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Garry Tan (@garrytan) is a designer and engineer turned early stage investor as a Managing Partner and co-founder at Initialized Capital. In 2019, Tan was listed at #21 on the Forbes Midas List having invested in Instacart, Coinbase, Flexport, Plangrid, Hellosign and many others. Prior to founding Initialized, Garry was a partner at Y Combinator for nearly five years where he advised and funded over 600 companies and more than a thousand founders. With all of that, Garry is incredibly talented and insightful, humble, thoughtful and empathetic.

In this episode, Garry talks about building the world he want to live in, how refugee ancestors has influenced his worldview, navigating the idea maze as a founder, his $200M mistake and how parenthood has changed his life.

Updated on April 17

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Jeff Morris Jr. (@jmj) is a full time angel investor and the founder of Chapter One. This is a conversation about the impact this global coronavirus pandemic is having on millions of lives, and the challenges and opportunities of post-pandemic future.

Updated on April 05

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Mike Solana (@micsolana) is VP of brand and community at Founders Fund. For episode #12, I chatted with Mike about having the courage to speak your mind, self-censorship, the rising tide of socialism in the United States and the power the stories we tell ourselves both as individuals and societies have to dramatically alter the future we end up living in.

Mike runs creative programming for Founders Fund, including F50, the firms annual summit and Shop Talk, the firm’s professional networking series. He’s also creator and producer of the firm’s awesome podcast, Anatomy of Next, which just went into a new season. Mike also just launched a personal podcast called Problematic which I highly recommending checking out.

Prior to joining Founders Fund, he edited non-fiction for the Penguin Group (USA). There, he acquired and developed New York Times bestselling work in the fields of technology, politics, philosophy, and humor. Mike is one of the best follows on Twitter and you can follow him @micsolana. Whether you agree with him or not, Mike has the courage to speak his mind, his cultural commentary is next level and if nothing else he will definitely push your thinking. I hope you enjoy this conversation with Mike Solana.

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Karlyn Borysenko (@DrKarlynB) is an organizational psychologist who helps organizations and teams find happiness and fulfillment at work through her company, Zen Workplace. For episode #10, Karlyn and I had a wide-ranging discussion about her experience in an online knitting group that turned her off to cancel culture, taking part in the New Hampshire primary and meeting every Democrat presidential candidate and her decision to go to a Trump rally to try and understand how her political opponents think.

Karlyn came on my radar when my dad told me about a viral medium essay she wrote called “I’ve been a Democrat for 20 years, here’s what I experienced at a Trump Rally” which has been read by over 3 million people. I didn’t read the article initially but when I heard Karlyn interviewed on a talk radio program I occasionally listen to, DMed her on Twitter and she agreed to come on the podcast. What could be more paradoxical than a registered Democrat going to a trump rally?

We also talked about the importance of shared values like free speech, thinking for yourself and attributing good intent to you those you disagree with. We recorded this conversation in March as COVID19 was ramping up so we also offered up from fresh takes on how the world was shifting that may or may not age well and that’s ok. It was nice to escape Silicon Valley and talk to someone from a completely different part of the country. I hope you enjoy this episode with Karlyn Borysenko.

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Sahil Lavingia (@shl) is the CEO of Gumroad and a prolific entrepeneur, writer, painter and thinker. For episode #8, I chatted with Sahil about the challenges of building startups and his viral essay “reflecting on my “failure" to build a $1B company”. We also escaped the world of tech and startups to talk about moving from San Francisco to Provo, Utah – the most conservative and religious city in America and lessons he learned about breaking outside our ideological bubbles and engaging with people we disagree with in a friendly way.

Lastly, we offered up some very amateur political analysis on the 2020 Presidential Race including some surprising similarities between Trump and Bernie. Full disclosure, we recorded this episode the week before Joe Biden’s South Carolina and Super Tuesday comeback so take it with a grain of salt. Sahil is a fascinating individual and I really loved how wide ranging the conversation was. I hope you enjoy this episode with Sahil Lavingia.

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Katherine Boyle (@ktmboyle) is a venture capitalist based in San Francisco and former journalist. For episode #7, I chatted with Katherine about escalating tensions between the media and tech industries, her path to becoming a venture capitalist and the threat that declining economic mobility poses to future generations.

Katherine Boyle is a partner at General Catalyst, a bi-coastal venture capital firm where she leads investments in early stage companies with uncommon missions. She's invested in the likes of Anduril Industries, Nova Credit, Spring Discovery and co-leads General Catalyst's seed platform. Prior to becoming an investor, she was a reporter at The Washington Post, and is passionate about the future of media.

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Kamal Ravikant is an entrepreneur, investor and best selling author of three books: Love Yourself, Live Your Truth, and Rebirth. On this episode, Kamal shares his views about fear, forgiveness and how your internal mentality can shape your external reality.

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James Beshara (@JamesBeshara) is a modern day renaissance man – an entrepreneur, angel investor, podcaster, author, musician. James is a prolific creator who operates with passion and he’s probably one of the most honest entrepreneurs I’ve ever met. James founded three startups including Tilt which was acquired by Airbnb in 2017 where he was Global Head of Airbnb Music. James has angel invested in dozens of startups like Gusto, Mercury Bank, Halo Top Ice Cream, Bolt and many others, including several multi-billion dollar companies, and is now a full-time angel investor.

This year, he launched the Below The Line podcast which is, without any exaggeration, my favorite new podcast of 2019. James is an advocate for mental health, a lover of philosophy, a beacon of honesty in the tech community and someone who always willing to help–he’s personally been very helpful in the launching of this podcast and now as our third guest. James has a book coming out next month called Beyond Coffee which you can check out at beyondcoffeebook.com and you call follow him on Twitter @JamesBeshara.

Check out our PodcastNotes from part 1: https://podcastnotes.org/2019/10/25/james-beshara-entrepreneurship-mental-health-creativity-paradox-podcast

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Trae Stephens (@traestephens) is a venture capitalist at Founders Fund with partners like Peter Thiel, Brian Singerman, Cyan Banister and Keith Rabois, where he invests across sectors with a particular interest in startups operating in the government space. He’s also Co-founder and Executive Chairman of Anduril Industries with Palmer Luckey, who founded Oculus, which was acquired by Facebook in 2014. Anduril is a defense technology company focused on developing autonomous systems for U.S. military and is by far one of the most interesting, and for some controversial, new startups in the last two years. In our conversation Trae described it as a real-life Stark Industries from Ironman.

Previously, Trae was an early employee at Palantir Technologies, where he led teams focused on growth in the intelligence/defense space as well as international expansion, helping large organizations solve their hardest data analysis problems. Prior to Palantir, Trae worked as a computational linguist within the United States Intelligence community. He began his career working in the office of then Congressman Rob Portman and in the Political Affairs Office at the Embassy of Afghanistan in Washington, D.C. Trae is a publishing a paper on Just War Theory In the Age of Technology later this month and you can follow him on Twitter @traestephens. Our conversation with Trae was a wide-ranging and illuminating. We hope you enjoy the episode.

Read Trae's latest piece: The Ethics of Defense Technology Development: An Investor’s Perspective
https://medium.com/@traestephens/the-ethics-of-defense-technology-development-an-investors-perspective-45c71bf6e6af

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James Beshara (@JamesBeshara) is a modern day renaissance man – an entrepreneur, angel investor, podcaster, author, musician. James is a prolific creator who operates with passion and he’s probably one of the most honest entrepreneurs I’ve ever met. James founded three startups including Tilt which was acquired by Airbnb in 2017 where he was Global Head of Airbnb Music. James has angel invested in dozens of startups like Gusto, Mercury Bank, Halo Top Ice Cream, Bolt and many others, including several multi-billion dollar companies, and is now a full-time angel investor.

This year, he launched the Below The Line podcast which is, without any exaggeration, my favorite new podcast of 2019. James is an advocate for mental health, a lover of philosophy, a beacon of honesty in the tech community and someone who always willing to help–he’s personally been very helpful in the launching of this podcast and now as our third guest. James has a book coming out next month called Beyond Coffee which you can check out at beyondcoffeebook.com and you call follow him on Twitter @JamesBeshara.

Check out the PodcastNotes for this episode: https://podcastnotes.org/2019/10/25/james-beshara-entrepreneurship-mental-health-creativity-paradox-podcast/

Show notes:
• 1:05 Introduction of James Beshara
• 2:18 Background of how the Paradox Podcast came to be
• 5:50 Why James is bullish on podcasts
• 8:24 Why radical honesty is a core part of James' life
• 15:45 Why James, a Catholic Texan, has gravitated to eastern philosophy and how meditation has impacted James' life
• 26:08 The genesis of James' serial creativity
• 28:56 Fact vs Fiction: the reality of being a founder
• 46:35 Why nuance still matters in the age of sound bites
• 52:10 How James became an angel investor and leveraged his own life challenges to help a new generation of founders
• 1:00:59 preview of James Beshara episode two available 11/1/19

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Jennifer Fearing (@jenniferfearing) is one of the most successful, innovative, and admired lobbyists in California. She left a lucrative corporate consulting career to advocate on behalf of issues that are close to her heart, especially animal issues. Jennifer successfully ran the 2008 Proposition 2 campaign, also known as the Prevention of Farm Animal Cruelty Act. She has led successful efforts to ban the sale of ivory and shark fin soup, to ban the use of hounds when hunting bears and bobcats, and championed numerous other issues related to animal welfare.

Jennifer spent eight years working for the Humane Society of the United States and in 2014 founded Fearless Advocacy, a lobbying firm dedicated to advancing the public policy agendas of causes she believes in. Clients include Pew Charitable Trusts, Pesticide Action Network, Defenders of Wildlife, the California Association of Nonprofits, Oceana, California Wildlife Officers Foundation and more. A graduate of UC Davis and Harvard’s Kennedy School, Jennifer has been featured on the Capitol 100, an annual list of the most impactful people in-and-around California government.

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Michael Davidson (@MPDavidson) is the CEO of GenNext (@gen_next), an organization that recruits business leaders in the private sector, educates them on critical issues like economic opportunity, education and global security and empowers them to have a direct impact both inside and outside of government. Michael is a super sharp guy who cares about the restoring the marketplace of ideas, reviving civics, and solving the leadership deficit in this country.

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