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

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 http://www.athleticgreens.com/tim —My all-in-one nutritional insurance policy. 99Designs http://www.99designs.com/tim — 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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Tim Ferriss?

  Brian, sound test, what did you have for breakfast?

• 0:02Speaker 01

  I had an omelet.

• 0:04Tim Ferriss?

  An omelet, what was in the omelet?

• 0:06Speaker 01

  Peppers, onions, onions, peppers, tomatoes, with no meat.

• 0:12Tim Ferriss?

  I love how you reordered those ingredients. The mind of Brian at work.

• 0:18Speaker 02

  At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question?

• 0:25Speaker 03

  No, it would have seemed inappropriate to ask.

• 0:29Speaker 02

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 0:40Tim Ferriss?

  This episode is brought to you by Athletic Greens. I get asked all the time, if you could only use one supplement, what would it be? And my answer is inevitably Athletic Greens. It is your all-in-one nutritional insurance. I recommended it in The Four Hour Body, did not get paid for that. And I travel with it to avoid getting sick. I take it in the mornings to ensure optimal performance. It just covers all my bases. If I can't get what I need through whole food meals throughout the rest of the day. And you can get 50, oh my God, 50% off, yes, 50% off if you go to athleticgreens.com/tim. That's athleticgreens.com/tim. Check it out. It's tasty, but more important, it will help you not screw up when you're doing your nutritional planning.

• 1:25Tim Ferriss?

  So for me, it just covers the bases, takes a load off my mind, puts a lot in my body. And check it out, athleticgreens.com/tim.

• 1:36Tim Ferriss?

  This episode is brought to you by 99designs, your one-stop shop for all things graphic design related. I have used 99designs for everything from banner ads to book covers, including sketches and mockups that led to The Four Hour Body, which later became number one New York Times, number one Wall Street Journal. And the brainstorming, a lot of it took place with designers from around the world. And here's how it works, whether you need a t-shirt, a business card, a website, an app thumbnail, whatever it might be, you submit that project and designers from around the world will send you. sketches and mockups and designs, you choose your favorite and you have an original that you love or you get your money back. It's that straightforward. And many of you who are listening have already used it and created some amazing things that

• 2:21Tim Ferriss?

  I'll be sharing in the future. But in the meantime, if you want to see some of my competitions, some of the book covers, as well as get a free $99 upgrade, go to 99designs.com/tim. That's 99designs.com/tim.

• 2:38Tim Ferriss?

  Hello, midnight mad hatters. This is Tim Ferriss. It's very late and I am sing-songing my intro to you in a sultry voice because there are people sleeping in my house and I don't want to wake them up. But I had to record this intro because I want to get this episode to you ASAP. It is a really fun one. For those of you who are joining 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.

• 3:21Tim Ferriss?

  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 is 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.

• 4:01Tim Ferriss?

  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. So of his investments, to give you an idea, include endeavors to cure age-related diseases and radically extend human lifespan

• 4:46Tim Ferriss?

  to 100+, 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 Gingko Bioworks and synthetic genomics, replicate the human visual cortex using artificial intelligence, companies Vicarious, mine precious resources off of asteroids, companies Planetary Resources, and many others. So Brian is not only a scrappy, rags-to-riches story, but he is someone who succeeded and had a massive success story in a technical

• 5:29Tim Ferriss?

  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, 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. I don't think that was the real request. And we did not have a spare backpack, but

• 6:11Tim Ferriss?

  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

• 6:54Tim Ferriss?

  you could talk about, since we first discussed doing the podcast together, how you've been thinking about it?

• 7:00Speaker 01

  Yes, I guess I, 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, you know, 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?

• 7:20Tim Ferriss?

  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, 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, 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?

• 7:51Speaker 01

  So I, my family and I, we were really close. I have four, 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 through, true throughout high school. For example, most, you know, when people are in high school, they don't like their parents or 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 we had a great time as a family. And for fun, we would watch the Dukes of Hazzard and the A-Team on Friday nights and we'd go get a special combo meal at Hardee's. We didn't really have much money, but we

• 8:35Speaker 01

  just, I guess I have a lot of sweet memories from growing up and being close to the family.

• 8:39Tim Ferriss?

  And what, so it sounds like your mom was one of the cool moms. What do you think, correct me if I'm wrong, but what, what characteristics of hers or?

• 8:50Tim Ferriss?

  Habits of hers or otherwise enabled her to be the cool mom and not the shunned mom. What were the contributing factors?

• 8:58Speaker 01

  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 to the street and

• 9:09Tim Ferriss?

  This is just in front of your house or?

• 9:10Speaker 01

  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, you know, it was producing quite a flame. And then her green Taurus rolled around the corner down, 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 like cars blowing up.

• 9:39Tim Ferriss?

  Right.

• 9:39Speaker 01

  So I walk over to 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, that's fair.

• 9:57Tim Ferriss?

  That's a very

• 9:58Speaker 01

  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.

• 10:04Tim Ferriss?

  Do you, so do you think it was, it's a very Dalai Lama like response to a potential gasoline bomb? Do you, do you think, you know, from the time that I lit the Dalai Lama's lawn on fire, I can say, um, I'm kidding. That's not what I did. But the, the, uh, 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 that then other parents were to their kids?

• 10:34Speaker 01

  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 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.

• 10:55Tim Ferriss?

  Did you ever get in, did you get in trouble at school or not so much?

• 11:00Speaker 01

  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, was it mostly an obsession for you as a baseball fan?

• 11:45Speaker 01

  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. Were you a popular kid in grade school, high school? No, so, well, so in eighth grade,

• 12:12Speaker 01

  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 like 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 like, 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.

• 12:57Speaker 01

  I just loved having friends. And I loved to dance in between the different groups because they saw the world so differently, right? It wasn't just like this, this mono understanding of the world. And so. I really enjoyed maintaining friendships and that was my first experience in and learning like 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.

• 13:29Tim Ferriss?

  Hmm. 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, the skaters, fill in 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?

• 13:52Speaker 01

  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 sincere and 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.

• 14:07Tim Ferriss?

  Did you think of yourself, or let me rephrase that, when, when did you first start thinking of yourself as an entrepreneur?

• 14:17Speaker 01

  Um, I think when I, when I, well, I guess I lived in Ecuador for two years and I came home to the, 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

• 14:38Speaker 01

  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, 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, 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, you know, 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.

• 15:13Tim Ferriss?

  What gave you that confidence?

• 15:16Speaker 01

  So I assessed my skills, what I was really good at, and I couldn't really find much.

• 15:21Tim Ferriss?

  This is when you were 21 or was it before that?

• 15:23Speaker 01

  Yeah.

• 15:23Tim Ferriss?

  Okay.

• 15:23Speaker 01

  Well, cause I wasn't good at necessarily great at school or science or biology. I didn't really have any skills in of note. And so I figured, you know, I, 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.

• 15:41Tim Ferriss?

  And then what was, so you've decided on the, on the, on the report card, the skill assessment, the self audit of life, you're like, okay, persistence, check.

• 15:50Speaker 01

  Yeah.

• 15:50Tim Ferriss?

  Good on tap dancing with, with uncertainty. Check box number two. Where did you go from there?

• 15:59Speaker 01

  So I, I was trying to find a cell phone and I was really frugal. I've always been very frugal and I found this guy on 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, you know, smart and energetic. Why don't you come cell phones for me? I'll pay you 40 bucks per activation. And I thought, perfect. Like I'd never, I never understood this whole idea that I would trade 60 minutes of my time for $8.25 an hour. Like it seemed crazy to me. And so he'd said that to me, I thought, okay, I'll make 80 bucks an hour. I can do two per hour. And I said, dill. So I sold phones for him for two days. And then I was on the porch of this lady's house and she had screamed, 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?

• 16:43Speaker 01

  And I, I left the sale and 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, 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 students to sell phones for me and I paid my way through college doing that.

• 17:03Tim Ferriss?

  And when you were first selling to people like this woman with the kids screaming on the porch, was that like a, a door knock type of sales approach? Or how were you? No kidding. So it's like the knock, knock, wipe the feet on the door mat. Like, what was, what was the opening, what was the opening line? When somebody opened the door?

• 17:21Speaker 01

  Well, I was A B testing the different approaches. I could walk throughout campus and ask students. 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.

• 17:37Tim Ferriss?

  Yeah. So one of the, one of my very close friends, 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, 10 terabytes, big deal.

• 17:53Speaker 01

  Right.

• 17:54Tim Ferriss?

  Big storage area network installation at the time. 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 interacting with people socially, even though his, his sort of bedrock skillset was technical. Now, did you, so let's see, you had, 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 it's a lot happened, I'm sure, between that and Braintree, but what was the sort of montage version of that?

• 18:35Speaker 01

  Well, the short version is the cellphone company went remarkably well, but it was not going to make me enough money to retire by 30.

• 18:42Tim Ferriss?

  Right.

• 18:43Speaker 01

  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.

• 18:53Tim Ferriss?

  Sounds, sounds perfect.

• 18:54Speaker 01

  We did everything wrong. No, we did have a, we actually built something, we got customers.

• 18:59Tim Ferriss?

  And this was also in Uton?

• 19:00Speaker 01

  Yes.

• 19:00Tim Ferriss?

  Yeah.

• 19:00Speaker 01

  And we had revenue, so like, we actually built something, but in reality, like, we, we were not set up to succeed. So that failed. And then on the heels of that, I started, I joined another guy to do real estate development. And the short of that is we, 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 on Monster and the other job sites at the time, nobody would hire me. Like, it was just, I think it was so clear that I was, 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...

• 19:36Tim Ferriss?

  Additional skills, loyalty, fierce loyalty to employer.

• 19:40Speaker 01

  And then I read, I saw the newspaper one day, it 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 sides. I'll become your right-hand man. I'll do whatever you want me to do. And no one responded. And so at this 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. 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 posting in, again, I think it's Monster. It was selling credit card processing door to door. And basically it was like, if you can- So business to business?

• 20:25Speaker 01

  Yes. Like marching up and on the street, walking into a retailer or a restaurant. Let me help you set up a merchant account and get a point of sale system. Yes. Or mostly change. Everyone already had existing service. Got it, got it. And so the requirement was like, if you could fog a mirror, you could work these guys. It's a hundred percent commission. Like what's, they don't care if you don't succeed. Right, right. But to your point on the sales side, I would go to inside of business. I figured out pretty quickly. The industry was really messed up. Like the technology was terrible and people were just generally plagued by the industry because it's just unscrupulous. All this dishonesty and complexity. And so I figured out that was the hook.

• 21:06Speaker 01

  Because my product had zero differentiation. It was exactly the same as 500 other providers that walked in the door, you know, every day. Right. And so I'd walk in, I'd say, all right, Tim, like right when you saw me walking in, you'd be like, all right, sales guy, all right, 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 a hundred dollars. 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 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.

• 21:51Speaker 01

  Following this really simple formula of just selling honesty and transparency in a broken industry. That's super interesting. And-

• 21:59Tim Ferriss?

  So a couple of questions, I just want to rewind for a second. With the real estate company, what were, if you're comfortable talking about them, like what were the bad, what were the worst decisions? What were the fatal mistakes?

• 22:10Speaker 01

  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.

• 22:16Tim Ferriss?

  Mixed-use means residential plus commercial.

• 22:18Speaker 01

  Exactly. Yeah, bottom floor, small shops. And Fannie Mae came in, they were our equity investor. I was, 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.

• 22:35Tim Ferriss?

  Storage for just all of their extra stuff that they wanted to take out of the big house and move into?

• 22:40Speaker 01

  Exactly.

• 22:40Tim Ferriss?

  This community living space.

• 22:42Speaker 01

  So then sales stalled in phase one, the bank got anxious, so.

• 22:46Tim Ferriss?

  Ah, got it. So just didn't account for that?

• 22:48Speaker 01

  Yeah.

• 22:49Tim Ferriss?

  That need.

• 22:49Speaker 01

  That was the big blunder.

• 22:51Tim Ferriss?

  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 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. I was like, ah, okay, here we go. So smiling, smiling and dialing.

• 23:24Speaker 01

  Yep.

• 23:25Tim Ferriss?

  And one of the things I did was very similar to what you did with

• 23:31Tim Ferriss?

  taking the potential objection and putting it right up front, which was like, I'm the same as every other guy?

• 23:36Speaker 01

  Yes.

• 23:37Tim Ferriss?

  Product, different label, same thing, except for this, right?

• 23:41Speaker 01

  Yes.

• 23:42Tim Ferriss?

  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.

• 23:55Speaker 01

  Yes.

• 23:55Tim Ferriss?

  And only called when I thought I could get the higher-ups who would

• 23:57Speaker 01

  Yeah.

• 23:58Tim Ferriss?

  work longer hours. But I would.

• 24:01Tim Ferriss?

  I would do my homework so I could guess what they were currently using, like Solaris boxes or whatever it's running on their industry. 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.

• 24:15Speaker 01

  Yes, yes.

• 24:16Tim Ferriss?

  And I would take all of the potential weaknesses and just put them right up front. What, you at that point had already had experience hiring salespeople. How did you, what did you look for in salespeople? Or how did you, how did you hire the people with the highest likelihood of success? Or train them?

• 24:35Speaker 01

  Their ability to connect with other people and earn their trust.

• 24:38Tim Ferriss?

  And what are the correlating behaviors or qualities that allow them to do that?

• 24:46Speaker 01

  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, you know, it spans differences of personalities and experiences in life. But if someone feels like someone is really trustworthy.

• 25:12Tim Ferriss?

  And how do you read that when you meet someone?

• 25:15Speaker 01

  If I trust them.

• 25:17Tim Ferriss?

  Okay, I'm just gonna, I'm gonna dig a little bit more.

• 25:18Speaker 01

  All right.

• 25:19Tim Ferriss?

  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?

• 25:32Speaker 01

  Yeah, I don't know. I guess, 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 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 I think it's a fairly accurate, I think most people can read that.

• 26:01Tim Ferriss?

  How this is a bit of a lateral step, but I just saw, and I want to say it's called Ex Machina.

• 26:09Speaker 01

  Yeah.

• 26:11Tim Ferriss?

  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 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.

• 26:51Tim Ferriss?

  Before a computer can read all of those micro expressions and so on, and come to the same type of trust or not trust conclusion? If you were a betting man,

• 27:07Tim Ferriss?

  and this was the Price is Right of technology.

• 27:10Speaker 01

  I don't think I'm qualified to answer. I will say that 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, like this visceral reaction inside of me. And so as you talk about 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, you know, computer interfaces. I think that

• 27:55Speaker 01

  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.

• 28:08Tim Ferriss?

  Do you think we will have sort of Turing test level interactions with machines within the next five years?

• 28:16Speaker 01

  If I'm a betting man, I'll go longer. I'll say, I'll say a decade at least.

• 28:21Tim Ferriss?

  A decade at least. Interesting. All right. Did the credit card processing business or that experience, you became the number one salesperson?

• 28:31Speaker 01

  Yeah.

• 28:33Tim Ferriss?

  Where did, obviously very interrelated, not exactly the same, but how did that, how did you go from there to Braintree?

• 28:40Speaker 01

  I did it for a year and

• 28:44Speaker 01

  it was amazing because it was this terribly broken world with the technology was just, 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.

• 29:01Tim Ferriss?

  To disrupt it. It was just so ripe.

• 29:03Speaker 01

  Yeah, for, for the right technology and the right disposition as a company to, to be honest and transparent and treat customers so they were thrilled.

• 29:11Tim Ferriss?

  And did you have any technical background?

• 29:14Speaker 01

  I didn't. No.

• 29:14Tim Ferriss?

  Did not?

• 29:15Speaker 01

  No.

• 29:15Tim Ferriss?

  So no computer science?

• 29:17Speaker 01

  No.

• 29:17Tim Ferriss?

  No mechanical engineering, electrical engineering? What was the, and you had one kid at home at that point?

• 29:24Speaker 01

  Two.

• 29:25Tim Ferriss?

  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?

• 29:42Speaker 01

  Yeah. So we, 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 backend processors for it. And I think I had like nine 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.

• 30:24Tim Ferriss?

  Where, where was OpenTable based?

• 30:26Speaker 01

  California.

• 30:27Tim Ferriss?

  It was.

• 30:27Speaker 01

  Yeah.

• 30:28Tim Ferriss?

  And they somehow found you.

• 30:29Speaker 01

  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, you know, this huge global network of restaurants and they stored credit card data when people made reservations. And they had the compliance issue. And so they came to us and they said, like, we have this big problem. And we said, we can fix it. And of course, like, I had no idea if I could fix it.

• 30:50Speaker 01

  But we did a deal with them and that's when we became a software company. But it was, it was a bet the company decision.

• 30:56Tim Ferriss?

  So in the beginning, then, Braintree was like your previous company that you worked for as a salesperson. It's kind of a commodity.

• 31:04Speaker 01

  That's right.

• 31:04Tim Ferriss?

  Business. But you had the relationships.

• 31:06Speaker 01

  That's right.

• 31:07Tim Ferriss?

  So at 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?

• 31:21Speaker 01

  We met at a local meetup in Chicago and we.

• 31:23Tim Ferriss?

  What kind of meetup?

• 31:25Speaker 01

  It was actually Matt Maloney and Mike Evans from Grubhub. They just went public and Karan Goll, 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.

• 31:53Tim Ferriss?

  No kidding. And how did you get so connected with the, 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?

• 32:10Speaker 01

  Yeah.

• 32:10Tim Ferriss?

  Or were you? I don't know.

• 32:11Speaker 01

  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, 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.

• 32:47Tim Ferriss?

  And so that's how you developed, that's how you sort of got your, your foot in the door with the tech world.

• 32:52Speaker 01

  Yeah, that's right. And then the, then the, so when I started Braintree, 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 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 like exceptional people to work.

• 33:27Tim Ferriss?

  And do any of those, those questions come to mind, kind of high level vetting questions for good engineers?

• 33:35Speaker 01

  On the technical side, sure, there's a lot. On the personality side, the, so we would, what I would try to communicate when we hired someone was that we, 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 interactions, working with other engineers. So we're in it for the long term. And so I tried to flush that out in interviews of, we're here to do something epic and special. So if that appeals to you, great. If not, then.

• 34:13Tim Ferriss?

  How do you, now maybe this comes back to the, the spider sense, but how do you vet people who are BSing and, and acting in an interview to get a job versus people who are the true believers?

• 34:25Speaker 01

  For, well, so I guess for non-engineers, I would write this, these posts on Craigslist to recruit people. And at the very top of the page, so the assumption was first, the person reading your job ad is not the person you want to hire.

• 34:36Tim Ferriss?

  That was the assumption?

• 34:38Speaker 01

  Yes.

• 34:38Tim Ferriss?

  Okay.

• 34:38Speaker 01

  That the person reading the ad knew the person you wanted to hire.

• 34:41Tim Ferriss?

  Ah.

• 34:41Speaker 01

  So the very first statement was, "I will pay you $5,000 if you refer the most capable person you know."

• 34:48Tim Ferriss?

  Ah.

• 34:49Speaker 01

  And then the, 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-

• 35:03Tim Ferriss?

  But the "do not apply" was first.

• 35:05Speaker 01

  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 a critical math around everyone around you is 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, about, you know, what you do every day and who you work with."

• 35:45Tim Ferriss?

  How did you choose the name Braintree?

• 35:47Speaker 01

  I, 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 had 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.

• 36:19Tim Ferriss?

  No kidding? I didn't realize that. Braintree, Massachusetts?

• 36:23Speaker 01

  Yeah.

• 36:23Tim Ferriss?

  Wow. I had no idea. So you, so you have this advisor, open table, opens a lot of doors, or changes the direction of the company, it sounds like?

• 36:35Speaker 01

  Yeah, that's right.

• 36:36Tim Ferriss?

  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?

• 36:50Speaker 01

  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. 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 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.

• 37:32Tim Ferriss?

  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?

• 37:51Speaker 01

  Yeah, a personal hero of mine is Ernest Shackleton.

• 37:55Tim Ferriss?

  Oh, yeah. I'll let you, I'll let you reintroduce people.

• 37:58Speaker 01

  Yeah, right. So we probably share a mutual love.

• 38:00Tim Ferriss?

  Yeah.

• 38:00Speaker 01

  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, 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

• 38:44Speaker 01

  in my life because I, 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 of the course. But I want to start with that as the contemplation.

• 39:05Tim Ferriss?

  So it's kind of like a what would Shackleton do bracelet?

• 39:09Speaker 01

  There you go. Yeah. Better said.

• 39:12Tim Ferriss?

  Shackleton, uh, why did you move to Chicago?

• 39:15Speaker 01

  To pursue an MBA.

• 39:17Tim Ferriss?

  Oh, no kidding?

• 39:18Speaker 01

  Yeah.

• 39:19Tim Ferriss?

  Why did you, are you glad that you got an MBA?

• 39:22Speaker 01

  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, um, I mean, the MBA, MBA was, was helpful, but I don't know. Um, 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.

• 39:56Tim Ferriss?

  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.

• 40:16Speaker 01

  Yeah.

• 40:16Tim Ferriss?

  And the only way that they could relocate was to get an MBA, say to Chicago, New York, SF.

• 40:23Speaker 01

  Yeah.

• 40:23Tim Ferriss?

  Uh, do you think the 120K or whatever it might be would be worth it?

• 40:31Tim Ferriss?

  If someone, if, if someone, if, if one of your kids was considering getting an MBA?

• 40:34Speaker 01

  Yeah.

• 40:35Tim Ferriss?

  And let's just say they were kind of of that age now.

• 40:37Speaker 01

  Yeah.

• 40:38Tim Ferriss?

  What, what might you ask them?

• 40:41Speaker 01

  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, get 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 in my mind, immediately went to like, how are these people paying for their rent? Are their marriages still intact? Right? Like, are they emotionally just too stressed out to function? The way I thought was so was was

• 41:25Speaker 01

  so colored by my experience as an entrepreneur. And it was such a dramatic difference in how my peers thought.

• 41:31Tim Ferriss?

  People coming in from like Ernst and Young.

• 41:33Speaker 01

  From larger corporations. Yeah.

• 41:34Tim Ferriss?

  Make their pay grade jump.

• 41:35Speaker 01

  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 it's not to say that education is not helpful. There certainly is in certain regards, but.

• 41:58Tim Ferriss?

  There are different types of education.

• 41:59Speaker 01

  That's right. Yeah.

• 42:00Tim Ferriss?

  What's the most valuable thing you took from business school? Or from that experience? Let me say that.

• 42:09Tim Ferriss?

  We can come back to it.

• 42:10Speaker 01

  Yeah.

• 42:10Tim Ferriss?

  Or you're giving me the look.

• 42:16Tim Ferriss?

  Or we can drop it.

• 42:17Speaker 01

  I'm not sure.

• 42:17Tim Ferriss?

  Okay. Well, that's, that's, that's a fine answer. I think more people should have that as an answer.

• 42:22Speaker 01

  Maybe that is the answer.

• 42:26Tim Ferriss?

  I was telling my brother, we're talking about some, some really kind of deep philosophical questions. And I said, I just haven't figured it out. And you said, maybe that's what you figured out.

• 42:35Speaker 01

  Exactly. Totally true.

• 42:37Tim Ferriss?

  Maybe that's not an answer you need to find. So with with Braintree, then let's, let's kind of look at what what turned Braintree into a rocket ship? Or what was what led to that perception at the very least?

• 42:54Speaker 01

  So I, early on, I had to figure out how to get customers without any money, which is a hard problem to solve.

• 43:01Tim Ferriss?

  Common problem.

• 43:02Speaker 01

  Right, exactly. And so what I did is I, I knew that computers, you know, computer software engineers were the target that I needed to appeal to them. And I knew there were different communities, like Python, dot net, Ruby on Rails. Java, they all hung out in these different communities and each community had certain characteristics about how they worked 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 onboard, 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.

• 43:47Tim Ferriss?

  Now, did you figure this out by looking at message boards? How did you go about doing it?

• 43:50Speaker 01

  No, I found actually a couple of academic research papers that, yeah, that actually measured sociability and interconnectedness, and had like these maps, the diagrams that showed where these nodes were and who, how they interconnected. And then I focused on Ruby on Rails, and we got a couple leaders, and they're like, you know, 37 signals and a few others GitHub.

• 44:06Tim Ferriss?

  It's a good one to have. 37 signals, this is a good one to have.

• 44:09Speaker 01

  Yeah, Jason and David were amazingly good to us. Like, they would tweet out all the time, and they referred out all their friends. They were fantastic. And so, we basically built the business on word of mouth, because we, we tried so incredibly hard to be exceptional in what we did. So they'd come on, and they would love it, what we, what we built, and how we treated them, and they would tell others.

• 44:28Tim Ferriss?

  So I wanted, 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 the, 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 everyone, when you want everyone to be your customer, customer, no one is your customer. Especially when you have no money. You need the, the kind of cost per acquisition to be as low as possible.

• 45:01Speaker 01

  Right, right.

• 45:01Tim Ferriss?

  Ideally, zero. And so when I launched either Four Hour Workweek, 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, the highest rebroadcasting ability. And very much similar to your, your chattiest checkbox, right? And I, I determined that I also wanted 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.

• 45:36Speaker 01

  Right.

• 45:36Tim Ferriss?

  Primarily. And, and then after, if I, if I hit a critical mass in that

• 45:43Tim Ferriss?

  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.

• 46:01Speaker 01

  Exactly.

• 46:02Tim Ferriss?

  But I wanted to identify the people who are kind of disproportionately creating the most online content.

• 46:08Speaker 01

  Exactly.

• 46:09Tim Ferriss?

  At that time.

• 46:10Speaker 01

  Yep.

• 46:11Tim Ferriss?

  And, okay, so you target Ruby on Rails. And was there a particular tipping point where you were like, holy moly?

• 46:19Speaker 01

  Okay.

• 46:20Tim Ferriss?

  Well. Any particular kind of hockey stick or breakthrough moments that come to mind?

• 46:25Speaker 01

  Yeah, so we, let me think, so we got as customers within the first couple of years, 37signals, GitHub, Uber, Airbnb, Living Social when they were on their tear. I mean, we had so many of the fastest.

• 46:42Tim Ferriss?

  You had the all-star team.

• 46:43Speaker 01

  We did. We had some of the best companies in the whole world using us. And that their growth fueled of 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, is 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.

• 47:03Tim Ferriss?

  Who were you in that period of time competing against? Who were your primary competitors?

• 47:10Speaker 01

  Initially, it was the old guard, like CyberSource and authorized.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.

• 47:33Tim Ferriss?

  Right.

• 47:34Speaker 01

  Doing their thing.

• 47:35Tim Ferriss?

  And so when you met with the Ubers, the Airbnbs and so on, how did you convince them to work with you guys?

• 47:44Speaker 01

  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 that we just found out they were customers when they were going through the underwriting process. But we did target some of these companies individually, but most of it was organic.

• 48:00Tim Ferriss?

  Got it. And aside from the word of mouth, what are other things that facilitated them finding you naturally?

• 48:10Speaker 01

  Being exceptional. This was the thing I said continually, again and again 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 so much so that I want to write them a love letter. If we solve that, everything else would take care of itself because they'd walk away and that night when they're out with their friend getting a beer, they're going to bring us up because they had 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, like, we see you're coding to the API and they're having problems. Can we help? Like,

• 48:55Speaker 01

  who does that? Like, who practically reaches out? So we tried to do these small things that created these really great experiences for people.

• 49:01Tim Ferriss?

  Now, could you explain, just for people who are non-technical out there, so, application programming interface?

• 49:06Speaker 01

  Oh, yeah, sorry.

• 49:07Tim Ferriss?

  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?

• 49:16Speaker 01

  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.

• 49:29Tim Ferriss?

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

• 49:50Speaker 01

  Exactly.

• 49:51Tim Ferriss?

  And that's the API.

• 49:52Speaker 01

  That's right.

• 49:53Tim Ferriss?

  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 experience.

• 50:02Speaker 01

  Yeah, making your services broadly available to a broader ecosystem of engineers.

• 50:06Tim Ferriss?

  Your story reminds me of...

• 50:10Tim Ferriss?

  A story told by one of my favorite people out there, a guy named Derek Sivers. I don't know if you know.

• 50:13Speaker 01

  I know Derek.

• 50:14Tim Ferriss?

  So Derek is, 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

• 50:57Tim Ferriss?

  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 email confirmation, and no one was doing that.

• 51:11Speaker 01

  Yes.

• 51:11Tim Ferriss?

  And so it spread, it was such a small detail with huge implications for brand loyalty, for PR, for acquisition, for all of these things. And it was so easy to do.

• 51:25Speaker 01

  Yep.

• 51:26Tim Ferriss?

  Right? It was not something that a big company couldn't do, it was just something a big company wouldn't do.

• 51:31Speaker 01

  Yes.

• 51:31Tim Ferriss?

  Typically, right? What are other, 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?

• 51:52Speaker 01

  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 like 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 like the thing came up that everyone was worried about or they wanted to talk about but no one dared.

• 52:36Tim Ferriss?

  So what would be, when would those awkward pauses come up? You say, does anyone have any questions? And then you just let it sit?

• 52:42Speaker 01

  Exactly.

• 52:43Tim Ferriss?

  Like, we're gonna, we're gonna wait until we have some questions?

• 52:44Speaker 01

  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 is-

• 52:51Tim Ferriss?

  The pink elephant expanding?

• 52:52Speaker 01

  Exactly. The thing is true in life is that everyone always has a pebble in their shoe, always. 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 we, you know, in the company and if we addressed it openly in the town hall setting, it'd be great. And so I would let these long pauses go and someone would finally raise their hand and say like, all right, like, I'm really bothered that we hired someone for this role instead of promoting someone internally, right? Like, what's going on? And it was great because these were really hard questions to answer. And so I encouraged like brutal, honest feedback. And if they criticized me, even better, right? If they

• 53:33Speaker 01

  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.

• 53:43Tim Ferriss?

  This was at a company Christmas party?

• 53:45Speaker 01

  Company Christmas party. We're in the buffet line. And I say, so like, how's you know, so and so doing? Like, he's four months in and how's he enjoying life? And she says, like, it's amazing. Like, he is happy. And he comes home and he's energized and he loves his coworkers. And it's so different from what he was, how he felt before. And I thought, yes, like, 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, how to get it. Now, of course, like, I couldn't go interview everyone all the

• 54:29Speaker 01

  time. It would be awkward. But just knowing that the data sources were out there to gather to build a, you know, a good team was really helpful.

• 54:38Tim Ferriss?

  So you said, you know, if they criticize me, all the better. What would you, how would you prompt people to be brutally honest? Because you're the you're the big boss, right?

• 54:46Speaker 01

  Right.

• 54:47Tim Ferriss?

  Uh, 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, what, what did you say? In either case?

• 54:59Speaker 01

  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, you know, sensitive about it. And then I would just, um, I guess in dialogue, I would try to typically own things myself to make them feel comfortable that they could bring it up and we could discuss it openly.

• 55:23Tim Ferriss?

  How would you do that?

• 55:25Speaker 01

  So if we talked about, um, I'm trying to think of like a recurring theme that came up. Um, 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 going to 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.

• 55:53Tim Ferriss?

  Got it. So it's not, it's no longer your job to worry about it. It's my job to worry about it.

• 55:56Speaker 01

  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.

• 56:07Tim Ferriss?

  So the, um,

• 56:10Tim Ferriss?

  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 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, you're very methodical. Uh, and one thing that I've personally struggled with is, uh, 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.

• 56:54Tim Ferriss?

  I want the bad news because I feel like the good news will take care of itself. Does that make sense?

• 56:58Speaker 01

  Yeah.

• 56:58Tim Ferriss?

  And I think as a result of that, uh, 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.

• 57:21Speaker 01

  Right.

• 57:22Tim Ferriss?

  Or I just forget about that.

• 57:23Speaker 01

  Yep.

• 57:25Tim Ferriss?

  How, 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, and that level of happiness that the significant other reported?

• 57:42Speaker 01

  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 is always going to feel left out because like I was just involved as you know, him or her in doing this. And so it is tricky, but I, I always highlight, we did, 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.

• 58:25Tim Ferriss?

  Right. The positive reinforcement.

• 58:26Speaker 01

  Yes.

• 58:27Tim Ferriss?

  And you did, how often did you do the town hall meetings?

• 58:31Speaker 01

  We did either weekly or bi-weekly. We kind of fluctuated over the years.

• 58:34Tim Ferriss?

  What day of the week?

• 58:35Speaker 01

  Friday.

• 58:36Tim Ferriss?

  Friday?

• 58:36Speaker 01

  Yeah.

• 58:36Tim Ferriss?

  Why Friday?

• 58:38Speaker 01

  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 we, and I guess regroup on the essence of why we existed, right? That we weren't just there to make a paycheck. We were there to build something exceptional and to continually talk about that was important.

• 59:07Tim Ferriss?

  When you were building Braintree, when do you feel like you were at your? Your peak powers, in other words, like when were you pitching a no hitter in the World Series? Like, at what point in building Braintree was that?

• 59:21Speaker 01

  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 of years to ramp up to start processing, you know, significant sales. So I don't know if I could identify a single point. It's just this slow, steady build.

• 59:46Tim Ferriss?

  When were you under the most, when did you feel under the most pressure?

• 59:53Speaker 01

  Always.

• 59:55Tim Ferriss?

  Okay, so the, the, where I'm trying to lead this is when, 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?

• 1:00:17Speaker 01

  Yeah, so I guess if I think about the broader context of life, I mean, I had

• 1:00:23Speaker 01

  two children when I started Braintree and then, 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 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 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

• 1:01:09Speaker 01

  fellow founders, people who get you and understand you.

• 1:01:12Tim Ferriss?

  Right.

• 1:01:13Speaker 01

  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 it's not to say people in 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 you and I have where We can talk as if we were journaling.

• 1:01:44Tim Ferriss?

  Right.

• 1:01:45Speaker 01

  Right. I mean, to get to the real raw and good stuff of life. But I think that that would have been very helpful during those darkest times, during the moments where it was the hottest.

• 1:01:55Tim Ferriss?

  Yeah. I had a book inscribed for me, actually it's right there. The Psychedelic Explorer's Guide had Jim Fadiman on the podcast and I thought his inscription was so great. He said, 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.

• 1:02:17Speaker 01

  Yeah.

• 1:02:17Tim Ferriss?

  We go on these hikes, but having those, those people who can identify with the pressures that you're feeling.

• 1:02:23Speaker 01

  Yeah.

• 1:02:23Tim Ferriss?

  What were other coping strategies that you had or routines that were helpful when you felt you were shouldering all of that burden?

• 1:02:32Speaker 01

  Yeah. So I always looked for hobbies that would consume my mind, where I could escape myself because these things-

• 1:02:39Tim Ferriss?

  You could change the channel.

• 1:02:40Speaker 01

  Exactly, yeah.

• 1:02:41Tim Ferriss?

  For a brief period of time.

• 1:02:42Speaker 01

  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 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 gonna 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. 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.

• 1:03:17Tim Ferriss?

  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?

• 1:03:25Speaker 01

  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.

• 1:03:38Tim Ferriss?

  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.

• 1:03:54Speaker 01

  Yeah.

• 1:03:54Tim Ferriss?

  Is it-

• 1:03:57Tim Ferriss?

  How cost prohibitive is it to become involved with aviation in some capacity?

• 1:04:02Speaker 01

  So I think I paid a few thousand dollars over the course of the lessons.

• 1:04:06Tim Ferriss?

  Got it.

• 1:04:07Speaker 01

  Something like that.

• 1:04:08Tim Ferriss?

  Over what period of time?

• 1:04:09Speaker 01

  I believe it took me 90 days.

• 1:04:11Tim Ferriss?

  Got it. So I mean, all in all, not pocket change, but not like buying a Gulfstream.

• 1:04:16Speaker 01

  That's right.

• 1:04:17Tim Ferriss?

  And this is something I've, I've, I've a number of friends here in the Bay Area who use aviation as their way of changing the channel, right? So that they're not constantly watching sort of

• 1:04:31Speaker 01

  Yes.

• 1:04:31Tim Ferriss?

  Uh, BBC news or whatever the hell their world happens to be.

• 1:04:35Speaker 01

  That's right.

• 1:04:38Tim Ferriss?

  Let's see, the, um, 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?

• 1:04:53Tim Ferriss?

  We're in that rough range.

• 1:04:54Speaker 01

  Yeah. I admired people who had.

• 1:04:59Speaker 01

  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 a significant amount of resources through building businesses and were 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 so 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.

• 1:05:34Tim Ferriss?

  So who were, who were some of those people or who are some of those people?

• 1:05:37Speaker 01

  Well, I mean, growing up in Utah, John Huntsman was

• 1:05:41Tim Ferriss?

  I don't know who that is.

• 1:05:41Speaker 01

  So he built, um, I'm not even sure what company he built, but he was enormously wealthy. And of course the Marriott's are in there as well, but there were a few families in the community that had accumulated significant resources and they, they like one, I think Huntsman had as 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 a, I thought that was really remarkable that you could make huge contributions potentially to humanity.

• 1:06:10Tim Ferriss?

  So this is, 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?

• 1:06:18Speaker 01

  It is, yeah.

• 1:06:18Tim Ferriss?

  So could you explain to people what the OS Fund is?

• 1:06:22Speaker 01

  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 it tastes like, what areas would I focus on? And I looked through thousands and thousands of ideas. And I was always thinking about it. And I studied during that time a lot of about science and technology. And the realization 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

• 1:07:06Speaker 01

  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 like the one of the biggest moments in the history of mankind, or humankind, how do we, the biggest question for me was, what kind of world are we going to build?

• 1:07:28Tim Ferriss?

  Yeah.

• 1:07:29Speaker 01

  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.

• 1:07:38Tim Ferriss?

  Yeah, it is really a fascinating time. And we have this sort of Cambrian explosion of potential, where, you know, what, what happens when you can create virtually anything?

• 1:07:49Speaker 01

  Yes.

• 1:07:50Tim Ferriss?

  You can download a recipe for a, a, a, a virus that could cause an epidemic.

• 1:07:57Speaker 01

  That's right.

• 1:07:57Tim Ferriss?

  Or a weapon.

• 1:07:58Speaker 01

  That's right.

• 1:07:58Tim Ferriss?

  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?

• 1:08:10Speaker 01

  Yes.

• 1:08:10Tim Ferriss?

  Why operating system?

• 1:08:12Speaker 01

  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, 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, my, what we think about is the companies we invest in are doing world changing things at

• 1:08:55Speaker 01

  the operating system level. So if they're successful in their endeavors, it would radically change the world.

• 1:09:00Tim Ferriss?

  Right. So the foundational

• 1:09:01Speaker 01

  That's right.

• 1:09:02Tim Ferriss?

  level upon which everything else

• 1:09:03Speaker 01

  That's right. So just like a computer has an operating system at its core that determines how it works. And then there's applications that sit on top. Everything in life has an operating system.

• 1:09:12Tim Ferriss?

  And what are some of the investments that you've made thus far in the, in the OS fund?

• 1:09:18Speaker 01

  Yeah. Human longevity led by Craig Venter is they're trying to radically extend healthy human life, you know, into the hundreds. And they're doing it by using the whole human genome and then adding data like the the metabolome and phenotype data, and then using advanced machine learning to learn about disease and, and create personal therapeutics. If they're successful, it would change medicine.

• 1:09:41Tim Ferriss?

  Right. As we know it, in a really fundamental way.

• 1:09:43Speaker 01

  Yeah.

• 1:09:45Tim Ferriss?

  Any others?

• 1:09:46Speaker 01

  Uh, 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, the producing in the lab that otherwise would be required in nature. And as we climb up the complexity of scale, we can do much more complicated things like work on antibiotic resistance and carbon capture. But the idea, Tim, like your biology, I'm biology, our world runs on biology.

• 1:10:23Tim Ferriss?

  Right.

• 1:10:24Speaker 01

  The fact that this could be a programming language we could actually predictably use is remarkable.

• 1:10:29Tim Ferriss?

  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 the, to the fragrances, for instance, that would be considered, is that considered synthetic biology?

• 1:10:45Speaker 01

  No, so they design the organism, just like you, 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 biology.

• 1:11:01Tim Ferriss?

  Interesting, okay, so you're just kind of removing a few ingredients in a pre-existing recipe and letting kind of the chef, I eat the organism, produce.

• 1:11:11Speaker 01

  So it's like this new-

• 1:11:12Tim Ferriss?

  A different food product.

• 1:11:13Speaker 01

  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.

• 1:11:20Tim Ferriss?

  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.

• 1:11:34Speaker 01

  Yeah.

• 1:11:35Tim Ferriss?

  And genetically modified food. What is your perspective on that?

• 1:11:39Speaker 01

  So I think that-

• 1:11:40Tim Ferriss?

  Because I, just from a personal, personal standpoint, there are cases where they can change the genetics slightly to make something, say, more resistant to-

• 1:11:51Speaker 01

  That's right.

• 1:11:51Tim Ferriss?

  Pests.

• 1:11:52Speaker 01

  That's right.

• 1:11:53Tim Ferriss?

  Then we, they're, they're start, it seems like we get into an area also where they're taking something from like a fish and putting it into a plant or something like that.

• 1:12:01Speaker 01

  Yes.

• 1:12:01Tim Ferriss?

  And then I get a little uneasy, and I'm not sure if that's well-founded or not.

• 1:12:05Speaker 01

  Yep.

• 1:12:06Tim Ferriss?

  Because we start getting into, you know, I think of all of the, all of these sort of horrifying mad scientist novels that I read when I was a kid.

• 1:12:16Speaker 01

  Yeah.

• 1:12:17Tim Ferriss?

  But do you, do you think any of those fears are well-founded, or what are the risks of that going wild?

• 1:12:24Speaker 01

  Okay, so I'll answer your question in a different way.

• 1:12:26Tim Ferriss?

  Perfect.

• 1:12:26Speaker 01

  You may not find satisfactory, but- I think.

• 1:12:30Tim Ferriss?

  It was a very, very poorly worded question. So thank you for saving my ass in the first place.

• 1:12:35Speaker 01

  So if we start with this premise that we have these incredibly powerful tools of creation, we can program anything. Okay, 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 and 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 exploring now with the OS fund is what I call our social operating systems. And there are systems of cooperation and reconciliation. So in that category falls like governance

• 1:13:17Speaker 01

  and capitalistic systems, right? These belief and value frameworks that drive our behavior 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.

• 1:14:03Tim Ferriss?

  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, you know, 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 there's like, you're stuck in a cave and there's one fat guy plugging the exit, and there are 10 people in the cave are going to starve to death.

• 1:14:42Speaker 01

  That's right.

• 1:14:43Tim Ferriss?

  You kill the fat guy. I mean, just it's mathematics.

• 1:14:45Speaker 01

  Right.

• 1:14:46Tim Ferriss?

  Pure and simple. And.

• 1:14:49Tim Ferriss?

  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. That's right. Who are hiring philosophers to try to advise. That's right. 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 it has to choose between, you know, hitting the five, you know, octogenarians on the sidewalk, the old ladies, or swerving the other direction and hitting a car that has a four-year-old in it. Yes, yes. So how do you make those value judgments, right? And what I'm so curious about, number one, that's a, that's a very multifaceted, thorny,

• 1:15:33Tim Ferriss?

  potentially subjective question to tackle, but you have to program these vehicles or entities. That's right. 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 is not, not only the, the complexity of the technology on its own is, is a, is a, is a big audish, uh, sort of big audacious challenge and problem to tackle, right? By good. Right. Let's just say, uh, sort of ethically wired technicians and technologists in the valley and elsewhere, right? Right.

• 1:16:14Tim Ferriss?

  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, 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, respond to incentives. Right, right. And so it's like the reward in a capitalist society, say, and then the punishment of a, of a legal system. Yes, exactly. Put you in prison. Yep. When politicians, many politicians are completely incentivized in the short term

• 1:16:55Tim Ferriss?

  for reelection and not envisioning the long-term implications of some of these massive decisions. That's right. Massive decisions. How do you contend with that? Like, or how have you, how have you thought about this? That's why I think it's such a hugely important area to focus because.

• 1:17:15Speaker 01

  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. Right? Oftentimes, that's why, for example, like, social operating systems are so incredibly powerful, but also they're invisible. Like, 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, right? These massive, powerful influences in our life that drive our decisions, and we don't even know it.

• 1:17:49Tim Ferriss?

  Right, that are subconscious.

• 1:17:51Speaker 01

  Exactly, yep. 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, you know, 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?

• 1:18:08Tim Ferriss?

  Yeah, what are the assumptions?

• 1:18:09Speaker 01

  Yes.

• 1:18:10Tim Ferriss?

  And the if-then's that are built into the lowest level?

• 1:18:13Speaker 01

  Exactly.

• 1:18:14Tim Ferriss?

  That affect our decisions on, you know, the eighth layer?

• 1:18:16Speaker 01

  Exactly.

• 1:18:17Tim Ferriss?

  And we've never tracked it back to that low level, because maybe we absorbed them during childhood through 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?

• 1:18:35Speaker 01

  Yeah, so at Braintree, 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 of being sprayed by cold water, the monkeys learn, don't climb up the ladder to get the bananas, because we're going to be sprayed by cold water. And so they take one monkey out and put a new monkey in, and the new monkey, of course, sees the bananas, it's like, hey, like, I'm gonna go grab a banana. But when it tries to go up the ladder, the other monkey grabs it and pulls it back. Like, I don't want to get sprayed by cold water, you're a new guy here, so like, don't mess with it.

• 1:19:16Tim Ferriss?

  I'm gonna teach you the rules.

• 1:19:17Speaker 01

  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.

• 1:19:31Tim Ferriss?

  Have ever experienced it.

• 1:19:32Speaker 01

  Exactly. And so what I always tried to wonder is, where is that in my life? Like, what am I assuming that is invisible, that I cannot see?

• 1:19:40Tim Ferriss?

  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, is very valuable, where they would have, say, I think it's a Skinner box that was used, where they would subject animals to shocks.

• 1:19:55Speaker 01

  Yeah.

• 1:19:56Tim Ferriss?

  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.

• 1:20:15Speaker 01

  Yes.

• 1:20:15Tim Ferriss?

  And get shocked.

• 1:20:15Speaker 01

  Yes.

• 1:20:16Tim Ferriss?

  So where does that exist in your own life? What are some cases, if you're comfortable discussing them, where you've discovered that? Whether at brain tree in a business capacity or otherwise?

• 1:20:27Speaker 01

  Yeah, let me think about that. So many. I mean, I guess, being human is remarkably tough, right? We do 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.

• 1:20:42Tim Ferriss?

  Right.

• 1:20:42Speaker 01

  And I guess a couple of years back, maybe a decade ago, I got into irrational behavior, reading Dan Ariely's book, Predictably Irrational, and Thinking Fast and Slow.

• 1:20:52Tim Ferriss?

  Yeah, Thinking Fast and Slow, Danny Kahneman.

• 1:20:53Speaker 01

  Yes, exactly. So I started reading all these books, and I became increasingly convinced of my own, what, 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.

• 1:21:35Tim Ferriss?

  Yeah, there's, 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.

• 1:21:54Speaker 01

  Oh, that's right.

• 1:21:54Tim Ferriss?

  And it was like, you know, 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 how, you know, changing the pricing and removing or adding options affected the the average order size.

• 1:22:07Speaker 01

  Yes.

• 1:22:08Tim Ferriss?

  So fascinating.

• 1:22:09Speaker 01

  Yes.

• 1:22:09Tim Ferriss?

  Uh, or adding in basically, not a red herring, it's not, I don't think 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.

• 1:22:23Speaker 01

  Totally.

• 1:22:24Tim Ferriss?

  Which would have been the cheapest before, but you would have then not chosen it.

• 1:22:27Speaker 01

  Exactly. 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.

• 1:22:35Tim Ferriss?

  Same thing with wine.

• 1:22:36Speaker 01

  Yeah.

• 1:22:36Tim Ferriss?

  Very common. Uh, when you are feeling, and maybe, 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?

• 1:22:50Speaker 01

  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, right, just saying it out loud, like, yeah, I actually, I can, I got this, but I just need to get that off my chest, 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 at any time of the day and say anything, right, no judgment on my side, just say it out loud, do it. And I think there's just, it's, it's hard to do hard things, I guess, as Ben Horowitz would say.

• 1:23:23Tim Ferriss?

  I am.

• 1:23:23Speaker 01

  And, um, having the ability to be vulnerable and honest and transparent and raw with other people is immensely helpful for me.

• 1:23:32Tim Ferriss?

  Yeah. But you weren't always, you didn't always do that.

• 1:23:37Speaker 01

  No, I was extremely private and guarded and I owned everything, I didn't dare come out, you know, let go and.

• 1:23:42Tim Ferriss?

  I think, I think men are particularly bad at that.

• 1:23:45Speaker 01

  I agree.

• 1:23:46Tim Ferriss?

  I, uh, 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,

• 1:23:59Tim Ferriss?

  I think it points to something I've noticed about myself and I tend to be stuck in my kind of prefrontal cortex.

• 1:24:04Speaker 01

  Yeah, yeah.

• 1:24:05Tim Ferriss?

  But if, 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.

• 1:24:15Speaker 01

  I agree.

• 1:24:16Tim Ferriss?

  Just by, by relying on the sort of internal pro and con list.

• 1:24:20Speaker 01

  Yeah.

• 1:24:21Tim Ferriss?

  And like schematic of something that is purely emotional, or maybe based on some operating system flaw that you're experiencing.

• 1:24:25Speaker 01

  Yeah, yeah.

• 1:24:26Tim Ferriss?

  So yeah, just calling a friend.

• 1:24:29Speaker 01

  Yeah, but that's like 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 that 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 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.

• 1:25:08Tim Ferriss?

  I find also, you know, my version of talking to someone very often is journaling in the morning.

• 1:25:15Speaker 01

  Yeah.

• 1:25:16Tim Ferriss?

  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.

• 1:25:27Speaker 01

  I agree. It's magical, right?

• 1:25:29Tim Ferriss?

  Yeah. And I think that, you know, 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.

• 1:25:38Speaker 01

  Yeah.

• 1:25:39Tim Ferriss?

  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, you, which don't have to have rapid fire answers.

• 1:26:01Speaker 01

  Okay.

• 1:26:02Tim Ferriss?

  You can, so you can take it however you want.

• 1:26:03Speaker 01

  I'm not very witty or quick. Okay, so I'll try my best.

• 1:26:07Tim Ferriss?

  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 a hundred dollars that has had a significantly positive impact on your life?

• 1:26:25Tim Ferriss?

  I have water, so take your time.

• 1:26:26Speaker 01

  Okay.

• 1:26:29Speaker 01

  Um, I would probably say.

• 1:26:34Speaker 01

  I don't know.

• 1:26:35Tim Ferriss?

  Okay, we'll come back to it.

• 1:26:36Speaker 01

  All right.

• 1:26:36Tim Ferriss?

  We'll come back.

• 1:26:40Tim Ferriss?

  Do you identi- 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?

• 1:26:50Speaker 01

  So I love biographies. I've read probably a hundred 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, there's a few.

• 1:27:06Speaker 01

  One, we talked about before Shackleton. He, he resonates with me at a deep level. Uh, two, I read this book called A Good Man by Mark Shriver, about his dad, Sarge Shriver, who worked in the Johnson administration and started the Peace Corps and, and, um, 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, um, that three, I'd probably say, uh, Viktor Frankl's Man's Search for Happiness.

• 1:27:41Tim Ferriss?

  Happiness or meaning?

• 1:27:42Speaker 01

  Meaning, okay. Yeah.

• 1:27:43Tim Ferriss?

  Yeah.

• 1:27:44Speaker 01

  So thanks.

• 1:27:44Tim Ferriss?

  Very interrelated, though.

• 1:27:45Speaker 01

  Yeah, but the, so I've, one of the driving philosophies of life, I think it drives me the most is

• 1:27:53Speaker 01

  this, I guess I find the most beautiful is that we have the ability to author life in life. 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

• 1:28:11Speaker 01

  you get to design your own world. And so in my office, actually, I hired, I commissioned a graffiti artist.

• 1:28:15Tim Ferriss?

  Oh, you sent me a photo of this.

• 1:28:17Speaker 01

  Yeah.

• 1:28:17Tim Ferriss?

  I remember.

• 1:28:17Speaker 01

  Yeah, yeah.

• 1:28:18Tim Ferriss?

  No, explain it, please.

• 1:28:19Speaker 01

  Okay, so on one side is Gandalf the Grey and the other side is, 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 his book that's opened, blank pages with a pen. And then above it in graffiti is the word dream. And the concept behind it is, is J R R Tolkien and J K Rowling created worlds that we inhabited through the tool of text. Right. They wrote this stuff down and then we inhabited. And so they literally authored worlds. And we have that same ability as entrepreneurs to build companies, right? And everything we do, we have that, and 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

• 1:29:02Speaker 01

  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 gonna be painful. To me, it's so much more fulfilling than a secure and safe way to live life.

• 1:29:19Tim Ferriss?

  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 this default. I don't, was that the default belief system? Maybe it was, maybe despite the, the financial challenges. I mean, because I think I recall you telling me that your, your mom made some of your clothing that you wore to school.

• 1:29:45Speaker 01

  She did, yeah.

• 1:29:46Tim Ferriss?

  So it's, it's not like you sort of came in with every possible advantage that people might assume is required to think that way.

• 1:29:57Tim Ferriss?

  The authoring of your own world, so I'm gonna come back to that. And I realized the, the successful question, I think, could be broken down a few ways. So you just brought up with that biography, the first one, A Good Man, the, the thought in my head that you can model different people for different traits.

• 1:30:15Speaker 01

  Yeah.

• 1:30:16Tim Ferriss?

  Which has its own risks, because you might absorb bad habits.

• 1:30:19Speaker 01

  That's right.

• 1:30:19Tim Ferriss?

  If you're spending time with those people without realizing it. Uh, sort of like viruses in your, you know, bugs in the OS, I guess.

• 1:30:25Speaker 01

  Yeah.

• 1:30:26Tim Ferriss?

  But, uh, 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?

• 1:30:42Speaker 01

  So I'd say actually like a bunch of names pop up.

• 1:30:46Tim Ferriss?

  Yeah.

• 1:30:46Speaker 01

  People I've invested in at the OS Fund. So I mean Craig Venter.

• 1:30:50Tim Ferriss?

  Yeah.

• 1:30:50Speaker 01

  At Human Longevity, Peter Diamandis there as well. Josh Tetrick Hampton Creek. Jason Kelly at GoBioWorks, Daniel Fong at LightCell. Scott Phoenix at Vercarius. I mean, we have a great roster of incredibly passionate entrepreneurs. Mustafa Soliman 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 audacious and determined and very aggressive.

• 1:31:27Tim Ferriss?

  Got it. Okay. So now, let's see.

• 1:31:33Tim Ferriss?

  Do you define, would you describe yourself as aggressive?

• 1:31:36Speaker 01

  I am.

• 1:31:38Tim Ferriss?

  In what ways are you most aggressive?

• 1:31:41Speaker 01

  When I see something I want to go after, I can be pretty relentless.

• 1:31:47Tim Ferriss?

  And which entrepreneurs do you most admire for their? And I'll have to say, you'll have to choose either a smaller subset of the people you've invested with, or you can choose other people, which might be safer, but for their resourcefulness.

• 1:32:08Speaker 01

  All right. So.

• 1:32:13Speaker 01

  Let's come back to that. I know I'm going to have a lot of examples to think of. People who have faced near and certain death countless times, somehow they figured out to maneuver.

• 1:32:22Tim Ferriss?

  Right.

• 1:32:23Speaker 01

  Around the problems.

• 1:32:24Tim Ferriss?

  Right. To sort of Neo in the Matrix, do the back bend and dodge the bullets and come back to life.

• 1:32:28Speaker 01

  Yeah, exactly. I mean, that's the essence of entrepreneurship.

• 1:32:31Tim Ferriss?

  So that's actually.

• 1:32:35Tim Ferriss?

  That's actually a good segue. So what do you think an entrepreneur is? What is an entrepreneur?

• 1:32:44Speaker 01

  Someone willing to, I think entrepreneurs and explorers have a lot in common with Shackleton, that they chart, 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.

• 1:33:12Tim Ferriss?

  What are practices,

• 1:33:16Tim Ferriss?

  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

• 1:33:29Speaker 01

  Yeah.

• 1:33:29Tim Ferriss?

  nature of startups or small companies?

• 1:33:33Speaker 01

  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, you know, burning? Right. 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. Like, 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 along the way, but that was just simply to pay the bills. But

• 1:34:08Speaker 01

  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?

• 1:34:16Tim Ferriss?

  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, you have, 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, what is on the horizon? And if I look back, a very kind of macro

• 1:34:54Tim Ferriss?

  Timing way to at least narrow down the field a bit, so it's easier to find those people seem to be investing during recessions. So investing right after crashes. It left sort of the people who couldn't conceive of doing anything else, standing on the playing field.

• 1:35:12Speaker 01

  Yeah.

• 1:35:13Tim Ferriss?

  And the sort of fair weather investors, the fair weather entrepreneurs all went back to doing whatever they perceived to be.

• 1:35:19Speaker 01

  Yeah.

• 1:35:20Tim Ferriss?

  Chartered territory.

• 1:35:21Speaker 01

  Yeah, exactly. I guess I want to be careful. Like, I don't want to be like an entrepreneur definition snob. And right and suggest that.

• 1:35:28Tim Ferriss?

  I was gonna come out and pound the table and yell at you about that, but.

• 1:35:30Speaker 01

  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, 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.

• 1:35:52Tim Ferriss?

  And hmm.

• 1:35:56Tim Ferriss?

  Let me, let me dive in to a couple of other questions also.

• 1:36:01Tim Ferriss?

  Do you have a, a book that you've gifted often? Are there any books that you've gifted to other people often?

• 1:36:08Speaker 01

  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 Frankl, that's how I, he, his basic point is, no matter the conditions we surround ourselves in, we can author our life. Right? We can author whatever, however we respond. And I guess I'd also throw in there Siddhartha. Have you read that?

• 1:36:48Tim Ferriss?

  Herman Hesse, Herman Hesse, I guess in German.

• 1:36:51Speaker 01

  Love that book.

• 1:36:52Tim Ferriss?

  Yeah, that came up yesterday on a, on a walk with.

• 1:36:57Tim Ferriss?

  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 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.

• 1:37:35Speaker 01

  Right.

• 1:37:37Tim Ferriss?

  Because it pulls you out of your normal context.

• 1:37:40Speaker 01

  Yes.

• 1:37:40Tim Ferriss?

  In a way.

• 1:37:41Speaker 01

  Yes.

• 1:37:41Tim Ferriss?

  So you're not, your programs, your problem solving software isn't running.

• 1:37:46Speaker 01

  Exactly.

• 1:37:46Tim Ferriss?

  So it kind of blindsides you.

• 1:37:47Speaker 01

  New mental models.

• 1:37:48Tim Ferriss?

  Yeah.

• 1:37:48Speaker 01

  Yeah.

• 1:37:49Tim Ferriss?

  Exactly. The, 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 going for about 60 minutes. So I'm probably in the, 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?

• 1:38:35Speaker 01

  Let's say I would put it in New York, and it would say, "Do an anonymous and random act of kindness today."

• 1:38:46Tim Ferriss?

  I like it. Why New York?

• 1:38:50Speaker 01

  For, if you're giving me the constraint of a single billboard.

• 1:38:53Tim Ferriss?

  That's right.

• 1:38:54Speaker 01

  And I want the broadest exposure, I'll go to New York where the density's highest.

• 1:38:58Tim Ferriss?

  Got it. I like it. Good answer. If you were giving advice to your 30-year-old self, what advice would you give?

• 1:39:21Speaker 01

  That

• 1:39:28Speaker 01

  no matter what comes your way, no matter how hard things feel,

• 1:39:35Speaker 01

  that I have the power to overcome and be at peace with it.

• 1:39:41Tim Ferriss?

  Good advice. I think that's a great place to to start wrapping up. Is there anything else you'd like to share with the audience? Resourcefulness examples, anything else?

• 1:39:55Speaker 01

  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.

• 1:40:18Speaker 01

  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

• 1:40:31Speaker 01

  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, the good is subjective, of course, but but that we can actually change humanity in fundamental ways and that the rising generation, if we do it right, will have amazing ability to contribute to our well being.

• 1:40:57Tim Ferriss?

  And if there are, and I'm sure there are, new parents listening to this. And in fact, I have someone I know very closely who's about to have his first kid.

• 1:41:09Tim Ferriss?

  What are

• 1:41:11Tim Ferriss?

  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, try these two things, three things, whatever it might be with your kids.

• 1:41:25Speaker 01

  Yes, my personal philosophy is 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 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 are six groups making a documentary. And so I'm with the teacher working with-

• 1:41:57Tim Ferriss?

  Six groups of students?

• 1:41:58Speaker 01

  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 to classroom a positive or 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, and my daughter who's in preschool. But I would say, parents, they get engaged in the children's lives to be truly relevant,

• 1:42:43Speaker 01

  to understand the underlying context of who they like, who they dislike, who are the friends, who are the, the people who are, you know, 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.

• 1:42:57Tim Ferriss?

  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, are there any other traditions or rituals that you've developed with your kids?

• 1:43:16Speaker 01

  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?

• 1:43:28Speaker 01

  And they're jamming, like, you know, it's like 11, nine and five, 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 like 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.

• 1:44:09Tim Ferriss?

  What in your mind are common mistakes that parents make, aside from doing the opposite of the two things you just described?

• 1:44:17Speaker 01

  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 were 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.

• 1:44:37Tim Ferriss?

  What friends are for.

• 1:44:39Speaker 01

  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 and someone could get really hurt. And there were other parents more like myself, like, look, they all figured out, like, 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.

• 1:45:05Tim Ferriss?

  Physics.

• 1:45:05Speaker 01

  Yeah, exactly.

• 1:45:06Tim Ferriss?

  In the flesh.

• 1:45:06Speaker 01

  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.

• 1:45:24Tim Ferriss?

  Yeah. Well, they're taught that they're fragile. I think therefore they develop the belief that they're fragile.

• 1:45:29Speaker 01

  Yeah.

• 1:45:30Tim Ferriss?

  I mean, now granted, I think back, 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.

• 1:45:41Speaker 01

  Exactly.

• 1:45:42Tim Ferriss?

  Like 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.

• 1:45:48Speaker 01

  Exactly.

• 1:45:49Tim Ferriss?

  I was just like, oh my God, but. All of those things taught me ultimately like the either this too shall pass or like, okay, 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.

• 1:46:05Speaker 01

  Exactly. Yeah. So we got in a four wheeler, uh, two weeks ago, my 11 and nine year old. 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? What were 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 going to get into a problem. They ran into a tree going slowly, but right? They talked about it, which was, I thought was really helpful.

• 1:46:48Tim Ferriss?

  Well, you know, it's, and, uh, I just think it's, I think you're a fascinating guy. I think you're a very inspiring guy. And as I think forward to yet someday having kids myself, I, I love asking you these types of questions and, uh,

• 1:47:03Tim Ferriss?

  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, um, second, where can people learn more about you, about the OS Fund and so on?

• 1:47:17Speaker 01

  Uh, osfund.co, CO is where all of our investments are. And, um, I'm active on Twitter. So happy to have ongoing discussions about the various things we talked about, but-

• 1:47:28Tim Ferriss?

  What's your Twitter handle?

• 1:47:30Speaker 01

  Uh, Brian underscore Johnson with a Y.

• 1:47:33Tim Ferriss?

  Got it. At Brian underscore Johnson. I'll put that in the show notes as well. Uh, any, any parting thoughts or comments?

• 1:47:40Speaker 01

  No, Tim, I just love this. We've, we've had fantastic conversations, you know, uh, over time. So this is fun to actually do this, um, formally. And, uh, you know, I really enjoy the friendship.

• 1:47:50Tim Ferriss?

  Likewise, man. And this is, 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, so.

• 1:48:36Tim Ferriss?

  Thank you, my friend. I appreciate that a lot. Appreciate it. So to be continued. Everybody, I hope you enjoyed this. This was a blast for me. We're going to continue to hang out, but off the record. And if you'd like to chat with Brian, ping him on Twitter, let us know what you think. Certainly, if there's anything that struck you, please let me know what was most memorable in the comments 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/podcast. And until next time, thank you for listening.

• 1:49:15Tim Ferriss?

  This episode is brought to you by 99designs, your one-stop shop for all things graphic design-related. I've used 99designs for everything from banner ads to book covers, including sketches and mock-ups that led to the Four Hour Body, which later became number one New York Times, number one Wall Street Journal. And the brainstorming, a lot of it took place with designers from around the world. And here's how it works. Whether you need a T-shirt, a business card, a website, an app thumbnail, whatever it might be, you submit that project, and designers from around the world will send you sketches and mock-ups and designs. You choose your favorite, and you have an original that you love, or you get your money back. It's that straightforward. And many of you who are listening have already

• 1:49:58Tim Ferriss?

  used it and created some amazing things that I'll be sharing in the future. But in the meantime, if you want to see some of my competitions, some of the book covers, as well as get a free $99 upgrade, go to 99designs.com/tim. That's 99designs.com/tim.

• 1:50:17Tim Ferriss?

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• 1:51:02Tim Ferriss?

  For me, it just covers the bases, takes a load off my mind, puts a lot in my body, and check it out, athleticgreens.com/tim. And until next time, thank you for listening.