The Tim Ferriss Show - #81: The Rags to Riches Philosopher: Bryan Johnson's Path to $800 Million

Episode Date: June 12, 2015

Bryan Johnson is an entrepreneur and investor. He is the founder of OS Fund and Braintree, the latter of which was bought by eBay in 2013 for $800 million in cash. Bryan launched OS Fund in 2014 with $100 million of his personal capital to support inventors and scientists who aim to benefit humanity by rewriting the operating systems of life. He cultivates real-world mad scientists. Our conversation includes his rags to riches story (and strategies), his philosophical hardwiring, negotiating/sales tactics, and even parenting. We cover a ton of ground with a fascinating and deep mind. Bryan's investments include endeavors to cure age-related diseases and radically extend healthy human life to 100+ (Human Longevity), make biology a predictable programming language (Gingko Bioworks & Synthetic Genomics), replicate the human visual cortex using artificial intelligence (Vicarious), mine an asteroid (Planetary Resources), reinvent transportation using autonomous vehicles (Mattternet), and reimagine food using biology (Hampton Creek), among others. Enjoy! Please check out the sponsors for this episode, which I’ve used myself: Athletic Greens —My all-in-one nutritional insurance policy. 99Designs — Your one-stop shop for all things graphic design related. I used them for the book cover mockups for The 4-Hour Body, which later hit #1 New York Times. Show notes (links, resources, books, etc.) from this episode can be found on my blog here: http://fourhourworkweek.com/podcast.***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Brian, sound test. What did you have for breakfast? I had an omelet. An omelet. What was in the omelet? Peppers, onions, peppers, tomatoes with no meat. I love how you reordered those ingredients. The mind

of Brian at work. At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question? Now would you see an appropriate time. What if I did the opposite? I'm a cybernetic organism living tissue over metal endoskeleton.

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Friday is only available if you subscribe via email. I do not publish the content on the blog or anywhere else. Also, if I'm doing small in-person meetups, offering early access to startups, beta testing, special deals, or anything else that's very limited, I share it first with Five Bullet Friday subscribers. So check it out, tim.blog forward slash Friday. If you listen to this podcast, it's very likely that you'd dig it a lot and you can of course easily subscribe any time. So easy peasy. Again, that's tim.blog forward slash Friday. And thanks for checking it out. If the spirit moves you. Tim Ferriss, the Tim Ferriss show for the first time, don't take my lack of seriousness for lack of content. We have a very important mission here on the program, which is to deconstruct world-class performers, to interview people

like billionaire investors, chess prodigies, actors like Arnold Schwarzenegger, and so on and so forth, and everything in between. We have athletes, we have memory champions, and there are commonalities across all of these different disciplines. And my job is to tease out the beliefs, the routines, the rituals, the favorite books, all of the tidbits that you can apply in your own life. And this episode is no exception. Had a blast with this. My guest was a friend and very impressive entrepreneur and investor, Brian Johnson. That's Brian with a Y. He's the founder of OS Fund, which I'll explain in a second, and Braintree. He sold the latter to eBay in 2013 for $800 million in cash. Now, that is more than enough to retire and kick back in a hammock

and lather yourself with coconut butter for the rest of your life, but he is not one to rest on his laurels. He took the Elon Musk approach and took $100 million of his personal capital to launch the OS Fund. That was in 2004. And the entire fund is intended to support crazy inventors and scientists who aim to benefit humanity by rewriting the operating systems of life. And in this interview, he'll explain what that means.

But it is going to stretch you to think very, very big, hopefully much bigger than you thought possible for yourself. Some of his investments, to give you an idea, include endeavors to cure age-related diseases and radically extend human lifespan to 100 plus, Human Longevity, Inc. And we talk about this in this episode. Making biology a predictable programming language. So how can you program DNA and biology to produce what you want, like ginkgo bioworks and synthetic genomics?

Replicate the human visual cortex using artificial intelligence, companies Vicarious. Mine precious resources off of asteroids, but he is someone who, who succeeded and had a massive success story in a technical field without technical training. And also just a very deep, soulful, good guy. And all those things combined make for a fun conversation. I hope you enjoy it as much as I did. And without further ado, please meet Brian Johnson. Brian, welcome to the show.

Hi, Tim. Thanks for having me. And this is our take two. We had a rough audition start. We were sitting in a park and we had this guy fooling around in the bushes who then asked us if we had a spare backpack. I thought that was an odd request. Yeah, I think we were missing something. Yeah, I don't think that was the real request. And we did not have a spare backpack,

but we were put sufficiently on edge by this guy meandering around us, like doing concentric circles like a shark around somebody in a lifeboat that I decided it was better to do it inside. So we're at Casa Ferris. And I want to look at this in kind of a meta context, because I've been hoping to have you on the podcast for so long. And we were talking just before starting recording about what questions I might ask and giving you sort of an overview. And I had no idea that you'd done any prep, but I wanted you to tell me a little bit about it because you asked, how can we make this a home run? And I said, well, I think we'll want to focus on stories. And I will also typically judge it by how many notes people take. And you're like, well, that's really interesting. You should say that. So maybe you could talk

about, since we first discussed doing the podcast together, how you've been thinking about it. Yeah, so I guess I love efficiency. And so as I contemplate, if I'm going to spend 60 minutes of my time listening to something, I want some value. And so specifically, I want to have five, six, seven takeaways. And so I thought ahead of time, what could I do in the shortest amount of time that would create the most value in someone's life?

And so I think this made me very excited because I wanted to have you on, first of all. in the shortest amount of time that would create the most value in someone's life. And so I think this made me very excited because I wanted to have you on, first of all. But second of all, you'd thought about it very methodically, which shouldn't have surprised me at all. We've taken a lot of hikes together and had a lot of long talks, very wide ranging. And I think we'll get into a good amount of it. Let's start kind of at the beginning, and we'll bounce around sort of memento style throughout your life, I think. But what are some of your earliest, most formative memories from your childhood? So my family and I, we were really close. I have three brothers and one sister, and we were always up to no good. We lived in a small town in Utah, and we had nothing really to do but get into trouble.

But we were also very close, and we were best friends. It was true throughout high school. For example, when people are in high school, they don't like their parents. They'll shun them. They're embarrassed by them. But I would walk down the hallways with my arm around my mom, and she'd give high fives to my friends because she was there you know being a substitute teacher watching over her rambunctious boys but um we had a great time as a family and um for fun we would watch the dukes of hazard and the a team uh on friday nights and we'd go get a special combo

meal at hardy's we didn't really have much money but we just i guess i have a lot of sweet memories from growing up and being close to the family and. And it sounds like your mom was one of the cool moms. What do you think, correct me if I'm wrong, but what characteristics of hers or habits of hers or otherwise enabled her to be the cool mom and not the shunned mom? What were the contributing factors? All right, so one time I wondered what, if you filled a gallon, a milk gallon jug full of gasoline and you lit it on fire, I wondered what would happen. And so I went out into the street and- This is just in front of your house or?

Yeah, exactly. I took the gasoline that was otherwise used for the lawnmower and I filled up this carton and I went out on the street and I lit it on fire. And as expected, it was producing quite a flame. And then her green Taurus rolled around the corner coming down the street, coming home. And I thought, oh, no. So in haste, I kicked over the jug.

And now the gasoline spills on the street and into the gutter. And now it's rolling down the gutter, and there's cars there. So I'm having these images of cars blowing up. So I walk over to the gutter, and I stomp on the gasoline to put it out. And of course, that splashes. Now the lawn's on fire. So it's getting worse and worse. So anyways, we put the fire out.

And then the only thing she says to me, she says, Brian, you probably shouldn't do that again. And I said, all right. That's fair. But that's typical of my mom. She was supportive and kind. She kept us out of trouble the best she could, but she wasn't over the top, and we responded to that. So do you think it was... It's a very Dalai Lama-like response to a potential gasoline bomb.

Do you think... From the time that I lit the Dalai Lama's lawn on fire, I can say... No, I'm kidding. That's not what I did. But do you think then that that kind of moderation in discipline prevented the rebelliousness that you would otherwise see? Or do you think that it was that she was closer to you guys in some way than other parents were to their kids? We trusted her implicitly. And I think when she let go and we owned ourselves and our own behavior, I think we behaved accordingly. And so I did feel let go and we owned ourselves and our own behavior, I think we

behaved accordingly. And so I did feel responsible for my own behavior and it didn't, I was still just as mischievous, but I also knew there were boundaries and how mischievous I could be. And it was out of respect for her and that she did give us a lot of freedom to do what we wanted to do. Did you ever get in, did you get in trouble at school or not so much? So I successfully avoided really serious trouble my whole life, but just below the level that I think could have been really dangerous. But we did all sorts of things. And even now, I guess, as I look at my children as they grow up, the world has been sterilized dramatically in terms of what is and is not acceptable behavior.

In many ways, I'm grateful for the things we were able to do because we were able to explore and try new things out. But yeah, I stayed out of trouble mostly. Did you collect anything as a kid? Baseball cards. Baseball cards. How long did you collect baseball cards? For seven years.

I remember going down to the store and buying the tops, you know, 25 cards for $1.25. And was it mostly an obsession for you as a baseball fan? Was it a business? Was it a combination of that and more? I just loved having it and knowing that I had value or some rare card to show to friends when they came over. But no, it was just simply a way to splurge. I didn't like spending money very much, but that was the only thing i really spent money on uh were you a popular kid in uh grade school high school no so well so in eighth grade i remember i had these good friends in my neighborhood we were best buddies and i was annoyed because in school there were these cliques forming of jocks and stoners and nerds, like these typical things how people organize themselves. And they had these in-group characteristics where they would conform with each other's behaviors and say similar things.

And I was bothered because I wanted to be friends with everyone. And so I did this scrappy big data analysis where I went out and I evaluated all the different groups and the power structures within each groups, because there's always people within the groups who allow new members to join the group. Sort of the alpha. Exactly. Border guard. Yes. And so I would befriend these people and I would say, look, I come in peace and I just want to be friends. I have no agenda here. And I became friends, I think, honestly, with everyone in the whole school. I just loved having friends. And I love to dance in between the different groups because they saw the world so differently, right? It wasn't just like this mono understanding the world. And so I really enjoyed maintaining friendships. And that was my first experience in learning social dynamics because it wasn't

natural for me. I wasn't good looking. I didn't have expensive clothes. My parents, we actually had very little money. I wasn't funny. I wasn't witty. I wasn't necessarily super smart. So I didn't have the natural things that get you entrance into that kind of club. And did your analysis, when you were looking at, say, the power structure, when you went and interacted with the whoever it was, the rockers, the stoners, theers the skaters yeah on the blank did you take on sort of the characteristics of that group or did you have a uh did you have a base sort of personality and set of behaviors that went that traveled across the groups i just took an interest

in them i wanted to understand how they looked at the world what they experienced what they liked what they disliked i just was um sincere and i I've always been curious. And so I know I didn't try to become like them. I just wanted to be friends and understand them. Did you think of yourself, or let me rephrase that, when did you first start thinking of yourself as an entrepreneur? I think when I when I I guess I lived in Ecuador for two years and I came home to the states and

I guess this is probably not the answer you're looking for but I after living in Ecuador and seeing these people shackled in extreme poverty and seeing that they really didn't have a shot at life I came home with this burning desire that I wanted to spend my life improving people's lives.

And so I assessed what I could do. I looked at all the things you find in college like Model UN and helping do projects in Africa or wherever else, but nothing really spoke to me. And so I thought, you know what? I'll just become an entrepreneur. I'll build a successful business. I'll retire by 30 with abundance of resources, and I'll have freedom of time. And then I'll figure out a way to improve people's lives.

And so I think it really, at the age of 21, was the first time I set my sights really on that I can become an entrepreneur and build something of value. What gave you that confidence? So I assessed my skills, what I was really good at, and I couldn't really find much. This is when you were 21 or was it before that? Okay. Well, because I wasn't necessarily great at school or science or biology, I didn't really have any skills of note. And so I figured, you know, what I do have is I'm persistent, I'm determined, and I'm smart enough that I can figure stuff out on the fly. And so entrepreneurship seems like a good path for me.

And then what was, so you've decided on the report card, the skill assessment, the self-auditive life. You're like, okay, persistence, check. Good on tap dancing with uncertainty. Check, box number two. Where did you go from there? So I was trying to find a cell phone and I was really frugal.

I've always been very frugal. And I found this guy in the Yellow Pages. I met him at the mall and I bought a cell phone that was super cheap. And he said, hey, you look like you're smart and energetic. Why don't you come sell phones for me? I'll pay you 40 bucks per activation. And I thought, perfect.

I never understood this whole idea that I would trade 60 minutes of my time for $8.25 an hour. It seemed crazy to me. And so he said that to me. I thought, okay, I'll make 80 bucks an hour. I can do two per hour. And I said, deal.

So I sold phones for him for two days. And then I was on the porch of this lady's house and she had two screaming kids. And I had this thought. I thought, wait a second. If I'm selling phones for him, why can't others sell phones for me? And I left the sale. I ran home and I spent almost two solid days figuring out how to become a wholesale provider of cell phone service. And I figured it out and I started a company. And now I changed the commission structure. So now I was

making $300 per activation. And it was the first company I started and I hired college college students to sell phones for me, and I paid my way through college doing that. And when you were first selling to people like this woman with the kids screaming on the porch, was that like a door knock type of sales approach? It was. No kidding. So it's like the knock, knock, wipe the feet on the doormat. What was the opening line when somebody opened the door? i was a b testing the different approaches i could walk throughout campus and ask students yeah i could walk door to door so this was my second day and this was the day to test going up and down the street so yeah it was do you have a cell phone service

and if you don't then i've got a plan for you yeah so one of the uh one of my very close friends um a fantastic systems engineer i started working with when i graduated from college and went to a mass data storage startup mass at that point was like five terabytes ten terabytes big deal right big storage area network installation at the time uh he was so effective as a systems engineer because he had to do integration but he started off as a door-to-door encyclopedia salesperson that was his first entrepreneurial gig so he had to get really really good at overcoming objections and uh interacting with people socially even though he is his sort of bedrock skill set was technical uh now did you

so let's see you have the cell phones, that was your first business. What happened between there, and this is obviously a very large, or maybe not so large, but a lot happened, I'm sure, between that and Braintree, but what was the sort of montage version of that? Well, the short version is

the cell phone company went remarkably well, but it was not going to make me enough money to retire by 30. So I had to find something bigger. So I started a voice over IP company with three founders. And it was just before Skype and Vonage. And the short of that is we had the wrong team, wrong product, wrong timing. Sounds perfect. We did everything wrong.

No, we did have a problem. We actually built something. We got customers. And this was also in Utah? Yes. Yeah. And we had a problem. We actually built something. We got customers. And this was also in Utah? Yes. And we had revenue. So we actually built something. But in reality, we were not set up to succeed. So that failed. And then on the hills of that, I joined another guy to do real estate development. And the short of that is that failed because of some bad decisions we made. And so without income for two years, I was dead broke.

And so I applied for 60 jobs. I found a monster in the other job sites at the time. Nobody would hire me. I think it was so clear that I had no intention of staying a long time. I tried to make the resume look like it,

but just never was the case. So nobody would even give me an interview. And then- Additional skills, loyalty, fierce loyalty to employer. Exactly. And then I read, I saw fierce loyalty to employer. Um, and then I,

I read, I saw the newspaper one day. I had a list of the 50 richest people in Utah. And I thought, bingo, like that's what it is. I will write an email to these 50 people. I'll say I'm young,

I'm smart. I, I'm trying to become an entrepreneur, but I just need some money on the side. So I'll become your right hand man. I'll do whatever you want me to do. And no one responded. It's at this point, I'm like totally desperate point I'm like totally desperate I'm sure you I'm sure you get a fair amount of those emails these days I do and you know I'm empathetic to it yeah I totally am

so at this point I have no income I have a child at home and so I need to make ends meet and so I find this job uh posting in again I think it's monster it was selling credit card processing door to door and basically it was like if you so business to business yes yeah like marching up and on the street walking into a retailer or a restaurant let me help you set up a merchant account yes or get a point of sale system yes or mostly change everyone already had existing service got it got it and so i the requirement was like if you could fog a mirror you could work for these guys it's a hundred percent commission like what they don't care if you don't succeed right right but to your point on the sales side um i would go to inside a business i figured out pretty quickly the industry was really messed up like the technology

was terrible and um people were just generally plagued by the industry because it was just unscrupulous, all this dishonesty and complexity. And so I figured out that was the hook because my product had zero differentiation. It was exactly the same as 500 other providers that walked in the door every day. And so I'd walk in, I'd say, all right, Tim, right when you saw me walking in, you'd be like, all right, sales guy, all right, I'm not interested. I've got stuff to do. Then when you heard me say credit card processing, it's like, please leave.

Strike two. Yeah, like leave. So I would say, Tim, if you give me three minutes of your time, I will give you $100 if you don't say yes to using my service. And usually they'd say like, okay, that's interesting. Like, what does this guy have to offer? And I would open my pitch book and I'd walk them through the industry. Here are the providers.

Here's what they do. Here's how they do it. Here's what I do. I'm the same as everyone else, except for with me, you get, you know, honesty and transparency and great customer support. And so I became this company's number one salesperson. I broke all their sales records following this really simple formula of just selling honesty and transparency in a broken industry. That's super interesting. And, uh, so a couple of questions, I just want to rewind for a second. With the real estate company, if you're comfortable talking about them, what were the worst decisions? What were the fatal mistakes? So I'm really proud of actually what we did.

We launched a $50 million mixed-use project in one of the best places in Utah. Mixed-use means residential plus commercial. Exactly. Bottom floor, small shops. And Fannie Mae came in. They were our equity investor. We really put together a great project. The single biggest flaw was storage space. So empty nesters showed up to buy, and there wasn't sufficient storage.

Storage for just all of their extra stuff that they wanted to take out of the big house and move into this community living space. So then sales stalled in phase one. The bank got anxious. Ah, got it. So just didn't account for that need. Yeah, that was the big blunder. With the sales.

So I'm fascinated by sales because there's the good, the bad, and the ugly. And you often see it within one industry, right? And so this brings back a lot of memories for me because I was the lowest paid as a base salesperson at the startup that I worked for out of college. And they're like, hmm, you're really persistent. You're in sales. You're really persistent.

You have no technical background. You're in sales. Congratulations. And I was like, oh, okay, here we go. So smiling and dialing. And one of the things I did was very similar to what you did with taking the potential objection and putting it right up front, which was like, I'm the same as every other guy. Product, different label, same thing, except for this, right? Yes.

Which was the relationship piece. And I took a very similar approach when I was cold calling, which I did between like, I want to say like seven and eight and six and seven. So I avoided the times that the gatekeeper would be manning the phones. Yes. And only called when I thought I could get the higher ups who would work longer hours.

But I would, um, I would, I would do my homework so I could guess what they were currently using, like Solaris boxes or whatever. And then I would say, well, not sure if this is the right fit at all. If you're using this type of system, this type of system, or this type of system, it is not at all. And I would take all of the potential weaknesses and just put them right up front. You, at that point, had already had experience hiring salespeople. What did you look for in salespeople or how did you hire the people who had the highest likelihood of success or train them? Their ability to connect with other people and earn their trust. And what are the correlating behaviors or qualities that allow them to do that?

They had to be genuine. It couldn't be that they were manipulating them into believing them. It had to be truthful, right? That if I trusted you, that you were saying something, that I could believe you, and that would be true tomorrow as well. So I think that sincerity and being genuine go a long ways. And I think even if it spans differences of personalities and experiences in life,

but if someone feels like someone who's really trustworthy. And how do you read that when you meet someone? If I trust them. Okay, I'm going to dig a little bit more. So is that a visceral spider sense or is it a, that guy's not looking me in the eye? What is the, is it a gestalt of all those things? What is, what is it that leads you to feel that you can trust or not trust someone?

Yeah, I don't know. I guess, um, you know, I've always had an interest in people because I'm curious and I've always enjoyed friendships and I don't know if i could even articulate this it's just this subconscious process that happens that i read whatever the hundreds of data points that you read when you meet someone and you intuitively feel like yeah i i could trust this person and the more you gather of course the higher your confidence level becomes and of course like i make mistakes like everyone else but um i think it's a fairly accurate i think most people can read that how this work this is a a bit of a lateral step but i just saw and i want to say it's called ex machina yeah like uh which made me think of i guess it's deus ex machina which is

the the machine or god from the machine which is when it's a theater expression. I'm all over the place because I've had enough caffeine and coconut oil, but it's, it's when there was a plot, a plot problem that needed to be solved. And the writer couldn't find any other solution besides having like God descend from the rafters on a wire and be like, be gone problems. Therefore,

act three, it comes to a close. Good night, everyone. But, uh, ex machina, I think that's, there's a lot of debate about how Latin is pronounced, but no idea.

In any case, how long do you think it is? And we're in 2015, last I checked. Before a computer can read all those micro expressions and so on and come to the same type of trust or not trust conclusion if you were a betting man and this was the price is right yeah of technology i don't think i'm qualified to answer i will say that uh the other day i watched a video online where robots were walking along and then people were kicking the robots or tripping them or doing something to put up an obstacle. And I had this emotional reaction watching this happen, even though I knew they were robots, but watching humans be cruel to robots, this visceral reaction inside of me. ex machina and the progression of robotics to read our emotions and for us to interact with them the emotion's real right like our ability to connect with robots is significant as i watch

my kids interact with siri and even other low tech um you know computer interact interfaces i think that we will generally be surprised at how seamlessly the technology has rolled throughout society and how we just interact as we normally would. It will appeal to our emotions and all these things we read. Do you think we will have sort of Turing test level interactions with machines within the next five years? If I'm a betting man, I'll go longer. I'll say a decade at least. A decade at least. Interesting.

All right. Uh, did the credit card processing business or that experience, you became the number one salesperson. Yeah. Uh, where did, obviously very interrelated,

not exactly the same, but how did that, how did you go from there to brain tree? I did it for a year. And it was amazing because it was this terribly broken world where the technology was years behind and no one trusted it to different providers.

It was fragmented with hundreds of providers. And after doing it, I thought this is a perfect industry to start a company. And so I started Braintree. To disrupt it. Yeah. Because it was just so ripe.

Yeah, for the right technology and the right disposition as a company to be honest and transparent and treat customers so they were thrilled. And did you have any technical background? I didn't, no. You did not? No. So no computer science. No. No mechanical engineering, electrical engineering.

What was the, and you had one kid at home at that point? Two. Two kids at home. So what was the, do you remember the moment or the conversation or the walk in which you decided, yes, I'm going to forego this sales job where presumably you're making pretty good income and start this company. Yeah. So what I did to start Braintree is I had these customers in Utah. I was in Chicago at the time.

That's where I built Braintree, Chicago. And I went back to my 10 best customers in Utah, best meaning like most loyal and also making me the most amount of money. And I said, hey, I just started this company, Braintree. I would love it if you switched over your processing to me. And it was restaurants and retailers, so it was just terminals. I could use back-end processors for it. And I think I had like nine out of the 10 say yes,

if I remember right. And they collectively made me $6,200 a month. And it was enough for me to get going, hire some part-time help, and start the company. And the biggest transition we had is OpenTable showed up and they said, hey, we have 11,000 restaurants around the world. Where was OpenTable based? California.

It was. Yeah. And they somehow found you. So the co-founder, the founder of OpenTable, Chuck Templeton, was an advisor. And he knew of the problem they had internally where they had this huge global network of restaurants and they stored credit card data when people made reservations. They had the compliance issue. They came to us and they said,

we have this big problem and we said, we can fix it. Of course, I had no idea if I could fix it. But we did a deal with them and that's when we became a software company. But it was a bet the company decision. In the beginning then, Braintree was like your previous company that

you worked for as a salesperson. It's kind of a commodity business, but you had the relationships. That's right. So a couple of related questions. How on earth, as I assume, but correct me if I'm wrong, kind of an unknown quantity at that point, did you get Templeton as an advisor? We met at a local meetup in Chicago. What kind of an unknown quantity at that point, did you get Templeton as an advisor? We met at a local meetup in Chicago. What kind of meetup? It was actually Matt Maloney and Mike Evans from Grubhub. They just went public. And Karan Gol, who was a local entrepreneur.

But there was like five or six of us, and people were just getting together to have breakfast. And he and I hit it off, and he was clearly a great guy. I mean, he had the right disposition, the insights. He was advising people around the table. He was an advisor for Matt and Mike at Grubhub. And he came on, and he was my only advisor for the whole duration of when I was building Braintree.

No kidding. And how did you get so connected with these tech guys when you were not, at least from the first glance as an outsider looking in, not in the tech space, per se? Or were you? I don't know. No, I wasn't. I wasn't connected to software engineers at all, actually. And so I had one friend who I trusted as a good developer.

He has a good developer. People, he had a high, you know, he has a good reputation and I would make, I would post jobs online and then he would help me interview these people as they came in. And as I listened to the questions he asked and how he discerned what, what made a good engineer, I learned over time how to decipher.

And it took me a couple hires to get down. And then I found a couple of really good core engineers and i now had a benchmark to know what exactly to hire both in personality but also coding skills and we could then build it from there and so that's how you developed that's how you sort of got your your foot in the door with the tech world yeah that's right and then the then the so when i started brain tree i i had three main goals one is that i wanted us to be the best payments provider in the world for developers two that i wanted our I wanted us to be the best payments provider in the world for developers. Two, that I wanted our employees to say it was the best company they'd ever worked for.

And three, that our customers would write us love letters. And so on the employee side, I wanted people to literally go home and rave about work, to be so excited about the stuff they were working on and what they did and how they did it and their peers. And so having high-quality engineers was really important because no one likes to work with someone who is incompetent or causing a problem. So it was extremely important we got exceptional people to work. And do any of those questions come to mind, kind of high-level vetting questions for good engineers? On the technical side, sure, there's a lot.

On the personality side, what I would try to communicate when we hired someone was that payments was not necessarily changing the world. It wasn't like we're going to provide clean water for everyone in the world or whatever else. The stated objective that we were going to build an exceptional company, like a company with a soul that we really cared about. And so I wanted people who really cared about what they did, the quality of the product, the quality of the interactions, working with other engineers. So we're in it for the long term. And so I tried to flesh that out in interviews of, we're here to do something epic and special.

So if that appeals to you, great. If not, then... How do you now, maybe this comes back to the spider sense, but how do you vet people who are BSing and acting in an interview to get a job versus people who are the true believers? I guess for non-engineers, I would write these posts on Craigslist to recruit people. At the very top of the page, the assumption was first, the person reading your job ad is not the person you want to hire. That was the assumption? Yes.

Okay. The person reading the ad knew the person you wanted to hire. That was the assumption? Yes. Okay. That the person reading the ad knew the person you wanted to hire. Ah. So the very first statement was, I will pay you $5,000 if you refer the most capable person you know. And then below it, it would say, please do not apply if. And we'd list out characteristics of people who just weren't compatible with our environment. And so we wanted to be clearly distinctive in who we were.

And then we had a section that said, please do apply if. And so the goal was – But the do not apply was first. It was first, yeah, which had this great psychological effect. And then the please do apply if. We wanted people to jump out of their seats and say, this is the environment I've been dying to be in. Because the most exceptional people love to work with exceptional people. And they have a hard time dealing with people who are not that exceptional.

And so if you build critical mass around everyone around you, it's just really good. Then it feeds upon itself. And so we wanted to put that signal out to say if you feel like this in your current job, like you're the best guy in the whole company, best gal in the whole company. And everyone else around you is kind of driving you nuts. Like you can come over here and feel really good about, you know, what you do every day and who you work with. How did you choose the name Braintree? So it's funny. Being this small company, I went through this thought process of like, hey, I'm small and I'm insecure. So I'm going to come up with like National Federation of Merchant Services or using big words that connotate

strength and stability. And nothing felt right. And I just read the biography of John Adams, who was born in Braintree, Massachusetts. And I really admired John for his contributions to the world. And so I wanted to come up with a name that was meaningful to me personally. And it was Braintree. No no kidding i didn't realize that brain tree massachusetts yeah wow i had no idea uh so you so you have this advisor open table opens a lot of doors or changes the direction of the company it sounds like that's right did it make you nervous that you were betting the future of the company on one person effectively who is, I suppose, making promises or pointing to the future and saying, this is what we can do together? Well, so it was a big decision because I think I was 28 at the time and I grew up poor.

We didn't have any money. And as an entrepreneur, of course, I had never had any money. And so I've been broke my entire life. And at this point, we were making really good money. We were making, I think, something like, I don't know, $200,000 in net income a year. So it was the first time I actually made money in my entire life. And deciding to become a software shop meant we were pouring back all the cash back into the business because I was bootstrapping. I hadn't taken any outside capital. And so it was a huge decision on what to do. But it was also, I knew that, I intuitively knew the industry was broken.

I intuitively knew that if we got the right people there, we could build good software. And so to me, it was a must-go. Are there any, so you mentioned John Adams. Are there any books, biographies, or otherwise that gave you confidence and a kind of chutzpah to go for it in those early formative years? Yeah, a personal hero of mine is Ernest Shackleton. Oh, yeah. I'll let you reintroduce people.

Yeah, right. So we probably share a mutual love. Yeah. So 1914, he went on the Trans-Imperial Antarctic Expedition, where he tried to cross coast to coast the South Pole, Antarctica. And what I like about Shackleton, there's a whole bunch of things I like about Shackleton, but basically to this question is when he imagined what he wanted to do in the world, he chose the most audacious thing imaginable. At the time, it was nearly inconceivable that somebody could do that, and he chose to do it, and he prepped, and he did it, and they failed in their endeavor, right? But he's not remembered as a failure. He's remembered as the grit and how they actually overcame all the obstacles that came about during the expedition. He's hugely inspirational in my life because I apply what I call the Shackleton sniff test to everything I do in life, that I contemplate if I'm going about on this endeavor, does it meet the threshold that Shackleton applied?

That is this the most audacious endeavor I could possibly conceive? And in time, we'll iterate, we'll change, we'll pivot. That happens over the course. But I want to start with that as the contemplation. So it's kind of like a what would Shackleton do bracelet. There you go, yeah. Better said. Shackleton.

Why did you move to Chicago? To pursue an MBA. Oh, no kidding. Yeah. Why did you, are you glad that you got an MBA? I have mixed feelings about it. School, I was always so bored of school because I felt like the data rate was so slow.

It was like a 56K connection, right? Sitting in the classroom and the pace of speech and the data, it just, I wanted like a gig data transfer rate. I wanted to learn so much faster. And so school was just boring to me. And I mean, the MBA was helpful, but I don't know.

I guess I learned in different ways, mostly from doing. And I'd been in the trenches of entrepreneurship my whole life. And that's really how I prefer to learn. Then, of course, reading on my own and stuff like that. So let me ask you this. If you were counseling a young entrepreneur who was living somewhere they felt was, and I'm not saying Utah is this place, uh, except I've actually spent quite a bit of time there, but if they're living somewhere they feel doesn't allow them to surround themselves

with other, uh, highly ambitious, capable entrepreneurs. Yeah. And the only way that they could relocate was to get an MBA, say to Chicago, New York, SF. Yeah. And the only way that they could relocate was to get an MBA, say to Chicago, New York, SF. Yeah. Uh,

do you think the 120 K or whatever it might be would be worth it? If someone, if, if someone, if, if one of your kids was considering getting an MBA and let's just say they were kind of of that age now, what,

what might you ask them or so i remember the very first case study we did in school was about these guys who were they came up i think of the new new golf ball that was better than the golf balls and it was about their struggle over a two-year period of time to work through patents and ip and all the distribution channels and stuff like that and then we got together with the study group to talk about the case. And there were certain questions we were trying to answer. I forget what they were. But in my group, there were five of us.

And we were contemplating things like cost models and distribution channels. And my mind immediately went to, like, how are these people paying for their rent? Are their marriages still intact? Are they emotionally just too stressed out to function? The way I thought was so colored by my experience as an entrepreneur, and it was such a dramatic difference than how my peers thought. People coming in from like Ernst & Young. From larger corporations, yeah.

Make their pay grade jump. It was just dramatic. And so I guess I would say to my son that the skills you need to succeed in a certain track of life may not require that education. That the core set of persistence and determination and then just the ability to learn and adapt quickly are much better suited for trying to do this. And that's not to say that education is not helpful. It certainly is in certain regards. There are different types of education. That's right, yeah. What's the most valuable thing you took from business school or from that

experience? Let me say that. We can come back to it. Yeah. Or you're, you're giving me the look or we can drop it. I'm not sure. Okay.

Well, that's, that's, that's fine answer. Um, I think more people should have that Okay. Well, that's a fine answer. I think more people should have that as an answer, quite frankly. Maybe that is the answer. I was telling my brother, we were talking about some really kind of deep philosophical questions,

and I said, I just haven't figured it out. And he said, maybe that's what you figured out. Exactly. Totally true. Maybe that's not an answer you need to find. So with Braintree then, let's kind of look at what turned Braintree into a rocket ship, or what led to that perception at the very least. So early on, I had to figure out how to get customers without any money,

which is a hard problem to solve. Common problem. Right, exactly. And so what I did is I knew that software engineers were the target that I needed to appeal to them. And I knew there were different communities like Python,.NET, Ruby on Rails, Java. They all hung out in these different communities. And each community had certain characteristics about how they work together, how collaborative they were, how chatty they were. And my theory was, if I could find a community of engineers that were

chatty and that helped each other through a word of mouth referral basis, and I could get a few of the leaders in that group to come on board, then it would spread throughout the community. And then we'd go to adjacencies. And so I did this analysis of looking at the characteristics, and I found that Ruby on Rails was the most conducive, that they were very tight. Now, did you figure this out by looking at message boards? How did you go about doing it? No, I found actually a couple of academic research papers that actually measured sociability and interconnectedness, and had these maps, the diagrams that showed where these nodes were and how they interconnected. And then I focused on, the diagrams that showed where these nodes were and how they

interconnected. And then I focused on Ruby on Rails. And we got a couple of leaders. And they're like 37signals and a few others. GitHub came on. 37signals is a good one to have. Yeah, Jason and David were amazingly good to us. They would tweet out all the time.

And they referred out all their friends. They were fantastic. And so we basically built a business on word of mouth because we tried so incredibly hard to be exceptional in what we did. So they'd come on and they would love what we built and how we treated them, and they would tell others. So I want to really underscore what you just said because I think it's so important

for anyone who's considering launching a product or service or business, and that is that your first target is not the entire market, right? And when I talk to people about, say, book launches, a lot of people want everyone to love the book. And when they write and promote and market a book to appeal to everyone,

when you want everyone to be your customer, no one is your customer, especially when you have no money. You need the kind of cost per acquisition to be as low as possible right ideally zero and so when i launched either the four-hour work week or was formulating the marketing plan i mean you and i have a lot of shared dna we've observed this before across a lot of different areas but i wanted to identify the market i could communicate with that would have the highest rebroadcasting ability. And very much similar to your chattiest checkbox, right?

And I determined that I also wanted it to be a market that I understood ideally belonged to. And that was the kind of 20 to 35-year-old tech-savvy males in San Francisco, New York, primarily. And then after, if I hit a critical mass in that particular demographic and psychographic, say my goal was, I think it was 10,000 books per week for two weeks, and I could try to identify kind of the conversion rates and so on to hit that number, then I knew through word of mouth that would bleed out, both in age range, it would jump from male to female.

But I wanted to identify the people who are kind of disproportionately creating the most online content at that time. Yep. And okay, so you target Ruby on Rails, and was there a particular tipping point where you were like, holy moly? Okay.

Well. Any particular kind of hockey stick or breakthrough moments that come to mind? Yeah. So we, let me think. So we got as customers within the first couple of years, um, you know, 37 signals, GitHub, Uber, Airbnb, living social when they were on their tear. I mean, we had so many of the fastest. You had the all-star team.

We did. We had some of the best companies in the whole world using us. And their growth fueled credibility, of course, in our brand that we were able to provide great services to them. So we had this exceptional client base. That's what it was. Once these guys hit their growth trajectories, right, and then once the reputation started spreading that we were a great provider, people loved using our service, it just really built upon itself. Who were you in that period of time competing against? Who were your primary competitors?

Initially, it was the old guard like Cybersource and Authorize.net and then processors like First Data and Global, which were really great targets because they were dinosaurs in technology. And then Stripe launched, I think, about a year or two after us, and they're obviously a fantastic company. And so they became formidable competitors. And then, of course, PayPal was always there doing their thing. And so when you met with the Ubers, the Airbnbs, and so on, how did you convince them to work with you guys? So we did do some outbound.

We did track a lot of these companies down, but most of these companies signed up on their own. We just found out they were customers when they were going through the underwriting process. We did target some of these companies individually, but most of it was organic. Got it. And to what do you – aside from the word of mouth, what are other things that facilitated them finding you naturally? get internally is that if we paid attention to creating an environment where people who interacted with us would walk away and say, unbelievable, right? The software is amazing.

The support is amazing that I just love this company. And I so much so that I want to write them a love letter. If we solve that, everything else will take care of itself because they'd walk away and in that night when they're out with their friend getting a beer, they're going to bring us up because they have this amazing experience with us where we solved all their problems. And we did small things like we would,

the integration team, we would see when someone was coding to the API and if they were having problems with it, we'd reach out and say, hey, we see you're coding to the API and they're having problems. Can we help? Like, what?

Like, who does that? Like, who practically reaches out? So we tried to do these small things that created these really great experiences for people. Now, could you explain, just for people who are non-technical out there, so application programming interface. Oh, yeah, sorry.

So no, no, no, we're fine. I love to kind of, it's a very important concept in a lot of tech. So what does coding to the API mean? So they were programming their software to speak to our software. And there was a certain way that they would do that.

And so a lot of the value of how that's done would be, is our software easy to work with? Does it make sense? You know, it just,

yeah. And so your software is behind the scenes handling transactions. So it's kind of like you have in a restaurant, front of the house, the maitre d',

the waiters and so on. Then you have back of the house, the restaurant, and you need those, the people in the restaurant never front of the house, the maitre d', the waiters, and so on. Then you have back of the house, the restaurant, and you need those. The people in the restaurant never see the people in the back with all the flames and cuts and burns on them, but you need a very reliable way for the front of the house to talk to the back of the house. Exactly. That's the API.

That's right. And it's a super, super important concept. It's how also, I mean, correct me if I'm wrong, but it's how a lot of companies grow very quickly is by making that a seamless that's right experience yeah making your services broadly available to a broader ecosystem of engineers it um your story reminds me of um a story told by one of my favorite people out there a guy named derek sivers i don't know if you know i know derek so derek is uh uh i certainly hope to have him on the podcast sometime, but sort of a philosopher king in the programming world, a really fascinating guy, great teacher also, really great teacher.

But he had a very similar focus on details with CD Baby, the company that he started, grew, and then later sold. And I remember he told me, and he wrote about this in his book as well, and if you guys search, I think I put this on my blog. If you just search Derek Sivers letter and then Ferris, I'm sure it'll pop up. Sivers, S-I-V-E-R-S, Sivers.org, really amazing guy. But when people would get their order confirmation email, it was this hilarious kind of elaborate story of like,

your CD has been carefully pulled off the shelf and placed on a satin pillow and then wrapped in paper by a japanese origami specialist and it was this just very personable uh email confirmation and no one was doing that yes and so it it spread it was such a small detail with with huge implications uh for for brand loyalty for pr for acquisition for all these things and it was so easy to do yep right it was not something that a big company couldn't do it was just something a big company wouldn't do yes typically right what are other uh what are other um whether it's and i hesitate to use this term, but growth hacks or say rituals, routines, or rules within Braintree that allowed you guys, helped you guys grow as quickly as you did?

Yeah. So one thing I focused on a lot was the second goal, which was that employees would say it was the best place they ever worked. And it was this ongoing quest to figure out how to make that happen. Again, my goal in my mind was they go home and rave about what they do on a daily basis. They feel good in life, right? They love it. And so I always wanted to know what people were feeling and thinking, because if I didn't know that, then I couldn't change or build certain things. And so I tried all the normal things. We did town halls every week. And it was more like group therapy than it was company updates

where I would let these long, awkward silences persist until the thing came up that everyone was worried about or they wanted to talk about, but no one dared. So when would those awkward pauses come up? You'd say, does anyone have any questions? And then you you just let it sit exactly like we're gonna we're gonna wait until we have some questions exactly so like i knew there's like one or two things on everyone's minds i could feel the pressure build all week right i mean the one thing i learned the pink elephant expanding exactly like the thing is true in life is that everyone always has a pebble in

their shoe always right there's something bothering us. And that sometimes by just acknowledging it, it addresses the problem. But it seemed like every week we'd build up this tension in the startup and in the company, and if we addressed it openly in the town hall setting, it would be great. And so I would let these long pauses go, and someone would finally raise their hand and say, all right, I'm really bothered that we hired someone for this role instead of promoting some of this internally. What's going on? And it was great because these were really hard questions to answer. And so I encouraged brutal, honest feedback. And if they criticized me, even better.

If they could criticize me, then anything was for open game. But one thing, I was at this Christmas party one year, and I was talking to the significant other of one of my employees this was at a company christmas party company christmas party we're in the buffet line and i say so like how's you know so and so doing like he he's four months in and how's he enjoying life and she says like it's amazing like he is happy and i he comes home and he's energized and he loves his coworkers. And it's so different from how he felt before. And I thought, yes, this is the data I want. Because I want to know the significant other knows the most about how that person feels in life based upon what they do on a daily basis.

And so it was a constant quest of trying to find out the right data source of how people feel in life to build an exceptional company and knowing where to go for that data and how to get it. Now, of course, I couldn't go interview everyone all the time. It would be awkward. But just knowing that the data sources were out there to gather to build a good team was really helpful. So you said, if they criticize me, all the better.

How would you prompt people to be brutally honest? Because you're the big boss, right? Right. Would you send out an email outlining the goal of the town hall? Or would you get up and talk for a few minutes in the beginning and try to encourage people to let that stuff out? What did you say in either case? So one, I think it's a disposition. I tried to be self-deprecating where I would make fun of

myself for things I did or mistakes I'd made. I'd try to openly broadcast those so that they felt comfortable that I owned up and I wasn't sensitive about it. And then I would just, I guess in dialogue, I would try to typically own things myself to make them feel comfortable that they could bring it up. We could discuss it openly. How would you do that? So if we talked about, I'm trying to think of like a recurring theme that came up. Maybe if it came up like two or three times, I could say like, look, like this honestly is like my deal because you guys have brought this up two or three times now. I've not done something about it that's adequate. So clearly I'm not doing what I should be doing because you're doing your job of being honest and transparent with me i have not taken the responsibility of actually acting

on this so i'm gonna go think about this put together a plan and do it but in the meantime like this is my problem and my mistake so i try to own things like that got it so it's not it's no longer your job to worry about it it's my job to worry about yeah like i hear you you did a good job thank you for being honest and transparent because that's what I asked of you. And you don't have the power to fix that yourself. This is like a more community problem. So it's in my. So the, um, the observation I've had on multiple occasions and, um, is, uh, you're very persuasive, but I don't think you'd be very good at lying. And I could be, maybe you're so good that I would never notice. I don't know, but I'm, I'm making, I'm just kidding, obviously. Uh, but I don't think you'd be very good at lying. And I could be, maybe you're so good that I would never notice. I don't know, but I'm just kidding, obviously.

But I don't think you'd be good at lying. And you seem, even though you don't have technical training, you seem very scientifically minded and sort of an engineer at heart. Does that make sense? I mean, you're very methodical. And one thing that I've personally struggled with is, and maybe this is through a lot of competitive sports. Maybe it's just from being, um, working solo so often. Uh, I don't want, I generally don't want, or it's personality type.

I don't want people to tell me what's going right. I want the bad news because I feel like the good news will take care of itself. Does that make sense? Yeah. news because I feel like the good news will take care of itself. Does that make sense? And I think as a result of that, I recognize that one of my kind of deficiencies as a manager of people is that I'm not very good or consistent in giving positive feedback. I don't feel, I erroneously believe that because I don't necessarily need that, other people probably don't need it. Or I just forget about that. How did you address that within Braintree?

Because I think it's, at least in my experience, it is important to maintain morale of the troops and so on. What did you do to help kind of maintain morale and that level of happiness that the significant other reported i would tell stories i would tell stories about people and exceptional efforts now it's always a double-edged sword because if you tell a story about one person you're not telling a story about the other person and one person's always gonna feel left out because like i was just involved as you know him or her in doing this and so um it is tricky, but I always highlight, I did weekly emails as well. And I wanted to tell stories of people who went above and beyond the call of duty, either in building their software or a customer service interaction, or even helping a coworker

do something. And those stories resonated with people, right? They saw what their peers were doing and it was influential on how they behaved. So I wanted to build a culture of a certain behavior, and I told stories to reinforce that. Right, the positive reinforcement. Yes. And how often did you do the town hall meetings? We did either weekly or biweekly. We kind of fluctuated over the years. What day of the week?

Friday. Friday. Yeah. Why Friday? It's a different vibe in the company. People are kind of reflecting upon the week. The tensions kind of build up. We're going into the weekend.

Monday morning is a little bit frantic. But Friday, I find people more pensive and reflective and that it was a good time for us to dig deep and find out what was really bothering us and how – and I guess regroup on the essence of why we existed. We weren't just there to make a paycheck. We were there to build something exceptional and to continually talk about that was important. When you were building Braintree, when do you feel like you were at your peak powers? In other words, when were you pitching a no-hitter in the World Series? At what point in building Braintree was that? I don't think I could identify it.

It was just so gradual and over time that we started these companies like Uber and like Airbnb. They hit their growth stride, and it was amazing that we were powering all their payments. And it was just so gradual and slow because companies come on brand new, and it takes them a couple years to ramp up to start processing significant sales. So I don't know if I could identify a single point. It's just this slow, steady build. When did you feel under the most pressure? Always. Okay. Okay, so where I'm trying to lead this is when you can try to think of when you were operating at a very high level under very high stress, what did your morning routine look like?

The first, say, hour of your day or two hours of your day. Yeah, so I guess if I think about the broader context of life i mean i had two children when i started brain tree and then um you know i had three by the end and we had my first two children were colicky so they're crying all night and so not being able to sleep very well at night then getting up the next day and going to work and then dealing with all the stuff you deal with. It was a pretty tough time in life. And, um, I mean, there were some dark moments. It's, it's, I guess something you and I have talked about on our walks is that I generally view advice. I'm very skeptical of advice because it's so contextual and it can be deceptively, um, unhelpful because you don't understand what's packed into that advice.

But one piece of advice I think is helpful for entrepreneurs that I wish someone would have told me is the importance of surrounding yourself with fellow founders, people who get you and understand you. That all those years as a founder, I felt like I owned everything. I owned energy. I owned growth. I owned the success. It was all me. And I didn't have any co-founders. So that's not to say people on my team didn't shoulder that, right?

But as the founder, you do feel an extra level of burden. And I had no outlet for it. I owned energy at home. I owned energy at work. And it was tough. It took a toll. And so over the past couple of years, i've created these friendships like you know like like you and i have where we can talk as if we were journaling right right i mean to get to the

real raw and good stuff of life but um i think that that would have been very helpful during those darkest times during the thing the moments where it was the hottest yeah i um i had a book inscribed for me actually it's it's right there. The psychedelic explorers guide had Jim Fadiman on the podcast. And, uh, I thought his inscription was so great. He said, um, you know, to Tim, a companion on the path. And I was like, that's it. And I think, I mean, we're literally companions on the path. We go on these hikes, but having those, those people who can identify with the pressures that you're feeling yeah what were other coping strategies

that you had or routines that were helpful when you felt you were shouldering all that burden yeah so i always look for hobbies that would consume my mind where i could escape myself because these things you could change the channel. Exactly. Yeah. For a brief period of time. Totally. Because like it loops and loops and loops.

And if you try anything else, it just loops. Even when you're having conversations, like you're just obsessed with trying to build your company. And so one day I had a hard day at work and I was walking home. I thought, you know what? I'm going to go fly an airplane.

Like maybe that will do the trick. And I did this discovery flight and the guy took me up and he's like, if you can do the following things, you can fly. And he did like this really hard turn up and down. I got sick and I was like, oh, I can never do that. It's so crazy and hard. But I thought about it the next morning. I thought, no, I can actually do this. And so I started flying and I lost myself in aviation. I absolutely love it. And so that really helped that I could find a different place to park my mind and focus. Is, is a discovery flight where like you're in the passenger seat of a new car and they show you what the car can do is that what a discovery flight is basically

yeah you go up and he's like hey so if you want to get your license you have to perform the following maneuvers like here's a steep turn you know 30 degrees and and so he was just showing me basically how the plane operated and what i would need to do. And I think for a lot of people listening, they think of learning to fly as a very, very, very, very expensive thing. I think they associate it with, say, owning a private jet. But that is not the case, right? I mean, as far as I understand it. I mean, I have friends who work jobs here who have gotten into aviation.

Yeah. Is it, how cost prohibitive is it to become involved with aviation in some capacity? So I think I paid a few thousand dollars over the course of the lessons. Got it. Something like that. Over what period of time? I believe it took me 90 days. Got it.

So I mean, all in all, not pocket change, but not like buying a Gulfstream. That's right. And this is something I've, I've, I've, I've a number of friends here in the Bay area who use aviation is their way of changing the channel, right? So that they're not constantly watching sort of, yes, BBC news or whatever the hell their world happens. That's right.

Let's see the, when you were 21, I think you said 21. When you were 21 and you thought of the word successful, who was the person who came to mind at that point for you? We're in that rough range. Yeah. I admired people who had... I guess I had a number of buckets in my mind of who I admired, but one bucket that

appealed to me because I thought I could potentially be like them was those who acquired significant amount of resources through building businesses and we're now using those resources to do good in the world, that they had freedom of time. They didn't need to show up for a job and they didn't write all that kind of stuff. And i identified with that because i think i thought it matched up with my potential skill sets and something i could potentially achieve in life so it really it was freedom of time to do the things that you cared about the most in life so who were who were some of those people or who are some of those people growing Growing up in Utah, John Huntsman was – I don't know who that is.

So he built – I'm not even sure what company he built. But he was enormously wealthy. And, of course, the Marriotts are in there as well. But there were a few families in the community that had accumulated significant resources. And they – one, I think Huntsman had a cancer institute at the University of Utah and others that they were able to move the needle in significant ways that other people just couldn't. And I thought that was really remarkable that you could make huge contributions potentially to humanity. So this is actually, I think, a good segue to one of your current projects.

I think it's fair to say, primary project, the OS Fund? It is, yeah. So could you explain to people what the OS Fund is? Yeah, so the context is, I guess at 21, I made that goal that I wanted to spend my life improving people's lives. And over the 14 years or so as I was building my companies, I thought a lot about this.

Like, what would it look like? What would it feel like? What would it taste like? What areas would I focus on? And I looked through thousands and thousands of ideas. And I mean, I was always thinking about it. And I studied during that time a lot about science and technology. And the realization that I came to is that the reason why our time and place is so unique in the arc of humanity

is we literally now have the tools to build the kind of world we can dream of. So if you take computer software and biology, genomics, AI, virtual reality, 3D printing, we can literally program our existence. So I think oftentimes of like Da Vinci, where he had his great sketchbooks, where he designed a flying machine, and did these really amazing ideas, but he couldn't build it. He didn't have the tools. We can literally build anything today. And so as I realized that, I thought, this is one of the biggest moments in the history of humankind.

The biggest question for me was, what kind of world are we going to build? And that's when I started the OS Fund, is trying to invest in these tools of creation that will so dramatically affect the kind of world we build. Yeah, it is really a fascinating time. And we have this sort of Cambrian explosion of potential

where what happens when you can create virtually anything? You can download a recipe for a virus that could cause an epidemic. That's right. Or a weapon. That's right. Or at the same time, obviously use that knife, that surgical knife to repair or build as opposed to damage. Right.

What now OS refers to operating system. Yes. Why operating system? So it's a metaphor. I like a lot that the biggest changes in history, the biggest improvements in history have happened at what I call the operating system level. So, for example, like germ theory, that we tried to figure out what was causing disease and death for a long time. And when we figured out there was this thing like bacteria that caused infections and death.

And then once we figured out sterilization and antibiotics and vaccines and good personal hygiene, we radically extended healthy human life. But it was finding out there was this core problem of bacteria. And every major change we've had has been at this level. And so instead of playing with things at a different level, what we think about is the companies we invest in

are doing world-changing things at the operating system level. So if they're successful in their endeavor, it would radically change the world. Right, so the foundational level upon which everything else. That's right. So just like a computer has an operating system at its core that determines how it works and there's applications that sit on top, everything in life has an operating system. And what are some of the investments that you've made thus far in the OS Fund? Yeah, Human Longevity, led by Craig Venter,

is they're trying to radically extend healthy human life into the hundreds. And they're doing it by using the whole human genome and then adding data like the metabiome and phenotype data and then using advanced machine learning to learn about disease and create personal therapeutics. If they're successful, it would change medicine. As we know it in a really fundamental way.

Any others? Yeah, we just made an investment in Ginkgo Bioworks, which they're basically making biology programmable. So just like we use computer code today to render a website or process a credit card transaction or fly an autopilot system in an airplane we can program the same thing in biology for today they're doing fragrances and flavors they're producing in a lab that otherwise would be required in nature and as we climb up the complexity scale we can do much more complicated things like work on antibiotic resistance and

carbon capture but the idea tim like your biology'm biology, our world runs on biology. The fact that this could be a programming language we could actually predictably use is remarkable. Right. Well, what is it? I mean, I guess DNA is what, ATCG, right? I mean, it's something along those lines. I'm getting out of my depth here into my ignorance pool pretty quickly.

But to the fragrances, for instance, that would be considered, is that considered synthetic biology? No. So they design the organism just like you take yeast for brewing beer, right? You take an organism and you can alter within the production of that organism what it produces. So it's actually a natural in production. You're just altering the organism that produces it. So it's not synthetic natural in production. You're just altering the organism that produces it. So it's not synthetic biology. Interesting.

Okay, so you're just kind of removing a few ingredients in a preexisting recipe and letting kind of the chef, i.e. the organism, produce a different food product. Exactly. It's this new era of industrial engineering where it's going to change all the processes we created during the first industrial revolution.

Now, what is your, and you may not have a strong opinion here, and if not, that's totally fine, but people get very excited, positively and negatively, about the term GMO, genetically modified food. What is your perspective on that? So I think that... Because just from a personal standpoint, there are cases where they can change the genetics slightly to make something, say, more resistant to pests. That's right. Then it seems like we get into an area also

where they're taking something from a fish and putting it into a plant or something like that. And then I get a little uneasy and I'm not sure if that's well-founded or not. Because we start getting into, I think of all of the um, all of the sort of, uh, horrifying mad scientist novels that I read when I was a kid. Yeah. Uh, but do you, do you think any of those fears are well-founded or what are the risks of that going wild? Okay, so I'll answer your question in a different way.

Perfect. You may not find satisfactory, but I think... It was a very, very poorly worded question. So thank you for saving my ass in the first place. So if we start with this premise that we have these incredibly powerful tools of creation, we can program anything. That obviously means – and couple that up with we have this distributed environment now where anybody can pull up a computer terminal in anywhere in the world at whatever age and program, right, either through biology or computer software. So we have all these tools.

So we have a world full of makers that have these powers. So with that, what you build affects me and what I build affects you. And so one thing that I'm and allow us to reconcile our differences. So we're going to have some really big questions to answer. And we have to decide as a society through our reconciliation systems, do we modify our genetics in our children? Do we do GMO, right? What is appropriate for AI in terms of what people build? So we have really big questions to answer. And I think that one of the best areas we could focus on would be how these social operating systems are constructed and calling attention to them as being technologies that can in fact be built, changed, and better aligned with the realities of our current time. The big question topic is a really fascinating one to me for a whole host of reasons. I remember as an undergraduate, some of my favorite classes were philosophy classes, introduction to metaphysics or whatever. And you had, say, utilitarian philosophers, I think that's the right term, like Peter Singer, for instance, very controversial. I think most of his controversy

is unearned. I think it's politicized and so on. But the question of doing the greatest good for the greatest number of people, how do you make decisions if that's your objective, right? And that would mean if you're stuck in a cave and there's one fat guy plugging the exit, and there are 10 people in the cave who are going to starve to death, you kill the fat guy. I mean, it's mathematics, pure and simple. And that used to be primarily just a thought exercise, sort of an academic ivory tower thought exercise. And now you have companies working on, say, autonomous vehicles and AI who are hiring philosophers to try to advise how to answer these questions when, say, an autonomous car is barreling down the highway or the Golden Gate Bridge and all of a sudden has to choose between hitting the five octogenarians on the sidewalk, the old ladies, or swerving the other direction and hitting a car that has a four-year-old in it. So how do you make those value judgments? And what I'm so curious

about, number one, that's a very multifaceted, thorny, potentially subjective question to tackle, but you have to program these vehicles or entities to behave. That's, that's, that's the, you know, the set of rules they're programming. At the same time, what I really worry about and, and, uh, is not, not only the, the complexity of the technology on its own is, is a, is a, is a big audition, uh, uh, sort of big audacious challenge and problem to tackle, right? By good, let's just say, sort of ethically wired technicians and technologists in the Valley and elsewhere, right?

That's challenging in and of itself. But how do you address the, ultimately a lot of, say, these like whether it's like a bill of rights or an arbitration agreement to to manage these social contracts where everyone's a maker yes will be dependent on it would seem and i want you to challenge me on this if you don't agree with this uh would be dependent on legislation right there will be sort of the the way that you know economics is how humans among other things things, respond to incentives. So it's like the reward in a capitalist society, say, and then the punishment of a legal system.

Yes, exactly. When politicians, many politicians, are completely incentivized in the short term for re-election and not envisioning the long-term implications of some of these massive decisions. Yeah, that's right. Massive decisions. How do you contend with that? Like, or how have you thought about this? That's why I think it's such a hugely important area to focus because when people make decisions, you're looking really at the surface layer.

But the beliefs and values that are driving that are embedded very deeply. Oftentimes, that's why, for example, social operating systems are so incredibly powerful, but also they're invisible. They just are woven into the fabric of our lives, and we don't know they exist. And when we do see them as existing, we just consider them as givens or fixed. And so what we're hoping to do is to call attention to what they are, these massive, powerful influences in our life that drive our decisions, and we don't even know it. That are subconscious. Exactly. And that identifying them, that they really are social technologies that are driving these decisions. And so if we go to use, I guess, a technical term, like if we go deeper in the stack,

if we go down to the operating system level, like what are these core beliefs and these core values? Where do they come from? What are they assuming? Yeah, what are the assumptions and the if-thens that are built into the lowest level that affect our decisions on the eighth layer? Exactly. And we've never tracked it back to that low level

because maybe we absorbed them during childhood through uh religion that wasn't of our choosing whatever it might be or of our choosing for that matter how do you personally try to identify those for yourself in your own personal decision making and so on yeah so at brain tree one of the principles i consistently communicated was challenge all assumptions and the story that i accompanied with it was there's five monkeys in a room there's a basket of bananas at the top and the monkeys of course want to climb the ladder to get the banana but every time a monkey tries they're all sprayed with cold water and so after a few times being sprayed by cold water the monkeys learn don't climb up the ladder

to get the bananas because we're going to spray by cold water and so they take one monkey out and put a new monkey in and the new monkey of course sees a banana is like hey like i'm gonna go grab a banana but when it tries to go up the ladder the other monkeys grab it and pull it back like i don't want to get sprayed by cold water you're a new guy here so like don't let me teach you the rules exactly so then they systematically pull every monkey out. And now you have five new monkeys in. Anytime a new monkey comes in and tries to climb the ladder, they grab the monkey and pull it back. But none of the five have ever been sprayed by cold water.

Have ever experienced it. Exactly. And so what I always try to wonder is, where is that in my life? Like, what am I assuming that is invisible that I cannot see? And, of course, when the circumstances change, in a situation like that, you am I assuming that is invisible that I cannot see? And of course, when the circumstances change in a situation like that, you have learned helplessness, right? Where they would say, take a, I mean, these are horrible experiments, but ultimately the data, I think it's very valuable where they would have say, I think it's a Skinner box that was used where they would subject animals to shocks. And there were some animals who could

move from one side to the other and avoid the shock, you know, from a pain on the floor to another pain, and then others that would get shocked no matter what. And then if they moved them into a new box where that was no longer the case, where they could avoid the shock, those who had learned it was futile to try to move would just lay on the floor and get shocked. So where does that exist in your own life? What are some cases if you're comfortable discussing them where you've uh discovered that whether it brain tree in a business capacity or otherwise yeah let me think about that um so many i mean i guess

being human is remarkably tough right because we just so like you and i before this discussion we were talking about all the funny irrational things you and I both do that's inconsistent with our thought patterns. And I guess a couple years back, maybe a decade ago, I got into irrational behavior, reading Dan or really this book, particularly Irrational, and Thinking Fast and Slow. Yeah, Thinking Fast and Slow, Danny Kahneman. Yes, exactly. So I started reading all these books, and I became increasingly convinced of my own um what i was fickleness and inability to actually act rationally in life and once i became aware of that i think i became much softer in my opinions and confidence levels in life where i i want to question thoroughly everything i do all

the time and of course i miss all layers a lot of time but i try to be present in knowing that when i make a decision there's all kinds of layers behind it, many of which are probably flawed. And if I went back and evaluated it. So I suppose it's just being present and knowing it exists and how flawed we are in our abilities when really we think we're perfectly logical and consistent all the time. We're just not. Yeah. Dan Ariely's book is great, Predictably Irrational. Also a lot of really solid business

takeaways in terms of how people... I remember the example he gave in a presentation. I'm not sure if it's in the book. I'm blanking of the checkout process that The Economist magazine tested. Oh, that's right. And it was like, get the print edition for this amount by itself, get the digital edition for this amount by itself, or get both for this amount. And changing the pricing and removing or adding options affected the average order size. Yes.

So fascinating. Yes. Or adding in basically not a red herring. I don't think it's the right term, but a straw man of an option that they don't even really want you to choose. But they'll add the cheaper option just so they know you'll, because they know that 50% of the people will take the middle option, which would have been the cheapest before, but you would have then not chosen it. Just like restaurants, I think put like the most expensive pricey item in the top right corner to say like, here's a $75 option. Everything else is cheap at $32. Same thing with wine. Yeah. Very

common. Uh, when you are feeling, and maybe and maybe the answer is you don't feel this way, but when you're feeling, say, overwhelmed, how do you unpack that and try to reduce the sources of that overwhelm? I've gotten so much better over the years. Now I just call a friend and just say, you know what? I'm feeling overwhelmed and I feel terrible and I don't think I can do this. And just saying it out loud, like, yeah, actually I can. I got this. But I just need to get that off my chest and I'm feeling overwhelmed and I feel terrible and I don't think I can do this. And just saying it out loud, like, yeah, actually, I can. I got this. But I just need to get that off my chest and I'm all right. And so when I deal with – when I work with entrepreneurs now, people I'm investing in or otherwise, I say, like, if you want to chat any time of the day and say anything, no judgment on my side, just say it out loud, do it.

And I think there's just – it's hard to do hard things i guess as ben horowitz would say and um having the ability to be vulnerable and honest and transparent and raw with other people is immensely helpful for me yeah but you weren't always you didn't always do that no i was extremely private and guarded and i owned everything i didn't dare come out you know let go and i think uh i think men are particularly bad at that um i agree i um yeah i've struggled with this myself and uh you're so on point it's such a simple answer seemingly self-evident and obvious right but uh I think it points to something I've noticed about myself, and I tend to be stuck in my kind of prefrontal cortex. Yeah, yeah.

But if you haven't kind of thought your way, if you haven't rationalized your way, or that's not the right, reasoned your way into a problem, it's hard to reason your way out of it. I agree. Just by relying on the sort of internal pro and con list and like schematic of something that is purely emotional

or maybe based on some operating system flaw that you're experiencing. So yeah, just calling a friend. Yeah, but that's what I love about the friendships I have is I can go into a conversation and I know when I leave, two things will happen. One is they will have challenged my mental models. I can't see my mental models and I can't challenge. I can't

see my mental models and I can't challenge myself very well, but someone else can see it so clearly and they can just call it out. Right. And number two is when I leave the conversation saying like, I want to become a better person. Right. And I want to do more in life and I want to work harder. Like those are the two things I think I value the most in the interaction. So it's, I want to be that for other people, right. That when they bring something to me, I can flip it and say, yeah, here's a different model for you to contemplate. And two, hopefully when they leave, they say, you know what? Yes, like I can do this and I've got that much more energy to go about it. I find also, uh, you know, my version of talking to someone very often is, uh, journaling in the morning just to take what I feel. For instance, if I'm feeling

overwhelmed or having some type of problem or source of anxiety, putting it on paper makes me realize how absurdly unfounded it is. I agree. I agree. It's magical, right? Yeah. And I think that it can be, if you don't have a friend to call who's going to challenge you in that way, just putting it, freezing your thought on paper can provide you with a sufficient mirror in which you can see. It's completely ridiculous. Like I thought I had, you know, I looked like the elephant man.

And in fact, it's just a tiny little pimple on the side of my head. Like, stop freaking out. It's not a big deal. And it's transient or reversible or both. So a couple of, just to shift gears for a minute, a couple of rapid fire questions that you can, which don't have to have rapid fire answers. Okay. So you can take it however you want. I'm not very witty or quick.

Okay, so I'll try my best. I think you're fast enough. In the last, say, six months to a year, or the first thing that comes to mind, what is something, a purchase you've made for less than $100 that has had a significantly positive impact on your life i have water so take your time okay um i would probably say i don't know okay we'll come back to it all right we'll come back uh

do you i did i mean that's that's that's not the right question because it gives you an out. What historical figure do you identify with? So I love biographies. I've read probably 100-plus biographies. And I don't know if there's one person in particular, maybe just a collection. Actually, no, actually, I'd say there's a few. One we talked about before, Shackleton.

He resonates with me at a deep level. Two, I read this book called A Good Man by Mark Shriver, about his dad, Sard Shriver, who worked in the Johnson administration and started the Peace Corps. And he was a remarkable man, an exceptional father, a good friend, loyal. And he is a mental model of the kind of person

I want to be in life. So that three, I'd probably say, Viktor Frankl's Man's Search for Happiness. Happiness or meaning? Meaning, okay, yeah thanks very interrelated though yeah but the so i've one of the driving philosophies of life yeah i think it drives me the most is this i guess i find the most beautiful is that we have the ability to author life in life a little bit better but we we can choose not to take default routes we can choose to take different paths that we can design and do whatever we want and i find that's why i find entrepreneurship so appealing is that you get to design your own world and so

in my office actually i hired i commissioned a graffiti artist oh you sent me a photo of this i remember yeah yeah no explain it please okay so on one side is Gandalf the Grey, and the other side is Harry Potter. And they have their wands and staffs pointed up, and it's this exploding energy in the middle of the air with this book that's open blank pages with a pen. And then above it in graffiti is the.R.R. Tolkien and J.K. Rowling created worlds that we inhabited through the tool of text. They wrote this stuff down, and then we inhabited it. So they literally authored worlds. And we have that same ability as entrepreneurs to build companies. In everything we do, we have that, especially our tools of creation now that we're investing in at the OS Fund. So I wanted to use pop culture figures because i wanted my kids to see this that they have that ability to do that in life that they don't need to say yes to the default options

that they can carve their own path and even though it's incredibly hard it's going to be painful to me it's so much more fulfilling than a secure and safe way to live life. And I think it's also just worth kind of rewinding and pointing something out to folks, which is you didn't come from, as far as I know, I mean, a wealthy family where that was the kind of default. Was that the default belief system? Maybe it was.

Maybe despite the financial challenges. I mean, because I think I recall you telling me that your mom made some of your clothing that you wore to school. She did, yeah. So it's not like you sort of came in with every possible advantage that people might assume is required to think that way. The authoring of your own world. I'm going to come back to that.

I realized the successful question, I think, could be broken down a few ways. You just brought up with that biography, the first one, A Good Man, the thought in my head that you can model different people for different traits, which has its own risks because you might absorb bad habits if you're spending time with those people without realizing it. Sort of like viruses in your,

bugs in the OS, I guess. But that person correlated to the values, right? So modeling that person based on values. If you were modeling, who is an entrepreneur or who are entrepreneurs that you admire for their aggression? So I'd say actually like a bunch of names pop up yeah people i've invested in at the os fund so i mean craig venter

yeah i have longevity peter diamandis uh there as well uh josh tetrick hampton creek um jason kelly inco bioworks daniel Fong at LightSell, Scott Phoenix at Vicarious. I mean, we have a great roster of incredibly passionate entrepreneurs. Mustafa Suleiman from DeepMind. I wasn't an investor there, but I find him immensely inspiring. But these entrepreneurs think differently about the world, and they're going after extremely hard challenges. And I'd say they're going after extremely hard challenges and i'd say

they're audacious and determined and very aggressive uh got it okay so now let's see do you define would you describe yourself as aggressive i am, in what ways are you most aggressive? Um, when I see something I want to go after, uh, I can be pretty relentless. And, um, which entrepreneurs do you most admire for their, and I'll have to say you're, you'll have to choose either a smaller subset of the people you've invested with, or, uh, you can choose other people, which might be safer, but for their resourcefulness. All right. So let's come back to that. I know I'm going to have a lot of examples to think of people who, who have faced near and certain death countless times,

somehow they figured out to maneuver around the problems. examples to think of people who who have faced near and certain death countless times somehow they figured out to maneuver right around the problems right to sort of uh neo in the matrix do the backbend and dodge the bullets and come back to life yeah exactly i mean that's the essence of entrepreneurship so so that that's actually uh that's actually um a good segue. So what do you think an entrepreneur is? What is an entrepreneur? Someone willing to... I think entrepreneurs and explorers have a lot in common with Shackleton.

That they head off in uncharted territory and they maintain this ability to adapt to circumstances that are chaotic, unknown, and extremely challenging. And they can maintain some order in all the chaos to actually achieve a goal. What are practices, experiments maybe, that people could perform to help them develop those characteristics. Is there anything else that you find sort of ports well over to that chaotic, uncertain nature of startups or small companies?

So I guess we, I have a lot of conversations with people who want to start their own thing. And one of my favorite questions to ask is, is this an itch or is it burning? So it's just an itch. It's not sufficient. And it gets to this point of how badly do you really want it? And for me, I burned the boats.

There was no way I was going to get a job. And so failure was never an option. I had to make this work and i did have jobs on the way but that was just simply to pay the bills but um failure just wasn't a solution i would accept and so i think i want to get at entrepreneurs that how badly do you want it what will you do to get there yeah I find it very difficult in the current environment to identify those people because things are so frothy right now. A lot of people who would otherwise be risk intolerant and fearful of uncertainty are jumping into the fray as founders. I mean,

and this, look, a lot of my very close friends come out of McKinsey and places like that. But when people with very high paid consulting jobs are then jumping into startups, I start to wonder what is on the horizon. And if I look back, a very kind of macro timing way to at least narrow down the field a bit so it's easier to find those people seemed to be investing during recessions. So investing right after crashes, it left the people who couldn't conceive of doing anything else standing on the playing field. And the fair weather investors,

the fair weather entrepreneurs all went back to doing whatever they perceived to be charted territory. Yeah, exactly. I guess I want to be careful. doing whatever they perceive to be. Yeah. Chartered territory. Yeah, exactly. I mean, I guess I want to be careful. Like I don't want to be like a,

an entrepreneur definition snob and suggest that I was going to come out and yell at you about that. But, but I mean like these attributes are held by people within companies who are starting their companies who are working with larger institutions, right? But it's, it's,

uh, it's just inherently people who can create, do, and see what others cannot or will not do, right? That they will blaze something that others will follow or benefit from. Hmm. Let me dive in to a couple of other questions also. Do you have a book that you've gifted often? Are there any books that you've gifted to other people often?

I have gifted A Good Man to quite a few people and Shackleton and Viktor Frankl's book. The Good Man I gift because if we contemplate how, like I wonder what would my son or daughter say about me? What kind of biography would they write? And that's a model for me I would want. Shackleton, that's how I want to behave in life. And Frankel, that's how I – his basic point is no matter the conditions we surround ourselves in, we can author our life. We can author however we respond.

And then I guess I'd also throw in there Siddhartha. Have you read that? Hermann Hesse, I guess in German. I love that book. That came up yesterday on a walk with someone I won't name because it was a private conversation, but a very, very successful guy that I also admire a lot for his sort of deep thinking on important philosophical questions.

Siddhartha came up. That's also come up, I think, with my conversation with Josh Waitzkin, who was on the second interview ever on this podcast, who is the basis for Searching for Bobby Fischer, known as a chess prodigy, but really I don't think it's appropriate because he's applied his kind of learning framework to many different areas. But that book comes up a lot.

It's a very sort of allegorical, but oftentimes I think that deep truths can be explored more effectively in fiction than in nonfiction. Because it pulls you out of your normal context. Yes. In a way. a way yes you're not your your program your problem solving software isn't running so exactly blindsides you new mental models yeah yeah exactly uh the um i had a profound question that just escaped my semi-ketogenic brain or ketotic brain.

I'm probably right on the, I think we were talking about this just before and I had 0.6 millimolars because I fell out of ketosis and then I'm just getting back in. I had some coconut oil, but I think that's kept me gone for about 60 minutes. So I'm probably in the no man's land, the gray zone of substrate suffering. What, if you could have,

if you had a huge billboard you could place anywhere and you can put whatever text you want on it where would you put it and what would it say let's say I would put it in New York and it would say do an anonymous and random act of kindness today. I like it.

Why New York? If you're giving me the constraint of a single billboard, and I want the broadest exposure, I'll go to New York where the density is highest. Got it. I like it. Good answer. Um, if you were giving advice to your 30 year old self, what advice would you give?

That, um, that no matter what comes your way, no matter how hard things fill, that I have the power to overcome and be at peace with it. Good advice. I think that's a great place to start wrapping up. Is there anything else you'd like to share with the audience? Resourcefulness examples? Anything else? Yeah, you know, one thing,

so I do a lot of projects with my kids. And, like, for example, we started a few businesses together and we wrote a children's book together. And as I think about the coming generation of makers and doers, that they're the people who will define our world so dramatically. If I think about who they aspire to be like

and what kind of things they want to do and how we write the operating systems of their aspirations and endeavors, I think that I'm encouraged by watching my own kids grow up that I see a bright future that we can trust these incredibly powerful tools of creation can be used for, for good things. They go to subjective, of course, but,

but that we can actually change humanity in fundamental ways and that the rising generation, if we do it right, we'll have amazing ability to contribute to a, to our wellbeing. And if, if there are, and I'm sure there are new parents listening to this.. And if, if there are, and I'm sure there are, uh, new parents listening to this. Uh,

and in fact, I have someone I know very closely who's about to have his first kid. Yeah. Um, what are a few activities or experiments or collaborations that you would encourage them to have with their kids or habits? It could be anything, but just general general try these two things three things whatever it might be with your kids so my personal philosophy is i i try to be relevant in my kids lives

and so for example in my my sixth grader he's in a public school and they don't have any technology in the school and so i've been working with the principal to bring technology in the school and the way we're doing it is we're running a test in his class where they are using the scientific method to say if we bring technology into the classroom will it improve our educational experience and so they have to test it out and use pros and cons and go through the whole process and then each of the then there's six groups making a documentary and so i'm with the teacher working with six groups of students yeah six groups of students within the class and they each are making like a three- to four-minute documentary on the process of testing the scientific method of does – is technology in the classroom a positive for a negative experience, or what are the pros and cons? And so I'm working with his teacher to do that and doing the filmmaking and plotting out the storyboarding and identifying what the scientific method looks like. And that gives me all these opportunities to talk about everything that's relevant in his life

in ways that are meaningful. And so when we have conversations, I'm not just saying, hey, how's your day? Fine. And that's the end of conversation, right? But it's relevant. And so the same is true with my fourth grader and my daughter who's in preschool. But I would say parents that get engaged in the children's lives to be truly relevant, to understand the underlying context of who they like, who they dislike, who are the friends, who are the people who are saying mean things to them, what are they worried about in school. So that's been helpful in my relationship with my kids, and I think it's really helped us form a very strong bond. Are there any traditions that you've built into the family that are non-obvious?

Christmas is very common for a lot of people, of course. But are there any other traditions or rituals that you've developed with your kids? Yeah, so when we sit down for dinner, I always have a question for them. Like last week on Saturday night, we had this discussion of what does it mean to be good? And they're jamming. It's like 11, 9, and 5, and they're jamming on this question of what it means to be good. And I raise all kinds of questions like what you think is good is not necessarily what I think is good. We have these different interpretations, and is there a single definition of good and so my five year old's raising her hand offering up her input which is amazing but they walk away they're

surprisingly bright and have these amazingly good insights so i try to have these significant conversations with them and sometimes it lasts like 10 minutes before chaos breaks out in the house you know but at least we have this moment where we can connect on really serious questions and they can explore these philosophically, which I have found to be beneficial in both their development, but also our relationship. What in your mind are common mistakes that parents make aside from doing the opposite of the two things you just described? So we were, this is up for opinion, of course, but we were at a, my five-year-old had this little party

for her preschool and I took her over and we were at the park and there was this merry-go-round and there was like 20 kids on the merry-go-round. It's like there was some older kids going really fast around and like sometimes a kid would fall, like fall in the dirt and get trampled by their friends. That's what friends are for. Exactly.

So, but there was like two camps of parents that broke out. One camp was like, no way is my child going to be involved in this terribly dangerous endeavor, which is a reasonable thing to say, right? Because it's pretty dangerous. Someone could get really hurt. And there were other parents more like myself, like, look, they'll figure it out. If they get hurt, I'm sure that they'll recover. And it'll be a great experience for them to learn about, about big objects moving very fast.

And right. These principles of physics in the flesh. So, I mean, my daughter got on and she was in the mix of all this stuff, but I'm certainly of the philosophy that I like kids to go explore and do on their own. And if they make mistakes,

that's fine. They can learn. But if we, if there's too much inherent protection structure, that they just forego those learning experiences. Well, they're taught that they're fragile. I think, therefore, they develop the belief that they're fragile. Yeah.

I mean, now, granted, I think back to, I mean, I'm sure you probably have this, like, gasoline, gallon of gasoline in the street example. I think back to some of the stuff I did where I'm just like, I cannot believe I was allowed to do that. Exactly. Like, skateboarding off of ramps in the middle of the street example i think back to some of the stuff i did where i'm just like i cannot believe i was allowed to do that exactly yeah skateboarding off of ramps in the middle of the street where i like flip over and like smash my head on the asphalt and concuss myself exactly she's like oh my god but yep all of those things taught me ultimately like either this too shall pass or like okay like you like you earned your lumps. Now you know not to do that, but you also know like you, you were able to weather the storm and get through it.

Exactly. Yeah. So we got in a four wheeler, uh, two weeks ago, my 11 and nine year olds. And I said, okay, I'm going to put your helmets on. I'm going to give you a two minute lesson on how to go, how to go forward and how to go backwards, how to break. I'm going to give you some lessons, like don't go into a ditch. Don't go on a hillside that you'll turn over but i'm expecting you to now go out for five minutes and come back safely and tell me how you did it like what were your thought processes how'd you stay safe or the risks you took but i want them to do it and i'm not going with you right so you go and come back and they came back in one piece but it was a good experience for them to tell me like okay dad this is how we looked at the risk this is how we thought that we potentially weren't getting to a problem they ran into a tree

going slowly but right they talked about it which was i thought was really helpful well you know it's and uh i just think it's i think you're a fascinating guy i think you're very inspiring guy and as i think forward to yet someday having kids myself. I love asking you these types of questions. And this has been a blast. So number one, thank you very much for taking the time. I always love having these conversations. This is our first one on the record. And second, where can people learn more about you,

about the OS Fund, and so on? OSfund.co, C-O, is where all of our investments are. And I'm active on Twitter, so happy to have ongoing discussions about the various things we talked about. What's your Twitter handle? Brian underscore Johnson with a Y. Got it. At Brian underscore Johnson.

I'll put that in the show notes as well. Any parting thoughts or comments? No, Tim, I just love this. We've had fantastic conversations over time, so this is fun to actually do this formally, and I really enjoy the friendship. Likewise, man. I'm so glad that I was able to try to give people a view

into these conversations that we have. It's so much fun for me, and I always come away with a bunch of things that I want to try or a bunch of assumptions I want to test. And I think you're really good at not only helping to prepare people for what could be a very glorious future of sort of infinite creation, but also giving them the belief in the first place that it's possible. And so I really believe that you're a force for good. So thank you for spreading confidence in the world. And I think you're trying to really leave sort of a dent in the universe and an impact. Thank you, my friend.

I appreciate that a lot. Much appreciated. So to be continued, everybody, I hope you enjoyed this. This I appreciate that a lot. on the blog, fourhourblog.com, all spelled out. You can find the show notes for this episode and every other episode by going to fourhourworkweek, all spelled out, fourhourworkweek.com forward slash podcast. And until next time, thank you for listening.