my family beyond with things way. Remember, just because you're doing a lot more doesn't mean you're getting a lot more done. Don't confuse movement with Progress. Way living, a paradoxical time where we have more comfort but less peace, more connectivity, less connection, more information, less wisdom. The purpose of this podcast is to explore these natural tensions with independent voices. Who will push our thinking tha This is the paradox. Podcast. Getting enough. You know I'm not good at it. You can learn quite a lot from experience. That's one thing.

Something after that have the will and determination to do anything about it. Everyone welcome to another episode of the paradox podcast I'm your host, Kyle Tibbits for episode number 10 Me of a super special guest. Gary Tan is a designer and engineer turned early stage investor. As a managing partner and co founder of Initialized Capital In 2019 Gary was listed at number 21 in the forms minus list, having invested in insta cart coined based Flex Sport Plan Grid Hello Sign and many others prior to Oh, I see. Gary was a co founder of Block platform Pasta Rhys, acquired by Twitter in 2012. Before that, he was employing Number 10 Volunteer, where he was a founding member of the engineering team for volunteers, financial analysis product and also designed Palin Tears logo. He has a B S and computer systems engineering from Stanford, and you can find him on his weekly started flog on YouTube and Instagram, and his videos are packed with valuable advice for entrepreneurs.

Gary is incredibly talented, and it's Saiful. I think what struck me most about our conversation is how humble, thoughtful and empathetic is. Hope you enjoy this episode with very tan Gary. Thanks for joining me on the Paradox podcast were about three weeks into the shelter in place order here in the Bay Area, and I think you're really the first region toe to move pretty aggressively with putting that in place. I'm Rob's recording from our respective quarantine locations, so still very much under some level of locked down. How are you doing on a personal level? And how do you think this battle against Kobe 19 is going?

Oh, I'm good. The hardest part is the child care, as you probably know as well. I've been really worried about Corona virus since January. Once you actually saw what China did, I think once you've been there, you realize they're not going to do things that are totally unnecessary. And that was one of my major major fears. You know, Is that what it would take to sort of tamp down on it? And now that we're seeing the curves starting to flatten, or at least the models are indicating that we're flattening the curve, that's a huge relief to me. And there's, ah, you know,

sort of. We're not done. We're not near the peak yet. It's in a few weeks out. But to see this outside of China and to see this shelter in place, actually having an effect and being very thankful for San Francisco, for California and for the leadership of, you know, these are side of the country. It's really great. Currently, it looks like we will have enough ice, you beds in California for the cases that are expected. And that means really, really great things for, you know, the people of California. And so, yeah, that's that's the best we can hope for.

Yeah, I share your sort of cautious optimism. I think that earlier on, probably in January and February when I was following folks like Apology and Scott Gottlieb that we're doing really great citizen journalism. I would say I was more worried because it felt like these folks were sounding the alarm. But there was not any urgency at all within the general populist within the media within, through the government to take this very seriously. And so I probably felt sort of most worried about Kobe, 19 in February as he saw kind of this this train wreck coming and we were totally unprepared for it. But then, as the level of concern really ratcheted up, I felt more confident that we might have a chance that actually battling against it and I think I think it's so interesting is each city. Each state almost has its own curve, and so we're seeing a curve in Washington state that looks very different than the curve and say New York City or even the curve in San Francisco. But we can look internationally to Italy and certainly South Korea and other countries that handle that far better than we did and have some optimism that we might be able to get through this, hopefully, sooner rather

than later. Program had amazing essay that came out yesterday about this, that you can tell a lot about countries in their media by how they handled this crisis. And his exhortation was we should probably remember this. We should remember the initial reaction from some of the people that there was skepticism about about the research about science, about, you know, the medical opinion that was coming out, and that matters. But it matters to our government, and it matters to how we make decisions and policy. If we respect science, frankly and for certain is pushed back reality. And it's never been more important than you can see this in, You know, the response of South Korean Taiwan. You know, the society still respect science and medicine, and in the worst was sort of saved off.

Yeah, they still respect science and medicine on one hand, but they also generally respect individual liberty on the other hand, and so it's a great model for us. We want to go the China direction of a pretty, harsh, authoritarian ish locked down which was effective for them. In the end, there's a lot of free societies Japan, South Korea that did much better than this that we did. We're just gonna have to make some cultural adjustments to really be able to live in this new world. And I agree with you that whether it's taking some lessons from this about how the media handled this, Howard government handled it even down to just basic individual things like hygiene and potentially wearing a mask in public transportation. There's some things in our cultural DNA that we should adopt and program into our society that will give us more resilience against stuff like this in the future. So I'm optimistic about some of the longer tail

effects as well. My partner Alexis of Hanyang, who he created, read it. And one of the things he's been talking about is the realization that there is 1/5 estate. So, you know, 1st 3 estates, obviously the three branches of government fourth estate being media as a check on that. And then now there's 1/5 estate that is citizen journalism in the form of apology, string of awesome. You definitely highlighted that very fundamentally for me, and it was astonishing how few people sort of took that very seriously early on and how it became our reality. But that's what we get to see all of the time. That's one of the most exciting things about society today is that the Internet will sort of present truth to us earlier, and we get to sort of determine what we believe sooner. Abs, That's a positive

view of yeah, where it's gonna decentralizing media in a sense, by having the rise of citizen journalists and also just as consumers and contributors to that discussion online. We're all ableto make up our minds for ourselves, and we already have to question everything you know. It's been demonstrated very clearly in this crisis that these narratives just shift so fast from like, absolutely master and effective to now Master recommended. We've seen the these narrative shift on No, just the flu. Thio. Oh, well, the flu is worse to Oh my gosh, the world is ending, and we've gone like the full gamut on these narratives in the course of like 30 days like multiple sort of narrative art. So I think it's been a great lesson, and I think we'll see a lot of decentralized media and citizen journalists coming up out of this and hopefully, like a 1,000,000 biology's will bloom out of the the wake of this. So I'm optimistic about that for sure. Switching gears a little bit So you're a full time investor in managing partner at initialized Capital. How has your sort of energy or focus shifted as this pandemic has ramped up here in United States?

Yet the great thing about how initialized works is we're actually eight partners, and we are able to work completely remote. So how we even make decisions is through software. We have two rounds of blind voting. Ah, lot of our discussion happens of resumed slack, and we sort of built the firm from the beginning to be remote first. So the only difference is I have a much shorter commute.

That's awesome. We'll get back to investing and founding companies and building startups in a little bit. But could you share a story from your childhood that really strongly influenced who you are today?

Yeah, absolutely. I grew up in the Bay Area, and one of the hardest things to realize now, as someone who works in tech, is the level of mistrust of tack in the Bay Area where you know, I'm in town, tingly. And I grew up in Fremont, you know, studied at Berkeley while I was in high school. I went to Stanford for undergrad and tech actually brought me from a very hard time in my life When I was a child, when I was a child of immigrants, my father struggled with alcoholism. My mom was a nurse assistant. She didn't speak English very well. She had a hearing impediment.

And, you know, we moved around a lot as a kid. You know, my dad got sick from his alcoholism. I remember being at times food in a secure, you know, growing up in one in two bedroom apartments. And you know, what really saved me was computers. I had discovered how powerful media could be. And, you know, the thing that got me into computers was actually my seventh grade teacher. I knew that I was really into desktop publishing, So this is,

you know, right before the website became a thing before the internet became a thing, you could go in tow, you know, Adobe Page maker. I think it was all this page maker at the time and you could make page layouts just like a newspaper. Only you could publish it yourself. And then I needed a way to get it out to my classmates on second parade and my teacher, Mrs Whitaker took my sort of 10 pages of underground newspaper and photocopied it for, you know, the 100 students in my class. And that became part of what maybe learn how to make Web pages. And I loved being that young, putting up a Web page that was a scene and then, having basically adults read it like it was written like a normal newspaper, you know,

wasn't that advanced? But I guess that's the level of Internet discourse. If you know your 14 year old King pass. You know, nobody knows that you're a dog on the Internet, right? But that's what taught me how to code. That's what opened up the Internet to me when I was, you know, 12 14 16 and that became a very fundamental part of my life and my first jobs making Web pages actually help me help my parents pay for their down payment for their home. Wow. And so for the Internet, you know this know how this ability to create things for other people became a very fundamental part of my life. And that's why today I just really want a lot more people to participate in. That lets out of one of my, you know,

foundational memories is that technology has remade my life and is remaking so many lives, and I just want a lot more of that right now. We're just at the beginning end of it like people talk about history being I wouldn't be great to live in the sixties. Wouldn't be great to live, you know, in the time of Jesus, it wouldn't it be great to live in like all of these

other times I'm like, Wouldn't it be great to live right now? Because right now in the that came online, no exact. That's an awesome story, and there's actually so much to unpack there. It sounds like there was probably kind of this magic moment where you're creating almost your first product, that's it, newspaper and your online, and you're learning to code and to build something from scratch literally something out of nothing, right kind of 01 moment that's very special. And then you have teachers printing stuff out, handling distribution for you. So it must have been kind of the very first moment of Oh, this is what creation is like. This is kind of lovely. Entrepreneurship is like and probably at that age,

you didn't fully have the context. Oh, are the understanding of what that fully would become. But it certainly was a seed that got planted that altered the entire course of your life. And you also mentioned, like, sort of the temporal, the timing nature of these things. And it's almost like that story, 10 years prior or 10 years later may not have been his profound. You're kind of like right at that moment, right? That special moment where spark of the Internet was just getting lit. And so that's that.

That is true right now, like there's, you know, a 16 year old or 12 year old out there right now. Who is discovering this? But instead of making you know underground newspaper, they're making an app. They're making a website. There's so much happening right now. It might be on tic tac

exactly. There were still so early in the cycle of what the Internet and what technology can do to help us create things from scratch. That it's not too late, I think, is an important message for people to understand.

Yeah, mark and reason when he came to the Bay Area from you. Why, you see, I think that's one thing he talks about, that he felt like he missed it. You know that the desktop revolution, personal computers, a computer on every desk and in every home that had already happened and he had missed it. And, you know, this is the creator of the Web browser.

It's good perspective. I think Thio keep in our minds. We contextualized these things. So your background, obviously you started early on coding Web sites and you have an engineering background. You were employing number 10 Palin Tear, founder of Phosphorus, which was acquired by Twitter. Now that you're an investor, what do you miss about being a founder in an engineer? And I think on some level you're still on entrepreneur because you've started with your co founder, Alexis, this firm. But what do you miss about kind of being in the trenches and building day today?

The biggest thing. It's actually really mundane and it sounds insane to say, because it's also the part that most founders really can't stand. But I miss the cycle of getting an email from a real user who uses your software. And then it's broken for that, nor you. It just doesn't quite do what they want. And being able to take that, go into the code editor, fix the thing, roll the website and then reply within an hour. Oh, yeah, that thing, it got fixed. And I've actually ended up making some of my closest professional friends from that people who I still we're gonna follow each other to this day From the kernel of that sort of moment, it's yeah, really, really fast cycle times and then building relationships literally through the software that you make is something on this a lot.

Yeah, I guess one of the most stark contrast between being an entrepreneur and being an investor are the cycle. Times has been entrepreneur. You're shipping stuff all the time. You're talking to customers. You're getting feedback like you said, from people that are using your product in the cycle times or crazy fast, and the learning curve, as a result, is is generally steep. I think investing is tough because the time horizon on when you understand what they're doing, a good job is much longer. Sometimes it's 5 10 years before even understand whether your investments are paying off such a look of probably other signals to figure out if things were going well, what are some of the signals that you look at now to kind of keep you in that creative flow?

Honestly, I am really blessed to be able to work with Founders, period, because you get to see that story play out a week to week, month, a month. And I think that our role is sort of soft advisors is that at best, it's sort of like being a chiropractor. It's like minor adjustments that end up becoming much bigger impact. And that's what we're sort of hoping for

analogy. You created a video while back to been creating lots of awesome videos about your $200 million mistake, and I kind of stuck in my mind as just a really interesting story, and I think that Silicon Valley is littered with the stories of folks that miss joining a company super early or they went one path instead of another. And I think they have to deal with the psychology of maybe missed opportunity because there's just opportunity at times, everywhere. And so you end up missing some really big things. He'd retell that story a little bit and just talk about both the story and the psychology around. Missed opportunities and maybe your perspective on it Now, now that you have some distance from that original story,

Yeah, absolutely. I was 22 23 years old. I had just graduated from Stanford and computer Engineering, and I went up to Microsoft was 2003. So the Web felt like it was fully dead by then, which is kind of insane, because that was the year. I think Facebook got started. And I have spent five years writing database backed websites, and I said, Well, I guess that's over. So that's like the first thing that was wrong. But that was the narrative right? And I think that that's something that kind of comes up over and over again in my life, that you kind of can't accept the mainstream narrative all the time,

and I think you're a big believer in this Like what I learned, Certainly from this experience, but over and over again, Is that you know, what do you believe that nobody else believes? And in that particular moment, you know, Facebook was spawned in the moment that people thought the Web was dead. And that was the exact wrong thing to do, right? So for me, I went off to a Windows mobile. I wanted to work on mobile devices. That was sort of the consensus thing that would be next. And the funny thing about that is the iPhone still didn't come out for another five years. So timing matters a lot,

and Microsoft was very safe. It gave me great health insurance. My parents were proud of me. And about that time, friends of mine went to start a company with Peter Thiel. And I was one of the first people they called. And so they flew me down at his expense. He took me out to dinner at his restaurant, freeze, Um, which I think actually close very quickly.

A terrible dinner, actually. But it made for a really great intro in the book where he talked about how terribly overly competitive

the restaurant. Yes, he learned in a very, very hard lesson that restaurants are not the kind of things you want to invest in your own. But he said, Hey, what are you doing in Microsoft? You are actually wasting your time. And he was so sure about this that he was willing to write me a check for one whole year salary, not. It was a zero risk opportunity for me. And you know, when aspect of privilege that I had at that point that I didn't even realize yet was as someone with a technical background who loved to build the only risk that I could take is not taking risk. And that was a really crazy inversion at that moment, and that's why it cost me $200 million. I know this is the universe sort of saying, Here's the thing that you need to work on,

like, who else could you start a company with other than the people you knew for years has started projects with like, you know, these were people I had known for a long time and being funded by someone who, you know, maybe he wasn't a billionaire at that moment, but he was extremely well known. In fact, I had ask him to come speak at Stanford multiple times, and he did, and he was very generous with his time. So for these things, to a lineup and for me to still say no. Yeah, that was a very powerful moment for me to realize What is reality, right?

My reality was really straight off the pages of Time magazine. Perhaps right TechCrunch didn't exist yet. Twitter didn't exist yet. I was sort of asleep in a way. I was, you know, they were working on enterprise software. Enterprise software was not hot at all. You know, the cool thing to do back then was to work on consumer software. But I think that I spent too much time thinking about what other people thought was hot and especially what the media thought. And the reality is all of those things where the lagging indicator they're talking about exciting, interesting things happening in rooms that aren't being covered 6 to 9 months after the fact, right. And so, you know, Palin tear at that moment was exactly one of those rooms to be in to create the future that just sort of happens all of the

time. Yeah, it's fascinating to because it sounds like Peter Thiel was one of the best people that could have given that sort of message to you because obviously referencing 01 again, he talks about being in this sort of mimetic competition as a lawyer, like in law school, and then joining a talk to your firm and then finally realizing I'm competing in this game because society says I should Or maybe my parents are proud of me. Or there's a scoreboard that I'm kind of operating against and just finally realizing I just need to get off this escalator entirely. And I just need to walk out the door and go do something else, which again, with no media with no cultural narrative out there to support that, that is a truly sort of original thought, or what people might call contrarian to be like The best thing to do is to leave your law profession or to leave a really great job at Microsoft. So you're a fan of Westworld, by any chance. You know, when I watched the first I think season or two, I lost.

To be honest, ever since my daughter was born. It's Yeah, yeah, and marijuana and frozen to know Florence to that. But I should get back into it cause I do have an

HBO now, so I just, uh I just bring it up because there's a very deep team in that No spoilers around awakening right both in the sort of robotic host world, but also in the real world for humans. So and I think my $200 million mistake is really a little bit of a story of an awakening. Like I was asleep and then I woke up,

and life has this way of kicking you back onto the path that maybe you were supposed to be on. So you started joining his employee number 10 it talent here. It's not as if you completely miss the volunteer boat and talk a little bit about just that experience. And he juxtaposed against your experience at Microsoft in terms of that continued reawakening that occurred as you went off, sort of the script that had been laid out for you in

your own head. Yeah, not to get too esoteric, but the big realization is that every organization is basically a machine and you individual human beings. We're not, you know, parts of a machine where people and then some of us who want to take the risk have the ability to make new machines. And that was what I got to see up close and personal in parent here being worth getting multibillion dollars now thousands of employees. There were definitely things that you needed to do early on. So what I learned was really how powerful and how important it is to create these new machines. Being a part of Microsoft was really being a cog in a machine that was built many, many years ago on backs of a few very giant monopolies, office and windows. And even when you were at a company like that, that was trying to do something brand new, which was Windows Mobile, it was very hard to sort of leave the orbit of the two major profit centers.

Where has and this is sort of Ah, common refrain for me is that I realize it's way more fun to be ah, pirate than to join the Navy. There just some people who were actually built for it, right?

Yes, some people are built for the Navy, and some people have the disposition of a pirate, and so you have to sort of pick your lane on some level. And I think, like you said, there's so much inertia around a Microsoft or Google or a Facebook at scale that it could be difficult, obviously, launching new products there. And if you're someone who really likes that creative process on having a very blank canvas, it makes sense to sort of be drawn towards the Pirates side of the ledger.

Yeah, I mean, a lot of it comes back to pure agency again. The thing I miss the most about product at some level is that fast feedback loop. But then, also, the reason why I could do that is that I had 100% agency, Um, and so if you want to create, it's a short feedback loop. Plus, agency makes a really big difference. But that's also why it's very powerful to go and join a start up and get as much agency as possible and do that. And then that prepares one the most to be the captain of that pirate ship someday down line.

Definitely. I love that we're continuing with the with the metaphor, switching gears a little bit. Can you talk about how having refugee ancestors that escaped other countries to come to United States have its influence, your worldview? And do you think that having immigrant parents were being an immigrant yourself gives you an advantage when it comes to founding or building a company?

Yeah, absolutely. So both my mom's side and my dad's side basically fled sort of the 20th century. And in Asia, China in particular, was a very intense place to be throughout the 20th century. On my mom's side, my grandfather ran textile factories in south China of those factories. He had to abandon it because of the Communist revolution, and they fled to Myanmar, where they, you know, literally had to take whatever they could turn it into gold so it into their pockets and flee. And then they had to do it again from Myanmar when there was anti Chinese rebellion and that, honestly, is a part of my history. And what helped me really understand Bitcoin Very early on,

we in the West have incredible privilege, and in Corona virus would just put that in the face just now that, hey, these things are all a little bit made up. Those in power don't have a complete crystal ball. Sometimes they don't act in it. They should. And that's one of the world we live in. All of that really underscores what you get to do here in America the at the end of the day. That's the beauty of coming thio. A free society. You can run a business the way you want. You have actual ownership and you have rights and that those are all things that we don't count as blessings nearly as often as we should.

Completely, I agree I don't have immigrant parents, but I think my sense just in a meeting with and talking with immigrants across every part of society, from the uber driver from Kenya to the founder of a company. I think the common thread or the connective tissue that I always here is they just have such a deeper appreciation for the freedoms that we have here at a visceral deep level, and I think that the disadvantage of being born here and I guess I can say this is someone who's born here and doesn't have immigrant parents is. It's very easy to take it all for granted. It's almost like a fish doesn't know it's in water, right, That's its environment. And it just thinks that AH, free society is the default when really it's if anything, it's sort of the exception, not the rule throughout history and so having parents, grand parents that live through the 20th century, which the majority of it was actually pretty awful, probably one of the most horrendous in history.

I think we tend have historical revisionism, but yeah, it was very easy to just completely lose gratitude around the freedoms that we have. And I think that's my gratitude is such an important thing to try to instill in your life toe, try to gain perspective, and I think the Corona virus thing to your point. It has sort of put a pause on society and giving us a moment to reflect on okay, this is a really challenging situation. There's an economic crisis, is a health crisis. People losing their jobs, people are losing their lives. This is a dark time, but a bit of the paradox there is that, you know, it's been a real blessing to spend time with my family.

So hopefully that gratitude is something that we can build a muscle around. Absolutely. This may be a bit of a connected question and actually stems from a tweet that you fired off. I think it was at the end of last year. But do you think that sort of this belief in free markets, which is, in my opinion, connected to a free society, is declining in the West? And what might be some of the factors that are causing people to lose faith in the free market as a vehicle for lifting people up out of poverty out of dire circumstances? I think certainly your backstory that you shared earlier in the conversation is, in my opinion, that is the epitome of the American dream. But talk a little bit about that, and whether you think the American dream is still alive and well, or whether it's on a respirator.

No, I mean honestly, you know, testimony. You know, God bless America. I naturalized that you as a U. S citizen. And any time I go to another country and then come back, honestly, I want to kiss the ground because there's a lot here that we totally take for granted. You know, I think it's a tough time to your point. I think people are forgetting what we have, and I think the hardest part is probably around the argument around privilege. The reality is like we all have a crazy amount of privilege and then at the same time, there is sort of this ongoing debate around exceptionalism and whether or not people should strive or cans drive,

I hope that we never lose that. You know, I think that people can really fundamentally effect there their life through their own hands and as long as that's reflected, sort of in society. I think that there's a chance, right? Even I think it's hard to ask people to take personal responsibility at the same time. We need systems that airfare and, you know, I also see that other side. They're definitely a systemic, totally systemic flaws in society around stuff, and we're not done fixing those right and so it's not purely a right versus left thing. I think it's both,

Yeah, I totally agree. It's We have a two front war where we need to continue to fight for quality of opportunity, expanding opportunity for more people. We have so much work to do on that front, without question, and anybody that pretends that we don't I think is completely kidding themselves. On the other hand, I think you mentioned agency earlier in the important of agency, whether it's starting a company, you're just in your own life and having a sense of efficacy that you can really have an impact on the way your life goes. And we won't encourage that at the same time as we're trying to fix on improve society at the systemic level. And I think in some ways they're interrelated. The more people that are able to leverage the agency and the gifts that they have in the talents, they have to do good and to create things of value. I didn't give more people that will be helpful in the fight to change and fix the systemic problems as well. And so bad scenario is where on both fronts,

you say, look, things are really bad. Things were broken across the board and we have very little chance of fixing them, and so you sort of de motivate people on the agency side and you say, because things were messed up, you don't really have a chance of achieving whatever you want to achieve. That's where our chances of actually keeping the American dream alive probably do start to decline on some level, because perception on some level is reality. People have to believe this stuff. Americans just really a set of ideas and beliefs, and we all come from different backgrounds and different families and different religions. And that's the beautiful thing about America. Is this melting pot? But if we lose faith in some of the ideas, some of the core ideas that have really pulled us together,

particularly when especially prior to Corona virus, you've been very cold, part and very polarized. I think that is a cultural challenge that I worry about. But more people need to hear on people like you.

I mean, I think that technology has a rule to play here because the stagnant view of society is that this is all zero sum and there are many, many zero sum games in the world, and the only lever we have is actually technology can one plus one equals three. I think that over and over again. Increasingly, that can't be true. The more we have people who are founders who are making companies that are actually solving real problems, you know, that's just pure value that gets sort of sent out into society. And if we can make the pie bigger than that's how we make space for everyone, that's right. Technology is literally the thing in society that is the most growth mindset. And that's why I think it's very, very important to foster new invasion and new companies and to get more people to start these companies. Because if someone's right, then we have a service that you make society better.

Like it or not, right, it's not perfect. Anytime you move the cheese like they're people who get hurt, and I think tech leaders do you need to spend time thinking about that. But let's not throw the baby out with the bathwater here. You know there is still a march forward, and you know, it's easy to say it's going backwards. I think we're going forwards and as almost people are thoughtful about how this is happening, I'm still pro tech. You know, I'm still a technological utopians like I think that we can get Thio Gene Roddenberry's

planet, but I don't have a technological utopian, but I'm certainly attack optimists. I think tech is a It's a tool, right, and this is why I worry a lot about more the societal layer underneath it and these things are intertwined, so they're very complex. But I think that if we motivate people, empower people and tech leaders look at these things with a great sense of empathy around what they're doing and the changes that they're leading to because they are building a different world. They're essentially seeing a world that they want to build in there, trying to create it, which is very hard. And I think if it's done in the right way, with the right empathy and the right kind of motivations, I do think we can definitely improve the world, and I think that you mentioned building things that matter and solving real problems. Chris Dixon wrote that famous Bog posts about the idea maze and navigating the idea. Maze is a founder. Can you talk a little bit about how you think about the idea maze and how influences maybe the founders that you choose to bet on?

Yeah. I mean, I love Chris and you know, he was one of my angel investors when we were working on my start up in 2008. Such a brilliant guy. But the idea me is is really sort of a true north around this because actually posted the video this morning on you know why now, why you write so actually, taking a step back, the idea mazes Fascinating because it's sort of Presupposes itself a tournament model. You know, Silicon Valley starts off at the top with many, many people who were trying to start all kinds of different startups solving sometimes similar or, you know, same space type problems. And then they go off into the maze and some of them I hit a brick wall and then the start up guys and some of them make it all the way to the center of the maze and they win. Then you have a multi $1,000,000,000 start up. And so the salient fact of that is,

can you tell what is going on with the maize based on who else has gone in and what have they tried? There's a great quote from Alcoholics Anonymous. At the end of the day, that's insanity is doing the same thing over and over again and expecting different results. And so this is probably the thing that I've been spending a lot of time trying to figure out how it to Saul's. I'm definitely trying to address some of the obvious dead ends in the maze through my YouTube general. Um, the basic problem, if you look at, you know, 10 startups that fail. And one startup that succeeds is that it's actually very hard to disentangle the quality of team or lack of skill from the lack of execution. And then there's a whole timing piece. There's so many different variables that this is very much in art and not a science at all. The closest thing to a solution that I've been thinking about doing is some sort of open knowledge graph or sort of ontology for, oh,

business activity, maybe rank ordered by U. S. GDP, eh? So you could sort of tag every startup and the amount that was raised. I mean, crunch base should probably do this and then, like

actually starting to map the idea maze a little bit, right? If you're Tom, map

the maze. Yeah, I'm That would actually help founders a lot and probably help me seize a lot. And that sort of treating the startup game as almost a research project, right? But that framework is super useful because it actually gives you parameters to make the situation better. The bad version of this in Silicon Valley is again a tournament model, not that different than trying to become partner at a law firm, right? It's, you know, grist for the mill. But I often worry about this because that's the part that I think is zero sum. And that's not the world that I want to live in, right.

I love your idea of Maybe this is part of the motivation. Like you said, with your YouTube videos or trying to map the maze a little bit is it's very high leverage if we can get all the folks that are either founding companies or building companies or thinking about doing either of the two Thio have a higher resolution picture in their mind of how to navigate the idea mates, because if you can propagate that across a network of people not just in the Bay Area, in sort of the core of Silicon Valley, but across the world. You have more entrepreneurs and founders that have a better chance of building the right thing. And in a non zero sum world, there's many people that can get to the middle of the maze and win. It's not, you know, I get there first. You have to lose for me to win type of thing. And so that seems very high leverage to create something like that. And to do it from the standpoint of not trying to maybe build a company or monetize that per se. Maybe there is a company there. Maybe there's not, but just to do it, to improve up level, the whole ecosystem, Yeah.

I mean, the thing is, this is already happening in the minds of veces across Sand Hill and around the world. And then everyone has their incomplete maze. Yeah, they only see you know, the pitches that they take. I think that that's why this is one of the most interesting times to live in the world to date, because what the Internet and what software lets us do is Prince End basically the individual right. The limitations of I only have 120 hours of wakefulness times 3 65 times. However many years I get to be on the earth and the Internet and software done right allows us to bridge that across many

people. Yeah, the way bees build like a hive or something like that, you can all contribute to something that is a multi generational, durable knowledge source that could be passed on from generation of creators and entrepreneurs.

That's the most meaningful thing you can do in your life, right? The great quandary in life is that you know, the more free you are, the fewer sort of dependencies you have on other people, the more disconnected you are from them and and vice versa. That's why the man's search for meaning is often about being a part of something greater than themselves. Yeah, and we live in this time now where that is literally what is happening. Using software.

Yeah, that's a really good point. I hadn't even connected those things before, but that's a great reference toe. Two man search for meeting. How do you think in a Post Cove in 19 World it seems like the idea maze thing still holds true. It's just that we're in a very, very interesting paradigm shift where, ah, lot of maybe themes that we've talked about for years are gonna get accelerated. Maybe some are gonna get decelerated. The world coming out of this is gonna look fundamentally different. Then it certainly looked a month or two ago. How do you think about that? How do you think about navigating the postcode 19 world, both as an investor that's placing bets on founders and as a founder who's dealing with a whole new set of inputs in terms of how reality it shifted?

That's a very deep question. I think there's sort of a pessimistic view and an optimistic view. Pessimistic view is Kimmy. Overall financial system sort of survive this. If you look at earnings, if you look at activity, this is sort of unprecedented in modern times. And what if the overall financial system suffers greatly? The SP A loans are very inefficient mass job loss. It's very hard to restart these businesses that makes the recovery very slow. And that's where you're seeing you know, people like Tomas, but, you know, honestly, We also have sort of said that to some of our companies that you maybe need to be prepared for 30 months of runway, which,

yeah, actually longer than what a lot of people actually have, and that's very dangerous. The optimistic view is that we also have a money printer that hopefully, perhaps guided by some software, increasingly could even learn more effective that you know, if we have that money printer and it is applied judiciously improperly, which is a big if there can be a V shaped recovery. And while startups will suffer, some get massive injections of basically zero CAC that they can turn into enterprise value like insta cart or refund of that meal kit company called Gobble. That's very, very quickly, and especially for consumer startups, just zero cactus, so powerful, incredibly powerful.

So they're gonna be cases where they're sort of slingshot stories that are actually amazing, and then a lot of it is a little bit out of our own power. It's up to the Fed. It's up to our government and the FDA, the banks and these were very large systems that you know. It's not clear what will

happen yet, You know, I think there's an incredible level of uncertainty, and anybody that has any level of certainty about how this is gonna play out is almost by definition wrong. And so who

was prepared for the worst? Basically, the best that anyone can do right now.

Completely. So you and your business partner, Alexis, or both dads. And he has a really great podcast called business debt, which was very cool idea for a podcast. How is parenthood change your life? And how do you find a balance between work and family, particularly, and quarantine, But just more in general?

Yeah, I think the biggest challenge for I mean people told me, You just don't have a visceral understanding of it until it actually happens to you. I just can't work the way I did in my twenties, in my early thirties. You know, I could take, you know, 100 hour weeks and max it all the way out and really optimized for work and to the detriment of all other things. And that's just not something you can do when you have a family and you have really responsibility to these little ones who, you know, you didn't have to have him, and that's something that I think about every single day. And it, uh, it means that we have to work a way smarter. It means that we have to actually invest very deeply in our organizations and in basically again trying to get leverage on whatever hours in the day that you can work.

And that's extra true right now with no child care. So you know, one thing that we've really encourage our portfolio founders to do is, you know, especially founders, don't have kids really take note and realize how hard it is for the parents and their organizations Right now, like, be a extra mindful of that because you know people who don't have kids, Man, you're learning French like fleas.

On a personal day, it's great. They binge all. Tiger King.

That's right. It's

lacking. In plus one episode, I barely snuck it in one night. Parenthood's interesting in the sense that definitely my thirties have been very different for my twenties in terms of just my time and my my availability to just kind of work all the time. But on the upside, I would say it isn't really interesting, forcing function around focusing and prioritizing in the right area is because you have limited time, right as a parent, because you're going to spend time with your family and you should. I also think it just gives you sort of a deeper reason for why you're doing what you're doing. I think back to my 21 year old South and I was, you know, just me and just by myself. And I was just working and and it's a great time to really learn a lot of skills and to put, you know, 80 100 hours weekend. But compared to now,

I would not want to go back to that because I think I might have a much deeper appreciation for why I'm doing the things that I'm doing and who I'm doing it for. I mean most, like explicitly, right? It's just you won't provide for your family. You want to provide for this next generation that's coming up behind you, so they have a shot to go and do what they want to do. And so I think being a parent has been one of the most mind altering mindblowing experiences. I think that people undersell it and they're certainly challenges. I'm not here saying it's it's easy all the time. But be a parent, it will. It will alter your mind in a lot of different ways. Yeah, that's been my experience,

Dad. Bod is a real

thing. Head out of your body chemistry, too. So you're creating all these awesome YouTube videos. Talk about that impetus for wanting to do that. And what does? Being a creator and really just operating in a very creative mind set around, you know, cinematography and around filming and story. What does that? What does that do for you beyond just obviously creating really great content with really insightful advice? Yeah,

honestly, I started doing it because I met Casey Neistat in person. Alexis and I always was a big fan of his YouTube channel. And then after I meditated on it a while, I realized, you know, this is sort of a perfect bringing together of all of my various interests. I love music. I love film, and then I have a way to have a direct relationship with possibly thousands of people. And then I have been doing Twitter for a long time. But now this could be a much more potent version of it where, you know, I sort of basically spend like five or 10 minutes with people who follow me on YouTube and already that's been really powerful. It's just a different way. It's literally a different consciousness, actually,

and it's a brand new one that is very unnatural but also very interesting. And then it lets me sort of exercise. All of my creative juices isn't yeah, film and edit, and you choose music and put it all together in the matter of maybe two hours a week, maybe an hour and 1/2 a week.

That's pretty good. It's a really great way to scale yourself, right, because you're having conversations with founders and you're talking with people on Twitter. But the video is almost like the deep cut. I mean, you'll share something on Twitter and Twitter's gray. I love Twitter as well, but if folks want to go a level deeper and kind of have the face to face thing without you having to be in 1000 zoo meetings a day, that the YouTube channel is really great and you too has been around a while. It's very easy to sort of just take that medium for granted, but actually is really semi miraculous that a synchronously at any time folks can tune in to your latest thoughts and really almost have, like, a mentor mentee relationship at scale without needing toe. You know, card up your time in tow five minute increments from for 80 hours a week. So

I think one of the deeper things that, uh, let's talk a lot about is, you know, going back to the fifth Estate and going back to overall what's happening with the Internet today. This is actually a part of it. Just being able to have a direct channel two people is very powerful. And then, you know, while I respect the fourth Estate and a lot of my friends are actually reporters and you know, they're great, they serve a very important role in society and at the same time, like I also want to be ableto have a channel that is unmediated and only after Twitter gives me that, and I YouTube gives me, like a whole other style of that. But you not only can I say what I really want, what I think that you know people need to hear to just try to help them. I also can sort of highlight the people in my life who I think more people should pay attention to. That I need to have you on my channel

is what? We'll definitely do it as soon as Radha Corentin, Let's let's make that happen. I think you're right. I think it's about amplifying voices that need to be heard. And, yeah, not having a gatekeeper for everything that you want to get out into the world is a really powerful thing that the Internets provided to us. So we're in the last two innings, probably of the podcast. One thing that I wanted to try, and we can keep this relatively quick. I have not really tried this before. It's this idea of turning the tables where from the question you're the host of the podcast and so you can fire question my way, and I'm obviously unprepared for what it is. And you maybe I'm prepared to ask it, but just kind of a fun little segment. Then we'll get to the last few questions that I ask

Every guest. Yeah, of course. So in 2014 you posted. Ah, high rate of learning is the most bankable asset you can have in the start up world. And I'm curious, you know, it's been six years since then. Has that changed? You know, are there stories from the past six years that you really exemplify that? And how do you think that's evolved today in 2020?

That's a great question, I think. To be honest, it's probably one of the block post that I wrote back in the day that maybe has more or less stood the test of time. I think I still believe it pretty deep down in my core, if you're ever in a position where you're learning, starts to decline and you think about learning is some sort of curve or slope and it starts to plateau. Even if a lot of the other things are going well from like a work standpoint, I think that's a problem, because I think there's an opportunity cost of not continuing to climb whatever the next learning curve is. I think that the proof of this is and I kind of get to This is the end of the piece, which is that you look at people, the warren buffets of the world. You know, Charlie mongers, even people like Mark Cuban, whoever folks that have been successful in business by every conceivable metric,

Why do they keep playing the game? Why, you know what what, 80 years old is one buffet still sort of playing the game? And I think it's proof that learning actually is the end unto itself. And so, yes, I think when you're 20 25 30 35 I think a leading indicated on your success and work is gonna be climbing all these learning curves. The great thing about start ups can be, and this isn't universally true, But it can be that you're put in a position in a scenario where it's almost trial by fire and you're gonna learn a lot faster. Is this quick iteration cycles that you talked about? It's quick decision making, kind of the type to type one level, and so it's a great accelerant for your rate of learning, which I think ultimately earns compound interest and ultimately reflects in other metrics what you're looking at compensation or they're looking at the type of company work for anything like that,

The one caveat I would say is that Post is pretty startup centric, I think, for maybe of Silicon Valley audience, that's relevant. But I think for folks generally I think that sometimes going outside of your comfort zone and switching into an area, whether it's like you said, starting to make videos or doing a podcast, which is not something that really came naturally to me at all. I think that is where you start to learn is when you flex out of your little zone of comfort into new areas. And I think that beyond career and work, it's a good approach. Life this way Think parenthood is learning curve. I think becoming fit and learning how to be more mindful is a learning curve. And so I think I have a more holistic view on it. But I think generally the headline of learning being the most important metric certainly and work possibly in life. I think I'd still generally believe that

well, it's Ah, there's levels to it. Game sort of is infinitely deep.

Yes, like like like layers of an onion. Totally great stoker. These last few questions questions that I ask every gas you can take him in any direction that you want. The 1st 1 is a question that you already referenced earlier on. It's actually a modification of the Peter Thiel question interview question, but what is something that you believe that most people don't?

So most people believe there's too much capital chasing, too few ideas and too few good people, and I don't think that at all. I think that there are basically infinite problems to solve, and then they're actually infinite number of really, really sparked driven people, Your infinite. It's certainly not actually infinite because there are a finite number of people. But I do believe that given the right circumstance and the right, frankly, community, the right values, people can actually really change, really make a difference not only in their own lives but in the lives of the people around them. And the onus is on the people who are actually creating those systems to think through the needs of those people. So great founders of great designers and they're truly actually impacts. They're actually thinking about all the stakeholders.

You know, the customers, the people who are all sort of involved. It's a dance right you're throwing a great party and a great party planner started thinks about all of the things into that every last detail, and we need a lot more of those people. We need a lot more parties, and we need a lot more great party planners. And it's not easy to do any of those things is not easy to start a company, but that's what is needed because that's how we solve problems.

Yeah, the too much capital, not enough ideas to deploy it against is a mean that's pretty broad based. I mean, you hear all the time, and I think that obviously we know each other kind of Twitter and I followed you for a number of years. But in this conversation, really, what I'm hearing is that a big part of your life's work, whether it's you're investing and founders to initialize or building companies previously or doing the YouTube channel or sharing ideas broadly and freely, is around this idea that look, there's a lot of people that can build really great things. It's not as limited as we think. The ceiling is much, much, much higher than we can even imagine. And so by empowering people either with advice or with capital or with a word of encouragement or with an idea and insight. It's actually executing against that belief that most people don't hold. It's not super cool how, how intertwined that belief is with with what you d'oh,

that's the life work. That's what I signed up for. But it's testimony like, this stuff changed my life, and I believe and I see it. I see it over and over again. They're just amazing people who were doing things that really matter. And it's not all that, obviously. But let's not throw the baby out with the bath water right? There are bad actors in Silicon Valley. There are founders who are just in it for the money or the power. And, you know, that's always been true in society. But there are the good ones out there. Look for the helpers. Look for the builders.

That's awesome. I love that. What's a problem that you're concerned about that most people are not,

I think, um, going from very little privilege to a lot more. After graduating from Stanford, I realized now how much the credential matters, and the danger is that there's a credential trapped, then s O if you didn't go to the right school or you didn't get in through some application process, you didn't get into Oh, I see. You know, these are things that are gates to society that close people off from the futures that they want to have. And I think that's a very profound and dangerous Newman society. Yeah, I don't have a solution for it, but, you know, this is actually a fundamental theme of Westworld Thio. It's that people get, you know, sort of traps, and there needs to be a way to both awaken but then escape.

That's fascinating. Going back to the early part of the discussion around folks with the credentials. Maybe it's in the media and the government thio, um, be decision makers or narrative makers. I think what we've learned, especially in the last 30 to 45 days. Ah, lot of this stuff is broken. I mean, we look at the education system, we look at the college debt crisis. There's something fundamentally wrong about credential is, um and I think there's a There's like a rising backlash against it. It's unclear to me what the solution is. But I think, like you said,

if you want folks to be able to really improved their standard of living and chased after whatever it is that they want to dio credential is, um is antithetical to that. It's a problem that needs to be solved. And it means that a lot of the institutions that we have, whether it's I don't know some of the four year colleges or whether it's some of the media institutions or whether it's certain aspects of federal, local and state government that's gonna need to change, and I don't know what shape it's gonna take, I have no idea. Particularly now, I'm probably less certain now than ever on how that's gonna shift. But I think the thing that I am certain about is that it's going to need to shift because these old templates, these old models, for how we help people improve their lot in life. A lot of them are not working. So

deal talks about this recently. I think in the last year he talked about how some of the top colleges are. I won't name names, but they're actually like lions for a nightclub, right?

Yeah, Studio 54. I think it's what he calls what calls are for.

You know why? Why can't those credentials actually expand by a lot?

And you actually, with the Internet, there's no reason why I can't. It's just it's just literally. It's the nightclub thing. It's like if everyone's in your nightclub, your nightclubs, not that nightclub. So we're gonna have to. We're going to figure that out as a society last question. What is the best piece of advice

you've ever received? This is pretty easy, actually. When I was 16 years old, I interned at actually one of the first digital agencies in San Francisco called The Jason. See the founder of that firm and you're safe there ended up selling that company for think 50 or $80 million to one of the public official agencies. And the coolest thing is, he worked on the first Apple Online store, and I learned how to write pearl and right database applications working at that firm, and I asked him, you know, Well, you started this. How did you get all these people to work for you and how did you do all of this? And he took me aside and said, Well, you're an engineer right now,

and there's gonna be a really big impetus from every part of your life. You know, it's the guidance counselor to your professor, to your your parents, too. Put down one title on your resume, and I encourage you to not allow that to direct how you actually live your life and how you study and what you try to. D'oh! So you're not, you know, a Pearl database. Back end engineer. Learn design, learn front end engineering, learn marketing, learn sales.

Be a study of human psychology. Be a study of media. Be a study of business of corporate finance like there's no task or discipline that is beyond you. You can learn it all, And if you want to be CEO, you actually need to be able to do that. You don't have to be the best in all of those things. You should already be great at a few of those. But if you can understand and manage all of those functions that you will truly be fit to lead,

I think that's fantastic advice. Sometimes there is a cultural pressure to put people in boxes. We like to categorize everything. I think we over categorize things. And so to truly just break out of that and just say, you know what I'm not gonna be put in a box is a very liberating thing. And I think we want more people to do that. I think the more people that do that in society that just break the mold and continue to break the mold, the better society becomes because people are actually gravitating towards their true north and their true talents. So I love that advice. It's fantastic.

Not a number. I am a friend.

So if folks particularly early stage founders want to reach out, what's the best way for them to get connected with you?

So right now I am open D EMS on instagram. So that's sort of the best way to get in touch. Hit me with a follow and deal on any time.

Awesome. Well, Gary, this has been a fantastic conversation, really, really, truly enjoyed and so nice to actually connect face to face despite being in quarantine after several years of going back and forth on Twitter. But thanks for carving out time. I really, really appreciate how generous you were with your time

today. Thank you so much for having me.

We appreciate you taking the time to join us for this episode of the Paradox Podcast raining for commute length conversations with original thinkers that will push your perspective and pull you into the marketplace of ideas. If you're new to the podcast, we encourage you to check out our previous episodes. In episode number nine, I chatted with Jeff Morris Junior about investing in a post Cobain 19 future nonlinear career pass in times of economic uncertainty moving to Kansas to break into tak and the UN bundling of talent. So, uh, just applying Thio all these countries, it has, Um, I guess you could say bad luck or maybe worked out as it was meant to be, but I applied to be one of the 1st 15 employees. An uber. I rented a desk space at this place for the rocket space, which was probably the original way work in San Francisco. As sat next to the earlier per team. I have a table next to me,

and I applied to join the team maybe like a 50 page jack, and they want interview me applied to Twitter where my brother in law works. I think I would have been like a top 101 15 point there. Didn't get that on a planet. Airbnb is like a top 50 employees and didn't get that. So I was kind of like shit. I found a lot of good cos I wish I wasn't in the best back. Clearly an act for identifying good cos early. That was a good sign. That was a special time period to see. There was more white space. But then I want to sell us out West and that this team from a company called bizarrely, which is just raise like a $1,000,000 a day before the weekend, away from the folks that cash in culture and other people. It's just a really exciting idea. I follow the hiring manager on Twitter.

He posted a job. I was the first person applying to AM the next day they hire me a two month contract, depending on me moving to Kansas City within 24 hours, and I just said, Fuck it, I'm gonna go do this. At least it'll be you attack industry, and then I can kind of figure it out from there and ended up staying there for about 3/3 years. But that was that was my God, wasn't it wasn't glamorous. I did, because the city thio to break an attack. And I think it's used to, like, see people on Twitter and think they're different from you or they use like the pot was much more obvious. But for me,

it was like the police obvious path. Thio Get a Quick Housekeeping note. We just launched a new Web site for the podcast at Paradox podcast dot Co, which will have all episodes and everything you need to know about the podcast. If you enter email address and subscribe, you'll get new episode sent directly to your inbox 1 to 2 days early, and you can always drop us a line on the contact form. We read every single message and really value constructive feedback. That's a wrap for this episode of the paradox Podcasts. If you'd like to connect, you can follow me on Twitter at Kyle to bits. If you enjoyed the episode, please rate review S and iTunes to spread the word until next time.