper he wrote then. But that paper is another one of these huge things. He's asking questions that you don't answer over two years or five years. You answer over a thousand years. I think it's Augmenting Human Intellect is the title of that paper. So he's certainly somebody else that I think is a very interesting thinker.

There's something really interesting about the ability to ask an enormous question, but then actually to have other questions at every scale. So you know what to do in the next 10 minutes that will move you a little bit towards that, you know what to do in the next week. You also know what your job is for the next thousand years. Actually, I think Elon Musk's (my article on the magic of Elon here) vision of settling Mars is an interesting one. And maybe even potentially eventually terraforming it. That's not a five-year project. That's another big one. Well, even better making your humans an interplanetary species. That's an interesting sort of large-scale project.


So I have to ask if you don't want to answer this question, that's fine. Do you have a hypothesis for the 21st-century project?


All right, so a very obvious answer that I don't want to go down is to say it's artificial general intelligence or let's just rule that out. I think a more interesting answer. Let me give you the boring version of the more interesting answer. First, I want to say something about cryptocurrency, that the most interesting ideas around that have to do with finding new ways. I mean, what a new type of financial instrument ideally will allow people to do is to coordinate in a way that was not previously possible. So in 1471, there's the invention of modern maritime insurance and that enabled all sorts of exploration to take place that wasn't funnily possible, basically because it allowed people to pool risks. So as an investor you weren't going to lose everything you own if the ship didn't come back, instead you'd take a small loss and it was okay. So modern maritime insurance was this just wonderful invention.

I believe it's true that there's probably just an enormous number of such similarly sized, similarly important financial instruments waiting to be discovered. Historically, it's been very hard to deploy a new financial instrument. You need lots of centralized infrastructure. Basically, you needed to run a bank. And that's, to me anyway, potentially the most interesting thing about having truly decentralized currencies, which are fully programmable, is the ability for individuals who are not CEOs of banks to devise new financial instruments. And just start deploying them at scale. So an example of one that I very much like is due to Alex Tabarrok, it's called the dominant assurance contract. It's basically an idea. It's sort of Kickstarter on steroids. So it's a little bit complicated. In Kickstarter, as I'm sure you know, you have this situation where if you don't get your project funded to a particular level, everybody gets their money back and what Tabarrok proposed doing was really a sort of a much more extreme version of that.

He proposed to set up a situation where, let's say you want to fund, I don't know, let's say a public swimming pool somewhere, and let's say there's the swimming pool is going to cost $400,000. Where you run this sort of, this dominant assurance contract, a kind of Kickstarter++, to raise $500,000. So you're going to get $100,000 bounty on top. But if it does not succeed, if you don't get people invested at that level, you give back and there's an extra premium which you give back to the people who bought in initially. So the first person to put up 10 bucks might actually get $13 back. As you get closer to the $500,000 threshold, of course, people basically just get back whatever they put in and it's designed to incentivize people to make this actually work.

You actually set up a fully functioning market basically. People are now incentivized to provide public goods like swimming pools because they can potentially make a profit if it fails, but also people outside, you know, are incentivized to find things which are going to fail and invest in them actually increasing the likelihood that they will succeed. So you've set up this very interesting mechanism. It's basically Kickstarter. But I think if all the incentives are appropriately designed, it's probably likely to be significantly more effective at funding certain types of goods. I mean, it's never been tried at scale. The key point is that some of these cryptocurrencies actually potentially make it very easy to implement marketplaces like this. And that kind of thinking, it's plausible to me anyway that the 21st century, maybe that's what it turns out to be about. It's about actually inventing new types of markets. Which is really a means of inventing new types of collective action. Anyway, do I believe that? Not sure. That's a good science fiction novel. Anyway.


Well, Michael Nelson, thank you so much for coming on the podcast.


Thanks, David.

Hey again, it's David here. You can support the North Star Podcast by leaving us a review on iTunes, or you can share the podcast on Twitter or Facebook.

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North Star Media helps companies build brands on the Internet. Through blog posts, books, videos, and podcasts, like this one, we build trust and generate attention.

If you would like to learn more about North Star Media, you can visit my website,, or connect with me directly on Twitter at @david_perrell. If you enjoyed this episode, you'll also liked the episode with Tyler Cowen, who writes about economics, technology, and culture. In that episode, Tyler shares some seriously counterintuitive points on travel, the millennial generation and how he thinks about learning and the future. 

Key points in this episode

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Our guest this week is Kevin Kwok and this episode is a special treat. Kevin was an investor at Greylock Partners, where he mainly focused on marketplaces, cryptocurrencies, and autonomous vehicles.

Kevin is particularly interested in understanding the underlying structures that shape industries and the core loops that drive companies. And among other things is currently working on a class on loops, network effects, and growth models.

In this wide-ranging conversation, Kevin and I jump between various topics such as A/B testing cities in China, Saudi Arabia and the future of democracy, and why we have democracies in countries and dictators in companies. 

Then, Kevin distills lessons from five extremely long biographies — four of them about US President Lyndon B. Johnson and one of them about Robert Moses, the “master builder” of New York City. Drawing on those Caro biographies, Kevin talks about power, where it originates, and how to think about systems.

Kevin has an in-depth knowledge of political history, governments, technology and growing a company in the internet age. Today, we’ll weave all of those threads together.


Kevin on Twitter

Kevin’s Website

The Power Broker, Robert Caro

Lyndon B. Johnson Biographies, Robert Caro

Time Stamps

1:27 Kevin talks about Robert Caro and his biographies on Robert Moses and Lyndon B. Johnson

3:08 How systems are the underlying reason for power in governments and companies

6:49 Kevin’s observations on the significant similarities between governments, religions and companies 

10:27 Kevin defines his theory of loops and how they are a pattern that can be seen in the most successful businesses

14:03 Kevin’s observation on how successful governments and businesses use loops to scale

17:34 The two ways Kevin sees legibility, why it’s so important in creating synchronization  between founders and employees, and how it’s the reason for Uber’s success

22:32 Kevin’s fascinations with Stripe’s thoughtful leaders and their transparency in growing the company

28:26 Why the outcome of loops is a leverage effect and how leverage can remove constraints and compound systems for more gain and less effort

34:49 Kevin talks about China’s goal to urbanize more of its country through A/B testing and his opinion on the pros and cons of their strategy

40:35 A brief history of Saudi Arabia, and its implications about whether democracy is declining.

46:25 Kevin’s opinion on the future of currency and how cryptocurrency is reshaping markets and their functions

51:32 Kevin talks about how infrastructure shapes how residents interact with their cities and the underlying problems that can arise

57:44 Kevin’s take on the new trend of contrarianism, how we’ve seen this pattern before and how to be most effective with a contrarian view

1:00:20 How Steve Jobs was a perfect example of contrarianism followed by impact

1:01:58 Kevin talks about his current focus on loops and his hope that humans continue pushing and testing this frontier


“It’s too easy to see what other people are doing. It’s so easy to raise capital if you can paint a compelling case for why there’s a good return. The best companies are companies that have these internal compounding proprietary advantages that get better and are impossible for anybody else to do other than them. That’s what I mean by loops. There’s different ways this can look. For example, network events as people come and talk about them is an example of a loop. The value of the user increases as more people join the network and that’s an internal loop that other people, who don’t have your network and don’t have your users, can’t benefit from.”

“People try to figure out how to build these systems that are independent from their hours put in. Fundamentally, your scarce resource is your hours. There’s just some finite cap and the level of productivity you can get. You can get more productive but there’s a finite cap to how much more productive you can get on your hours. As long as your output is contrast by your hours, there always is some cap to it. The question is, how do you get increased leverage on that and, how do you keep increasing the leverage on that at some point? Ultimately, capital is actually less of a constraint if you have a working business model than just the cognitive load and your ability to actively work on different things.”

“Think about how much has been shaped structurally, without even realizing it, by the decisions that were made by people crafting the Internet standards. All of those decisions people made have had huge downstream impacts on every layer that has been built on top of them. I don’t think we regret that. I think that we look at it and we say, let’s make sure we do all of the good things there. Let’s also think about the mistakes we’ve made as we create other industries, whether that’s the current waves of finance, or the current waves of tech, or whatever. When you’re in these nascent periods of new industries, how do we make sure that we help the people who we trust to be making those decisions be there at the end.”

“I think that a lot of people talk about contrarianism as being against the grain, and having views that other people disagree with. Of course, the challenge is the decision of, ‘I have this view that people disagree with. Is that actually a good view or a view that people disagree with because it’s a bad view?’ Similarly, it’s hard to judge the people around you because it could be that you have a view that is mainstream in your community, but it’s actually a contrarian view in the larger view of people. My view of contrarianism is that the important part isn’t in having this view that everybody else disagrees with. The important part is bringing it to everyone else, taking that view and causing it to become non-contrarian.”

“The people we should be most excited about that have contrarian views are the people who don’t just have them, they then go make sure that those views stop being contrarian and we all believe them. In fact, it’s the people who we look back and say, was that even that contrarian of a view? Actually, we all believe it. And I think that there is too much of a focus on the standing apart and being the one with the unique insight versus the part which is, ‘how do you educate everybody else and bring that back into the mainstream consciousness?’. That is a lot of work and proves that what you were thinking about was actually valuable and important. That’s the part of it that I wish was more focused on, not the part where you just feel hipster.”



Kevin Kwok, welcome to the North Star.


Thanks for having me.


So you absolutely loved Caro biographies and I thought that would be a fun place to begin this podcast.


I'm glad I get to do my paid advertisement for Caro now. So Robert Caro has written five biographies right now, one of which is on Robert Moses who is kind of the person who built all of New York City. And then the other four are kind of four biographies of Lyndon Johnson who is probably everyone's least interesting president when they don't know about him. And then after reading the biographies, he’s by far the most interesting I think. The craziest thing about the biographies is that they are extremely long and so they're just these huge tomes that if you try to get someone to read, nobody will because they kind of look at it and then they are like, I would much rather go and read 10 books instead of reading one of those. And so it's super hard to get people to start with it. And Caro has certainly done himself no favors on that, but they're just the best books I think about understanding power, where it originates, structuralism, and how you think about the kinds of systems and people who understand how to figure them out and make them work for good or for bad. Which both, I think, you know, Moses in New York, then Lyndon Johnson and the Senate, and then the White House are both kind of the peak examples.


What is it about power that interests you so much? And is there a story that you can tell from one of the biographies that illuminates your interest in power?


Yeah, for sure. I think power is less the thing that interests me about the biographies as much as understanding systems. For most people, it's hard to understand the companies they work at or how the government functions or why New York grows and the way that it grows is something that feels too complex to kind of be legible and be understood. But then you look at, you know, someone who does it and you don't understand why they're able to do it. And unpacking that I think is just super useful to get people down the road of saying, wait, actually how do all of these systems work? And can I figure out the kind of thing in either the company I work at to make it work better or in the kind of why the government operates in the way it does.

And so to give you one example though, we could go on for infinite examples on this. I think if you look at Senate history, there really wasn't, you know, we now look at the Senate as kind of this dysfunctional organization that doesn't really ever produce meaningful bills, has a large impact. Uh, and that's not actually a recent phenomenon. I think that in general is actually how the Senate has always operated. But there's this brief period when Lyndon Johnson enters the Senate and then becomes majority leader where the just sheer volume of important bills that pass is ridiculous. Like most of the progressive bills we now look at whether that's kind of !medicare related or whether that's a punch of the public works or whether that's the civil rights act, all are kind of ones that Lyndon Johnson shepherded through and shepherded it through at a time where the southern senators had tremendous amounts of power.

And where they were not interested in civil rights or anything like this kind of being passed through. And so a lot of it is kind of him going into this sub 100 person organization understanding at both the kind of personal level, but also kind of where there a centralization of power, whether that was how to raise money better and funnel that to government. Whether that was how to set up the subcommittees that actually had the organizational power and had the kind of power to shape what moved down the pipeline of bills or whether that was kind of setting up a structure where he decided had people in all of the subcommittees and helped both expedite bills. And eventually, people went to him to kind of make sure that their bills will get passed.

But then that also gave him a tremendous amount of insight and knowledge and control what bills were getting passed and having leveraged with all the other senators. And so I think, you look at a bunch of those examples and then they're not dissimilar from how we look at companies now, right? Or how we look at any type of organization now of where are the natural places, where the constraints on the system are and where are the places where power resides and I think Lyndon Johnson certainly did not always do things for the greater good. He did things for his own personal power which sometimes was aligned with the greater good but oftentimes was not. And I think the interesting thing is how do you understand those systems? And then how do you hopefully have people who care about building good things out of those systems, understand them and use them.


Building off of that, even in that answer, you talked about companies, you talked about government and you strike me as somebody who looks at models and frameworks that sort of may be representing a lot of different domains with the world. How do you think about that?


Yeah. The thing that always strikes me about organizations is that whether you look at governments or religions or companies, all of them are kind of topologically equivalent. Like they're all kind of the same thing. There are organizations of people that have some set of rules for who's in the group. Some set of rules for how the group makes decisions and come to a consensus, some sort of rules for how they allocate resources and all of these things. And so you can look at them on a bunch of different factors and they vary right, for example, you looked at a lot of companies and companies kind of allow both the company and the employee to unilaterally decide if they want to be part of the company. Whereas governments, for example, kind of have this rule that says, hey, as long as you don't commit treason, if you're a citizen, you're a citizen.

And so they vary on different things. But actually, once you account for that, at similar orders of magnitude they're very similar. And so I think as an example, one thing I think about a lot with companies is are companies today are more similar to a companies a thousand years ago or are they more similar to city states a thousand years ago and what are then the lessons you can draw if you look at all the different things that are similar in some regard but different in others that you looked at and say, hey, you can actually learn some interesting lessons about how religions organize and structure themselves for crypto projects. Are there lessons for how the Senate operates for decisions within companies or things like that.


So how do you think about balancing the similarities between different structures but also the reality that as things grow and scale, begins to change the properties of something. Right? Because you could see similarities between different companies for example. But also there's an inherent tension between growth and wanting to sort of rest on those models, but things change as they scale.


Yeah. That's, that's a great question. I think the thing that always confuses people is that as their companies grow or as any organization grows by an order of magnitude on any dimension, whether that is customers or employees or a number of purchases or anything, it's just a fundamentally different company and a different system. And the things that you've built and the processes you have that work great when you're 10 people, stop working when you're 100 people and definitely don't work when you're 100,000 people. And so a part of it is that you have to be comfortable saying, how do I understand that even just being successful at the same thing, we are successful, that will by definition obsolete our competence at it because it will grow by order of magnitude and will be fundamentally different. And how do you understand what are those ecosystems and loops that you have? And you know, as they get to a new scale, how they change and what they need to transition to and what that looks like, that might be very different.


So we were at dinner about a month ago and we were talking about loops and you have some really interesting ideas in terms of the relationship between loops, sales, network effects, maybe even careers. So just gonna let you run with that.


Yeah. It's funny because I feel like I talk about loops with a bunch of people or on !twitter. And then I realized that everyone just asked me what loops are and I don't have a great explanation because I feel like it's not discussed super often. I think to kind of start from the beginning of it. I think one of the things that I've thought about a lot is if the two of us were going to start a company a thousand years ago, 500 years ago, the best way to start a successful company would be to get the government to give us exclusive trade routes between the US and India and guarantee that anyone else using those routes, the military or the navy would go stop them. And you could build a hugely successful business there.

And then in the 1800s or 1900s, the best way to do it would be to find some area, maybe a natural resource or building railroads or something like that and go build this business that is economy of scale after you have a bunch of proprietary relationships. And it'd be hard for people to both copy that or raise the capital to compete with it. But now you look at the most successful companies and certainly the tech companies and it's too easy to see what other people are doing. It's so easy to raise capital if you can paint a compelling case for why there's a good return on it. And so the best companies are companies that have these internal compounding proprietary advantages that get better and are impossible for anyone else to do other than them. And I think that's what I mean by loops and there are lots of different ways that can look.

For example, I think that, you know, network effects as people commonly talk about them, are an example of a loop where the kind of value to the user increases as more people join the network and that's an internal loop that other people who don't have your network and don't have your users can't benefit from even if they know that it's true. But I think that network effects are one subset, but there are lots of them and they're all over companies. And actually the interesting way to think about companies or sectors or any of these ecosystems is kind of the loops around them and what is compounding and not only what is compounding but what's constraining them, because when you look at something that's a loop the and keeps compounding, the thing that hurts it the most is wherever it is most constrained and is dropping off, right?

So I think that both for individuals and for companies, we don't currently track things like this. In fact, many of our metrics today are more geared around either funnels or other types of ways of looking at companies. But really as you think about how do you build companies and understand the sequencing of what compounds and why does it keep getting bigger. It's all about what are the loops you have and how do you strengthen them? And then what are the constraints on them and how do you remove those frictions, right? Whether that's financial capital or social capital or knowledge or having more employees or whatever it is.


What changed about the world that made loops super relevant?


It's a good question. I think that loops were always relevant, but the thing is the less data and iterations and the less at bats you have the less loops matter because if you look at an enterprise company and you know they need to land the government and they land the government and they're a public company and that's the entire business. Then you know, these loops don't really matter. What matters is, can you build a great relationship with the buyer at the whatever department in the government and can you get them on board, but then you look at the other extreme and you look at consumer marketplaces and it's not enough to say, I got dinner with that one buyer and they bought $25 thing on my website and now I'm golden. You have to say, hey, can I get 10 million people to go do that?

And it's just not possible for me to hand go to them and get to know them personally. I have to build a system that aligns them with me and causes them to engage with me and then retain and then keep buying and then be happy and then keep spreading the word to other people. And so the more we have things that have greater amounts of data or customers, the more we have things where you have more interactions with the customers, the more that you have things where you can't just have the government dictate that you win or have one or two people decide who's the winner in the market. The more we get to a world where you have to build these internal systems that compound. And I think that's why we're still in the early days of it.

I think we'll look back in 10, 20 years and a lot of how we track things in companies, a lot of how we look at things will have shifted towards this because one model of companies or model of venture I look at is at one end of the extreme is enterprise sales where it is more knowable, what makes a company successful and which people could start a successful company and who are the customers. And then on the other side is consumer social or consumer marketplaces where even for the best investors, it's super hard to predict which one will figure out the loop and get traction with customers. But you know, the whole point of tech as an industry and venture as an industry to some degree is taking these things that are not yet understood about how we should think about metrics or how we should think about company building or loops and then making it understood and benefiting from that.

But hopefully, the things that are the frontier of our understanding today about company building, in 20 years, kids in college, will just look at you like you're dumb for even thinking that that was ever not understood in the same way that we look back at companies 20 years ago and we say, you know, of course. I think that exactly like that, you go back enough years, it wasn't in the mainstream consciousness about how to think about that. Now it's almost overused, right? Everyone kind of knows that's how they should think about that. And I think the question is how do you keep pushing all of these views that are usable and useful of how to think about companies or just how to think about any system forward collectively. Right?


And on that theme of pushing forward and pushing to the frontier where we were talking a bit about pushing the frontier of legibility. Can you do a quick background on legibility and illegibility and talk about what you mean by pushing the frontier of legibility?


Yeah, for sure. So I think that there are two ways I think about legibility, which I'll go into. I think the first is that legibility in companies, which I view as kind of two things I've been kind of thinking about are legibility and synchronicity and companies. And so I think legibility to me and companies is, does each person at a company understand why the company works the way it does and what's important to the company and what are the loops that matter to the company? And I think that's super important because a lot of times people do their job well and then the company or their manager or whoever kills the project and they don't understand why and they don't understand why even though they did the thing that they were told to do, it didn't fit into the larger system of what the company wanted.

And the same is true for founders. You know, a lot of times founders have to figure out legibility of the market, right? And understanding where they fit into that. And I think that it's hard to measure and we don't really measure this but it's interesting to me to what degree does each person within a company understand the loops and the rest of the company so that they always know how they should kind of act and the things they should do that are most beneficial for the company. I think if you think about legibility as kind of everyone at the company trying to understand the company, synchronicity is kind of the flip of that, which is if you're the founder of a company, what is your ability to have everyone at the company synchronized with the things you want and on the same page and of kind of how you think about it and what actions are important and working towards those. And I think that these are the kind of the two feedback loops in both directions within companies that are their own system and loop, right. That when you have it really well, it's just significantly more productive and for better or worse. For example, I think that Uber had tremendous synchronicity, more so than many, many companies and it allowed them to act with super distributed teams in every city.


Almost a balance of their central headquarters, but also the local units that would go into every city, work with local government, understand the local dynamics of the market and they had good synchronicity between the two.


Exactly. You need the legibility of understanding what is actually what should be different for each market and having the teams on the ground there, but then you also need them to understand kind of what is actually the most important things that Uber as an entity cares about. Right. And those are things like liquidity and having a driver available within x minutes from anytime you call or having pricing that looks within a certain range and these kinds of metrics that you need to have kind of synchronicity across all of the groups on. I think that also is just as we talked about with Caro, I think that goes in both the benefits and the cons, right? Because it also means that if you have issues, those can get synchronized across the entire companies too.

But I think that one thing that Silicon Valley has done significantly better than many other industries is how to think about the internal structure of organization and how do you actually get leveraged. So instead of just adding more and more humans and hoping that it works well, but inevitably kind of falling over because it becomes harder and harder to coordinate. How do you actually figure out these systems so that you can coordinate people both on the team, or a lot of marketplaces if you look at Uber, Airbnb for example, I think that they don't have direct control over the hosts or the drivers, but they still need to have synchronicity and legibility with them of figuring out how to coordinate with them and have them act in ways that are beneficial for both them and the platform. And that's even tougher when you don't have direct control because they're your employees. All of the tech companies have been figuring out a lot of advancements in how do we think about company structure and you look at how Amazon or Stripe or all these companies very intentionally think about it and you know, there's a lot of mistakes made, but it also is kind of pushing forward a bunch of this, right?


Talk about Stripe, I'm really interested in stripe and I think that in terms of its impact on the world, it's very under-covered and definitely understudied.


Yeah, absolutely. I certainly think that there are many people who know Stripe much better than me and I definitely don't know all the details of it. But I think there are a few things that are fascinating about Stripe. I think certainly one of them from a company organization standpoint is that the Collison brothers, even from afar, are just very clearly thoughtful leaders who are consciously thinking about knowledge. It's baffling to me given the demands of their jobs, how they have the cognitive time and any of the ability to spend the amount of time they do just soaking up knowledge and thinking about how to kind of structure their company better and structure or their system better.

But you just look at them and they're super intentional about it. Right? And I think that whether that's the internal tooling they built out for kind of improving communications internally, which they've blogged a bit about or whether that's kind of how they think about the emails being open and shared and having a default to that so that people can have as much information as possible. Whether that's just kind of seeking out the best practices from other companies and always kind of trying to figure out how to improve. I think that one thing you look at is that people talk about A players and B players and C players and companies and there's always the adage of kind of you want people who are not afraid to hire the best people to join them versus afraid that people will kind of replace them.

But I actually think there's another accede to that, which is how much do you bias towards people who will build things in the same way that they have been built versus people who will rethink how to build these systems. And don't get me wrong, I think that a lot of times the best practices that have been established are great and so in a lot of places you do want to hire the person who has built out with VP sales at the company that was the last generation of what you're building and can immediately bring you to all of those best practices. And so that's kind of one accede to me. And then there's another accede which is, are people willing to look at kind of the situation of your company in particular and say, hey, actually should we rethink how it's done and would it be more beneficial or should we obsolete this business unit entirely and would that actually be beneficial?

And then am I not afraid to do that. And I think the harsh truth is that most companies, getting to the best practices is kind of a baseline requirement. And if you can't do that at some speed, you don't really earn the right. You just don't have the time or the money or the ability to experiment with new models that might not work. And the payoff could be much higher, but you might not find out whether it worked or not for a while. Then you look at companies like Stripe that kind of do operate at a great level, and then still are able to find the time and say, hey, actually we should still rethink these systems and figure out if there are ways to build it better. And that's how you build very special companies.

Because I think that as an example if you look at marketplaces and you look at Uber, it wasn't common knowledge to think about network effects at a local level when Uber started and when Lyft started, people didn't do city teams in the same way. They kind of launched nationally and both of those companies kind of really pioneered, at least for the mainstream consciousness, this idea that actually it might be advantageous to launch city teams because there might be these loops that are better done at the city level versus at the national level. Now, you look after Uber and Lyft and there were so many marketplaces that all kind of created city teams and launched. Actually, it's not obvious that was always beneficial. I think you look at a lot of these teams and they kind of copied this new norm that kind of became standard instead of also thinking for their sectors, hey, actually if you looked at it, what is the correct scope of my network effect and what's the best area, whether that's the city level or the state level or just the local neighborhood or even one block and saying what actually makes the most sense.

And so for example, if you look at the scooter companies that are popping up everywhere in the US and whether they'll be successful or not, what's fascinating is that their natural zone is not quite cities. They work much better on the Venice boardwalk. Then they work in the middle of some suburban neighborhood in Los Angeles.


Wouldn't work in Houston.


Right, right. So the question is if you look at that, how do you figure out how you deploy the people in your organization, how do you think about the metrics and what scope you should be tracking them and how do you think about what are those loops and what is the natural scope of them so that you can best build the business and have it compound. And I think that, you look at companies that are just super thoughtful about it and it's incredible and you know, part of the challenge is, how do you find people who have that bias, but also how do you have a cadence of shipping and progress that is fast enough that you know, have the time and ability to spend those resources thinking about it.


It seems like leverage, is sort of the outcome of loops. So loops keep spinning. Perhaps as the network effect grows, they spin faster and faster and over time you're building leverage. And that's something I think about in terms of building a career. I've been thinking about maybe we're moving from a world of career ladders to actually spinning different loops and going where which ones are spinning faster and faster, and then that's where we direct our attention. So how would you think about this in terms of a personal career?


Yeah, a few things on that. So the first is, I think the way I've thought about careers, which I think is very much to your point, is there is compounding and unconstraining. And so I think unconstraining is that the reality is most of us, probably all of us are constrained on different things. In fact, most people think that money is the constraint because for most people money is the constraint, right? And if you're living paycheck to paycheck, money is the thing that is kind of constraining your ability to decide what you want to do and to pursue or to optimize for the long-term or all sorts of decisions. And then for a bunch of us, not that money is not a constraint to some degree, but then you get passed some point where you're worried about paying rent or paying for food and money becomes less the constraint.

And then there are other things that might be the constraints such as knowledge and learning about things or who you know or all sorts of other areas. And so I think one way I look at it is that you should always have a view of what are the constraints on you. And that's kind of you as a loop, right? What are the constraints that are kind of blocking you? And if they were unconstrained you would act meaningfully different and you would feel like you had more autonomy to decide what you wanted to do. And then I think the second half of that is compounding. And so how do you build out these loops and how do you build out loops that actually have the ability to compound for you? So for that, I think there are two ways I look at it. One way is for you doing whatever you like, whether that's your podcast or whether that's your business, how do you build it so that you doing it today versus you doing it a year from now, it's better, easier, higher quality, lower costs, all of these good attributes a year from now versus today because otherwise it's kind of, there's been no progress. Right? And it's kind of finitely limited.


It's like the red queen effect of always trying to spin faster and faster. One thing I'm always thinking about is how do I build leverage so that I can achieve, it sounds obvious, but the goal is how to achieve more without running faster and faster and that sort of by building that leverage so that once something comes, you can just automate or have the connections to see something and make it happen.


For sure. The red queen effect is a good way to put it because I think that the natural state of most things in the world is default and tropic and so the natural state of things is that, you find a successful business, competitors will see that and come to challenge it that the things that you've been doing eventually they will degrade slightly over time. And so that's why it's important to find the things that are naturally compounding because actually, the default is that things will naturally kind of revert to the mean. Right? And so you have to find these areas that compound, whether that's on your time or whether that's building out systems around you that kind of will help scale up your work, whether that's with people or with the kind of products you build because otherwise the natural status for them to kind of all revert to the mean.


It was funny, we were with some friends last week. I was in Austin and we were talking about the spectrum of typers to tappers and typers are hardcore workers, hands-on-keyboard people and they are the workers of an organization. They generally have less leverage, but then my buddy, he was with the CEO of a sixty-billion-dollar of a Japanese firm and he said that his biggest insight from spending a bit of time with him was that he was a tapper and that he had so much leverage on his time that his career could all be done by tapping on a smartphone screen. And the fundamental insight was that he's not doing work. Rather he's directing the flow of a gushing river and he's directing the flow of water.


Yeah. That's interesting. I think that there's a lot of truth to that. There's also, not to take away from the former, there's a lot of just how does work get done? Right. And the reason I think eventually people will think about how to build these systems that are independent from their hours put in is that fundamentally your scarce resource is your hours. And so there's just some finite cap and the level of productivity you can get more productive, but there was a finite cap to how much more productive you can get on your hours. And so as long as your output is constrained by your hours, there always is kind of some cap to it. And so the question is how do you get increased leverage on that?

Right? And how do you keep increasing the leverage on that at some point because ultimately capital is actually less of a constraint if you have a working business model than just the kind of, not even hours, but just your cognitive load, right? And your ability to how many things you can really kind of keeping your mind and be actively working on. And so I think everyone eventually either intuitively struggles with it or tries to explicitly build out these systems of how do I build systems around me or my company so that I can kind of get more leverage on this and be able to keep scaling it up without it being affected by the fact that I only have x hours to work per day even if I cut into my sleep.


Gonna change directions here. I think both of us are pretty interested in cities. And personally, I'm fascinated by city-states. Actually, one of the things sort of on my long-term bucket list is I'd really like to travel to Singapore and Hong Kong to Dubai and compare and contrast the different city-states from culture to economics to politics. And I know you've talked a lot about city-states, but also from sort of an A, B test perspective. What do you mean by that?


Yeah, so I think one of the areas on cities, and this is specific to China. When I was talking about this in good ways and bad ways, I think that China seems to A, B test cities in the same way that companies in the US A, B test features. And look, there's a lot of bad about that too, right? I mean, I think that when you A, B test cities, whichever is the B test that did not work out that well has a lot of people's lives affected. On the other side though, it means that they're integrating a bunch on experimenting with how should you structure cities and how do you improve cities the most? And so I think that if you look at China right now and I think China's plan is to urbanize more people in the next few decades in China than people who live in the United States.

And if you think that the, the best way to improve human well-being is actually urbanization, which I think a lot of the data points to, of all the network effects of cities. Then it makes a lot of sense, but it also is a insanely daunting thing to say, how do I intentionally manufacture over 300 million people moving into cities that do not exist today. I think that when you think about that challenge and how, how you build that, it's a lot of different experiments that they've done on a scope that in a lot of other countries we don't do for better or worse. And you contrast that to a lot of the debates people have in San Francisco on housing policy for example. It's just a much higher both centralization of power and bias to action, which has a lot of downsides but also has a lot of upsides.

And so I think the contrast to that to me is if you look at democracies, I think that one of the, kind of weak points of democracies, the one that people commonly talk about is majority rule. I think that's discussed a lot and because it's discussed a lot of people think about how to mitigate it a bunch, which is good. I think that one of the less commonly discussed ones is that democracies don't represent future stakeholders. And so democracies are greater representing all of us who are around today, but they don't represent the people who will be affected 10 years from now by our decisions or 50 years from our decisions because they don't vote. Sometimes they're not alive. And the way in governments we deal with this is that for the most part, we think that the people today it's their children who will be the future stakeholders.

And so it's okay because they'll kind of think about the interests of their children. So even then, if you look at a lot of how we make funding decisions for a lot of government institutions, we don't seem to account for kind of how it's handled down the road. But when you look at a lot of the areas that there's a lot of disagreement on such as housing policy or immigration or areas like this, I think that a lot of the problems come down to the fact that a lot of the people who care about those decisions are not part of the process of deciding those decisions. And so it's not the immigrants, it's not the future citizens who are currently living in other countries who get to weigh in on what immigration policy should be and it's not the people who don't live in San Francisco but would live in San Francisco if housing was cheap enough, who'd get to weigh in on that.

And that creates this misaligned incentives where people aren't being irrational. They're actually representing their interests. Right? And you know, people who own houses should want their houses to increase in value. People who live in a country, at least some set of them would not want other people to come in. And I think that in so far as you think that those kinds of things are important. There is a question which is how do we kind of fix these issues or mitigate these issues in our democracies so that we do represent these stakeholders and I think historically two ways we've done is we've either said, hey, here's why it obviously is economically beneficial even for the people who are already there to have San Francisco grow in size and more people move here and grow the economy or another way we've done it as we've had cultural norms or we've said, hey, you know, America is built on this norm of being built by immigrants and welcoming immigrants.

And I think both of those and other strategies are powerful, but both of those seem to be weakening. And as they weaken, then the question is how do you make sure, as long as you think these are good things for cities to have, how do we get these benefits? So without the downside so that we can get the benefits that countries like China have with kind of growing their cities without the downsides of kind of totalitarian rule or pollution or a bunch of centralized control that's not representing the interests of the people. Right.


So we've talked about America, we've talked about China, but I see that you're really interested in Saudi Arabia. Why?


Yeah, yeah. I feel like over the last few years, certainly there's a handful of countries that I feel like I've just personally and certainly for no professional interests, spent a lot of time thinking about and researching and Saudi Arabia is one of them. I think Saudi Arabia is fascinating right now because it kind of hits on a lot of trends that are happening in the world right now. And so for example, one trend is that Saudi Arabia is this fascinating country where, people, most people don't quite know what to make of it. It sort of is, you see a lot of reports and you say on one hand it looks like they're cracking down on corruption or improving women's rights or opening up to foreign investment. And then, on the other hand, you also look at it and you say it looks like it's centralizing power and becoming less democratic.

Not that it was entirely democratic at all ever, but it's becoming even more centralized in power and actually trending towards kind of a dictatorship and cracking down and imprisoning political enemies. And so you look at these two sides and I think it's hard for a lot of people to weigh what's happening. But I think, you dig into it a bunch and what's happening kind of also then explains a bunch of kind of structurally what's been happening in the Middle East. And so one example is over the last five, 10 years, MBS, who is the current ruler, has kind of been involved in a tremendously done coup of the other royal families in Saudi Arabia. And you look at that and one part of it is a lot of the conflicts in the Middle East, a bunch of them can be traced back to the fact that MBS was kind of in command of the external facing parts of Saudi Arabia.

Whereas the other sides of this internal coup were in charge of the internal facing government organizations. And so having a bunch of conflicts happen in the Middle East actually make it more important to centralize power with the external facing side of this government. And helped him gather power, build relationships with the military, cement those relationships as he then went to kind of cement his power in the throne. A lot of the movements on both liberalizing externally but solidifying rule internally or are very interconnected, right? And you need to have the external allies aligned with you as you kind of deal with a bunch of the internal conflicts. And then finally, I think that it also is just an interesting data point on this trend where I think a lot of us, if you think about the core things that you believe in and if at the top of that heap of things that you believe in but don't hold very strongly is kind of what's your favorite breakfast food.

And then at the bottom of that heap is your belief in maybe for some people democracy or their religion or free speech or whatever areas they care most about. I think that one of the questions we're dealing with today is, is there a reason democracy is structurally trending away as the dominant form of government? Because if you look around the world empirically and Saudi Arabia, China included are good examples of this. It feels like there was a time years ago where it felt like the world was getting more democratic. It actually feels like the world is getting less democratic now. And there was a question of why that's happening. You know, for example, I think one reason you might say it's happening is that it's actually becoming more possible for countries to understand the needs and what is going on at a local level in their countries.

And you look at China for example, and you go back a thousand years in China. It was impossible for people in the central government to truly coordinate with all of the local provinces at any reasonable time-frame. And so there's just a natural decentralization that happens there where you need. We're even if we say it's under one ruler, you have to let local officials decide things because it'll take eight weeks to hear word back for any decision. Whereas you look at China now and because of all of the information technology that has been created and because of all of these things, it's more possible than ever for a government to understand what's going on and all of the local provinces and in the best form of that say, hey, actually what are the things they want and what are the things they need?

And so it's become easier and easier for centralized authoritarian governments to both control, but also provide for and understand what they should provide for, of people around their countries. And that has made democracy seem to trend downward, which I think for a lot of us as a pretty frightening thing, but it's a thing that I think you should always assess whether the thing that you don't want to happen. Is it a temporary blip that it's fading away or is there some structural reason? And if so, how do you either try to mitigate that or how does that influence your views on it?


My question to you is sort of a meta question, but there is this sort of this spectrum from people in crypto land who say this time is different, things will never be the same to people often in finance. A lot of the literature is, this is just a cycle, we go in cycles of the market is going well, the market drops, the market goes well, the market drops. How would you think about the words this time is different in terms of something like government and democracy?


Yeah, yeah, for sure. I think that also in the crypto point, I think that that is also a super fascinating question because, on the crypto side, I think that it's exactly as you say, right? People who are involved in crypto say well we reshape a bunch of the markets of how things function. This will be fundamentally different. And then people in both tech and finance say, actually, there may be some changes, but it will kind of reconverge back on the same thing. And to some degree, I think both are correct. I think that the way things work is you can change a lot of things. Now eventually people will recentralize as they figure out where are the dominant places to centralize power within these ecosystems.

And so we don't yet know where that is in crypto. I think eventually people will figure those out. But to the point, and part of the reason I think a lot of people, myself included, are interested in crypto right now is that the decisions made in this kind of formative early part of these industries. If you think these industries will become important, which I think we don't know if certainty, but there is a decent likelihood that crypto could, a lot of decisions made. Whether consciously or unconsciously in the kind of days where this is kind of still wet clay end up having huge downstream effects. So for example, if you look at privacy norms in the US, I think that a lot of decisions that were made by both the CEOs of companies like Facebook or Snapchat or other companies that are at the forefront of kind of both the communication mediums that people use for this as well as kind of a video recording or other areas, the decisions they made and the people who influenced them kind of had an outsized impacts on social norms around those areas.

Now, not to say that the government doesn't help get involved in it and not to say that the people don't, you know, in some ways regulate and socially regulate their decisions, but they have a lot of impact. And so if you care about those impacts, then what's important is kind of being in zone of those decisions and how those decisions are made or being able to impact the people making those decisions so that they do think about the consequences of them and they think about what the downstream impacts are and you look at the Internet today and the, there's many volumes of kind of debates that were had on internet standards and for the most part, we don't remember them now at all, but you think about how much has been shaped just structurally without even realizing it by the decisions that were made by people kind of crafting the internet standards.

And all of those decisions people made have had huge downstream impacts of every layer that has been built on top of them. And so I don't think we regret that per se, but I think that you look at it and you say, hey, let's make sure we do all the good things there. Let's also think about the mistakes that we've made as we've created other industries. Whether that's the current waves of finance or whether that's the current waves of tech or whatever. And say, hey, when you're in these nascent periods of new industries, how do we go make sure that we help the people who we trust to be making those decisions be there at the end. Right? And I think that's not unique to crypto.

I think that's also the same if you look at governments, you look at AI, you look at a lot of these areas, a lot of us personally won't be able to affect a bunch of those, but to the degree you can, you want the people who you trust to be making the decisions that you think are most aligned with how you think decisions should be made to be the ones at the table who have a say. And the reality is the table stakes for being at that table in many of these industries is building the companies that have the dominant loops and are the dominant companies of their industries because they're the ones who get to kind of have a seat at that table to decide what our norms will be for AI or what are norms will be for crypto or any of these areas.


Even something as simple as the words we use shape how we act and whatnot. And also we were talking about cities earlier and when you think about building the infrastructure of a city, a city that depends on highways operates very differently from a city that depends on public subways and whatnot, which operates then again, very differently from a city that has roads designed for bikes and people who are walking, right? So the infrastructure that we build at the beginning will then shape the topology, the culture, and basically the modes of action that arise later.


100 percent. And maybe that's a good reroute to the beginning of a Robert Caro because I think his first book about Robert Moses who kind of built out much of what people look at in New York City is a really good example of this because Robert Moses, he basically was unchecked in his power in building things in New York, which has a lot of downsides. And I think that the flip side of the critique of a lot of things going on in San Francisco right now where people say, hey, I wish we built more is what happens after Robert Moses where for decades after Robert Moses, people. I think Jane Jacobs is the most known among these said, a lot of things that he built weren't great. And some of that was terrible views and decisions he had.

And I think there's a lot of things we can point to there. And then part of it was also areas where he was one man and didn't have full legibility on what the city needed or wanted or how to prepare for the future. And so to give you some examples of this, he built the highway systems in and around New York City and at the time there were very few people driving on highways or in cars and he kind of was one of the first people. And then a lot of the people who then ended up building a bunch of the highway systems for Eisenhower across the US where people who worked for him and he built these highways and he refused to put public transit lines along them. And his view was why would you need this? 1. The highways you can more than handle the capacity of cars that are driving.

And 2. Another view he kind of had or people suspect he had, which is he was slightly elitist. And he said, cars are the rich and public transit is the poor. And actually, I want to make it much easier for the rich to get out to these places and not have the poor able to do it. And so you look at these decisions and they had huge impacts for a bunch of reasons. So one reason, one impact they had is that a bunch of these decisions he made that were either racist or discriminatory against the poor, just created ghettos within New York, made it impossible for people who are poor to afford to go out. And the same way that people who were rich were, they had real impact on real people's lives. And Robert Caro, I think he does a great job of both capturing how Robert Moses accumulates power and understanding it while also capturing the real stories of the people whose lives were affected by it in terrible ways.

So that you understand that we shouldn't just love this. We should understand that these decisions have very real impacts. And you know, there's one section of the book where he goes through one block that was affected by the decisions that Robert Moses made and talks to the children and grandchildren of people who lived on this block that was raised for one of Robert Moses' project and how their lives were affected by that and how crushing it was to their families and how much it impacted even two generations later, their children and your grandchildren. And so I think that there's that side of it. And then on the other side, you look at it and his refusal to build public transit lines along the highway has kind of still, we are feeling the impact of that because obviously now cars are ubiquitous and everywhere and the highways he built to handle that.

And the reality is highways period can handle that without building public transit, LRT systems which just can handle significantly more people. And so you look at a lot of these decisions people make around how we structure our cities or structure of companies. And these decisions have huge downstream impacts and so I think it's fascinating to see all these decisions being made a lot of times without the full understanding of the downstream impacts and without other people understanding that these are very important decisions. And that's kind of why I think the Caro books are just great at this because they make, you realize that once you take the time to understand how these ecosystems develop and the downstream impacts of them, you understand why all of these things are important and they show how one person can have a huge impact on it.

One person who understands the system and kind of where the vulnerabilities of it are and where the weaknesses are in it can have a huge impact on it. And you know, hopefully, that will be people who have good intentions doing that. Right? And using that. And that's why I kind of want a lot of my friends and other people to read the Caro biographies to kind of understand that and be able to be in position for those. But it also means that it helps you understand when you see people who are making bad decisions about it, right? And whether intentionally or not and kind of understanding that the importance of things like housing policy or things like public transit, whether that looks like bike lanes or highways or LRT or whatever because they have a just huge impact on everything else within these cities.


The last question before a couple of quick ones at the end, you had a thought about contrarianism a couple of weeks ago that I've been thinking a lot about. I think perhaps we've gone a bit too far with it and often in the name of contrarianism we miss the mark about what it's really about. So I'd love if you could riff on that for a bit.


Yeah, for sure. I think that contrarianism has become obviously a very mainstream area where ironically everyone wants to be contrarian now and what's interesting is that I think I've always been fascinated by these concepts where everyone is a big fan of them, but we don't unpack them further. And so for example, I think network effects is another example of these areas where everyone knows that they should say they are contrarian or they have network effects, but then you really push on kind of like, what do you mean by that other than just I have good things. So I think that a lot of people talk about contrarianism as kind of being against the grain and kind of having views that other people disagree with.

And of course, the challenge is the decision if I have this view that people disagree with. Is that actually a good view or is it just a view that people disagree with because it's a bad view. And similarly, I think it's hard to judge if you're contrarian enough from the people around you because it could be that you have a view that is mainstream in your community, but that view is actually a contrarian view in the larger view of people. But my view of contrarianism is that the important part of it is not about having this view that everyone else disagrees with. The important part is bringing it to everyone else and actually taking that view and causing it to become non-contrarian because a contrary view that stays controlled forever. It's just something that is-


It's all intellect, no action.


Yeah, it's useless, right? It's useless both for you and for the world. And so the interesting thing is actually having views that are not the consensus views of the world, but then doing your work to make sure they become consensus to the world if they are better, and don't get me wrong, I think that part of that is getting rewarded for it, right? And figuring out how to generate value from that, whether that is in building a company or whether that is in finding people who are like-minded.


I think a great example of that is Steve Jobs. His vision for the future of computing, a contrarian that many people doubted. There are all the stories that we know, but then he goes out and profits from it by giving his vision to the world. And I think that to your point, that's why he's revered in society.


Absolutely. And I think that the best thing to look at in contrarianism is how successfully they obsoleted their view from being contrarian, right? Because the people we should be most excited about who have contrarian views are the people who don't just have them, they then go make sure that those views stopped being contrarian and we all believed them. In fact, it's the people who we looked back and we say, hey, was that even that contrarian of a view? Actually, like we all believe it, right? I think that there's too much of a focus on the kind of standing apart and, and being the one who has the unique insight that nobody else has versus the part which is how do you go educate everyone else and bring that back into the mainstream consciousness and actually that is a lot of work and that is the thing that proves that what you were thinking about was actually valuable and of importance. And when I think about contrarianism, that's the part of it that I wish was more focused on versus the part where everyone can kind of feel hipster and feel that they're the special person with special thoughts on it.


Totally. So a couple of questions about you. The first one I'm going to steal from Tyler Cowen (my episode with Tyler here), he and his interviews saying what is your production functions? So what helps you stand out, be different, and have these ideas that you've shared with us today?


I don't know to what degree I stand out or have done well or I'm different. The view I care about is in understanding how systems work and the structuralism of that and I find that the people who I get along super well with and could talk for hours with are people who share that curiosity about trying to understand systems. When I think about on a kind of 50 year time horizon, what are the bets that I would want to take and would want to live by and then when you're retired and 50 years later if you're wrong, you're like, well, I'm still glad I took that bet. But it could have been wrong. I think the first one is kind of a on this idea that there is value in understanding systems and actually part of what we all should be doing is pushing this frontier of understanding the world and understanding why things work the way they do and then actually testing it and seeing if it is true in our theories on that were true.

And so I think that is a bet I'd take any day of the weekend and I think is just natural gravity I have. And then I think the second one, which is tied to that on the people side, it's just finding people you resonate with who kind of are interested in thinking about the same types of things you do. Because at the end of the day, just like companies have loops and network effects. I think that people are ultimately the loop and network effects for each other. And the reality is we write biographies about companies and people and because of how we write biographies, we always view them as kind of the start of the company is when the company was incorporated and then it was built from there. When the reality is that the companies were all started 20 years before that of the set of people who how the founders knew each other, the people who they bounce their ideas off of the people who they would go then and higher. And so all of the compounding companies and governments and organizations to me seems to stem from the people you surround yourself with and how you resonate with them. And so I think that also is kind of how I both draw most of my ideas is from those discussions and also kind of how I stress test my ideas is kind of pushing on those with people who are curious about those same things or who are in other fields and you find the consilience between the fields.


Well Kevin, thank you so much for coming on the North Star.


Yup. Thank you so much.

Hey again, it’s David here one more time.

At North Star Media, we help companies build brands on the internet, and through content, we help them build trust and generate attention. And we do it through blog posts, books, videos, and podcasts like this one.

You can support the North Star Podcast by leaving a review on iTunes. Or you can share the podcast on Twitter or Facebook.

To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell. And if you enjoyed this episode, you’ll like the episode with Albert Wenger, a partner at Union Square Ventures. In this conversation we talk about Albert’s fourth coming book, World After Capital, and how technological progress has shifted scarcity for humanity. When we were foragers it was food that was scarce, during the Aquarian age it was a fight for land. Following the industrial revolution, capital became scarce. With digital technologies, scarcities are shifting once more. We need to figure out how to live in a world after capital, where the only scarcity is our attention. 

Key points in this episode

Listen Here: iTunes | Overcast Keep Up with the North Star Podcast Introduction

My guest today is Sara Dietschy, a YouTuber and content creator based in New York City. 

With more than 300,000 subscribers, Sara’s created a docu-series, a daily vlog and recently launched a new podcast called The Creative Exchange.

Sara is one of the most inspiring people I know.

Before she moved to New York, Sara grew up in Dallas, went to college to study computer science, dropped out, and moved to Nashville. Through her work, Sara explores the intersection of technology and creativity. Sara rocks the YouTube scene with her sincerity and a contagious zest for life. 

The internet spells the end of oppressive creative regimes, the death of gatekeepers and the fall of Hollywood. On the Internet, agility is essential. In this day in age, vlogs showcase the everyday experiences of real people with real stories that exist in real life. 

We live at a time where people have deep and intimate relationships with their favorite YouTubers — people they’ve never met before that feel like their best friends. Millennials and Gen Z have the luxury to ask what is my passion and use the internet to build a career.

On the internet, people want to connect with individuals, not massive companies or a bland television ad. They want to connect with people, not companies, and it’s influencers like Sara that are leading the charge.

In this episode, Sara explains how she rose to Youtube stardom and the characteristics she’s noticed between herself and other successful influencers. 

Sara and I go back to her time as a musician — an on-stage performer who played in front of large audiences. We talk about all the Sundays Sara spent at a local Megachurch in Dallas, where she played in a band and was blown away by top-notch production quality. 

We discuss what it means to do work you love, and the power of staying busy, how Sara’s built a career around the vlogosphere.

Finally, we talk about her first viral moments, how she forced herself to become extroverted and the takeover of new media. 


Sara’s Youtube Channel

Sara’s Podcast, The Creative Exchange

Sara’s Instagram

Sara’s Twitter

Sara’s Facebook

Sara’s Website

Sara on Medium

Time Stamps

1:27 Sara talks about who she is and what to expect from her Youtube channel

2:14 How Sara turned from a basketball-loving tomboy into a musician

6:39 Sara’s first love and how it gave her the most creative highs of her career thus far

7:28 Her transition from music to videography and how her church was the driving factor for her moving behind the lens

10:08 Her move to Nashville and how she leveraged value in turn for artist’s time for her first docu-series called Creative Spaces

11:35 Sara’s belief that the harder you work the luckier you get and how she notices serendipity in her life the more she works towards her goals

12:50 Sara’s, very calculated, first viral moments featuring TWO shoutouts from Casey Neistat

17:01 Sara talks about her passion for creativity and what motivates her throughout the process

18:20 The one characteristic Sara has found in common amongst all of her passionate friends and interviewees

24:36 The three pillars Sara believes makes a good Youtube channel

26:26 Sara’s Youtube career, from 0 to over 300,000 followers

33:09 Sara talks about why audiences relate to an individual over a brand

36:22 The clear divide between Hollywood and new media, as proven by the Cannes Film Festival

39:52 Sara’s rule to always be working on something or learning about topics outside of her job in order to have that essential escape

45:40 The changes happening in New York City and Sara’s prediction that Hudson Yards is becoming the next Midtown

50:32 How our ecosystem is built around cars and how storytellers may impact the sharing economy

51:41 Where Sara’s inspiration comes from and how she works with deadlines

55:53 How Sara trained herself to become more extroverted so she could meet more creatives

58:32 Sara’s vision for the future and her perspective to see it as a never-ending journey

1:00:24 How Sara sees her future on Youtube


“Serendipity I think is huge. Being in a place where things are happening is a big deal. If you want to make music videos for country stars for the rest of your life, you have to be in Nashville. If you want to be a creative business type and you want flavors from different industries, be in New York. If you want strictly entertainment and acting, you have to be in LA. I fully believe in location helping tremendously.”

“Everyone who is doing something that they love, and it’s never all rainbows and butterflies, but to the people who are doing what they love-it’s because they have gone through so many things before that to figure out what they want to be doing now. I think a lot of people wait around, and wait for something to hit them. They wait for their passion to hit them and it so doesn’t happen that way.”

“I myself, as much as a person who creates it and consumes it, am so much more motivated by people in the real world. Instead of watching Wolf of Wall Street, I’m going to watch a couple of Gary Vaynerchuk Vlogs. I am way more inspired by seeing the behind the scenes of a CEO in real life than a fabricated story of this crazy Wall Street dude.”

“I think if you just have these huge massive goals-like one massive goal every five years-I don’t think it’s the healthiest thing. If you don’t achieve it, you’re destroyed. If you do achieve it, you’re going to be empty inside and be like, what’s next? I always have these miniature things in my head, I want to meet these five people, I want to do these five things. If they happen sick, if they don’t, move on to the next thing. It’s taught me to be stoked on the journey because you’re never going to arrive.”


You can support the North Star Podcast by leaving a review on iTunes. Or you can share the podcast on Twitter or Facebook.

To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell. And if you enjoyed this episode, you’ll like the episode with Kyle Chayka, who writes about the intersection of art, architecture, and how the internet is transforming society. We also talk about Kyle’s time in Beijing, the co-evolution of fashion and internet culture, and the present, past and future of minimalism.

Key points in this episode


My guest today is Paul Cooper, who spends his days exploring ancient and modern ruins. 

I’m going to begin this introduction with a hot take: Paul has one of the best Twitter accounts in the world.

Ruins are special. They freeze a moment in time forever. They remind us of the shortness of life and the inevitable entropy of history. Paul's book, River of Ink, is predicated on the idea of bringing ancient cities back to life in a fictional context.

In this episode, we talk about the academy in the internet age, compare functional and sacred architecture, and dream about time travel. We explore the strange and perplexing history of the Roman Colosseum and investigate letters written on clay tablets in ancient Mesopotamia. And now, I invite you to enjoy this journey through space and time, as we explore the many shades of human history.

Note: Since I enjoyed this podcast so much, I wrote a short blog post about it.

Useful Links

Paul’s Book, River of Ink 

  Find Paul Online




Paul’s Website


Learn More About Paul

The Timeless Allure of Ruins, Paul’s BBC Feature

Paul’s The Atlantic Articles


Show Notes


1:00 How Paul’s childhood, surrounded by castles in South Wales, inspired him to study ancient ruins


1:53 Paul’s first novel, River of Ink, depicts a fictional story of the events that could have taken place during a real thirty-year gap in Sri Lankan history 


3:31 Paul’s most surprising takeaway from his year living abroad in Sri Lanka


4:07 Paul is captivated by the spark in imagination that occurs when walking through ancient ruins, a passion he shares with his 39,000 Twitter followers


5:29 Paul questions the transition a building undergoes from functioning structure to ancient ruin


7:26 Why are there flowers in the Colosseum that don’t exist anywhere else in Europe? Paul explains the answer botanist Richard Deacon discovered explaining the ancient mystery


10:38 Ruins: A place where the future is spontaneously canceled. Paul’s observation on ruins and their story as a place where the future was spontaneously canceled


12:34 Paul explains the tension between a building’s first few years and the inevitability that one day it will have to be torn down


15:14 Paul asks: "At what point can you say a ruin is "finished" and it’s permitted to destroy it?"


25:32 Paul talks about the invention of writing and how it has shaped ancient architecture, philosophy, and mathematics


28:24 Get a short peek into Paul’s second book, set in the Assyrian Empire


29:33 If Paul could travel back in time, what would he see? These are his top three choices


31:29 Paul explains the similarity between ancient ruins and ghost towns


39:32 Paul talks about the interplay between ruins in time and what they represent today, explaining how these structures feel oddly static when you enter them


41:40 Paul’s eerie story of a haunted church in Norfolk and why he believes these stories exist


43:55 Paul’s realization that for thousands of years, each person visiting a ruin has brought a different perspective, causing a continuous variation from the truth of ancient structures and historical stories


45:42 Paul’s opinion on what people in the year 5,000 will find the most interesting about today’s civilization


49:57 How the Internet is reshaping academia


53:03 Paul’s observation of the new self-education movement

You can support the North Star Podcast by leaving a review on iTunes. Or you can share the podcast on Twitter or Facebook.

To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell. And if you enjoyed this episode, you’ll like the episode with Tyler Cowen, a columnist at Bloomberg who writes about economics, history and culture. In the Two Blundering Fools episode, Tyler shares seriously counterintuitive points on travel, the millennial generation and how he thinks about the future.


“Every ruin is a place where a physical object was torn apart and that happened because of some historical force. If a building is ruined, an economic ruin, a closed down factory, it’s been blown up by a bomb, or it’s been abandoned because people moved away-It’s because huge historical forces have washed over it. Each ruin shows a place where the future was just suddenly cancelled. The next day didn’t happen, it was just a ruin. So, each one is a window into a particular historical moment where something changed. That’s what really fascinates me everyday about them.” 

“Writing is such an incredible thing. It restructures the way we think. Once you know how to read, it’s impossible not to. If I showed you a page of words and said don’t read this, you wouldn’t be able to. Your brain has been forever changed by being taught the ability to read. The ability to store information outside of our brains suddenly frees us up to do a whole load of incredible things. A pre-literate society has a certain amount of knowledge passed down from the ancestors, who have gathered that knowledge very carefully. And we have to expand so much effort to keep that knowledge together. We have to put it in lists, make it rhyme, do it in patterns. All of these things simplify and help us remember the knowledge passed down from the ancestors. Once we can write down on clay or paper and make the material remember for us, we’re freed up to do a whole load of interesting things like examine philosophy or mathematics.”

“When people in previous ages have looked at ruins, what they see is what we’ve been describing. There was a cataclysmic event, something went wrong here, and they try to tell stories about why that might have happened…Ruins don’t mean anything by themselves. They seem like a kind of place that slightly resists meaning. People try to give meaning to them. They try to tell stories about them that make sense about what must have happened.”

“Everyone who comes to a ruin brings a different perspective and a different story and a different meaning. And all the time, the ruin is just sitting there, kind of meaning nothing. It doesn’t mean anything by itself. It needs somebody to come along and give it meaning. And so in that way, the ruin forms a battle ground. Everybody is in this five way tug of war about what this crumbling mass of bricks in the desert means and that’s what makes them incredible places to study.”


Key points in this episode

Listen Here: iTunes | Overcast | PlayerFM Keep Up with the North Star Podcast Summary

Today’s guest is Kyle Chayka, a Brooklyn based writer who has been published in New York Times, Verge, Business Week and more. His studies in International Relations at Tufts University led him to live in Beijing, where he initially noticed the impact social platforms were having on internationalization.

In 2015 he wrote his essay, Welcome to Airspace, dissecting the effect of the growing decentralized geography born from technology and digital platforms.

Kyle Chayka regularly questions the future of society as the internet becomes commodified through brand ecosystems. His article archive can be found on his website, as well as information on his upcoming book regarding the allure of minimalism, The Longing for Less. Aside from his writing endeavors, Kyle is the founder of Study Hall, a freelance journalist collective coordinating office space and live events for independent writers while promoting a digital community. 

In this conversation, we talk about the dangerous impact social platforms are having on cultures around the world and how living in the future has become a daunting lifestyle. Why can we visit coffee shops on opposite sides of the world with the same ambiance and aesthetic?

We talk about the effect of the digital nomad movement on cultures, countries and politics and the future impact of this lifestyle on the world.

And finally, we discuss how the internet has created a commodified identity, where humans are failing to interact successfully within this so called utopian future. You can read Kyle’s essay, Welcome to Airspace, and search his article archive on his blog, linked below.

Related Articles That I've Written Quotes

“The problem is that all the coffee shops look the same no matter where you go.”

“There’s a decentralized geography in the world now that exists mostly because of technology and digital platforms. The coffee shop theory of Airspace is that all these coffee shops look the same because all of the same people are going to them, no matter what country they are in.”

“The way you game the system is by trying to look like everything else that has a good rating.”

“Beauty to me is different ways of aesthetic appreciation and not just looking for beauty in things that aren’t stereotypically beautiful.”

“The future is this catastrophe.”

“People are moving into places they don’t understand or don’t engage with the local community and that can be super destabilizing.”


Find Kyle online:

Kyle’s Blog





Read Kyle’s articles:


Welcome to Airspace (1:37)

Reign, Supreme (31:15)



Mentioned in the show:

Kinfolk (2:28)

Brian Eno Music for Airports (26:05) 

Rent The Runway (28:49)

Airbnb (43:39)

Bleep (44:39)

Neo Yokio (48:35)

Everlane (57:19) 

Gucci (59:05)

Lot (1:00:41)


Show Topics

1:40 The inspiration behind writing Welcome to Airspace, his essay about the decentralized geography occurring in the world as a direct effect of technology and digital platforms.


4:13 Kyle’s connection between Airspace and rating based platforms like Foursquare and Airbnb


5:10 How Kyle’s initial passion for aesthetic and art was established and how he fell in love with the idea of different perspectives inventing new ways of looking at the world


8:03 Kyle’s definition of beauty and how he gained his appreciation for things that aren’t stereotypically beautiful


9:28 How architecture has shaped Kyle writing career and his opinion on humans’ inability to avoid being impacted by architecture as an art form


11:28 Why Kyle’s writing focus is on architecture and how it encompasses the entirety of the human experience


12:15 Kyle’s take away from medieval art as a representation of the same globalization happening today


15:50 How fashion is the fastest moving cultural form as a direct result of digital platforms instantly exposing what is fashionable to cities on the opposite side of the globe


17:42 How national identities are becoming more blurred as cosmopolitan cities in different countries become more and more like each other and distinct from the conservative cities surrounding them


19:40 Kyle on the reason why the digital nomad has become a global trend


21:08 Kyle’s opinion on the long term consequence of the digital nomad lifestyle as it gentrifies countries and promotes political agendas and urban spaces to be built around long term tourists instead of the local population


22:30 How social media is the driving force behind decentralized geography and how the cro-nut can be invented in New York and sold in Beijing within the same week


27:30 Why social platforms are an intersection between identity and ambiance and how users are taking advantage to brand themselves and their companies


31:15 Kyles thoughts on Supreme and how it’s a constellation of markets and experiences


33:14 How the internet has become a commodified place where things aren’t accessible and systems are implemented to exchange identity for monetization


34:16 Kyle’s observation of what was the future ideal and what is the future reality


38:03 How humans are interacting with these future needs and where the next step is for understanding and fixing the problems they are creating, such as the Bitcoin trend


40:20 The new dystopian idea of getting into brand ecosystems and staying in them for years by having one company sell a consumer everything they need to live and commodifying another person’s identity


43:47 Kyle’s experiences in Bejing, China and how it shaped his futuristic perspectives on internationalization within new communities and artistic influence


47:03 Kyle’s opinion on how digital platforms are manipulating identities yet giving users the most freedom they have ever had to express themselves


52:36 Kyle on the shift from TV and radio programs controlled by one CEO to on demand platforms that removed the boundaries 


53:53 Kyle on his book Longing For Less and the shift behind minimalism across lifestyles, music, architecture and philosophy

You can support the North Star Podcast by leaving a review on iTunes. Or you can share the podcast on Twitter or Facebook.


To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell. And if you enjoyed this episode, you’ll like Geoff’s Manaugh’s perspectives on how technology is changing architecture in the Burglars, Buildings and Blueprints North Star episode.

Keep Up with the North Star Podcast

Key points in this episode


Today’s guest is Matt Levine, a columnist at Bloomberg covering finance, Wall Street and the broader business world. Before blogging, Matt spent four years as an investment banker at Goldman Sachs, structuring and marketing corporate equity derivatives. Before that, he worked as a mergers & acquisitions lawyer and a high school latin teacher. He’s also a graduate of both Harvard and Yale Law School. Matt’s newsletter, Money Stuff is always fresh and I admire Matt’s ability to discuss complex topics in fresh and engaging ways.

In this episode, we talk about Matt's career shift from banking to blogging — from Goldman Sachs, huge and famous, to DealBreaker, teeny and scrappy. Matt shares the ideas that have shaped his worldview and his process for writing. We talk about the books that have influenced him the most, both inside and outside the financial sphere. I particularly enjoyed learning about the Iliad.

“The tech startups are like the great laboratories for these questions now because what has happened weirdly is that the people with the best tech startup ideas have what seems to be enormous leverage over the people with the money.”


Find Matt online:


Mentioned in the show:


Books mentioned:


People mentioned:

Show Topics

1:00 - Introduction to the episode and a bit of background info on Matt. 2:32 - Matt detailing his financial background, his general background, and where he comes from.

4:19 - How Matt got into classics, a bit on his experiences in college, and his job out of college.

7:00 - The books that have shaped Matt’s perspective and worldview the most and bit on what took him into the world of finance, marketing, and accounting. Also, what some of his experiences were in that field.

11:21 - The aspect of puzzles in these fields of M&A and Matt detailing his journey from investment banking to blogging.

13:40 - How Matt’s day is structured to write, read, do deep work, and not be exhausted afterward. Also, a bit on Matt’s way of writing and learning.

15:55 - Matt detailing how he has learned to easily sift through a lot of the false information that’s commonly found and find true information. Discussion about the reality of financial investing that’s commonly mis-portrayed in the media.

20:14 - Which sorts ideas and life experiences beyond the bank that come up all the time that have been foundational for Matt’s way of approaching the world. Some discussion on law in general, lawyers, and contracts.

“You get a certain amount of legal realism baked into you in law school I think and a certain amount of skepticism about the magic functions and words in contracts.”

24:59 - Matt’s partial background in academic finance and how this has helped him understand more in the field of investing. Discussion on shareholders, share buy-backs, and running companies.

“The tech startups are like the great laboratories for these questions now because what has happened weirdly is that the people with the best tech startup ideas have what seems to be enormous leverage over the people with the money.”

31:44 - The people that have influenced Matt the most and some discussion on how blogging has changed over the years.

35:30 - What some of the main goals are that Matt tries to accomplish everyday and a bit on the writing that he does.  

37:49 - Topics and things that Matt finds the most fascinating to write about and figure out. Discussion on shareholders, index funds, writing, and investing.

Hey again, it’s David here one more time. You can support the North Star Podcast by leaving us a review on iTunes. Or you can share the podcast on Twitter or Facebook.

To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell. And if you enjoyed this episode, you’ll like the episode with Tyler Cowen, another columnist at Bloomberg who writes about economics and culture. In the podcast, Tyler shares counterintuitive insights on travel, the millennial generation, and how he thinks about the future. Thanks again for listening.

Key points in this episode

Listen Here: iTunes | Overcast

Subscribe to my Monday Musings Newsletter to Keep Up with the Podcast

Tyler Cowen is an economics professor at George Mason University. He runs the Mercatus Center, which bridges the gap between academic ideas and real-world problems. He blogs every day at Marginal Revolution, writes for Bloomberg, and hosts his own podcast called Conversations with Tyler. He writes about economics, arts, culture, food, and globalization.  

As I prepared for this episode, I settled on three things that I wanted to focus on: how Tyler thinks about travel, the rise of China and India, and how he learns so much. Enjoy this exploration of knowledge and culture, and I hope you laugh with us along the way. 

I particularly recommend Tyler’s most recent book, Stubborn Attachments.


David:             Tyler Cowen, welcome to the North Star.

Tyler:              Thank you for having me.

David:              So tell me a little bit about where you grew up in northern New Jersey. What was growing up like for you and what were you into as a kid?

Tyler:              I was born in Kearny, New Jersey, Hudson county, which was a blue collar town, and my father climbed some kind of career ladder from having been bankrupted at thirty, to being upper, upper middle class, so I caught different parts of that income stream. I went to a great high school where I had four or five close friends who were super smart and had a blast. We were like a nerd fest before nerds were cool and I learned something every day but not from the teachers. I loved it and I just knew New York City.

David:              Well, let's dive into it. I think that one thing that's really interesting about the Internet is I like to say it rewards obsession in a way that the world didn't use to and I think a byproduct of that is nerd culture is, is cool now.

Tyler:              You know, I specialized in the style of learning before there wasn't an internet and then when the Internet came along, I feel it made me like 20 times more productive. So I'm very lucky to have gotten this extreme productivity boost at about age 40, which is very rare in careers. There are people who might have some kind of productivity turning point when they're 29 or 22, but to get it at age 40, it's given my life a very different trajectory.

David:              So I know you wrote a book about that, but talk about what was that productivity boost like, how do you think about productivity, and how did that boost manifest itself?

Tyler:              Well, I worked very hard for years at trying to absorb more information and absorb it quickly and order it effectively and when the way you do that is driving around to used bookstores and carry used books home and read them, well, that's a wonderful thing to do, but when you can just go to your iPad or your laptop and whoosh, it's all there, you're going to do a lot better.

Tyler:              Whereas people who say do research, they've been made more productive by the Internet in other ways, but they're less concerned with absorbing information. So I feel I've gotten a relative gain compared to many other people.

David:              So does that mean that you're hopping around between different subjects? Like if I go on marginal revolution, I could go from traveled economics to then yesterday, right, about North Korea and America. So are you hopping around or how has that style of learning changed over the years?

Tyler:              I have long-term study plans, like part of my long-term study plan is to understand India and China much better. So that's kind of a 10 year project that I'm always in the middle of, but of course using the Internet to help me makes it much easier. Plus travel, travel being a key to learning. We'll get back to that. Uh, and then during the day I just try to keep up with the flow, the flow of good articles and new ideas.

Tyler:              And you know, the flow always beats me. But you wake up at seven, you go to bed at 11:00 PM, there's interruptions, you exercise, you eat, but the day is the flow, the flow is your day, like it or not.

David:              Dodging bullets and trying to survive. So there was analogy I got a couple months ago of if, if you're learning is a ship, when you try to steer something for long-term, so say that you want to learn about India in the next 10 years. The advice that I got which I thought was quite good was just steer your ship. So change your twitter feed, change your social streams one or two degrees. How do you think about it?

Tyler:              I view myself as a prisoner of my passions. So what helps me is to be very motivated to do what I do. So I don't sit down and strategize like what's my optimal career plan?

Tyler:              I just think what'll keep me involved and I figure they kind of compound interest on that learning will just accumulate and as long as I'm having fun, I'll stay motivated like way past other people and that's going to go well for me. So it's almost a deliberate absence of strategy except for motivating me.

Compounding fuels success in almost anything. Albert Einstein once called it the 8th wonder of the world.

— ᴅᴀᴠɪᴅ ᴘᴇʀᴇʟʟ ✌ (@david_perell) October 23, 2017

David:              What are those core passions?

Tyler:              Travel of course, food, just social science and generally walking through the world on a given day and you see things like you go to Barnes and Noble, they offer like a loyalty card, buy more books with us, we'll give you a discount and you think, well, why are they doing that? How does that make economic sense? And you want to try to figure it out so you just want to try to figure things out. It's almost a Sherlock Holmes like game and there's always more and more and more and more and more and it drives you crazy, but it's fun.

David:              What is it about China and India in particular that appealed to you?

Tyler:              Obviously they're two highly populous countries. The US could have a billion more people and we'd still be, you know, the third most populous country in the world. China now by at least one measure has the world's largest GDP and I'm an economist. India is probably headed to having the world's largest GDP. So it does go back and think, imagine you're a British person in 1910, like what should you study? Where should you travel? Well, the United States. To complain that you don't like the pollution or not all the food is what you expect. It's irrelevant, right? You go to the United States, if you don't, you're kind of a dummy. So for me right now, China, India, that's like the United States in 1910. I feel obliged to learn it more by obligation, but it's fun. It's also a passion.

David:              So when you're going about learning something like China, India, of course you'd go to the Bloomberg New York Times, but I think that there is, to back to nerd culture, there are probably certain sections of the Internet of the world that will give you a very rich experience that the average person wouldn't get.

David:              You seem to be very good at that. How have you been thinking about studying China in India in a way that most people wouldn't think about?

Tyler:              China and India I consider hard to learn because when you read about their histories, things don't fall into intuitive categories that maybe they do for Chinese people for instance, but all the different dynasties, they tend to blur together. You could read the same Chinese history book a bunch of times in a row and at the end you're still confused and you don't really know how to place it all, so to pick some side areas, so for me, Chinese food or Indian classical music or certain features of Chinese geography or ethnic regional culture and to learn those well and just keep on attacking the elephant from all these different sides rather than just, "Oh, I'm going to sit down and read this book on Chinese history.".

Tyler:              That tends not to work. It works really well for like Paris or the Florentine Renaissance, but for unfamiliar parts of the world and I look for these sideways in the door.

David:              Well, let's dive into China first. Where in China have you been and what have the really striking experiences been for you during your travels set?

Tyler:              My goal is to go to all the provinces in China in a significant way and not just putting a toe in. I'm past the halfway point. My favorite part of China is the west and the southwest, especially Yunnan province. It's highly exotic. It's about half regional minorities. That has some of China's best food. It's extremely reasonably priced that has remarkably little pollution by Chinese standards. People are very friendly, uh, there are actually quite pro-american because of the history of America. Helping them out in the war against Japan is just amazing fun.

Tyler:              I think right now it's probably the best trip in the world is to go to western China.

David:              Wow. So western China and eastern China, of course, because we're just talking about GDP, it seems like most of that would be concentrated in eastern China. So let's start with western China. What is it about it that makes it so interesting and is it authentic to what's happening in China because it is so different demographically.

Tyler:              Authentic is a tricky word. So if you go to Oregon is not authentic America. Well yeah, but it's not typical either. Nor is New Jersey. So southwestern China, it's just accessible and it's fun. So Beijing I love. It's fantastic. Everyone should go multiple times, but in some ways it's a tough slog. A lot of the city is ugly. The pollution can be awful and it's so large. It's not really walkable for the most part, although it's walkable within neighborhoods.

Tyler:              You can go to Beijing and think you don't really like China. That's the wrong impression. So I would say Udon, it's like this backdoor into China and it will open up ways of thinking about China and then when you go to Beijing you'll like Beijing a lot more. So you know, to get to Udon, you probably have to go through Beijing to fly there. So yeah, stop in Beijing for a day, but find the back doors that get your passions and that's going to be western China.

David:              And now in terms of what I would consider, I don't know if this is totally true, but that's how I model China. There are four big mega cities. You know there's, there's the manufacturing center, Hong Kong, Shanghai and Beijing. Can you talk about the differences between them?

Tyler:              Well, Guangzhou and Chongqing are also mega cities.  Some people believe Chongqing, which now has been made its own province is bigger than any other locality in China. We don't even know because there are so many people who are within China, in essence, illegal migrants. We're not sure how many people are are there. The different parts of China until recently have not been economically integrated, so they have cuisines that are quite unlike each other, maybe more unlike each other than different European cuisines. Visually, some parts will look the same because these mega cities have been built up recently using more or less common patterns so you can have the deceiving impression that you're going to the same place over and over again, even though you're traveling to many parts of China, but European say that about the US often like "Oh, the whole country feels the same." If you live here, you know, it's not true, right? There aren't really significant differences.

Tyler:              So to go to Hunan Province or to go to Shenyang in the northeast, which is near North Korea, or go to, you know, Chengdu in Sichuan and forgive all my pronunciations which are not proper Chinese. Uh, you're seeing much more diversity than anything you're likely to do in either Europe or the US. You're seeing what's now the world's most important country. Again, I can't stress how favorable the prices are. You can stay in a five star luxury hotel in most parts of China other than Beijing or Shanghai for less than $100 a night and it will be, you know, a wonderful quality experience and the best food in the world, you know, a meal will never have to cost you more than $20 unless you order a highly unusual dish like shark fin soup. So if you're on any kind of budget, there was no reason not to go.

Tyler:              Crime is close to zero for women overall it's quite safe. I mean everywhere it has some problems, but as the world goes, one of the best areas to travel in solo if you're a woman. The main reason not to go is air pollution. But again in the west that's a much smaller problem.

David:              Right. I was reading that there have been 16,000,000 new bikes installed in China in the last year and a half and, and a lot of people are saying that the changes in transportation there may do something at least to help boost the air pollution, which I thought was interesting, but I want to dive into infrastructure. How has being in China, uh, changed the way that you think about infrastructure and sort of the way that you think about how development happens?

Tyler:              Infrastructure is their specialty. They have, what is one of the world's two or three best train systems given how large the country is, that's important. A remarkable thing about traveling and mainland China is you can wake up in the morning and one city and be in almost any other part of China the same day just by taking a train trip and you'll see amazing things on the way. But in terms of planning your journey, everything is within a day without having to mess around with flights and with flights, you don't see what's in between. So you can go like Beijing to Shiyan see the terracotta warriors, that's maybe about six hours. So there's this remarkable sense of freedom you have because of the infrastructure. Along so many dimensions, now they are probably more innovative than we are. And to see that is impressive, we Americans are so complacent and smog. We think where the world's innovators, the Europeans lag behind true on average, but China does something like the payment system.

Tyler:              There's this way quicker and much better and you'll come back here and curse, like having a, you know, stick your chip in the thing and it doesn't always work. They're rebuilding their world in some ways. They're outdoing us.

David:              In terms of innovative. How do you define innovative and in what sense do they have an advantage by by not having had the PC and being able to jump straight to sort of a mobile first world?

Tyler:              In some cases, they're just not locked into older systems as you mentioned. Also, this is more disturbing. We should be bothered by this by having less rule of law. They can just "do things and get them done" and that's not always a good thing. A privacy law. They don't have the concerns you would have in Europe or the United States, but a Chinese payment typically is you take out your smartphone, you scan a qr code, it can be done in a second and a half.

Tyler:              The error rate seems to be very low. Uh, it's processed perfectly well. It's cheaper, better, quicker and more convenient than what we do and they beat us and we're not really catching up. And we need, uh, to absorb that lesson for the first time maybe ever. But at least for a long time, the US now has a peer country. Like Soviet Union was never that peer, only with weapons were they a peer. China in terms of creativity and GDP. Arguably right now is a peer. You ought to go and learn from your peer, right? How can you not do that?

David:              Yeah. I couldn't agree more. I was talking to a friend last night. I think Hong Kong might be a good place or Shanghai might be a good place to spend a couple of years, but I want to talk about travel in terms of how do you think about travel?

David:              So I'll be honest, I did a euro trip recently and I didn't get quite the experience that I wanted because before we had never really come to a consensus on what does travel mean and it's not something that a lot of younger people, at least in my, in terms of my friends really think about. So how do you think about travel and what are you looking to do when you do travel?

Tyler:              I like to go weird places. So I did a European trip this summer. It was in August. I went to Macedonia. The country where people hardly ever go. Most of the tourist are either Russian or Serbian. Uh, but certainly not many Americans are there. Again, it's completely safe. Prices are very favorable. I had perfect weather, beautiful sights, tenth century monasteries, all kinds of sculpture. Remarkably good cheeses, breads and meats, wonderful food, wonderful lake fish. A lot of history. A lot of geopolitics you understand much better why the Balkans are messed up and just like how Bulgaria, Greece, Macedonia, Serbia, Kosovo fit together together.

Tyler:              I've tried reading that in books. I can't grasp it. I go there, but the mix of going there and the books, somehow it all works and you see this country where the politics are so different from what we're used to in Europe. You just again have to reexamine everything. So I say to people like, go weird, like yes, at some point you should see Paris, but if all you do is see Paris, maybe you'll be a little bored. Where did you go?

David:              In Europe?

Tyler:              Yeah.

David:              We went to Amsterdam, Berlin, Prague, Vienna, and Budapest.

Tyler:              You should have seen Paris! Those are all the same, it's like an airport shopping mall.

David:              I couldn't agree more and exactly. And then, so over the new year's I was in Chile.

Tyler:              One of my favorites by the way.  

David:              So my dad is a total nut. And so what we did was, it was new year's day and we went to go see some hieroglyphics up in the Atacama desert in the northern part of the country. It's the driest place in the world.

Tyler:              And one of the best trips you can take.

David:              Yes, it was wonderful. So it's new year's day and we'd go to the person at the front of the hieroglyphics and we say at where's the closest place to get lunch? And he said, it's new years day, it's all closed. So he said, but I have a friend, she can cook you food. So we go into this little town, all adobe houses, just a gravel streets. And this woman, Sherry and her husband had left her. She was quite lonely unfortunately, but we spent the entire afternoon with her. She, you know, she had chickens in the backyard, llamas in the backyard and it was the richest experience I had in a long time traveling.

Tyler:              And the food there is excellent, right? It's quite safe. Infrastructure is surprisingly good given how remote it is and there's some magic to Chile, some kind of warmth but also efficiency where it just hits that sweet spot and it's both familiar and exotic at the same time.

David:              Yeah. All right, back to India. So, now we'll get into India. So how have you been thinking about learning about India? I know at least in India is much, it's very different in terms of there's a lot of different languages, lots of different cultures. I think a lot of westerners don't realize that.

Tyler:              I've been quite a few times to India. I've never gotten sick. I'm very fortunate. Some people do. I'm not sure how to weigh this risk, but I've done all kinds of things. Eating what I've wanted and just been fine every day. Maybe it's just because I travel a lot. Indian classical music I think is one of mankind's greatest creations ever. I would say going to the classical music festival in Chennai in December, I took my daughter to that. We both loved it. For food, India and China. Clearly the two best countries in the way better than any Michelin Guide and way cheaper. Everything is new and fresh and undiscovered and diverse. India's tough in a way that China isn't. So, China is poorer than what we're used to, but there's some grinding poverty in the countryside, but for the most part going around is not depressing. In India it can be. The air pollution can be worse than in China. The population density, the cities are out of control in a way you would not say about China. Chinese cities are way less dense than outsiders expect.

Tyler:              Hong Kong is much denser than most parts of the typical Chinese city would be. So being in a Chinese city is a lot more pleasant than people expect, especially, uh, if it's not a major city, but India, my goodness, traffic, monsoon, disease. But there's something about the notion of ideas there. The religion, spirituality kind of syncretic something that is just magic and creative and nowhere else in the world do you get it and you're just bombarded with it the whole time. And people fall in love with India and they should. And you will. It's tough. I could, you know, you gotta be ready.

David:              Talk more about the spirituality aspect because it's almost become trendy to talk about the eastern thought and, and, and whatnot. And I'm not discrediting it, but I think it's miss misinterpreted by many westerners.

Tyler:              Keep in mind, I'm not myself a religious person. I wouldn't even say I'm spiritual. I don't really believe in anything in particular. So when I say it's rich in religion and spirituality, that for me actually has mixed sides and it may be partly a reason why India is not richer or has problems with public health, but the old saying when it comes to religion, every Indian is a millionaire, maybe is true, but don't think it's an entirely positive thing. But the ways in which religious ways of thinking suffuse the entire culture, uh, there are few other countries where that runs so deep and so thick and also in a diverse way. You have multiple religions including Christianity. And to learn those by going to India is one of the things you get there. It's one of the world's largest countries with Muslims, right? Maybe it's number three and I think. Indonesia number one, Pakistan, number two.

Tyler:              I'm not sure if India is ahead of Bangladeshi behind it for Muslims, but obviously it's significant for Muslim culture. Janes, different kinds of Hindus, Sikhs and every city, every state is so different in a way people will engage with you is so fresh and this kind of deep burning curiosity to somehow incorporate what you know into what they think. Uh, to me there is very strong and I find very attractive.

David:              This is going to be sort of part of a broader question. Are you reading books, blogs and we'll start there and then we'll get to the distinction between books and blogs and different forms of media.

Tyler:              If it's India and China, uh, I take very different approaches. India, I find reading books much more useful than for China. Maybe it's because of the history intersects with European history more. But reading books on India, a lot more sticks with me than with China. Uh, I haven't found that many good blogs on India. It may just be my defect, but if you just read plenty of books on India and go and in terms of cinema and music and cuisine, try to actually learn things about those before you go. Fashion, design, textiles, studying history of Indian textiles is one of the best ways to learn Indian history and it can structure your tourism and where you go and maybe even what you buy. So there were more entry points for India. Whereas for Chinese music, I mean I've tried, I liked Chinese opera, but I don't find it that useful. A lot of it to me, I just don't enjoy Chinese popular music. I enjoy much less than Indian popular music. So for China it's much more important that I be there and talk to Chinese people, which you can do here as well of course.

Tyler:              So I approached those two countries in a very different way. And India also I find I have a kind of stamina problem. I'm in very good health. I walk a lot, travel a lot, but it's hard for me day after day to be outdoors in Indian cities all day long. Just like pollution, noise, different indignities. I can't do it. Uh, with China, unless it's a very smoggy day I can. In India I paced myself much more. I spent a lot more time indoors. It's a little bit inefficient.

David:              So let's get back to different forms of media. How do you think about books versus blogs? It's something that I debate a lot with my friends. Um, how do you think about it and what advice would you give to younger people as media begins to shift like it is.

Tyler:              I mean mostly books are still better. There's way more knowledge in books than blogs and it's easier to find out how good a book is by reading reviews. Not that reviews are perfect, but you get a sense, you know, maybe blogging peaked about 10 years ago and I'm happy that I'm still blogging. Like our readership actually is not down at all. It's maybe up a little, but I don't think in general, blogs are a good way to learn about countries. They're very good for a particular food scenes. Like where should I eat in Mumbai? There'll be a food blog about Mumbai that will be way better than any book and then use the blog. But history of India, you know, just read some good books and they're there, read Indian fiction. Find these other entry points, like history of Indian textiles.

David:              That's interesting that you talk about entry points. Is that something that you apply in other domains?

Tyler's secret to learning: Don’t try to learn things head on. Look for entry points instead.💡

— ᴅᴀᴠɪᴅ ᴘᴇʀᴇʟʟ ✌ (@david_perell) October 23, 2017

Tyler:              Everything always has entry points. If you try to learn things head on, I just find I fail usually, entry points I succeed. More motivated pieces, start to fit together.

David:              Recent example?

Tyler:              Well, take Macedonia, so I've been learning more about Macedonia history by studying, reading about Macedonian woodcarving. So by woodcarving you learn something about the religion, you learn something about the monasteries, you're learning what were the errors, where they were most creative, where it's just rereading political history I don't get-.

David:              Like reading the Wikipedia page.

Tyler:              That's right. So uh, there are always other entry points for any place and you know, they need to be ones that interest you, but basic ones are going to be food, music, art, design. Architecture is a very good one. Right. Architecture in Macedonia is very interesting. I read quite a bit about that.

David:              I'm curious to hear more about architecture and different from Macedonia to India to China.

Tyler:              Take the main city in Macedonia, Skopje. it had a complete makeover within the last 10 years. And they put up a large number of statues in a kind of older style, almost eastern European brutalist style. Many people hate them, some people quite like them for the most part. I liked them, but if you imagine some parts of Las Vegas, which are a bit garish and they put up big things to impress the viewers. A lot of Skopje looks like that, but it's done not In the kitschy way, but with, you know, uh, no wink from the eye and with no smile on the face, they just did it. And the city has been transformed and it's this major political issue and it was a dispute should they have spent so much money. So one way to learn Macedonia is to learn about the statues dispute.

Tyler:              And then so many of the statues are historically controversial. Like there's a statue of someone who would seem to be Alexander the great, but the Greeks can't claim Alexander the Great. So if it's explicitly Alexander, the Greeks get upset, will be more concerned with blocking their entry into the European Union. So it's Alexander, but it isn't Alexander and just by reading about the statute that both is and isn't Alexander the great at the same time is a great way to learn about Macedonian history, politics more generally, international relations. So I think architecture is one of the best entry points and it's something you always see, right? Like you can't avoid it anywhere you go. And if it's ugly, often so much the better.

David:              Now to China, the balance or the almost to the juxtaposition of totally modern these grand structures. And then the old.

Tyler:              It's hard to find good old things in many parts of China. There are the old neighborhoods which they're clearing out of Beijing, but there's still some left. Uh, those to me are very charming just to walk through them. I can do, you know, for hours that's fun and they'll have great places to eat. Chinese mega cities. Uh, they are an acquired taste. The last one I was in was Chongqing, which is in western China. It's, you know, maybe 20,000,000 people just in enormous number of skyscrapers and they're not that distinctive, but the rivers of the city and the way it's laid out, it nonetheless has a distinctive field and if you walk around it enough, you will get that. Uh, and the ugliness or at least the non attractiveness of the architecture I actually like it. It is something you need to learn, but it's, it's part of what being there means, you know, it's not all gonna look like Venice, nor do I want it to.

David:              So when you go into these cities and you're meeting people and trying to learn as much as you can, is that similar to the way that you conduct your Conversations with Tyler series? What is your philosophy of interviewing so to speak?

Tyler:              You know, I picked the people I want to talk to, so I'm very selfish. I'm not paid to do this, so I should have fun. On average, I spend maybe a month preparing for a guest. Maybe I'll have done that reading all right. But even then I'll reread it. So it's gotta be like, look, I want to spend a month doing this or like why, you know, I'm not, I don't care about you all listeners now and it's a way of focusing my reading. It's actually an entry point. So I'm going to interview Ross Douthat in December. I'm friends with Ross, he's a great thinker, awesome columnist.

Tyler:              But Ross for me is also an entry point actually into understanding Catholicism. And if I just sat down and read about the Catholic Church, a lot of it would be boring. But if I read, well I'm going to try to figure out what does Ross Douthat think about this Catholic issue. I learned so much more about Catholicism because Ross is my entry point. So I picked guests to be entry points.

David:              And then when you're actually doing the interview, what are you thinking about? What, what, how are you thinking tactically about that?

Tyler:              I don't know if people should emulate each other because you know, we're all different, but I take everything that person has done and I hold it in my mind all at the same time right before and during the interview. And that's extremely strenuous, so for me to do one of these interviews is the most strenuous thing I do in life. Much harder than giving a talk and I'm quite exhausted when it's over, even though they do much more of the talking because having to hold all the information in my brain, it's like playing a very hard chess game.

Tyler:              And then when the interview's over, I lose like 90 percent of it within half an hour. But maybe it's made my understanding of things deeper. Uh, but during the interview I feel I have access to kind of everything I've taken in, almost in a magical way. Uh, I'm not sure other people can or should emulate that, but that's how it is for me. It's very intimidating. I think people have realized now when they're interviewed by me, I kind of know some of their stuff better than they do and I'm not that slow, so I'm not trying to screw them over and make them look stupid at all. Quite the contrary. But when someone's trying to make you look really smart, it's actually harder than when someone's trying to refute you.

David:              That's interesting. In your interview with Ben Sasse, it was really wonderful. I've listened to it three or four times. I've read his books since and what really struck me was the notion of a multi career life, the idea that it used to be perhaps that you worked for a corporation the rest of your life or be a tenured professional like yourself, but now that's beginning to change. How should young people be thinking about that?

Tyler:              Yeah, teaching yourself how to learn and relearn. So there's all this talk, oh, I learn from my school, or you know, business will retrain me someday. No one retrains you, your business, your employer might help you, but you're retrain yourself. That's one reason why wage inequality is up. Not many people are good at this. So learning how to retrain yourself, I think getting mentors in any new area is very, very important. It's still underrated even though I think it's pretty highly rated. Uh, I mean, those are some basic tips I would give people.

David:              In terms of mentors, I'll push back on you a little. Is it worth taking the time to actually get a mentor in real life? Like what would the benefit of that when I could listen to your Conversations with Tyler series and all these other incredible podcasts and in some ways that are a similar mentorship. It's just not so personal.

Tyler:              It's great to do that, but a mentorship by being alive and physical makes so many things emotionally vivid for you. And I think for eighty percent of people, uh, that's extremely important. So the mentor is like another kind of entry point into something. And some click happens in your mind, like why something is important. You learn by meeting the person and interacting with them and it may just be two or three hours in your life. It doesn't have to be an ongoing thing. Right? Uh, and I think we still undervalue that, trying to meet those few right people who will open a few intellectual doors for you.

David:              So who have the mentors has been for you? I know your, when you were getting your, uh, PhD in economics and then, uh, Mr. Shelling, right?

Tyler:              At Harvard, he was an important mentor for me and also he gave me a vision of what it could mean to succeed that I hadn't quite had before, but my most important mentors, you know, I was a teenager. So there was a fellow named Walter Grinder. Probably my most important mentor. I met him, I'm guessing I was 14 and Walter at the time was not a, he's never had really worldly success, but he was the person I met who had read and understood more books than anyone else and he still would be one of the few like of anyone I've ever met who's read and understood more than anyone else.

Tyler:              And I just saw that in him and I thought like, well I want to be some version of this. And that was one of the biggest events in my life was meeting and getting to know Walter Grinder.

David:              Keep going on that. That's really interesting.

Tyler:              And I think it wasn't easy for me to see Walter. I didn't drive, he was a friend of my father's like we had some meals together. I met him some number of times or take the bus into New York, see him there, but it wasn't an amazing amount of contact, but the contact we had, I got that vision and I would always ask Walter, well, Walter, what should I read? And I would read what he recommended, but what he recommended was actually not important. What was important was to kind of see the wheels turning in his head, like how he thought about what he was reading was way more important than any particular book he recommended.

David:              Do you have rules for how you think about those things?

Tyler:              I don't know if there are rules, but thinking strategically and philosophically about management is one of the most important things almost anyone can do because it's hard for me to think of anyone who is as productive solo is with other people and other people can multiply both your impact and your learning by many, many, many times. Right? Like if you had to go to a bookstore and read all the books on management, they're kind of a harbor right? There are kind of like self-help books. They're cliches. It's like building a team is important, they're boring, maybe they're even wrong. So the entry points for management are so hard and I think they are people and it goes back to mentors. Maybe you can only learn whatever it is you know about management from mentors and not management books. But that, too, is oddly under appreciated for something that's so oversold. It's nonetheless underappreciated.

David:              In Stubborn Attachments. Your most recent, I don't know if I could call it a book, but it was something of that form. Yeah, output. You talked about the power of compounding and what is it? Of course it's important and finance and of course people have uh, many people have a elementary idea of it. But what do you made that sort of the, the core theme of that book? and why?

Tyler:              Yeah, so much of what people write is autobiographical. So I could give you a kind of objective philosophical answer as to why I think compounding is important. But I prefer to give you a biographical answer. So right now I'm 55 and I started on all the assignments at actually 13 or 14, so that's over 40 years of stuff. So I'm not old. I'm, you know, in good health and very full of energy. But like, no more years of history. I've had more years of learning. So the idea, you should have a very long time horizon and be totally determined and persistent and like none of us are really that able or smart at all. We're all kinds of blundering fools. But if you just get some rate of improvement and just let it keep on compounding, I mean you can do pretty well. I'm a big believer in that as a form of biography. Same is true with travel. I think every year I traveled better and more wisely and it's more fun for me because I learned things from the last time I travel. So you always want to be on some kind of cycle. Our curve where you're compounding.

David:              I'm glad I'm not the only blundering fool then. Um, so. So when did that become clearer and clearer to you? When did you begin to have an intuitive sense of that and then what were, as somebody who's 23 years old, somebody who's just beginning their career, what would I not understand about compounding that, you know.

Tyler:              In my early forties, I actually realized what I was doing, so I was doing it for over 25 years and not even knowing what I was doing, which makes me really a blundering fool. But the things I had learned much earlier, like started to pay off in my research and my books, like ideas finally gelled after 25 years. And also the Internet gave me a platform for putting them out there. My abilities to sort of think about and evaluate projects became sharper and a lot of things came together for me, you know, in my early forties, which is probably later than average. And then I kind of thought back then, you know, I've been kind of working towards this for a long time and I didn't even know it.

David:              The book, out of all the ideas that you've written about, the one that is truly fascinating to me is Average Is Over. Can you give a brief overview and how have your ideas from that book changed over time?

Tyler:              Average Is Over. I think it came out four years ago now. I'm not sure, but it basically looks at the implications of a world where computers can do so much and artificial intelligence is here and on the way. So I think if people just falling into two categories there, they've either found a way that the computer augments their skill and then they can do very, very well in life or they're in some way competing against computers and software and then the chance they lose is actually pretty high. Like if you were to play an ordinary travel agent 25 years ago, right now you're probably doing something else. Maybe you can plan boutique holidays or wealthy people, but odds are, you know, Expedia and Orbitz have outcompeted you. So this is driving some of the income inequality, which is not a comfortable reality, but I think it's one we have to face. And what we want to do is get as many people as possible on the better side of that division.

Tyler:              And part of the book is how to do that and how to think about this for your own career, your own skills.

David:              You mentioned self learning. What else would be the big important things?

Tyler:              Conscientiousness, persistence, determination, kind of very old school moral virtues I think matter much more now than they did 25 years ago. That's counter-intuitive. But if you just stick to some version of classical morality and keep a long time horizon, I think today opportunities have never been better. But of course it's not easy for most of us to do.

David:              Has in terms of opportunities then, has the Internet changed how you think about planning? Like are you're thinking about planning on shorter time horizons more opportunistically?

Tyler:              Yes, and I've never thought that much about planning anyway. That's one of the ways in which I'm a blundering fool.

David:              Haha, we're going to call this episode "Tyler Cowen is a blundering fool."

Tyler:              Haha. And again, everything I'm saying, I'm not recommending for other people. I would just stress how different people are, find your own way, but just to tell you how I've thought about it for myself, I said if I can find things that to me are fun, compounding will kick in in my favor and all the blunders I make in the meantime will come out in the wash. I really actively maybe recommend against that for most people. But that was my so-called planning, was to have fun.

David:              Wonderful. Going to do a little pivot here. You seem to have a big love for basketball and the NBA, but besides basketball, what do you love about the NBA?

Tyler:              It's drama, right? It's better than most theater, but it's actually happening. So what really matters to the people? You don't have to suspend belief. It's an entry point into understanding a lot about America.

Tyler:              The NBA in particular is an entry point to understanding a lot about race. The NBA is far more international than before and it's a way of being in touch with parts of American life and commercialization and also media and television that otherwise I wouldn't necessarily intersect with that much and it's just plain outright fun. And last night I watched the Wizards play their first game of the year.

David:              That John Wall dunk was crazy.

Tyler:              It was, it was kind of an awful ugly game and I'm not going to watch again for a while. I got it out of my system and I'll follow every game. And as the playoffs approach, I'll watch it a bit more. I'm going to a game December fifteenth with Philip Wallach. That'll be great fun. And he and I will talk social science.

David:              There we go. Well, I'm going to try to go tomorrow night, but I want to dive into the Wizards. I'm curious to hear about what you said about NBA in America, sports in America. I, uh, it was with some friends the other day and I argued that sports was actually the best way to learn about America and now I'm going to use your entry point theory. What do you have to say about that?

Tyler:              I had breakfast with George Will a few weeks ago when I said to him, you know, today you probably understand the country better if you read the sports page than if you read the news page. It's more like what people are actually doing. There's something quite normal that sports but sports. It's also extremely bizarre. You care so much about like your team, which is arbitrary. Like these guys. They're not from Washington. I don't even identify with Washington. I don't know them that might be bigger jerks than the Boston Celtics and I root, you know, very hard for them to beat the Celtics and you realize how much of like human nature is expressive. How much some of it's like politics. Uh, you know, how much in some ways sports, like mirrors hunting and some very old pastimes of male competition and bonding. It's also a way of studying how statistics matter, what you can measure and not measure. Management, teamwork. Sports is a wonderful entry point for all these things.

David:              Sports abroad in other countries. What have your experiences been? To go back to the beginning of this conversation.

Tyler:              I once saw a professional basketball game in New Zealand, which is a much lower quality of play, but that too is interesting. I tried to see a game in Spain. I failed to. I'd love to see professional basketball game in China. Uh, I consider that an under-explored area where I'd like to do more.

David:              Yeah.I find the relationship interesting, to go back to basketball. The relationship between China and America with the NBA.

Tyler:              A great entry point into China, is to read all of that stuff in Marbury. His experiences in China and you will see sides of China much more clearly than you would get out of reading a book on Chinese history.

David:              What is that story about again?

Tyler:              Well, Stephon Marbury was sort of a top player here, but not actually that good. And he shot the ball too much and he was out of control and not a great teammate. And uh, he had some injury problems. He quit. He reinvents himself in China and he's a huge success in China. They've even erected statues to Stephon Marbury and China's, he's a major endorser. He's had his own movie, I think for awhile a TV show. And how Chinese treat celebrities and how they think about African Americans and how they reward athletic excellence in ways in which they're either more tolerant or more rewarding or more brutal. Like compare the story of Stephon Marbury with China's own Yao Ming who it seems was bred, eugenically bred to be a star basketball player. That too, is insight into China. Basketball, one of the best entry points into China.

David:              Chinese celebrity. Let's go down that rabbit hole.

Tyler:              So, China of course is a big country and the media are very important and they have Wechat, which is more powerful than our Facebook. It performs some similar functions, but more. Uh, China has become a celebrity culture in a very short period of time. And in some ways it's copied a somewhat earlier version of American celebrity culture than we have now. Now it's in some ways more Internet based, but Chinese celebrity is a sign of China being domesticated and less authoritarian than you might think reading the news pages and it's very aspirational and to see what celebrity looks like and a culture that is much more aspirational than ours. Ours is much more complacent. That to me is a very interesting contrast.

David:              We gotta dive into the complacency. Compare the similarities and the differences in terms of complacency between China and America. Because when I see the data, I concur with your argument, but living in Manhattan, it's not what I feel whatsoever.

Tyler:              Manhattan, of course, is an outlier and when you say Manhattan, there are many Manhattan's. But if you think about China, my first visit was 1989. There were hardly any cars. Everyone was on a bicycle. Maybe you'd be lucky to have a bicycle. It was a very, very poor place. And now, uh, it's about as.... Well, it has a higher total GDP than ours, but it's better off than most other emerging economies per capita. They've had a 35 or more year run, that's one of the two or three most impressive runs in human history ever, and this is the only one for a billion plus people. So it could be the most important event in human history ever. Or one of the top three or four. So just that alone is like, oh my goodness. But there's still high risk in China.

Tyler:              If you don't get out there and like master something, that risk will come and get you and crush you. If you were born into an educated family in this country, that's typically not the case. Someone can take care of you or you can get a job or a degree where you get by. You can be a slacker. Um, China, people expect everything to change every 10 years. It has been for them. They're used to this, they consider it a norm. They're not complacent. Life there is much more stressful in most ways. It's much less pleasant in many ways. But it's also more real and at least in that one big way. And now they are determined to outdo us and they're making a real go with it. That's like, how can you not want to go and see that?

David:              Also as a young person, I first of all feel compelled to make that change, but also not something that, of course the American media is covering very much.

Tyler:              There's so many articles on millennials, right? Millennial this, millennial that. So in a sense, all ideas about millennials are covered whether they're true or false, but none of them seem to get any traction is I suppose how I view it.

David:              So how do you view the millennial generation?

Tyler:              They're the nicest, most tolerant generation we've had, but I don't think that's an entirely good thing. And so far they're slated to be a relatively complacent generation. Maybe somewhat less ambitious, taking fewer chances, wanting safe spaces, which makes sense given the constraints they had been faced. But I worry that they're not replenishing America's cultural capital for generations to follow.

Ah, the millennial question 😯😯😯 Millennials are the nicest, most tolerant generation we’ve ever had. But it’s not entirely a good thing...

— ᴅᴀᴠɪᴅ ᴘᴇʀᴇʟʟ ✌ (@david_perell) October 23, 2017

David:              Talk about those constraints. But also, I'm interested in the dichotomy of millennials are both complacent and entitled.

Tyler:              A lot of millennials grew up in families that had a lot of wealth, right, more than ever before. That leads to a sense of entitlement. There is way more helicopter parenting for these people than ever before, which I think is mostly a negative, but they also grow up in this slow job market. Sometimes very slow depending on their age, no fault of their own. They grow up in a much more globalizing world, so an investor is thinking like, should I hire this millennial or should I send my capital to Vietnam where someone will be just as smart, maybe harder working and do something for a tenth of the wage, and we see a lot of people choosing the ladder. I wouldn't say that it's anyone's fault, but it makes it a different world. You either decide, well, I'm going to be the next Mark Zuckerberg, and there's a class of people like that who've been phenomenal, or you just decide like, look, I can't really compete. It's gotten too hard, but these stocks have wealth or enough. I can protect myself. The Internet is fun. TV is great. Maybe people are into recreational drugs, whatever level or kind of sex nuanced way easier to get them before.

Tyler:              It's like, well, why not do that? That's pretty good. Right?

David:              Right. I mean it's funny because I see almost all so many of these ads in New York are surrounded around "It'd support you to just stay home and we will bring it all to you.".

Tyler:              That's why the Amazon will deliver whatever or Netflix streaming, everything's delivered now and that to me is the cultural negative even though obviously it's super convenient.

David:              So what is it about China and India? What is in the water there that is having things be different because of course they have the Internet.

Tyler:              Well they're much poorer so that's something bad in the water and they're growing at much higher rates because they're doing catch-up growth and the background level of risk there is very high, which again makes living there extremely unpleasant, not for the billionaires, but for most ordinary people, their incomes can fluctuate much more. Trying to get good healthcare in China, much, much harder than here at any price you may have to pay. And then bribe your doctor again. Even then the, you know, the pharmaceuticals you get might just be fake. You'll never really know until you live or die. We don't face that kind of challenge and our healthcare system is pretty screwed up, right? So, uh, that makes them less complacent.

Tyler:              So the idea that not all good things come together, I feel is very hard for America to grasp right now. And the fact that we've made our lives pleasant and safer, which on net, I favor that that's also very costly. Again, it's a point being made by myself, by others, but it's not appointed distraction.

David:              Yeah, I thought what you said on a previous interview was just that mediocrity is underrated.

Tyler:              That's right, mediocre life is a great life. Like if you can just keep it going live til 80, whatever your thing is, the Internet, the drugs, the sex, some nonlinear combination thereof. There were like, you have your three kids, uh, you know, it's going to be diverse, but like, that's really good. You cannot be starving, but you don't have to be Mark Zuckerberg. And if I think of myself, uh, you know, I'm not like really of wealth, but I think I have a better life than, you know, most really wealthy people. It's more fun, more challenging.

David:              Well, the final question I'm asking you is then, what are the tenants that you've looked for in terms of building that life and in terms of what has given you that life? What are the things you know, the pillars of what makes it so enjoyable for you?

Tyler:              You know, I think so much of what we are we're born with, um, so we admit that about yourself, like figure out what you're really good at, which is going to be something for almost everyone. Like try to build on that. Be pretty honest with yourself about what you're not good at. Like it has to be fun because you need to stay motivated and it's a more competitive world order. But the opportunities are there and uh, you know, do something different than what I did, but do something like I'm waiting for you to do something for me. Here I am impatient, wanting more fun. You do it, bring me stuff.

David:              OK, well now I want to hear more.

Tyler:              My main idea is not any idea at all. It's a method. It's a personal method and it's a method of learning. It's take wherever you're at and just try to push your understanding deeper. Don't spend time telling yourself that you're right and other people are wrong and try to talk about other people being wrong as little as possible. If someone bugs you in your twitter feed, don't let it bug you, either ignore them or stop following them because you'll start thinking how right you are and how wrong they are. That will screw up your learning path. Just like stay the compounding returns of learning more and more curious, better and deeper questions. Your current level of understanding is always that of a blundering fool in some way, but you want to be waltzing along that curve on the compounding returns and just always asking better questions and just obsess over that and so much getaway from like a fixed doctrine of, you know, whatever.  

Incredible advice. “My main idea is not any idea at all… it’s a method of learning. Always ask better questions and obsess over that."

— ᴅᴀᴠɪᴅ ᴘᴇʀᴇʟʟ ✌ (@david_perell) October 23, 2017

David:              Yeah, because that's what's so hard about about university is it like tells you almost what I know, what I need to do or know what I need to learn it. It's like the antithesis of curiosity.

Tyler:              Yes, and it's too homework geared, which is a crime. High school, all the more so and our education system is failing us and this thing called the Internet has come along and for actual learning has so out competed what we call education.

David:              It's not even close.

Tyler:              It's not even close and so much of the internet is free. It's not all free but free or fairly cheap and it works on principles that are so much better than what you're given in so many classes. So I think the time is right for some real revolution where what we call education in some ways becomes more like the Internet and we're going about it wrong.

Tyler:              So what we're doing now is we're taking education as we knew it and we're adding on the Internet, which I'm all for by the way. So you assign a YouTube video in your class and students email you again? Fine. No reason not to be excited about that, but the real gain is to make the Internet the center and they add on the education at the fringes and we're very far from doing that.

David:              So then as information becomes abundant, the scarce resources should then shift into something else. So what is becoming scarce?

Tyler:              Motivation, and that's the theme in my book Average Is Over that you asked about. How can you motivate yourself, how can you motivate others? The real scarce input is the preacher, the moral leader, the inspirer, the mentor or the role model. That is what is scarce in our world and we don't even know it.

Tyler:              And it's hard to produce, right? Actually we may get more of it through the Internet itself, but still it's hard to produce and for a lot of people, a lot of it has to be in person. Like you've read a lot of my stuff or heard me, but like now we meet the first time and I hope at least I'm something different to you. Maybe I'm worse?

David:              You're a blundering fool, Mr. Cowen. Hahaha.

Tyler:              Haha, well, I'm happy if I'm not different at all. So there's something about meeting the person where you reevaluate all the rest. That's just so fundamental.

David:              I'll tell you, this is what I feel with almost every single person. So with people who I ask of course are generally the people I tend to respect the most. So they start off through social media. What I found really interesting is they are there, they're almost like godly and then you meet them and you realize that they're human and then on like the far side of their humanity is their exceptionalism of like, you can do it, but because you can do it and you know how much work goes into that, then you begin to have this really deep admiration for many of these people.

Tyler:              Someone just emailed me a question. It was, what's your readers biggest misconception about you? And it's a brilliant question. Partly it's such a good question because I don't know the answer even though it's like about me. You think, oh, you know about yourself. But if people ask you a question about you, you don't know the answer to, it's a very good question.

David:             What did you respond with?

Tyler:              Uh, I asked the question back. (Both laugh)

Tyler:              The answer I got was uh, I'm more serious in print and on the blog and more a kind of genial or enjoying things or playful in person.

David:              You are very playful. You're very playful. But I knew that because because every interview, about five percent is funny. There's always humor and humor is just, it's very important to be able to humanize in that way.

Tyler:              It's the emotionally vivid thing. It's the entry point. Like humor is an entry point for learning almost anything.

David:              Huh, what do you mean by that?

Tyler:              If you want to learn about like cheese, don't read a cheese book. Start with the Monty Python skit about going into the cheese shop where he recites all the cheeses that they don't have. You learn names of cheeses much better that way than if you try to learn about cheese.

David:              So is humor like music in that sense?

Tyler:              Exactly. Music's a great way to learn about cultures and travel, humor. So the Monty Python skit where they try to summarize, proves it. If you don't know of it, watch it online. There's a competition, summarize Proust. You've got to do it in 10 seconds. Of course it's a many volume work with not even all that much plot, so it's hard to summarize and you see people being blundering fools trying to summarize it. And this gets over in two and a half minutes. The best way to start understanding Proust is to view something funny on Proust.

David:              There we go. Start a restaurant. So hopefully some ethnic food and podcast series. Well this was a great jumping point into Tyler Cowen. Thanks for coming on the North Star.

Tyler:              My pleasure. Thank you.

David:             Hey again, it's David here. One more time. You can support the Northstar podcast by leaving us a five star review on iTunes, or you can share the podcast on Twitter or facebook and to listen to other episodes or learn more about the North Star. You could connect with me directly at And you can always reach out on Twitter @david_perell. And if you enjoyed this episode, you'll also like the episode with Josh Wolfe, where we talked about the magic of learning, science, and economics.

Tyler Cowen's Books: 

Average is Over

The Great Stagnation

The Complacent Class

Stubborn Attachments


Other Links:

Proust on YouTube

Ben Sasse Podcast

Tyler's DC Food Guide

Tyler's Blog: Marginal Revolution

Tyler Cowen Twitter


Connect with Me (I love meeting new people):




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Today’s guest is Geoff Manaugh, who explores the intersection of architecture, technology, and landscapes. As a professor, he’s taught classes in both the United States and in Australia on topics such as blackouts, the future of cinema, geo-engineering, and the possibility of a San Andreas fault national park.

In the episode, we talk about how the geography of Los Angeles influences bank heists, the new subterranean structures in Singapore and Hong Kong, caves, and how technology is changing architecture.

This conversation will have you exploring new ideas, underground tunnels, sneaking through subway systems, and using blueprints to escape a prison. You can find Geoff online at his blog, BLDGBLOG.

“All of the buildings that we interact with every day tend to be completely overlooked and treated as something that isn’t even worth discussing, and yet that’s where we spend most of our lives.”

“The real world is so much more interesting than people think it is. There’s no reason to be bored — the world is cooler and more futuristic than you might think.”


Find Geoff online:

Mentioned in the show:

Books mentioned:

People mentioned:

Show Topics

1:53 - Introduction to Geoff and discussion on how he got into the architectural field.

3:15 - Diving into anthropology, ancient civilizations, and Geoff’s interest in both ancient structures and architecture.

5:10 - Some discussion on our current architecture and some speculation on us often being surrounded by a built environment. “All of the buildings that we interact with every day tend to be completely overlooked and treated as something that isn’t even worth discussing, and yet that’s where we spend most of our lives.”

7:50 - Discussing how the infrastructure and landscape of a city influence heists and crime. How our environment is much less passive than we think, and how it actively plays a role in influencing the way that we think and what we do.

11:12 - Figuring out how police view a city, taking advantage of various get-away routes, and the grey-areas often found in get-away routes.

12:55 - How burglars think differently about underground structures. Some discussion on tunneling and its relation to different types of landscapes under a city (sandy soil, bedrock, etc).

16:03 - How advances in technology influence architecture, security in the architectural world, and land boundaries.

18:55 - Speculating how well burglars actually know the building that they’re breaking into, how to easily find out the blueprints for a place, and discussion on burglars exploiting vulnerabilities within cities.

23:32 - How Geoff managed to get in touch with several burglars and learn from them. Also, how we unconsciously act like burglars in our lives.

28:19 - The emerging aspect of digital burglary and some discussion on this, as well as a bit on cryptocurrencies and investments. Also, thoughts on the actual definition of burglary and its relation to architecture.

32:14 - Discussing graffiti artists, people riskily exploring of architecture, and a bit on how we pay for city infrastructures, but yet we aren’t allowed to visit some of them.

34:35 - Geoff explaining various subterranean structures, caves, and underground tunnels. Also, how Singapore has begun to excavate outwards beneath the ocean for storage and other uses, architects designing artificial caves, Hong Kong’s future plans with underground infrastructures, and the powerful sense of awe that we can attain from architecture.

41:54 - Further discussion on the many things that we see, but do not consciously appreciate or really notice. Also, a bit of talk on the mysterious places left behind due to architecture evolving.

43:55 - The future of cities and architecture, and what Geoff is most excited about within these fields. The huge possibilities of technology merging with architecture. Also, a bit on quarantining people, isolating people, and relating both of these to architecture.

47:52 - Discussion on the architectural way of thinking and being efficient as a writer.

49:39 - Geoff’s connection to cinema and his perspective on cinema. A bit on what he’s done for cinema as an architect, as well.

51:12 - What has surprised Geoff while working in the television industry about bringing his book into the media network. Also, Geoff’s thoughts on transferring abstract ideas into a filmable scene.

Hey again, it’s David here one more time. You can support the North Star Podcast by leaving us a review on iTunes. Or you can share the podcast on Twitter or Facebook.

To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell. And if you enjoyed this episode, you’ll like the episode with Eugene Wei, a film editor who has worked in some of the worlds largest tech companies, as well as directly under Jeff Bezos. We discuss merging media with technology, company building, his lessons from Bezos, and more.

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Listen Here: iTunes | Overcast

Today’s guest is Eugene Wei, who's spent his career working at some of the world’s best technology companies including Amazon, Hulu, and Facebook. He joined Amazon in 1997 after graduating from Stanford and it was at Amazon that he watched Jeff Bezos turn a small little internet bookstore into “The Everything Store” that were all so familiar with. After leaving Amazon, Eugene moved to New York to become a film editor before moving to Los Angeles to become a director.

That summer he joined the company that would become Hulu, leading the product, design, editorial, and marketing teams. And since then, he founded and sold a startup called Erly, and worked as the head of product for Flipboard before joining the Facebook as the head of video at Oculus.

In this conversation, we talk about the spiritual significance of the second law of thermodynamics and its impact on movies, company building, and personal growth. We talk about the principles of communication and draw lessons from Jeff Bezos on how to communicate clearly and memorably. And finally, we take lessons from Eugene’s time living in Los Angeles and Silicon Valley and explore the ever-fascinating intersection of media and technology. And before we begin, you can find links to his blog, Remains of the Day, along with my favorite posts below. 


Find Eugene online:

Mentioned in the show:


Books mentioned:


People mentioned:

Show Topics

0:32  - Some information on the episode guest, Eugene Wei and a bit of background on his career.


1:58 - Introduction to Eugene, what life was like for him early on, and what he got into as a kid. Also, a bit on how he got into the filmmaking scene.


3:32 - Eugene on some of the biases from his parents that he faced regarding a career choice, and a bit on him convincing them to move out west and away from Chicago.


4:56 - What Stanford was like back when Eugene was growing up, how his parents felt about his choice to go there, what things he ended up exploring while there, and what he majored in.


6:55 - How learning with both sides of the brain influenced Eugene after college and how it has been useful for him in the professional context. “I think the general idea of following your interests so that you have an inherent sort of motivator for learning is just super-critical.”


7:54 - Thoughts on underestimating the advantages of a somewhat generalist education compared to an education in a specific field. How having a broad set of skills and a general education has helped him more than if he were to specialize in one field.


9:50 - Eugene on the importance of being deeply intellectually interested in his work.


10:32 - Eugene’s journey towards receiving a job with Amazon in 1997, the choices he made regarding college, and him realizing the growing wave that was the internet back then.


14:11 - Eugene discussing Born to Rebel, an influential book that he read while in high school, and how this impacted him. Also, Eugene discussing fighting the conformist nature that comes with being an older sibling, and some discussion on how the younger sibling likely has a rebellious nature.


15:40 - Further discussion on challenging the conformist nature, pushing yourself into new and challenging areas to grow, and Eugene talking about his decision to leave Amazon and go to film school. “To start over and be a student again forces you into a different frame of mind.”


17:35 - How leaving Amazon to start over and go to film school taught Eugene valuable lessons and positively impacted him.


18:28 - What the second law of thermodynamics is and how it played a role in Eugene’s journey. Some more on him pushing out of equilibrium for growth, as well.


22:01 - What Eugene did for work when he first got into filmmaking and some more thoughts on what the journey did for him. Also, a bit on his next job, which was working for the company that eventually became Hulu.


24:18 - Eugene’s thoughts about the different streaming platforms around that time that he began working for the company that eventually became Hulu.


25:45 - What Eugene learned about how the media and technology industries operate and where they intersect. Some thoughts on media and tech companies in general and thoughts on their futures, as well.


30:16 - Eugene describing the free agent model and its contrast with vertical integration. A bit more on how various media companies have changed and some of the strategies that they use. “In 2013, 18 of the top 25 films were sequels, prequels, or extensions of existing stories or popular streams.” “In box office earnings, sequels make 8 times as much as originals.”


35:10 - The self-perpetuating platforms that a majority of movies are now and a bit on how media companies look to buy story optionality to promote future stories.


37:49 - What it was like working for Amazon in 1997 and working close to Jeff Bezos. Also, what it was like watching a company like that grow and why Amazon originally started with selling books.


41:40 - What Eugene learned from Jeff Bezos himself and a bit of insight on how Jeff worked. Also, the importance of thinking based on first principles, and some guidelines necessary for developing these first principles. “To derive first principles, you need access to raw data or you'll forever be getting secondhand principles from other people.”


43:33 - Eugene further discussing developing first principles, accessing raw data necessary for developing them, and the necessity for failure.


44:58 - The unique ways that meetings are run at Amazon, why Jeff banned the usage of Powerpoint, how Powerpoint distorts people’s thinking, and some more things that Jeff did to improve various aspects of the company and its employees.


49:47 - Eugene on what you should do as a CEO once your company grows larger and more successful, and some thoughts on a few things that make successful and effective companies.


52:04 - How language is encoded in various media, the immense communicative aspects of visual media compared to literal, and some thoughts on us being visual learners. Also, how watching someone do their job is much more effective compared to reading about how to do that job.


1:02:08 - Story and narrative being a very powerful way to encode information in addition to media, and some more thoughts on visual and narrative mediums being the most effective ways to learn.


1:04:12 - The positive benefits that countries gain from gaining widespread TV for the first time and some thoughts on how TV can be beneficial to us.


1:05:49 - What Eugene’s favorite writers have in common and why they are his favorites. Also, a bit on the different style of directing by Terrence Malick. How Terrence uses the visual medium in unique ways to get closer to consciousness and what it’s actually like to perceive the world.


You can support the North Star Podcast by leaving a review on iTunes. Or you can share the podcast on Twitter or Facebook.

To listen to other episodes or learn more about the North Star, you can connect with me directly at and you can always reach out on Twitter at david_perell. And if you enjoyed this episode, you’ll like the episode with Tyler Cowen, an economist at George Mason with deep interests in food, music, art, and travel.

Key points in this episode


“The holy grail of design is small things that make a big difference.” 

Scott Belsky helps creative people, teams, and networks make ideas happen. 

In this episode, we talk about how Scott has merged the worlds of business, technology, and design. Scott shares insights on how to reinvent yourself throughout your career, and discusses the future of media and technology. I love what Scott had to say about design, where he draws from numerous trips to Japan where he was awestruck by the culture, their attention to detail and the care they bring to their craft. 

Today, Scott is Adobe’s Chief Product Officer and the Executive Vice President of Creative Cloud. He’s a product design and consumer behavior obsessive and founded Behance to organize the creative world and connect creatives with lucrative opportunities, before Adobe acquired the company in 2012.

He's a Venture Partner at Benchmark - a venture capital firm based in San Francisco, an early-stage investor, a Product Strategy Advisor to Adobe and Twitter's video efforts, and is co-founder and Executive Chairman of Prefer, a platform that empowers the careers of service professionals and enables people to find professionals they need from people they know. He’s also invested in many of my favorite companies including Sweetgreen, Uber, and Warby Parker. 


Connect with Me (I love meeting new people):

Please leave an honest review on iTunes. It helps people discover the podcast. 

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“I learned that courage was not the absence of fear, but the triumph over it. I felt fear more times than I can remember, but I hid it behind a mask of boldness. The brave man is not he who does not feel afraid, but he who conquers that fear.” 

Douglas Abrams is the founder of Idea Architects, a book publishing, and media company that works with visionary authors to create a wiser, healthier, and more just world.

Nobel Peace Prize Laureates, the Dalai Lama and Archbishop Desmond Tutu have both survived more than fifty years of exile. Both have endured the soul-crushing violence of oppression. And yet despite their hardships—or, as they would say, because of them—they are two of the most joyful people on the planet.

Doug recognized this and asked two simple, yet profound questions: How is this possible? And what can we learn from their example to cultivate more joy in the face of life’s inevitable suffering?

In celebration of the Dalai Lama’s 80th birthday, Doug traveled to Dharamsala, India, alongside Archbishop Tutu for a five-day conversation on the nature of human happiness and suffering, the two Nobel Peace Prize recipients traded intimate stories, teased each other continually, and shared their spiritual practices. 

Out of that, came Doug’s new book, The Book of Joy, a New York Times bestseller that probes the very nature of joy itself — the illusions that eclipse it, the obstacles that obscure it, the practices that cultivate it, and the pillars that sustain it. 

If you enjoyed this episode, you'll also enjoy the episode with Heather Hartnett, where we talk about eastern philosophies and western ways of living and working. 


Please leave an honest review on iTunes. Your ratings and reviews really help and I read each one.

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Albert Wenger is a partner at Union Square Ventures. Before joining USV, Albert was the president of through the company’s sale to Yahoo and an angel investor in Etsy and Tumblr. He previously founded or co-founded several companies, including a management consulting firm and an early hosted data analytics company. Albert graduated from Harvard College, where he studied economics and computer science and holds a Ph.D. in Information Technology from MIT. 

In this episode, we talk about what it was like to grow up in Germany, where Albert received an Apple II at a young age. As a teenager, Albert visited America for the first time when he stayed with a family in Rochester, Minnesota — the most impactful travel experience of his life.  We talk about how technological progress has shifted scarcity for humanity. When we were foragers, food was scarce. During the agrarian age, it was land. Following the industrial revolution, capital became scarce. With digital technologies, scarcity is shifting once more. We need to figure out how to live in a World After Capital — the title of Albert’s new book — where the only scarcity is our attention. 



Please leave an honest review on iTunes. Your ratings and reviews really help and I read each one

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Ari Paul is the co-founder and Chief Investment Officer of BlockTower Capital. He was previously a portfolio manager for the University of Chicago's $8 billion endowment. Ari earned a BA in political science from the University of Pennsylvania, and an MBA from the University of Chicago with concentrations in economics, entrepreneurship, strategic management, and econometrics & statistics. 

In this episode, we talk about Ari’s passion for poker, and what the game taught him about investing, risk, and table selection, a powerful concept that applies to just about every field. Ari recently identified what he calls “the opportunity of a lifetime” — cryptocurrency. It led him to start investing in cryptocurrencies, a decision that was guided by Ari’s commitment to stretching boundaries. Finally, Ari discusses his passions for backpacking and travel, and like so many guests, Japan was one of Ari’s favorites. 

Time Codes: 

2:30 - 6:20: Background and departure from science. 

6:20 - 9:35: Playing poker and complete information. Tilt. 

9:35 - 14:25: Table selection. Phil Ivey. Sharp Ratio. 

14:25 - 17:40: Childhood/youth. Building skills and transferring them to trading. 

17:40 - 20:30: Value investing vs. momentum investing. Path dependency for crypto. 

20:30 - 24:00: All heuristics are regime dependent. 

24:00 - 28:25: Shorter attention spans. Analogies. Changing minds. 

28:25 - 32:30: Backpacking. Consuming information vs. going off the grid. Stoicism.

32:30 - 35:40: Japan/Osaka/Kyoto. Accelerated living. 

35:40 - 40:00: Consciously stretching boundaries ("Life is lived at the margins"). Behavioral economics. Internalizing stereotypes. 

40:00 - 43:20: Stretching boundaries applied to cryptocurrencies. Principal component analysis. 

43:20 - 44:00: Specializing vs. building bridges in your career. 

44:00 - 45:30: Moving away from hard skills

45:30 - 49:20: Perspectives and trust building pre and post internet. Signaling. Psychological bias. Overconfidence vs. familiarity. 

49:20.- 50:10: We don't know people like we think we do. 

50:10 - 53:35: Blogging and personal brand. Blogging as a way to falsify ideas. Cunningham's law. 

53:35 - 57:45: Learning > Ego. Power laws. Combined talents out of necessity can create a combinatorial edge. 

57:45 - 59:50: The experience of starting a crypto fund. 

59:50 - 1:03:50: Agency when there's no roadmap. MBA students. 

1:03:50 - 1:08:45: Breaking through natural momentum. Anchoring. Status quo bias. Fat pitch. Crypto as the opportunity of a lifetime. Hard work, burnout, and compounding.


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Heather Hartnett is the CEO and founding partner of Human Ventures. She leads the Human Ventures team and advises each of Human Ventures’ portfolio companies. Heather brings a fresh new perspective to the technology scene and Business Insider recently featured Human Ventures as the first female-led startup studio in New York City. Heather was also named one of the 50 Most Influential Women in America by Marie Claire.

Before Human Ventures, Heather founded a FinTech company incubated within City Light Capital — a venture capital fund that invests in companies making social and environmental impacts. 

Heather and I talk about her childhood, and what she learned by traveling the world, focusing on the time she spent in Holland and India in particular. We talk about Heather’s favorite subject: people and the importance of having great energy, a singular vision, and how to get things done. 

We also explore the intersection of Eastern philosophies and western ways of living and working. Meditation plays a prominent role in Heather’s life and she serves on the Board of Directors of the David Lynch Foundation, which is dedicated to helping children around the world learn to meditate. Heather and I explore the impact of Transcendental Meditation on her life, her work, and her worldview. This was, without question, my favorite part of the episode. 


Recommended for New Hires at Human Ventures:



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Josh Wolfe is the co-founder and managing partner at Lux Capital, which invests in the intersection of science and technology at the outermost edge of what is possible. He partners with innovators challenging the status quo and even the laws of nature. The more ambitious, the better.

Josh is a published scientist himself. He's a founding investor and board member with Bill Gates in Kymeta, a company that makes cutting-edge antennas for high-speed global satellite and space communications. And before Lux Capital, Josh worked in investment banking and capital markets. Afterwards, Josh co-founded Kurion, which used advanced robotics, engineering, and chemistry to clean up nuclear waste. In 2016, the company was bought for $400 million. 

In this episode, we talk about it all: Biology, randomness, finance, consciousness, space, Brooklyn, investing, art, risk, and basketball. We start with what he learned growing up in Coney Island, a working class neighborhood in Brooklyn. Josh then shares his investment philosophy and why he likes investing in industries like lots of intellectual property, high barriers to entry and a limited talent pool. And finally, we talk about biology and the history of it— from single-celled organisms to the nature of consciousness — and Josh draws from his experience as a board member at the Santa Fe Institute. I hope you enjoy this wide-ranging conversation as much as I did. 

Show Notes: 

0:00 - 1:45: Growing up on Coney Island. Science, finance, and The Cyclone

1:45 - 3:15: Josh Wolfe's research background, the importance of persistence, introduction to capital markets

3:15 - 6:45: Learning new ideas. Identifying and avoiding BS. Risk and the value spectrum. Killing failure to find paths to success. 

6:45 - 9:10: Science fiction novels and the pursuit of truth. Gap between science fiction and actual science is closing. 

9:10 - 12:30: Competitive edge is paranoia and a competitive desire to have an information edge. 100-0-100 investing philosophy. Importance of humility and ambition. 

12:30 - 17:00: College and early career epiphanies. Embracing randomness and optionality. Avoid boring people. Dinner with Jim Watson, who discovered the structure of DNA. Appreciation for scrappy underdogs. 

17:00 - 20:00: A lot of fictional influences including TV, movies, and comic books. Avid consumer of information and any and all information. Curiosity born from information anxiety and overall competitiveness. 

20:15 - 21:45: The relationship between art & science

21:45 - 25:05: Mentors are a portfolio of the best ideas and role models such as Richard Feynman. 

25:05 - 29:10: Founding story of Lux. Henry Truman Quote: "There is nothing new in the world except the history you do not know." Competitive edges in investing. Intellectual honesty at Lux Capital. 

29:10 - 32:40: In history, there is no linear starting point. Red Queen effect and information consumption. Intellectual honesty, non-obvious ideas, and vigor. 

32:40 - 36:50: Consciousness, complexity. Daniel Dennett and Sam Harris debates. Bayesian updating. 

36:50 - 40:00: Complexity is chaotic phenomena with universal emergent principles. Lots of parallels with Entropy and the rest of the world. 



Connect with David:

Thanks to Conor Witt for producing this episode. 

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Shane Parrish is a partner at Syrus Partners and the mind behind one of my favorite blogs, Farnam Street. The blog is devoted to helping you develop an understanding of how the world really works, make better decisions, and live a better life. Shane writes about mental models, decision making, learning, reading, and the art of living. He draws from both the sciences and the humanities, expanding the intellectual horizons of his readers, helping them connect ideas, think in multidisciplinary ways, and cultivate meaning in their lives. 

I first discovered the blog in college and credit Shane for so much of my intellectual curiosity. He writes a weekly newsletter called Brain Food that covers all that he’s learned in the week beforehand. To help you cut through the noise, he includes his favorite books and articles with a high signal-to-noise ratio. He also hosts a podcast called The Knowledge Project. I recommend this episode with Rory Sutherland

In this episode, Shane reveals counterintuitive secrets to learning history through the lens of his recent trip to France. We also dissected one of my favorite mental models — why the map is not the territory. It’s a fascinating one that changed the way I see the world. I hope you enjoy this episode as much as I did. 


Connect with Shane: 

Connect with David: 

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"Everything you wear is a costume of some kind. Everything speaks to what you're thinking about, what you're feeling, what you represent, and where you're from - so it's very personal."

Greg Rosborough is the co-founder and design director of Abasi Rosborough. As a fashion designer, he thinks about the interaction between anatomy and functionality. He designs in juxtapositions, combining ancient with modern, minimal with monumental, and interesting with ease. 

Greg grew up in Tucson, Arizona where he attended the University of Arizona and worked for the men’s basketball team. Following Arizona, he moved to New York to study Menswear Design at FIT, where an internship at Ralph Lauren landed him his first job as a designer. He also founded UGallery, a curated online art gallery which now represents 500 artists and sells artwork in over 60 countries. 

In this episode, Greg tells the story of his first trip to New York as an 18 year old, his visit to Bergdorf Goodman, and how it inspired him to become a designer. We talk about his travels to Japan, Istanbul, and Morocco, his favorite books, and how he's fused ideas from various disciplines including architecture and the US Military to redefine the men’s suit. Greg was a 2017 LVMH (Louis Vuitton) Young Fashion Designer Prize Nominee. This conversation will give you a glimpse into the thinking and creativity behind Abasi Rosborough.


About Abasi Rosborough:

Greg Rosborough

Neil Patrick Collins - Episode Producer 

Greg Rosborough

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My guest today is Mark Broadie, a Golf Statistician and Professor at Columbia Business School. I first found Mark through his book Every Shot Counts, which transformed golf statistics and analytics forever. Marcus worked with many of the world's best golfers, including Francesco Molinari, and Justin Rose, who became the world's number one golfer as a result of their work together. In this episode, we explore the nooks and crannies of golf statistics, we talked about how different kinds of grasses influence players, why approach shots play the biggest role in success for top golfers. We discussed the math behind the drive for show and putt for dough theory, and dive into the reasons why Tiger Woods was so dominant for so many years. Now I live for conversations like this. I love them. And spending an afternoon with Mark talking about strategy, statistics, and golf, the so called greatest game ever played is about as good as it gets for me. And we begin the conversation talking about the strokes gained measurement system which Mark invented, and which dispelled many of the myths and misconceptions about the game of Golf. I hope you enjoy this episode.


Find Mark online:

People mentioned:

  • Tiger Woods

  • Francesco Molinari

  • Justin Rose

  • Phil Mickelson

  • Tommy Fleetwood

  • Rory McIlroy

  • Steve Stricker

Other mentioned:


1:45 Why drive for show, putt for dough is not really true, an elevator pitch of Mark’s strokes gained statistic, and which information on shots would Mark want access to that he doesn’t already have

10:25 Surprising conclusion about player performance around straight vs. dogleg holes, how does perception line up with statistic when it comes to player reputations, and correlations between birdies, bogeys, and driving distance

19:01 Is closer to the hole always better and what the exceptions to the rule, how the NBA changed it’s mind about three pointers, how Mark thinks about introducing changes to the way things are done in a sport, and the effect that different courses have on player psychology

32:12 The effect of different species of grass on the green on player performance, how some variants of grass are better for worse players, the horses for courses effect, and Mark’s counter-intuitive idea of which are the key holes on a course

40:51 How game theory affects driving decisions in 1:1 situations, what really separates the best players from the just good ones on a particular day among the pros, the TV highlight reel effect for long putts

53:54 How different golf course architects effect how players change their game, how ridiculously good Tiger Woods’ approach shot game was in his prime, and diving deeper into spin rates

1:05:00 How has being a golf statistician changed Mark’s own game, what the biggest mistakes that amateurs make, the most rewarding experiences that have come out of his work, and David and Mark piece together a story about the 2013 US Open

1:15:19 The next phase of Mark’s research that he is excited about

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