0:00
Brian's sound test, what did you have for breakfast? I had an omelet.
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0:01
An omelet, what was in the omelet?
0:06
Peppers, onions, onion onions, peppers, tomatoes. But no meat.
0:12
I love how you reordered those ingredients.
0:15
The mind of Brian at work.
0:40
This episode is brought to you by Athletic Greens.
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I get asked all the time if you could only use one supplement, what would it be?
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And my answer is inevitably Athletic Greens.
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So for me, just covers the bases, takes a load off my mind, puts a lot in my body.
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And uh check it out, athleticgreens. com/tim.
1:36
This episode is brought to you by 99designs, your one-stop shop for all things graphic design related.
1:39
I have used 99designs for everything from banner ads to book covers, including sketches and mock-ups that led to The 4-Hour Body, which later became number one New York Times, number one Wall Street Journal.
1:53
And the brainstorming, a lot of it took place with designers from around the world. And here's how it works.
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2:38
Hello, midnight mad hatters. This is Tim Ferriss.
2:41
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.
2:48
I don't want to wake them up.
2:50
But I had to record this intro because I want to get this episode to you ASAP. It is a really fun one.
2:54
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.
3:04
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.
3:19
We have athletes, we have memory champions, and there are commonalities across all of these different disciplines.
3:28
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.
3:38
And this episode is no exception. Had a blast with this.
3:40
My guest was a friend and very impressive entrepreneur and investor, Brian Johnson. That's Brian with a Y.
3:48
He is the founder of OS Fund, which I'll explain in a second, and Braintree.
3:53
He sold the latter to eBay in 2013 for 800 million in cash.
3:59
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.
4:09
He took the Elon Musk approach and took 100 million dollars of his personal capital to launch the OS Fund. That was in 2004.
4:20
And the entire fund is intended to support crazy inventors and scientists who aim to benefit humanity by rewriting the operating systems of life.
4:27
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.
4:39
Some of his investments, to give you an idea, include endeavors to cure age-related diseases and radically extend human lifespan to 100 plus, Human Longevity Inc.
4:48
And we talk about this in this episode.
4:50
Making a biology a predictable programming language.
4:53
So, how can you program DNA and biology to produce what you want, like Ginkgo Bioworks and Synthetic Genomics.
5:02
Replicate the human visual cortex using artificial intelligence, companies Vicarious.
5:07
Mine precious resources off of asteroids, the companies Planetary Resources, and many others.
5:13
So, Brian is not only a scrappy rags-to-riches story, but he is someone who who succeeded and had a massive success story in a technical field without technical training.
5:30
And also just a very deep, soulful, good guy.
5:33
And all those things combined make for a fun conversation.
5:36
I hope you enjoy it as much as I did.
5:39
And without further ado, please meet Brian Johnson.
5:47
Brian, welcome to the show. Hi, Tim. Thanks for having me.
5:51
And this is this is our take two.
5:51
We had a a rough audition start.
5:54
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.
6:01
I thought that was an odd request.
6:04
Yeah, I think we were missing something.
6:05
I don't think that was the real request.
6:08
And um we did not have a spare backpack.
6:10
Uh but we 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.
6:20
So we're at Casa Ferriss.
6:22
And uh 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.
6:28
And we were talking uh just before starting recording about what questions I might ask and giving you sort of an overview.
6:37
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?"
6:43
I said, "Well, I think we'll want to focus on stories and uh I will also typically judge it by how many notes people take."
6:52
And you're like, "Well, that's really interesting you should say that."
6:53
So maybe you could talk about, since we first discussed doing the podcast together, how you've been thinking about it. I love efficiency.
7:01
And so as I contemplate, if I'm going to spend 60 minutes of my time listening to something, I want some value.
7:07
And so specifically, I want to have, you know, five, six, seven takeaways.
7:11
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?
7:20
And uh so I think I 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.
7:29
Uh 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.
7:34
Uh let's start kind of at the beginning and uh 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?
7:51
So I my family and I we were really close.
7:54
Um I have four three brothers and one sister, and we were always up to no good.
7:59
We lived in a small town in Utah and we had nothing really to do but get into trouble.
8:05
But we were also very close and we were best friends.
8:07
Um it was through true throughout high school, for example, most you know, when people are in high school, they don't like their parents, they'll shun them, they're embarrassed by them.
8:15
But I would walk down the hallways with my arm around my mom and she'd give high fives to my friends cuz she was there, you know, being a substitute teacher watching over her rambunctious boys.
8:23
But um we had a great time as a family.
8:25
And um 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.
8:31
We didn't really have much money, but we just uh I guess I have a lot of sweet memories from growing up and being close with family.
8:38
And what So it sounds like your mom was one of the cool moms.
8:42
What do you think I Correct me if I'm wrong, but I mean what what characteristics of hers or habits of hers or otherwise enabled her to be the cool mom and not the shunned mom.
8:56
You know, what what were the contributing factors?
8:58
All right, so one time I 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.
9:05
And so I went out to the street and This is just in front of your house or Yeah, exactly.
9:10
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.
9:16
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."
9:25
So in haste, I kicked over the jug and now the gasoline spills on the street and into the gutter.
9:31
And now it's rolling down the gutter.
9:33
Uh uh and there's cars there.
9:35
So I'm having these images of like cars blowing up.
9:37
So I walk over the gutter and I stomp on the gasoline to put it out and of course that splashes. Now the lawn's on fire.
9:44
So I it's getting worse and worse.
9:46
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."
9:54
And I said, "All right, that's that's fair."
9:56
But a very That's typical of my mom.
9:58
She was supportive and kind.
9:58
She kept us out of trouble as much as she could, but she wasn't over the top and we responded to that.
10:05
Do you So, do you think it was That's a very Dalai Lama-like response to a potential gasoline bomb.
10:10
Do you Do you think you know, from the time that I lit the Dalai Lama's lawn on fire, I can say I'm kidding. That's not what I did.
10:16
But the the 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 than other parents were to their kids?
10:33
We trusted her implicitly.
10:33
And I think when she let go and we owned ourselves and our own behavior, I think we behaved accordingly.
10:40
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 in how mischievous I could be.
10:49
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.
10:55
Did you ever get in Did you get in trouble at school or not so much?
11:00
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 um 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 and is not acceptable behavior.
11:19
Um in many ways I'm grateful for the things we were able to do because we were able to explore and and try new things out, but um yeah, I stayed out of trouble mostly.
11:28
Did you collect anything as a kid? Uh baseball cards. Baseball cards.
11:30
How long did you collect baseball cards? For 7 years.
11:35
I remember going down to the store and buying the tops, you know, 25 cards for $1. 25.
11:38
And was it Was it mostly an obsession for you as a baseball fan? Was it a business?
11:46
Was it combination of that and more?
11:49
I just loved having it and knowing that I had value or some rare card to show to friends when they came over.
11:56
But no, it was just simply a way to splurge.
11:57
I didn't spend any money very much, but that was the only thing I really spent money on.
12:00
Uh were you a popular kid in grade school, high school?
12:05
No, so Well, so in in eighth grade I remember I had these good friends in my neighborhood. We were best buddies.
12:16
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 have these in-group characteristics where they would conform with each other's behaviors and say similar things.
12:28
And I was bothered because I wanted to be friends with everyone.
12:33
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.
12:43
Sort of the alpha Exactly. border guard Yes.
12:46
And so, I would befriend these people and I would say like I'm I come in peace and I just want to be friends. I have no agenda here.
12:53
And I became friends, I think honestly, with everyone in the whole school.
12:57
I just loved having friends.
12:58
And I loved to dance in between the different groups because they saw the world so differently, right?
13:03
It wasn't just like this this mono um understanding the world.
13:06
And so, um I really enjoyed maintaining friendships.
13:10
And that was my first experience in in learning like social dynamics because it wasn't natural for me. I wasn't good-looking.
13:16
I didn't uh have expensive clothes.
13:18
My parents We actually had very little money. I wasn't funny. I wasn't witty.
13:22
I wasn't necessarily super smart.
13:24
So, I didn't have the natural things that get you entrance into that kind of club. Hm.
13:27
And did 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.
13:38
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?
13:50
I just took an interest in them.
13:52
I wanted to understand how they looked at the world, what they experienced, what they liked, what they disliked. I just was um sincere.
13:59
And I I've always been curious.
14:02
And so, I know I didn't try to become like them.
14:03
I just wanted to be friends and understand them.
14:05
Did you think of yourself or let me rephrase that.
14:11
When When did you first start thinking of yourself as an entrepreneur?
14:17
Um I think when I When I Well, I guess I lived in Ecuador for 2 years and I came home to the to the states and uh I guess this is probably not the answer you're looking for, but I after living in Ecuador and seeing these people shackled in extreme poverty and seeing that they really didn't have a shot at life, I came home with this burning desire that I wanted to spend my life improve these improving people's lives.
14:45
And so, I assessed what I could do.
14:45
As I looked at all the things you find in college like Model UN and helping do projects in Africa or whatever else, but nothing really spoke to me.
14:54
And so, I thought, you know what?
14:55
I'll just become an entrepreneur.
14:56
I'll build a successful business.
14:58
I'll retire by 30 with abundance of resources and I'll have uh freedom of time.
15:02
And then I'll you know, figure out a way to improve people's lives.
15:06
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.
15:13
What gave you that confidence?
15:17
So, I assessed my skills.
15:19
Uh what I was really good at and I couldn't really find much.
15:21
This is when you were 21 or was it before that? Okay.
15:23
cuz I wasn't good at necessarily great at school or science or biology.
15:25
Um I didn't really have any skills in of note.
15:30
And so, I figured, you know, I What I do have is I'm persistent.
15:32
I'm determined and I'm smart enough that I can figure stuff out on the fly.
15:36
And so, entrepreneurship seems like a good path for me.
15:41
And then what was So, you 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. Yeah.
15:49
Good on tap dancing with with uncertainty. Yeah. Checkbox number two.
15:57
Uh where did you go from there?
15:59
So, I I was trying to find uh a cell phone and I was really frugal.
16:04
I've always been very frugal.
16:05
And I found this guy in the Yellow Pages.
16:07
I met him at the mall and I bought a cell phone that was super cheap.
16:09
And he said, hey, you look like you're you know, smart and energetic.
16:12
Why don't you come sell phones for me?
16:13
He said, I'll pay you 40 bucks per activation. And I thought, perfect.
16:16
Like I never I never understood this whole idea that I would trade 60 minutes of my time for $8. 25 an hour.
16:21
Like it seemed crazy to me.
16:24
And so, he said that to me.
16:24
I thought, okay, yeah, I'll make 80 bucks an hour. I can do two per hour. And I said, deal.
16:29
So, I sold phones for him for 2 days.
16:31
And then I was on the porch of this lady's house and she had screamed two screaming kids and I had this thought.
16:37
I thought, wait a second, if I'm selling phones for him, why can't others sell phones for me? And I I I left the cell.
16:44
I ran home and I spent almost two solid days figuring out how to become a wholesale provider of cell phone service.
16:51
And I figured it out and I started a company.
16:52
And now I I changed the commission structure so now I was making $300 per activation.
16:56
And that 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.
17:03
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.
17:12
So, it's like the knock knock, wipe the feet on the doormat.
17:15
Like Uh what was What was the opening What was the opening line when somebody opened the door?
17:20
Well, I was AB testing the different approaches.
17:22
I I could walk through a campus and ask students.
17:26
I could walk door to door.
17:26
So, this was my second day and this was the day to test going up and down the street.
17:31
So, yeah, it was, do you have cell phone service?
17:33
And if you don't, then I've got a plan for you.
17:38
So, one of the uh one of my very close friends, um a fantastic systems engineer, I started working with when I graduated from college and went to mass data storage startup.
17:48
Mass at that point was like 5 terabytes, 10 terabytes, big deal, big storage area network installation at the time.
17:56
Uh he was so effective as a systems engineer because he had to do integration, but he started off as a door-to-door encyclopedia sales person.
18:04
That was his first entrepreneurial gig.
18:06
So, he had to get really, really good at overcoming objections and uh interacting with people socially even though he his his sort of bedrock skill set was technical.
18:17
Uh Now, did you So, let's see.
18:20
You had You had the cell phones.
18:21
That was your first business.
18:23
Uh 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?
18:33
Well, the short version is the cell phone company went remarkably well, but it was not going to make me enough money to retire by 30. Right.
18:43
So, I had to find something bigger.
18:43
So, I started a voice over IP company with three founders. Mhm.
18:45
And it was just before Skype and Vonage.
18:48
And the short of that is we had the wrong team, wrong product, wrong timing.
18:52
We did We did Sounds Sounds perfect. We did everything wrong.
18:55
No, we did have a problem.
18:55
We actually built something. We got customers.
18:58
And this was also in Utah? Yes. Yeah. And we had revenue.
19:00
So, like we actually built something, but in reality like we we were not set up to succeed. So, that failed.
19:07
And then on the heels of that, I started I joined another guy to do real estate development.
19:11
And the short of that is we that failed because of some bad decisions we made.
19:17
And so, without income for 2 years, I was dead broke.
19:20
And so, I applied for 60 jobs.
19:22
I found on Monster and the other job sites of the time. Nobody would hire me.
19:26
Like it was just I think it was so clear that I was I had no intention of staying a long time.
19:31
I tried to make the resume look like it, but just never was the case.
19:34
So, nobody would even give me an interview.
19:35
And then Additional skills, loyalty, fierce loyalty to employer. Exactly.
19:40
Um and then I I read I saw the newspaper one day.
19:43
It had a list of the 50 richest people in Utah. And I thought, bingo. Like that's what it is.
19:46
I will write an email to these 50 people. I'll say, I'm young. I'm smart.
19:51
I I I'm trying to become an entrepreneur, but I just need some money on the side.
19:55
So, I'll become your right-hand man.
19:57
I'll do whatever you want me to do. And no one responded.
19:59
It's at this point I'm like totally desperate.
20:01
I'm sure you I'm sure you get a fair amount of these emails these days.
20:05
I do, and you know, I'm I'm empathetic to it. I totally am.
20:09
Um So, at this point I have no income. I have a child at home.
20:13
And so, I need to make ends meet.
20:15
And so, I find this job uh posting in again, I think it's Monster.
20:19
It was selling credit card processing door-to-door.
20:23
And basically, it was like if you could So, business-to-business? Yes.
20:24
Like marching up and down the street, walking into a retailer or restaurant.
20:28
Let me help you set up a merchant account.
20:31
Yes, or Get a point-of-sale system. Yes. Or mostly change.
20:33
Everyone already had existing service. Got it. Got it.
20:37
And so, I the requirement was like if you could fog a mirror, you could work for these guys. It's 100% commission.
20:42
Like what's They don't care if you don't succeed. Right. Right.
20:47
But to your point on the sales side, um I would go to a inside of business.
20:51
I figured out pretty quickly the industry was really messed up.
20:53
Like the technology was terrible, and um people were just generally plagued by the industry because it's just unscrupulous.
21:01
All this dishonesty and complexity.
21:03
And so, I figured out that was the hook because my product had zero differentiation.
21:08
It was exactly the same as 500 other providers that walked in the door, you know, every day. Right.
21:14
And so, I'd walk in and I'd say, all right, Tim.
21:15
Like the right when you saw me walking in, you'd be like, all right, sales guy.
21:18
All right, I'm not interested. I've got stuff to do.
21:19
Then when you heard me say credit card processing, it's like, please leave. Strike two. Yeah, like leave.
21:25
So, I would say, Tim, if you give me 3 minutes of your time, I'll give you $100 if you don't say yes to using my service.
21:33
And usually they'd say like, okay, that's interesting.
21:34
Like what does this guy have to offer?
21:35
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.
21:40
I'm the same as everyone else.
21:42
Except with me, you get, you know, honesty and transparency and great customer support.
21:47
And so, I became this company's number one sales person and I broke all their sales records.
21:50
Following this really simple formula of just selling honesty and transparency in a broken industry.
21:56
That's super interesting.
21:56
And uh So, a couple of questions.
21:59
I just want to rewind for a second.
22:00
With the real estate company, uh what were if you're comfortable talking about them, like what were the bad deci What were the worst decisions?
22:07
What were the the fatal mistakes?
22:10
So, I'm really proud of actually of what we did.
22:12
We launched a $50 million mixed-use project in one of the best places in Utah.
22:16
Mixed-use means residential plus commercial, right? Exactly.
22:19
Yeah, bottom floor and small shops. And Fannie Mae came in.
22:21
They were our equity investor.
22:23
I was We really put together a great project.
22:25
The single biggest flaw was storage space.
22:28
So, empty nesters showed up to buy, and there wasn't sufficient storage.
22:35
Storage for just all of their extra stuff that they wanted to move take out of the big house and move into Exactly.
22:40
this community living space.
22:40
So, then sales stalled in phase one. The bank got anxious. So, Ah, got it.
22:45
So, just didn't account for that Yeah. that need. the big blunder. Uh with the sales.
22:51
So, I'm I'm fascinated by sales because there's the the good, the bad, and the ugly.
22:58
And you often see it within one industry, right?
22:59
And uh so, this brings back a lot of memories for me because I was the the lowest-paid as base salesperson at the startup that I worked for out of college.
23:11
And they're like, hmm, you're really persistent. You're in sales.
23:15
You're You're You're really persistent.
23:17
You have no technical background. You're in sales. Congratulations.
23:20
And I was like, ah, okay. Here we go.
23:21
So, it's smiling for you know, smiling and dialing. Yep.
23:24
And one of the things I did was very similar to what you did with uh taking the potential objection and putting it right up front, which was like, I'm the same as every other guy. Yes.
23:37
Product, different label, same thing, except for this, right? Yes.
23:41
Which was the relationship piece.
23:43
And you know, I I took a very similar approach when I was cold calling, which I did between like I want to say like 7:00 and 8:00 and 6:00 and 7:00.
23:50
So, I avoided the times that the gatekeeper would be manning the phones. Yes.
23:54
And only called when I thought I could get the higher-ups who would work longer hours.
23:57
But I would um I would I would do my homework so I could guess what they were currently using, like Solaris boxes or whatever it was in the industry.
24:06
And then I would say, well, not sure that if this is the right fit at all.
24:09
Um if you're using this type of system, this type of system, or this type of of system, it is not at all. Yes. Yes.
24:16
And I would take all of the potential weaknesses and just put them right up front.
24:19
Uh what you you at that point had already had experience hiring sales people.
24:26
How did you What did you look for in sales people?
24:28
Or how did you How did you hire the people with the highest likelihood of success or train them?
24:34
Their ability to connect with other people and earn their trust.
24:39
And what are the correlating uh behaviors or qualities that allow them to do that?
24:45
The They had to be genuine.
24:48
Uh it it couldn't be that they were manipulating them into believing them.
24:52
They had to be truthful, right?
24:54
That if I trusted you that you were saying something that I could believe you, and that would be true tomorrow as well.
24:59
So, I think that that sincerity and uh being genuine go a long ways.
25:04
And I think even, you know, it spans differences of personalities and experiences in life.
25:08
But if someone feels like someone is really trustworthy, Mhm.
25:13
And how do you read that when you meet someone? If I trust them.
25:17
Okay, I'm just going I'm going to I'm going to dig a little bit more.
25:18
So, what is that a visceral spider sense?
25:19
Or is it a that guy's not looking me in the eye?
25:24
What is the Is it a gestalt of all those things?
25:26
What is What is it that leads you to feel that you can trust or not trust someone? Yeah, I don't know.
25:31
I guess um Yeah, I've always had an interest in people because I'm curious.
25:35
I've always enjoyed friendships.
25:39
And I don't know if I could even articulate this.
25:40
It's just this subconscious process that happens that I read, whatever, the hundreds of data points that you read when you meet someone. Mhm.
25:46
And you intuitively feel like, yeah, I I could trust this person.
25:51
And the more you gather, of course, the higher your confidence level becomes.
25:54
And of course, like I make mistakes like everyone else, but um I think it's a fairly accurate I think most people are can read that.
26:01
How This we're going This is a a bit of a lateral step, but I just saw I and I want to say it's called Ex Machina. Yeah.
26:10
Like uh which made me think of I guess it's Deus Ex Machina, which is the the machine or god from the machine, which is when it's a theater expression.
26:19
I'm all over the place cuz I've had enough caffeine and coconut oil.
26:22
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.
26:36
Therefore, act three it comes to a close. Good night, everyone.
26:38
But uh Ex Machina, I think that's There's a lot of debate about how Latin is pronounced, but no idea.
26:45
In any case, how long do you think it is?
26:47
And we're we're in 2015 last I checked.
26:51
Before a computer can read all those microexpressions and so on and come to the same type of trust or not trust conclusion.
27:03
If you were a betting man, and this was the Prices Right Yeah. of technology.
27:10
I don't think I'm qualified to answer.
27:10
I will say that uh the other day I watched a video online where robots were walking along, and then people were kicking the robots or tripping them or doing something to put up an obstacle.
27:23
And I had this emotional reaction watching this happen, even though I knew they were robots.
27:27
But watching humans be cruel to robots, like it was this like visceral reaction inside of me.
27:33
And so, as you talk about, you know, Ex Machina and the progression of robotics to read our emotions and for us to interact with them, the emotion's real, right?
27:41
Like our ability to connect with robots is significant.
27:45
As I watch my kids interact with Siri and even other low- tech um you know, computer interact interfaces, I think that we will generally be surprised at how seamlessly the technology is rolled throughout society and how we just interact as we normally would.
28:03
It will appeal to our emotions and all these things we read.
28:06
Do you think we will have Is there a Turing test level interactions with machines within the next 5 years?
28:16
If I'm a betting man, I'll I'll go longer.
28:18
I'll say I'll say a decade at least. A decade at least. Interesting. All right.
28:25
Uh did the credit card processing business or that experience you became the number one salesperson? Yeah.
28:32
Uh where did obviously very interrelated, not exactly the same.
28:35
But how did that How did you go from there to Braintree?
28:40
I did it for a year, and it was amazing because it was this terribly broken world.
28:46
With the technology just it was years behind, and no one trusted in different providers.
28:52
It was fragmented with hundreds of providers.
28:55
And after doing it, I thought this is a perfect industry to start a company in. So, I started Braintree.
29:01
To disrupt it cuz it was just so ripe.
29:03
Yeah, for it for the right technology and the right disposition as a company to to be honest and transparent and treat customers so they were thrilled.
29:11
And did you have any technical background? I didn't. No. Did not. No. So, no computer science. No.
29:17
No mechanical engineering, electrical engineering.
29:21
What was the And you had one kid at home at that point? Two. Two kids at home.
29:24
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?
29:42
Yeah, so we What I did to start Braintree is I had these customers in Utah.
29:45
I was in Chicago at time, so that's where Braintree in Chicago.
29:48
And I went back to my 10 best customers in Utah.
29:50
Best meaning like most loyal and also making me the most amount of money.
29:55
And I said, "Hey, I just started this company Braintree.
29:57
I would love it if you switched over your processing to me."
30:00
And it was restaurants and retailers, so it was just terminals.
30:02
I could use back-end processors for it.
30:06
And I think I had like nine of the 10 say yes, uh if I remember right.
30:08
And they collectively made me $6,200 a month.
30:12
And it was enough for me to get going, hire some part-time help, and start the company.
30:16
And the biggest uh transition we had is OpenTable showed up and they said, "Hey, we have 11,000 restaurants uh around the world."
30:23
And you just Where Where was OpenTable based? California. It was? Yeah.
30:26
And they somehow found you?
30:28
So, the co-founder or the founder of OpenTable, Chuck Templeton, was an advisor.
30:31
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.
30:40
And they had the compliance issue.
30:41
And so, they came to us and they said like, "We have this big problem."
30:45
And we said, "We can fix it."
30:45
And of course, like I had no idea if I could fix it then.
30:50
But we did a deal with them and that's when we became a software company.
30:52
But it was it was a bet-the-company decision.
30:55
So, in the beginning then, Braintree was like your previous company that you worked for as a salesperson, it's kind of a commodity That's right. business.
31:04
But you had the relationships. That's right.
31:07
So So, at uh a couple of related questions, how on earth as um I assume, correct me if I'm wrong, kind of an an unknown quantity at that point, did you get Templeton as an advisor?
31:21
We met at a local meetup in Chicago and we What kind of meetup?
31:23
Uh there I It was actually Matt Maloney and Mike Evans from Grubhub. They just went public.
31:27
And um Coran Capshaw, who was a local entrepreneur, but there was like five or six of us and people were just getting together to have breakfast.
31:35
And he and I hit it off and he was clearly a great guy.
31:39
I mean, he had uh the right disposition, the insights.
31:42
He was advising people around the table.
31:43
He was an advisor for Matt and Mike at Grubhub.
31:47
And he came on and he was my only advisor for the whole duration of when I was building Braintree. No kidding.
31:52
And um 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. Yeah. Or were you? I don't know. No, I wasn't.
32:11
I wasn't connected to software engineers at all, actually.
32:14
And so, I had one friend who I trusted as a good developer.
32:19
People he had a high, you know, he had a good reputation.
32:21
And I would make I would post jobs online and then he would help me interview these people as they came in.
32:27
And as I listened to the questions he asked and how he discerned what to what made a good engineer, I learned over time how to decipher it.
32:33
It took me a couple hires to get down and then I found a couple really good core engineers.
32:39
And I knew how to benchmark to know what exactly to hire, both in personality but also coding skills.
32:43
And we could then build it from there. Mm.
32:47
And so, that's how you developed That's how you sort of got your your foot in the door with the tech world. Yeah, that's right.
32:52
And then the Then the So, when I started Braintree, I I had three main goals.
32:56
One is that I wanted us to be the best payments provider in the world for developers.
33:01
Two, that I wanted our employees to say it was the best company they'd ever worked for.
33:04
And three, that our customers would write us love letters.
33:08
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.
33:17
And so, having high-quality engineers was really important because no one likes to work with someone who is incompetent or causing a problem.
33:22
So, it was extremely important we got like exceptional people to work.
33:28
And uh do any of those those questions come to mind, kind of high-level vetting questions for good engineers?
33:35
On the technical side, sure, there's a lot.
33:36
On the personality side, they So, we would what I would try to communicate when we hired someone was that we payments was not necessarily changing the world.
33:47
It wasn't like we're going to provide clean water for everyone in the world or whatever else.
33:51
The stated objective that we were going to build an exceptional company, like a company with a soul that we really cared about.
33:56
And so, I wanted people who really cared about what they did, the quality of the product, the quality interactions working with uh other engineers.
34:02
So, we're in it for the long term.
34:04
And so, I tried to flush that out We're here to do something epic and special.
34:09
So, if that appeals to you, great.
34:11
If not, then How do you now, maybe this comes back to the uh 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?
34:26
For Well, so I guess for non-engineers, I would write this these posts on Craigslist to recruit people.
34:29
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. That was the assumption? Yes. Okay.
34:37
That the person reading the ad knew the person you wanted to hire. Ah.
34:42
very first statement was uh I will pay you $5,000 if you refer the most capable person you know.
34:49
And then the Then below it, it would say, "Please do not apply if."
34:50
And we'd list out characteristics of people who just weren't compatible with our environment.
34:54
And so, we wanted to be clearly distinctive in who we were.
34:58
And then we had a section that said, "Please do apply if."
35:01
And so, the goal was But the do not apply was first. It was first. Yeah.
35:05
Which had this great psychological effect.
35:07
And then the please do uh apply if.
35:11
We wanted people to jump out of their seats and say, "This is the environment I've been dying to be in."
37:56
I'll let you reintroduce people. Yeah, right.
37:58
So, we probably share a mutual love. Yeah.
38:00
So, 1914, he went on the the Trans-Imperial Antarctic Expedition where he tried to cross coast to coast uh the South Pole, Antarctica.
38:11
And the what I like about Shackleton, I mean, there's a whole bunch of things I like about Shackleton.
38:14
Basically, to this question is when he imagined what he wanted to do in the world, he chose the most audacious thing imaginable.
38:23
At the time, it was it was nearly inconceivable that somebody could do that. And he chose to do it.
38:29
And he prepped and he did it.
38:29
And they failed in their in their endeavor, right?
38:32
But and he's not remembered as a failure.
38:35
He's remembered as as the the grit and uh how they actually overcame all the obstacles that came about during the expedition.
38:43
He's hugely inspirational in my life because I I apply what I call the Shackleton sniff test to everything I do in life.
38:49
That I contemplate if I'm going about on this endeavor, does it meet the threshold that Shackleton applied?
38:54
That is this the most audacious endeavor I could possibly conceive.
38:58
And in time, we'll iterate, we'll change, we'll pivot.
39:00
That happens over the course.
39:02
But I want to start with that as the contemplation.
39:04
So, it's kind of like a a what would Shackleton do bracelet? There you go. Yeah. Better said. Shackleton.
39:12
Uh why did you move to Chicago? To pursue an MBA. Oh, no kidding. Yeah.
39:19
Why did you Are you glad that you got an MBA?
39:22
I have mixed feelings about it.
39:22
School I I was I was always so bored at school because I felt like the data rate was so slow.
39:29
It was like a 56K connection, right?
39:31
Sitting in the classroom and the pace of speech and the data, it just I wanted like a gig data transfer rate.
39:35
I wanted to learn so much faster.
39:38
And so, school which boring to me.
39:41
And um I mean the MBA MBA was was helpful, but I don't know.
39:44
I guess I learn in different ways, mostly from doing.
39:49
And I'd been in the trenches of entrepreneurship my whole life, and that's really how I prefer to learn.
39:54
Then of course reading on my own and stuff like that.
39:55
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 cuz I've I've actually spent quite a bit of time there, but if they're living somewhere they feel doesn't allow them to surround themselves with other uh highly ambitious capable entrepreneurs. Yeah.
40:16
And the only way that they could relocate was to get an MBA say to Chicago, New York, SF. Yeah.
40:23
Uh do you think the 120k or whatever it might be would be worth it?
40:31
If someone if if someone if if one of your kids was considering getting an MBA. Yeah.
40:35
just say they were kind of of that age now. Yeah. Yeah.
40:38
What what might you ask them or So I remember the very first case study we did in school was about these guys who were they came in up I think with a new new golf ball that was better than other golf balls.
40:52
And it was about their struggle over a two-year period of time to work through patents and IP and all the get distribution channels and stuff like that.
40:58
And then we got together with a study group to talk about the case and there were certain questions we were trying to answer. I forget what they were.
41:06
But in my group where there were five of us and we were constantly doing things like cost models and distribution channels.
41:11
And in my mind it immediately went to like how are these people paying for their rent?
41:17
Are their marriages still intact? Right?
41:19
Like like are they emotionally just too stressed out to function?
41:20
The way I thought was so was was so colored by my experiences as an entrepreneur and it was such a dramatic difference in how my peers thought.
41:30
Are people coming in from like Ernst & Young to From larger corporations, yeah.
41:33
make their pay grade jump. It was just dramatic.
41:35
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.
41:43
That the course out of persistence and uh determination and then just the ability to learn and adapt quickly are much better suited for trying to do this.
41:54
And I mean it's not to say that education is not helpful.
41:55
It certainly is in certain regards, but There are different types of education. That's right, yeah.
41:59
What's the most valuable thing you took from business school?
42:04
Or from that experience, let me say that. We can come back to it.
42:09
Yeah, uh Or you're you're giving me the look. Or we can drop it. I'm not sure. Okay.
42:18
Well, that's that's a that's fine answer.
42:20
Uh I think more people should have that as an answer, quite frankly.
42:22
Maybe that is the answer.
42:26
Uh I was telling my brother we were talking about some some really kind of deep philosophical questions and I said I just haven't figured it out.
42:31
And he said maybe that's what you figured out. Exactly. Totally true.
42:37
Maybe that's not an answer you need to find.
42:40
Uh 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? Mhm.
42:54
So I early on I had to figure out how to get customers without any money.
42:59
Which is a hard problem to solve. Common problem. Right, exactly.
43:01
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.
43:10
And I knew there were different communities like Python . NET, Ruby on Rails Java.
43:17
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.
43:25
And my theory was if I could find a community of engineers that were chatty and that helped each other through a word-of-mouth referral basis and I could get a few of the leaders in that group to come on board then it would spread throughout the community.
43:38
And then we'd go to adjacencies.
43:38
And so I did this analysis of looking at the characteristics and I found that Ruby on Rails was the most conducive.
43:44
That they were very tight.
43:46
Now did you figure this out by looking at message boards?
43:48
How did you go about doing it?
43:49
No, I found actually a couple of academic research papers. Huh.
43:52
That yeah, that actually measured sociability and interconnectedness and had like these maps and diagrams that showed where these nodes were and who how they interconnected.
44:00
And then I focused on Ruby on Rails and we got a couple leaders in there like you know 37signals and a few other GitHub came on.
44:07
37signals is a good one to have.
44:09
Yeah, Jason and David were amazingly good to us.
44:11
Like they would tweet out all the time and they referred out all their friends. They were fantastic.
44:14
And so we basically built the business on word-of-mouth because we we tried so incredibly hard to be exceptional what we did.
44:24
So they'd come on and they would love what we what we built and how we treated them and they would tell others.
44:29
So I wanted to 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.
44:36
And that is that the your first target is not the entire market. Right?
44:43
And when I talk to people about say book launches, a lot of people want everyone to love the book.
44:49
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.
44:57
Especially when you have no money.
44:57
You need the the kind of cost per acquisition to be as low as possible, right? Ideally zero.
45:03
And so when I launched either the 4-Hour Workweek or was formulating the marketing plan I mean you and I have a lot of shared DNA.
45:09
We've shared 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.
45:23
And very much similar to your your chattiest checkbox, right?
45:25
And I I determined that I also wanted to be a market that I understood, ideally belonged to.
45:31
And that was the kind of 20 to 35-year-old tech-savvy males in San Francisco, New York primarily.
45:35
And and then after if I if I hit a critical mass in that in that particular demographic and psychographic, say my goal was I think it was 10,000 books per week for two weeks.
45:51
And I could try to identify kind of the conversion rates and so on to hit that number.
45:54
Then I knew through word-of-mouth that would bleed out both in age range, it would jump from male to female. Exactly.
46:01
Uh but I wanted to identify the people who are kind of disproportionately creating the most online content at that time.
46:08
And Okay, so you target Ruby on Rails and was there a particular tipping point where you were like holy moly. Okay.
46:20
Well, any any any particular kind of hockey stick or breakthrough moments that come to mind?
46:26
Yeah, so we Let me think.
46:27
So we got as customers within the first couple years 37signals, GitHub, Uber Airbnb, LivingSocial when they were on their tear.
46:38
I mean we had so many of the fast Did they Did they the the all-star team? We did.
46:43
We had some of the best companies in the whole world using us and that their growth fueled credibility of course in our brand that we were able to provide great services to them.
46:50
So we had this exceptional client base.
46:54
That's that's what it was.
46:54
Once these guys hit their growth trajectories, right?
46:57
And then once the reputation started spreading that we were a a great provider, people loved using our service.
47:01
It just really built upon itself.
47:04
Who were you in that period of time competing against?
47:09
Who were your primary competitors?
47:10
Initially it was the old guard like CyberSource and authorize.
47:13
net and then processors like First Data and Global uh which were really great targets because they were dinosaurs in technology.
47:22
Um and then Stripe launched I think about a year two after us and they're obviously a fantastic company. Mhm.
47:27
And so they became formidable competitors.
47:31
Um and then of course PayPal was always there Right. uh doing their thing.
47:33
And so when when you met with the the Ubers, the Airbnbs and so on, how did you convince them to work with you guys?
47:44
Um Many of the So we did do some outbound.
47:46
Like we did track a lot of these companies down, but most of these companies signed up on their own.
47:49
That we just found out they were customers when they were going through you know the underwriting process.
47:54
Um we we did we did target some of these companies individually, but most of it was organic. Got it.
48:00
And what do you what to what do you aside from the word-of-mouth what are other things that facilitated them finding you naturally? The being exceptional.
48:12
That I 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 interacted with us would walk away and say unbelievable. Right?
48:27
The software is amazing, the support is amazing that I just love this company.
48:31
And I so much so that I want to write them a love letter.
48:33
If we solved that everything else would take care of itself because they'd walk away and in in 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.
48:43
And we did small things like we would the integration team, we would see when someone is 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. Uh can we help? They're like what? Like who does that?
48:55
Like who who proactively reaches out?
48:57
So we tried to do these small things that created these really great experiences for people.
48:59
Now could you explain just for people who who are non-technical out there?
49:03
So application programming interface, API. Oh yeah, sorry. Right?
49:06
So no no no, we're we're fine.
49:08
I I love to kind of uh it's a very important concept, right? In in a lot of tech.
49:13
So what what is coding to the API mean?
49:15
So they're programming their software to speak to our software.
49:20
And there was a certain way that they would do that.
49:21
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.
49:28
And so your software is is behind the scenes Yeah. handling transactions.
49:33
So it's kind of like you have in a restaurant front of the house, the maitre d, the waiters, and so on.
49:38
Then you have back of the house the restaurant.
49:39
And you need those the the the people in the restaurant never see.
49:43
The people in the back with all the flames and cuts and burns on them.
49:45
But you need a very reliable way for the front of the house to talk to the back of the house. Exactly. That's the API. That's right.
49:51
Uh and uh it's super super important concept.
49:54
Um it's how also, I mean, correct me if I'm wrong, but it's how a lot of companies grow very quickly is by making that a seamless That's right. experience.
50:03
Yeah, making your services broadly available to the a broader ecosystem of engineers.
50:06
It um your story reminds me of um a story told by one of my favorite people out there, a guy named Derek Sivers.
50:12
I don't know if you know Derek.
50:14
So Derek is uh uh I certainly hope to have him on the podcast sometime, but sort of a philosopher king in the programming world.
50:22
A really fascinating guy, great teacher also, really great teacher.
50:23
Um but he had a very similar focus on details with CD Baby, the company that he started, grew, and then later sold.
50:35
And uh I remember he 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 search Derek Sivers letter and then Ferris, I'm sure it'll pop up. Sivers s i v e r s. Uh sivers. org, really amazing guy.
50:50
But when people would get their order confirmation email, it was like this hilarious kind of elaborate story of like, "Your CD has been carefully pulled off the shelf and placed on a satin pillow and then wrapped in paper by a Japanese origami specialist."
51:04
And it was this just very personable uh email confirmation, and no one was doing that. Yes. And so it it spread.
51:15
It was such a small detail with with huge implications. Yep.
51:19
Uh for for brand loyalty, for PR, for acquisition, for all these things.
51:23
And it was so easy to do. Yep. Right?
51:24
It was not something that a big company couldn't do.
51:28
It was just something a big company wouldn't do. Typically, right?
51:33
What are other uh What are other um whether it's and I I hesitate to use this term, but growth hacks or uh say um rituals, routines, or rules in within Braintree that allowed you guys helped you guys grow as quickly as you did?
51:52
Yeah, so one we one thing I focused on a lot was, you know, the second goal, which was that employees would say it was the best place they ever worked.
51:57
And it was this ongoing quest to figure out how to make that happen.
52:02
Again, my goal in my mind was they go home and rave about what they do on a daily basis.
52:07
They feel good in life, right? They love it.
52:09
And so I always wanted to know what what people were feeling and thinking because if I didn't know that, then I couldn't change or or build, you know, certain things.
52:18
And so I tried all the normal things like we did town halls every week.
52:23
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 was they wanted to talk about, but no one dared.
52:36
So what would be an When would those awkward pauses come out?
52:38
You'd say, "Does Does anyone have any questions?"
52:41
And then you just let it sit? Exactly.
52:43
Like we're going to we're going to wait until we have some questions. Exactly.
52:45
So like I knew there was like one or two things on everyone's mind cuz I could feel the pressure build all week, right?
52:49
I mean, the one thing I learned The pink elephant expanding. Exactly.
52:52
Like the the thing is true in life is that everyone always has a pebble in their shoe, always.
52:56
Like there's something bothering us.
52:58
And that sometimes by just acknowledging it, it it take it addresses the problem.
53:03
But it seemed like every week we'd build up this tension in the startup and we, you know, in the company and and if we addressed it openly in the town hall setting, it'd be great.
53:11
And so I would let these long pauses go and and someone would find their way to raise their hand and say like, "All right, like I'm really bothered that we hired someone for this role instead of promoting someone from internally, right? Like what's going on?" Mhm. Right?
53:24
And it was great because even really hard questions to answer.
53:27
And so I encourage like brutal honest feedback.
53:29
And if they criticize me, even better, right?
53:31
If they could criticize me, then anything was fair open game.
53:35
But one thing I I I was at this Christmas party um one year and I was talking to the significant other of one of my employees.
53:42
This was at a company Christmas party? Company Christmas party.
53:45
We're in the buffet line.
53:47
And I say, "So like how's, you know, so-and-so doing?
53:49
Like he he's 4 months in and how's he enjoying life?"
53:51
And she says like it's amazing. Like he is happy.
53:55
And I 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.
54:05
And I thought, "Yes, like this is the data I want."
54:08
Like cuz 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.
54:17
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.
54:24
And knowing where to go for that data and how to get it.
54:27
Now, of course, like I couldn't go interview everyone all the time, it would be awkward.
54:30
But uh just knowing that that the data sources were out there to gather to build a, you know, a good team Mhm. was really helpful.
54:36
So you said, you know, if they if they criticize me, all the better.
54:39
What would you How would you prompt people to be brutally honest?
54:45
Because you're the you're the big boss, right? Right.
54:46
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?
54:56
What what What did you say in either case?
54:58
So one, I think it's a a disposition.
55:00
I tried to be self-deprecating where I would make fun of myself for things I did or mistakes I'd made.
55:07
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.
55:13
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. How would you do that?
55:25
So if we talked about um I'm trying to think of like a recurring theme that came up.
55:31
Um maybe if it came up like two or three times, I would say like, "Look, like this honestly is like my deal because you guys have brought this up two or three times now.
55:37
I've not done something about it that's adequate.
55:39
So clearly I'm not doing what I should be doing cuz you're doing your job of being honest and transparent with me.
55:44
I have not taken responsibility of actually acting on this.
55:47
So I'm going to go think about this, put together a plan, and do that.
55:49
But in the meantime, like this is my problem and my mistake."
55:51
So I try to own things like that. Got it.
55:53
So it's not it's no longer your job to worry about it.
55:55
It's my job to worry about it. Yeah, like I hear you. You did a good job.
55:58
Thank you for being honest and transparent cuz that's what I asked of you.
56:00
And you don't have the power to fix that yourself.
56:02
This is like a more community problem, so it's in my So the um the observation I've had on multiple occasions and um is uh you're very persuasive, but I don't think you'd be very good at lying.
56:18
And I could be Maybe you're so good that I would never notice. I don't know.
56:20
But I'm I'm I'm just kidding, obviously.
56:21
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?
56:33
I mean, you have you're very methodical.
56:35
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.
56:49
I don't want people to tell me what's going right.
56:54
I want the bad news because I feel like the good news will take care of itself. Does that make sense?
56:58
And I think as a result of that uh I recognize that one of my kind of deficiencies uh as a manager of people is that I'm not very good or consistent in giving positive feedback.
57:14
Uh I don't feel like I erroneously believe that because I don't necessarily need that, other people probably don't need it. Right.
57:22
Or I just forget about that. Yep.
57:23
Uh How do How did you address that within Braintree?
57:27
Because I think it's at least in my experience, it is important uh to maintain morale of the troops and so on.
57:32
Uh What did you do to help kind of maintain morale and and that level of happiness that the significant other reported? I would tell stories.
57:43
I would tell stories about people and exceptional efforts.
57:45
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.
57:52
And one person is going to feel left out because like I was just involved as, you know, him or her in doing this.
57:55
And so um it is tricky, but I I always highlight We did I did weekly emails as well.
58:02
And I wanted to tell stories of people who went above and beyond the call of duty either in building our software or customer service interaction or even helping a coworker do something.
58:12
And those stories resonated with people, right?
58:14
They saw what their peers were doing and it was influential on how they behaved.
58:17
So I wanted to build a culture of a certain behavior and I told stories to reinforce that.
58:25
Right, the positive reinforcement. Yes.
58:27
And uh you did How often did you do the town hall meetings?
58:31
We did either weekly or biweekly.
58:31
We kind of fluctuated over the years. What day of the week? Or Friday? Friday. Yeah. Why Friday?
58:38
It's a different vibe in the company.
58:39
People are kind of reflecting upon the week.
58:40
Um the tensions kind of build up.
58:43
We're going into the weekend.
58:45
Monday morning is a little bit frantic.
58:46
Uh but Friday I find people are 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 re- and I guess regroup on the essence of why we existed, right?
59:00
That we weren't just there to make a paycheck.
59:01
We were there to build something exceptional and to continually talk about that was important.
59:04
When you were building Braintree, when do you feel like you were at your your peak powers?
59:13
In other words, like when were you pitching a no-hitter in the World Series?
59:17
Like at what point in building Braintree was that?
59:19
I don't think I could identify it.
59:22
It was just so gradual and over time that we started these companies like Uber and like Airbnb, they hit their growth stride.
59:30
And it was amazing that we were powering all their payments.
59:34
And um it was just so gradual and slow because companies come on brand new and it takes them a couple years to ramp up to start processing, you know, significant sales.
59:42
So, I don't know if I could identify a single point.
59:43
It's just this slow, steady build.
59:46
When were you under the most When did you feel under the most pressure? Always. Okay.
59:55
So, the the 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?
1:00:12
The first, say, hour of your day or 2 hours of your day.
1:00:16
Yeah, so I guess if I think about the broader context of life, I mean, I had two children when I started Braintree and then um yeah, I had three by the end.
1:00:28
And we had my first two children were colicky, so they're crying all night.
1:00:32
And so not being able to sleep very well at night and getting up the next day and going to work and then dealing with all the stuff you deal with.
1:00:40
It was a pretty tough time in life.
1:00:42
And um I mean, there were some dark moments.
1:00:45
It's it's I guess something you and I have talked about on our walks is that I generally view advice I'm very skeptical of advice because it's so contextual and it can be deceptively um unhelpful because you don't understand what's packed into that advice.
1:01:00
But, one um piece of advice I think is helpful for entrepreneurs that I wish someone would have told me is the importance of surrounding yourself with fellow founders, people who get you and understand you.
1:01:12
That all those years as a founder, I felt like I owned everything.
1:01:16
I owned energy, I owned growth, I owned the success, I it was all me.
1:01:20
And I had didn't have any co-founders, so uh that's not to say people my team didn't shoulder that, right?
1:01:24
But, as the founder, you do feel a extra level of burden.
1:01:27
And I had no outlet for it.
1:01:29
I owned energy at home, I owned energy at work. And um it it was tough. It took a toll.
1:01:35
And so over the past couple years, I've created these friendships like, you know, like like you and I have where we can talk as if we were journaling. Right. Right.
1:01:44
I mean, to get to the real raw and good stuff of life.
1:01:48
But, um I think that that would have been very helpful during those darkest times, during the thing the moments where it was the hottest. Yeah.
1:01:56
I um I had a a book inscribed for me.
1:02:00
Actually, it's right there.
1:02:00
The Psychedelic Explorer's Guide.
1:02:01
Had Jim Fadiman on the podcast and uh I thought his inscription was so great.
1:02:09
He said, "You know, to Tim, a companion on the path."
1:02:12
And I was like, "That's it."
1:02:14
And I think I mean, we're literally companions on the path.
1:02:16
We go on these hikes, but having those Yep.
1:02:17
those people who can identify with the pressures that you're feeling.
1:02:22
What were other coping strategies that you had or routines that were helpful when you felt you were shoulder shouldering all of that burden?
1:02:31
Yeah, so I always look for hobbies that would consume my mind, where I could escape myself because these things the channel. Exactly, yeah.
1:02:41
For a brief period of time.
1:02:41
Totally, because it's like it loops and loops and loops.
1:02:44
And if you try anything else, it just loops.
1:02:45
Even when you're having conversations, like you're just obsessed with trying to build your company.
1:02:50
And so one day I had a hard day at work and I was walking home, I thought, "You know what?
1:02:53
I'm going to go fly an airplane.
1:02:54
Like, maybe that will do the trick."
1:02:56
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."
1:03:01
And he did like this really hard turn up and down.
1:03:02
I got sick and I was like, "Oh, I can never do that. It's so crazy and hard."
1:03:05
But, I thought about it the next morning, I thought, "No, I can actually do this."
1:03:08
And so I started flying and I lost myself in aviation. I absolutely love it.
1:03:12
And so that really helped that I could find a different place to park my mind and focus.
1:03:15
Is Is it discovery flight where like you're in the passenger seat of a new car and they show you what the car can do?
1:03:22
Is that what a discovery flight is? Basically, yeah.
1:03:25
You go up and he's like, "Hey, so if you want to get your license, you have to perform the following maneuvers.
1:03:30
Like, here's a steep turn, you know, 30° and And so he was just showing me basically how the plane operated and what I would need to do. Mhm.
1:03:36
And I I think for a lot of people listening they think of learning to fly as a very very very very expensive thing.
1:03:43
I think they associate it with, say, owning a private jet.
1:03:46
But, that is not the case, right?
1:03:48
I mean, as far as I understand it.
1:03:50
I mean, I have friends who work jobs here who have gotten into aviation. Yeah.
1:03:54
Is it uh How How cost prohibitive is it to become involved with aviation in some capacity?
1:04:02
So, I think I paid a few thousand dollars over the course of the lessons. Got it. Something like that.
1:04:08
Over what period of time?
1:04:08
Uh I believe it took me 90 days. Got it.
1:04:09
So, I mean, all in all, not pocket change, but not like buying a Gulfstream. That's right.
1:04:17
Um and this is something I've 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?
1:04:27
So, that they're not constantly watching sort of Yes.
1:04:31
uh BBC News or whatever the hell their world happens to be. Um Let's see.
1:04:38
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? Or in that rough range. Yeah.
1:04:54
I admired people who had I guess I had a a number of buckets in my mind of who I admired.
1:05:03
But, one bucket that appealed me because I thought I could potentially be like them was those who had acquired significant amount of resources through building businesses and were now using those resources to do good in the world.
1:05:16
That they had freedom of time.
1:05:16
They didn't need to show up for a job and they didn't, right? All that kind of stuff.
1:05:20
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.
1:05:27
So, it really it was freedom of time to do the things that you cared about the most in life.
1:05:34
So, who were Who were some of those people?
1:05:36
Or who are some of those people?
1:05:37
Well, I mean, growing up in Utah, Jon Huntsman was I don't know who that is.
1:05:41
So, he built um I'm not even sure what company he built.
1:05:45
But, he was enormously wealthy.
1:05:45
And of course, the Marriotts are and they're as well.
1:05:49
But, there were a few families in the community that had accumulated significant resources and they they like one I think Huntsman had his 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.
1:06:02
And I thought that was a I thought that was really remarkable that you could make huge contributions potentially to humanity.
1:06:10
So, this is this is actually I think a good segue to uh one of your current projects.
1:06:14
I think it's fair to say primary project, the OS Fund. It is, yeah.
1:06:18
So, could you explain to people what the OS Fund is?
1:06:22
Yeah, so the context is I guess at 21 I made that goal that I wanted to spend my life improving people's lives.
1:06:26
And over the 14 years or so as I was building my companies, I thought a lot about this.
1:06:32
Like, what would it look like? What would it feel like?
1:06:34
What would it taste like?
1:06:35
What areas would I focus on?
1:06:36
And I looked through thousands and thousands of ideas.
1:06:40
And I mean, I was always thinking about it.
1:06:42
And I studied during that time a lot of about science and technology.
1:06:45
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.
1:06:57
So, if you take computer software and biology, genomics, AI, virtual reality, 3D printing, we can literally program our existence.
1:07:07
So, I think oftentimes of like DaVinci where he had his great sketchbooks where he designed a flying machine.
1:07:11
And he had these really amazing ideas, but he couldn't build it.
1:07:14
He didn't have the tools.
1:07:15
We can literally build anything today.
1:07:19
And so as I realized that, I thought, "This is like the one of the biggest moments in the history of mankind or humankind."
1:07:24
How do we Biggest question for me was, "What kind of world are we going to build?" Yeah.
1:07:28
And that's when I started the OS Fund is is trying to invest in these tools of creation that will so dramatically affect the kind of world we build.
1:07:38
Yeah, it is really a fascinating time.
1:07:38
I mean, we have this sort of Cambrian explosion of potential where, you know, what what happens when you can create virtually anything.
1:07:48
You can download a recipe for a a a a a a virus that could cause an epidemic or a weapon.
1:07:57
Or at the same time, I obviously use that knife that surgical knife to repair or build as opposed to damage, right?
1:08:05
Uh what Now, OS refers to operating system. Yes. Why operating system?
1:08:10
So, it's a metaphor I like a lot that the biggest changes in history the biggest um improvements in history have happened at what I call the operating system level.
1:08:22
So, for example, like germ theory.
1:08:24
That we tried to figure out what was causing disease and death for a long time.
1:08:27
And when we figured out there was a thing like bacteria that caused infections and death.
1:08:30
And then once we figured out sterilizations and antibiotics and vaccines and good personal hygiene we radically extended healthy human life, but it was finding out there was this core problem of bacteria.
1:08:41
And every major change we've had have been has been at this level.
1:08:44
And so instead of playing with things out of different level um my what we think about is in the companies we invest in are doing world-changing things at the operating system level.
1:08:55
So, if they're successful in their endeavors, it would radically change the world. Right.
1:08:59
So, at the foundational That's right.
1:09:00
level upon which everything else is That's right.
1:09:03
So, just like a computer has an operating system at its core that determines how it works.
1:09:06
And then there's applications that sit on top.
1:09:09
Everything in life has an operating system. Hm.
1:09:12
And what what are some of the investments that you've made thus far in the in the OS Fund?
1:09:17
Yeah, Human Longevity led by Craig Venter is they're trying to radically extend healthy human life, you know, into the hundreds.
1:09:25
And they're doing it by using the whole human genome and then adding data like the the metabiome and phenotype data and then using advanced machine learning to learn about disease and and create personal therapeutics.
1:09:38
If they're successful, they'll change uh medicine. Right.
1:09:40
As we know it in a really fundamental way. Yeah. Uh any others?
1:09:45
Uh yeah, we just made an investment in Ginkgo Bioworks, which they're basically making biology programmable.
1:09:54
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.
1:10:04
T- For today, they're doing fragrances and flavors that producing in a lab that otherwise would be required in nature.
1:10:11
And as we climb up the complexity scale, we can do much more complicated things like um work on antibiotic resistance and carbon capture.
1:10:17
But, the idea to like your biology, our biology, our world runs on biology. Right.
1:10:24
The fact that this could be a programming language we could actually predictably use is remarkable. Right. Well, what is it?
1:10:30
I mean, I guess DNA is about ATCG, right?
1:10:32
I mean, it's something along those lines.
1:10:34
So, I'm I'm getting out of my depth here into my ignorance pool I'm pretty quickly.
1:10:37
But, the uh so, the fragrances for instance, that would be considered Is that considered synthetic biology? No.
1:10:43
So, they design the organism just like you you take yeast for for brewing beer, right?
1:10:48
Um you take an organism and you can alter within the production that organism what it produces.
1:10:55
So, it's actually a natural in production.
1:10:57
You're just altering the organism that produces it.
1:10:59
So, it's not synthetic biology. Interesting.
1:11:01
Okay, so you're just kind of re- removing a few ingredients in a a pre-existing recipe and letting kind of the chef, I mean, the organism produce.
1:11:10
So, it's like this different food product. Exactly.
1:11:12
It's this new era of industrial engineering where it's going to change all the processes we created during the first industrial revolution.
1:11:19
Now, uh what is your and you may not have a strong opinion here and if not, that's totally fine.
1:11:25
But, people get uh very uh excited positively and negatively about uh the term GMO. Yeah.
1:11:33
Uh genetically modified food.
1:11:35
Uh what is your perspective on that?
1:11:39
So, I think that Because I just uh from a personal personal standpoint, there are cases where they can change the genetics slightly to make something say more resistant to That's right. pests. That's right.
1:11:52
Um then we they're they're start I 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. Yes.
1:12:01
And then I get a little uneasy and I'm not sure if that's well-founded or not. Yep.
1:12:05
Uh cuz I we start getting into uh you know, I think of all of the um all of these sort of uh horrifying mad scientist novels that I read when I was a kid.
1:12:16
Uh but, do you do you think any of those fears are well-founded or or what are the the risks of that going wild?
1:12:21
Okay, so I'll answer your question in a different way. Perfect. not find satisfactory.
1:12:27
But, I think It was a It was a very very poorly worded question.
1:12:31
So, thank you for saving my ass in the first place.
1:12:35
No, I So, I If If we start with with this premise that we have these incredibly powerful tools of creation. We can program anything.
1:12:42
Okay, that obviously means and and couple that up with we have this distributed environment now where anybody can pull up a computer terminal in anywhere in the country in the world and at whatever age and program, right?
1:12:53
Either through biology or computer software.
1:12:55
So, we have all these tools.
1:12:57
So, we have a world full of makers that have these powers.
1:13:02
So, with that, what you build affects me and what I build affects you.
1:13:06
And so, one thing that I'm exploring now with the OS Fund is what I call societies our social operating systems.
1:13:12
And there are systems of cooperation and reconciliation.
1:13:14
So, in that category falls like governance and capitalistic systems, right?
1:13:18
These belief and value frameworks that drive our behavior and allow us to reconcile our differences.
1:13:25
So, we're going to have some really big questions to answer.
1:13:29
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?
1:13:37
What is appropriate for AI in terms of what people build?
1:13:39
So, we have really big questions to answer and uh 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 and and um better aligned with the realities of our current time.
1:14:03
The big question topic is a really fascinating one to me uh for a whole host of reasons.
1:14:09
I remember as an undergraduate, some of my favorite cla- classes were philosophy classes.
1:14:15
Introduction to metaphysics or whatever.
1:14:16
And you had say utilitarian uh philosophers, I think that's the right term, like Peter Singer for instance.
1:14:22
Very controversial, I think.
1:14:24
Most of his controversy is unearned.
1:14:24
I think it's politicized and so on.
1:14:26
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?
1:14:33
And uh that would mean if there's like you're stuck in a cave and there's one fat guy plugging the exit and the 10 people in the cave are going to starve to death, you kill the fat guy.
1:14:42
I mean, just it's mathematics, right? Pure and simple.
1:14:47
Um and that used to be primarily just a thought exercise.
1:14:53
Sort of an academic ivory tower thought exercise.
1:14:54
And uh now you have companies working on say autonomous vehicles and AI who are hiring philosophers to try to advise That's right.
1:15:06
how to answer these questions when say an autonomous car is barreling down the highway or on the Golden Gate Bridge and all of a sudden has to choose between, you know, hitting the five uh you know, octogenarians on the sidewalk, the old ladies, or swerving the other direction and hitting a car that has Yes. four-year-old. Yes. Yes.
1:15:21
So, how do you make those value judgments? Yep.
1:15:25
And what I'm so curious about, number one, that's a that's a very multi-faceted, thorny, potentially subjective question to tackle, but you have to program these vehicles or entities That's right. to behave.
1:15:40
That's that's that's the you know, the set of rules they're programming.
1:15:44
At the same time, what I really worry about and 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.
1:16:03
Let's just say uh sort of ethically wired uh technicians and technologists in the Valley and elsewhere, right?
1:16:12
That's challenging in and of itself.
1:16:13
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.
1:16:28
will be dependent on it would seem.
1:16:30
And I want you to to challenge me on this if you don't agree with this.
1:16:32
Uh would be dependent on legislation, right?
1:16:35
There will be sort of the the way that you know, economics is how humans, well, among other things, respond to incentives, right?
1:16:41
And so, it's like the reward in a capitalist society say and then the punishment of a of a legal system that put you in prison.
1:16:50
When politicians, many politicians are completely incentivized in the short term for re-election and not envisioning the long-term implications of some of these massive decisions massive decisions.
1:17:04
How do you contend with that?
1:17:04
Like or how how have you how have you thought about this?
1:17:07
That's why I think it's such a hugely important area to focus because when people make decisions, you're looking really at the surface layer.
1:17:19
But, the beliefs and values that are driving that are embedded very deeply, right?
1:17:24
Often times That's why I That's why for example like social operating systems are so incredibly powerful, but also they're invisible.
1:17:31
Like they just are woven into the fabric of our lives and we don't know they exist.
1:17:34
And when we do see them as existing, we just consider them as givens or fixed.
1:17:40
And so, what we're hoping to do is to call attention to what they are, right?
1:17:46
These massive powerful influences in our life that drive our decisions and we don't even know it. Right.
1:17:49
Or that they're subconscious. Exactly. Yep.
1:17:51
And that identifying them that they really are social technologies that are driving these decisions.
1:17:55
And so, if if we go to use I guess a technical, you know, term, like if we go deeper in the stack, 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?
1:18:08
Yeah, what are the assumptions and if thens that are built into the lowest level Exactly.
1:18:14
that affect our decisions on, you know, the eighth layer. Exactly.
1:18:15
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.
1:18:27
How do you personally try to identify those for yourself in your own personal decision-making and so on? Yeah.
1:18:35
So, at Braintree, one of the principles I consistently communicated was challenge all assumptions.
1:18:42
And the story that I accompanied with it was there's five monkeys in a room.
1:18:46
There's a basket of bananas at the top.
1:18:47
And the monkeys, of course, want to climb the ladder to get the banana.
1:18:51
But, every time a monkey tries, they're all sprayed with cold water.
1:18:56
And so, after a few times being sprayed with cold water, the monkeys learn don't climb up the ladder to get the bananas cuz we're getting sprayed with cold water.
1:19:02
And so, they take one monkey out and put a new monkey in.
1:19:04
And the new monkey, of course, sees the bananas and is like, "Hey, like I'm going to go grab a banana."
1:19:08
But, when it tries to go up the ladder, the other monkeys grab it and pull it back.
1:19:12
Like, "I don't want to get sprayed with cold water. You're new guy here.
1:19:14
So, like don't mess with me." to teach you the rules. Exactly.
1:19:17
So, then they systematically pull every monkey out um and have you Now, you have five new monkeys in.
1:19:23
Anytime a new monkey comes in and tries to climb the ladder, they grab the monkey and pull it back.
1:19:28
But none of the five have ever been sprayed by cold water.
1:19:30
Have ever experienced it. Exactly.
1:19:31
And so what I always try to wonder is where is that in my life?
1:19:35
Like what am I assuming that is invisible that I cannot see?
1:19:40
And of course when the circumstances change in a situation like that, you have learned helplessness, right?
1:19:43
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. Yeah.
1:19:54
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.
1:20:02
And then others that would get shocked no matter what.
1:20:05
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 Yes. and get shocked. Yes.
1:20:16
So where does that exist in your own life?
1:20:19
What What have you What are some cases if you're comfortable discussing them where you've discovered that?
1:20:22
Whether at Braintree in a business capacity or otherwise.
1:20:27
Yeah, well let me think about that. Um so many.
1:20:29
I mean I guess being human is remarkably tough, right?
1:20:35
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. Right.
1:20:41
And I guess I a couple years back like maybe a decade ago I got into irrational behavior reading Dan Ariely's book Predictably Irrational.
1:20:50
And uh Thinking Fast and Slow.
1:20:50
Yeah, Thinking Fast and Slow, Danny Kahneman. Yes, exactly.
1:20:53
So I started reading all these books and I became increasingly convinced of my own um what I was fickleness and inability to actually act rationally in life.
1:21:03
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.
1:21:14
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.
1:21:23
And if I went back and evaluated it.
1:21:25
So I I suppose it's just being present and knowing it exists and how flawed we are in our abilities when really we think we're perfectly logical and consistent all the time. We're just not. Yeah.
1:21:34
There's Dan Ariely's book is great, Predictably Irrational.
1:21:38
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.
1:21:54
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.
1:21:59
And how changing the pricing and removing or adding options affected the the average order size. Yes. So fascinating.
1:22:10
Or adding in basically not a red herring, it's not the I don't think the right term, but a 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 people will take the middle option. Totally.
1:22:24
Which would have been the cheapest before, but you would have then Exactly.
1:22:27
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.
1:22:32
Everything else is cheap at $32. Same thing with wine. Very common.
1:22:38
When you are feeling and maybe it 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?
1:22:48
I've gotten so much better over the years.
1:22:52
Now I just call a friend and just say, you know what?
1:22:54
I'm feeling overwhelmed and I feel terrible and I don't think I can do this and right?
1:23:00
Just saying it out loud like yeah, I actually I can.
1:23:01
I got this, but I just need to get that off my chest and I'm all right.
1:23:04
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 anytime of the day and say anything, right?
1:23:12
No judgment on my side, just say it out loud, do it.
1:23:16
And I think there's just it's it's hard to do hard things I guess is is Ben or what would say. yeah.
1:23:23
And having the ability to be vulnerable and honest and transparent and raw with other people is immensely helpful for me. Yeah.
1:23:33
And but you weren't always You didn't always do that.
1:23:36
No, I was extremely private and guarded and I owned everything.
1:23:39
I didn't dare come out of you know, let go and I think I think men are particularly bad at that. I agree.
1:23:45
I uh Yeah, I've struggled with this myself. And you're so on point.
1:23:50
It's such a simple answer.
1:23:53
Seemingly self-evident and obvious, right?
1:23:55
But uh I think it points to something I've noticed about myself and I tend to be stuck in my kind of prefrontal cortex 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. I agree.
1:24:15
Uh just by by relying on the sort of internal pro and con list and like schematic of something that is purely emotional or maybe based on some operating system flaw that you're experiencing. Yeah.
1:24:26
Uh So yeah, just calling a friend.
1:24:29
Yeah, but that's like what I love about the friendships I have is I I can go into a conversation and I know when I leave two things will happen.
1:24:35
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.
1:24:42
But someone else can see it so clearly and they can just call it out, right?
1:24:45
And then number two is when I leave the conversation saying like I want to become a better person, right?
1:24:51
And I want to do more in life and I want to work harder.
1:24:52
Like those are the two things I think I value the most in the attraction.
1:24:55
So it's I want to be that for other people, right?
1:24:57
That when they bring something to me I can flip it and say, yeah, here's a different model for you to contemplate.
1:25:02
And two, hopefully when they leave they say, you know what?
1:25:05
Yes, like I can do this and I've got that much more energy to go about it.
1:25:08
I find also you know my version of talking to someone very often is journaling in the morning.
1:25:14
Just to take what I feel for instance if I'm feeling overwhelmed or having some type of problem or source of anxiety, putting it on paper makes me realize how absurdly unfounded it is. I agree. I agree. It's magical, right? Yeah.
1:25:30
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 can provide you with a sufficient mirror in which you can see it's completely ridiculous.
1:25:43
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.
1:25:47
Like stop freaking out, it's not a big deal.
1:25:48
And it's transient or reversible or both.
1:25:49
Um So a couple of just to shift gears for a minute, a couple of uh rapid fire questions that you can you which don't have to have rapid fire answers.
1:26:01
You can So you can take it however you want.
1:26:02
I'm I'm not very witty or or quick.
1:26:05
Okay, so I'll try my best. you're fast enough.
1:26:09
Uh In the last say 6 months to a year or the first thing that comes to mind, what is something a purchase you've made for less than $100 that has had a significantly positive impact on your life?
1:26:25
I have water, so take your time. Okay.
1:26:29
Um I would probably say I don't know.
1:26:34
Okay, we'll come back to it. All right. We'll come back.
1:26:38
Uh Do you I mean that's that's that's not the right question cuz it gives you an out.
1:26:45
What historical figure do you identify with? So I love biographies.
1:26:50
I've read probably 100 plus biographies.
1:26:57
And I don't know if there's one person in particular.
1:27:00
Might be just a collection.
1:27:02
Actually no, actually I'd say there's there's a few.
1:27:04
Um One we talked about before, Shackleton.
1:27:08
He he resonates with me at a deep level.
1:27:12
Uh two, I read this book called A Good Man by Mark Shriver about his dad Sargent Shriver who worked in the Johnson administration and started the Peace Corps and and um he was a remarkable man.
1:27:24
An exceptional father, a good friend, loyal, and he is a mental model of the kind of person I want to be in life.
1:27:32
So um that three I'd probably say uh Victor Frankl's Man's Search for Happiness.
1:27:40
That Happiness or Meaning? Meaning. Okay, yeah. Yeah. Yeah, yeah. So thanks.
1:27:44
Very interrelated though.
1:27:44
Yeah, but the So I have one of the driving philosophies of life thing that drives me the most is is I I guess I find the most beautiful is that we have the ability to author life in life.
1:27:59
Yeah, you're better but we we can choose not to take default routes.
1:28:01
We can choose to take different paths that we can design and do whatever we want.
1:28:05
And I find that's why I find entrepreneurship so appealing is that you get to design your own world.
1:28:11
And so in my office actually I hired I commissioned a graffiti artist.
1:28:15
Oh, you sent me a photo of this. I remember. Now explain it, please.
1:28:17
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 it's exploding energy in the middle of the air with this book that's open blank pages with a pen.
1:28:30
And then above it in graffiti is the word dream.
1:28:34
And the concept behind it is is J. R. R. Tolkien and and J. K.
1:28:36
Rowling created worlds that we inhabited through the tool of text. Right?
1:28:43
They wrote this stuff down and then we inhabited it.
1:28:45
So they literally authored worlds.
1:28:47
And we have that same ability as entrepreneurs to build companies, right?
1:28:50
And everything we do we have that.
1:28:52
Especially our tools of creation now that we're investing in at the OS Fund.
1:28:55
And so I wanted to use pop culture figures because I wanted my kids to see this that they have that ability to do that in life.
1:29:03
That they don't need to say yes to the default options.
1:29:05
That they can carve their own path.
1:29:07
And even though it's incredibly hard, it's going to be painful, to me it's so much more fulfilling than a secure and safe way to live life.
1:29:19
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 a wealthy family where that was the kind of is uh default I don't I Was that the default belief system? Maybe it was.
1:29:35
Maybe despite the the financial challenges.
1:29:38
I mean, because I think I recall you telling me that your your mom made some of your clothing She did. Yeah.
1:29:45
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.
1:29:55
Uh the authoring of your own world.
1:29:57
So I'm going to come back to that.
1:30:01
And I I realized the the successful question I think could be broken down a few ways.
1:30:06
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. Yeah. Right?
1:30:15
Which has its own risks, because you might absorb bad habits if you're spending time with those people without realizing it.
1:30:21
That's Uh sort of like viruses in your you know, bugs in the OS, I guess.
1:30:24
But but that person correlated to the values, right?
1:30:29
So modeling that person based on values.
1:30:31
If you were modeling who is an entrepreneur or who are entrepreneurs that you admire for their aggression?
1:30:42
So I'd say actually a like an bunch of names pop up. Yeah.
1:30:45
People I've invested in at the OS fund. So I mean Craig Venter. Yeah.
1:30:49
At Human Longevity, Peter Diamandis there as well.
1:30:54
Josh Tetrick Hampton Creek. Mhm.
1:30:54
Um Jason Kelly at Ginkgo Bioworks, Daniel Fong at LightSail.
1:30:59
Uh Scott Phoenix at Vicarious.
1:31:02
I mean, we have a great roster of incredibly passionate entrepreneurs.
1:31:06
Mustafa Suleyman from DeepMind.
1:31:09
I wasn't an investor there, but I find him immensely inspiring.
1:31:10
But um these entrepreneurs think differently about the world and um they're going after extremely hard challenges.
1:31:20
And I'd say they're audacious and determined and very aggressive. Uh Got it. Okay, so now let's see.
1:31:33
Do you define Would you describe yourself as aggressive? I am.
1:31:38
Uh in what ways are you most aggressive?
1:31:40
Um when I see something I want to go after, uh I can be pretty relentless. Mhm.
1:31:47
And um which entrepreneurs do you most admire for their And I I'll have to say you're you'll have to choose either a smaller subset of the people you've invested with or uh you can choose other people, which might be safer.
1:32:03
Uh but for their resourcefulness.
1:32:08
All right, so let's come back to that.
1:32:13
I know I'm going to have a lot of examples to think of.
1:32:16
People who who have faced near and certain death countless times, but somehow they figured out to maneuver Right. uh around the problems. Right.
1:32:24
Did sort of uh Neo in the Matrix do the backbend and dodge the bullets and come back to life. Yeah, exactly.
1:32:28
I mean, that's the essence of entrepreneurship.
1:32:29
So So that that's actually uh that's actually um a good segue.
1:32:35
So what do you think an entrepreneur is? What is an entrepreneur?
1:32:44
Someone willing to So I I think entrepreneurs and explorers have a lot in common. One like Shackleton.
1:32:50
That they chart they they head off in uncharted territory.
1:32:55
And they maintain this ability to adapt to circumstances that are chaotic, unknown, and extremely challenging.
1:33:04
And they can maintain some order in all the chaos Mhm.
1:33:07
to actually achieve a goal.
1:33:12
What are practices uh experiments maybe that people could perform to help them develop those characteristics?
1:33:22
Is there anything else that you find sort of ports well over to that chaotic uncertain nature of startups or small companies?
1:33:33
So I guess we I have a lot of conversations with people who want to start their own thing.
1:33:36
And one of my favorite questions to ask is is this an itch or is it you know, burning? Right.
1:33:45
So if it's just an itch, it's not sufficient.
1:33:46
And it gets to this point of how badly do you really want it?
1:33:52
And for me, I burned the boats.
1:33:52
Like there was no way I was going to get a job.
1:33:56
And so failure was never an option. I had to make this work.
1:33:59
And I did have jobs along the way, but that was just to simply to pay the bills, but um failure just wasn't a solution I would accept.
1:34:10
And so I think I want to get it on entrepreneurs that how badly you want it, what will you do to get there? Yeah.
1:34:17
I find it very difficult in the current environment to identify those people because things are so frothy right now.
1:34:24
Uh a lot of people who would otherwise be risk intolerant and fearful of uncertainty are jumping into the fray as founders.
1:34:34
I mean, you have And this look, I have a lot of my very close friends come out of McKinsey and places like that, but when people with very high-paid consult consulting jobs are then jumping into startups, I start to wonder what uh what is on the what is on the horizon.
1:34:48
And if I look back a very kind of macro timing way to at least narrow down the field a bit so it's easier to find those people seem to be investing during recessions.
1:35:01
So that's sort of investing right after crashes.
1:35:07
It left sort of the people who couldn't conceive of doing anything else standing on the playing field. Yeah.
1:35:12
And the sort of fair-weather investors, the fair-weather entrepreneurs all went back to doing whatever they perceived to be Yeah. charted territory. Yeah, yeah, exactly.
1:35:21
I mean, I I guess I I want to be careful like I don't want to be like a an entrepreneur definition snob.
1:35:24
All right, and suggest that I was going to come out and pound the table and yell at you about that, but But I mean, like these attributes are held by people within companies who are starting their companies, who are working with larger institutions, right?
1:35:36
But it's it's uh it's just inherently people who can create, do, and see what others cannot or will not do, right?
1:35:46
That they will blaze something that others will follow or benefit from. And Mhm.
1:35:53
So uh Let me Let me Let me dive in to a couple of other questions also.
1:35:59
Uh Do you have a a book that you've gifted often?
1:36:03
Are there any books that you've gifted to other people often?
1:36:08
I have gifted A Good Man to quite a few people and Shackleton and Victor Frankl's book.
1:36:15
Um The Good Man I gift because if we contemplate how Like I wonder what would my son or daughter say about me?
1:36:24
What kind of biography would they write?
1:36:26
And that's a model for me I would want.
1:36:28
Um Shackleton, that's how I want to behave in life.
1:36:30
And Frankl, uh that's how I He He his basic point is no matter the conditions we surround ourselves in, we can author our life. Um right?
1:36:42
We can author whatever how we respond.
1:36:43
And then I guess I'd also throw in there Siddhartha. Yeah. Have you read that?
1:36:47
Herman Hesse or Herman Hessa, I guess in German. I think it's Herman. I love that book. Yeah.
1:36:51
That came up yesterday on a on a walk with um uh someone I won't name cuz it was a private conversation, but a very very successful guy that I also admire a lot for his sort of deep deep thinking on important philosophical questions. Siddhartha came up.
1:37:07
Um that's also come up I think with uh my conversation with Josh Waitzkin, who was on the second interview ever on this podcast, who was the basis for Searching for Bobby Fischer.
1:37:16
Known as a chess prodigy, but really I don't think it's appropriate cuz he's applied his kind of learning framework to many different areas.
1:37:21
But that book comes up a lot.
1:37:24
It's a very sort of allegorical, but um often times I think that deep truths can be explored more effectively in fiction than in non-fiction. Right.
1:37:35
Uh because it pulls you out of your normal context Yes. in a way.
1:37:40
So you're you're not your your program your problem-solving software isn't running.
1:37:45
So you kind of blindsides you. New mental models. Yeah. Yeah, exactly.
1:37:48
Uh the um I had a profound question that just escaped my semi-ketogenic brain or ketotic brain.
1:37:59
I'm probably right on the I think I we were talking about this just before and I I had 0.
1:38:02
6 millimolars cuz I I fell out of ketosis and then I'm just getting back in.
1:38:07
Had some coconut oil, but I think that's kept me going for about 60 minutes.
1:38:09
So I'm probably in the in in the the no man's land, the gray zone of substrate suffering.
1:38:16
Uh What uh 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?
1:38:35
Uh let's say I would put it in New York and it would say do an anonymous and random act of kindness today. I like it. Why New York?
1:38:50
For if if you're giving me the constraint of a single billboard That's right.
1:38:54
and I want the broadest exposure, I'll go to New York where the density is highest. Got it. Uh I like it. Good answer.
1:39:01
Um if you were giving advice to your 30-year-old self, what advice would you give?
1:39:21
That um no matter what comes your way, no matter how hard things feel, that I have the power to overcome and be at peace with it. Good advice.
1:39:43
I think that's a great place to to start wrapping up.
1:39:45
Is there anything else you'd like to share with the audience?
1:39:49
Resourcefulness examples, anything else?
1:39:54
Yeah, you know, one thing so I do a lot of projects with my kids and like for example, we started at 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.
1:40:18
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 upper aspirations and and endeavors, I think that um I'm encouraged by watching my own kids grow up that I see um a bright future that we can trust these incredibly powerful tools of creation can be used for for good things.
1:40:42
It goes to subjective of course, but um but that we can actually change uh humanity in fundamental ways and that um the rising generation, if we do it right, will have amazing ability to contribute to a to our well-being.
1:40:57
And if 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. Yeah.
1:41:07
Um what are a few activities or experiments or collaborations that you would encourage them to have with their kids or habits.
1:41:20
It could be anything, but just general try these two things, three things, whatever it might be with your kids.
1:41:26
Yes, I my personal philosophy is I I try to be relevant in my kids' lives.
1:41:30
And so for example, my 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 uh are using the scientific method to say, if we bring technology into the classroom, will it improve our educational experience?
1:41:47
And so they have to test it out and use pros and cons and go through the whole process.
1:41:50
And then each of the and there's six groups making a documentary.
1:41:55
And so I'm with the teacher working with Six groups of students?
1:41:57
Yeah, six groups of students within the class and they each are making like a three to four-minute documentary on the process of testing the scientific method of does is technology in the classroom a positive or negative experience or what are the pros and cons.
1:42:11
And so I'm working with his teacher to do that and doing the filmmaking and 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.
1:42:25
And so when we have conversations, I'm not just saying, "Hey, how's your day?" "Fine."
1:42:27
And that's the end of conversation, right?
1:42:29
But it's relevant and so the same is true with my fourth grader and in my in my daughter who's in um preschool, but I would say parents that get engaged in the children's lives to be truly relevant, to understand the underlying context of who they like, who they dislike, who are their friends, who are the the people who are you know, saying mean things to them, what are they worried about in school.
1:42:52
So that's been helpful in my relationship with my kids and I think it's really helped us form a very strong bond.
1:42:58
Are there any um traditions that you've built into the family that are non-obvious?
1:43:03
Like 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?
1:43:16
Yes, so when we sit down for dinner, I always have a question for them.
1:43:18
Like uh last week on Saturday night, we had this discussion of what does it mean to be good?
1:43:28
And they're jamming like you know, it's like 11, 9 and 5 and they're jamming on this question of what it means to be good and I raise all kinds of questions like what you think is good is not necessarily what I think is good.
1:43:37
We have these different interpretations and is there a single definition of good?
1:43:42
And so like my 5-year-old is raising her hand offering up her input, which is amazing, but they walk away they're surprisingly bright and have these amazingly good insights.
1:43:48
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.
1:43:55
But at least we have this moment where we can connect on really serious questions and they can explore these philosophically, which um I have found to be beneficial in both their development, but also our relationship.
1:44:09
What in your mind are common mistakes that parents make aside from doing the opposite of the two things you just described?
1:44:17
So we were this is up for opinion of course, but we were at a uh my 5-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.
1:44:29
So 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.
1:44:37
That's what friends are for. Exactly.
1:44:37
So when there was like two camps of parents that broke out.
1:44:41
One camp was like, "No way is my child going to be involved in this terribly dangerous endeavor."
1:44:45
Which is a reasonable thing to say, right?
1:44:49
Because it's pretty dangerous and like someone could get really hurt.
1:44:51
And there were other parents more like myself like, "Look, they'll figure it out.
1:44:55
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?
1:45:02
These principles of physics. Yeah, exactly. In the flesh.
1:45:05
So I mean my daughter got on and she was in the mix of all this stuff, but um 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.
1:45:17
They can learn, but if we if there's too much inherent protection structured that they just forego those learning experiences. Yeah.
1:45:23
And well, they're taught that they're fragile.
1:45:24
I think therefore they develop the belief that they're fragile. Yeah.
1:45:28
I mean now granted, I think back to I mean I'm sure you probably have this like your gasoline gallon of gasoline in the street example.
1:45:37
I think back to some of the stuff I did where I'm just like I cannot believe I was allowed to to do that. Like Yeah.
1:45:41
Skateboarding off of ramps in the middle of the street where I'd like flip over and like smash my head on the asphalt and concuss myself.
1:45:48
I was just like, "Oh my god." But yeah.
1:45:51
All of those things taught me ultimately like the either this too shall pass or like, "Okay, like you earned your lumps.
1:45:58
Now you know not to do that."
1:46:00
But you also know like you you were able to weather the storm and get through it. Exactly.
1:46:05
Yeah, so we got on a four-wheeler two weeks ago, my 11 and 9-year-old and I said, "Okay, I'm going to put your helmets on.
1:46:10
I'm going to give you a two-minute lesson on how to go how to do go forward and how to go backwards, how to brake.
1:46:15
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.
1:46:26
Like what were your thought processes, how did you stay safe, what were the risks you took, but I want them to do it and I'm not going with you, right?
1:46:32
So you go and come back."
1:46:34
And they came back in one piece.
1:46:36
But it was a good experience for them to tell me like, "Okay, Dad, this is how we looked at the risk.
1:46:39
This is how we thought that we potentially would get into a problem." They ran into a tree. Going slowly, but right?
1:46:43
And they talked about it, which was I thought was really helpful.
1:46:48
Well, you know, it's and uh I just think it's I I think you're a fascinating guy.
1:46:52
I think you're very inspiring guy and as I think forward to yet someday having kids myself, I I I love asking you these types of questions and um this has been a blast.
1:47:03
So number one, thank you very much for taking the time.
1:47:08
I always love having these conversations.
1:47:09
This is our first one on the record and second, where can people learn more about you, about the OS Fund and so on? Uh OSFund.
1:47:16
co co is where all of our investments are.
1:47:22
And um I'm active on Twitter, so happy to have ongoing discussions about the various things we talked about, but What's your Twitter handle?
1:47:28
Uh Brian_Johnson with a Y. Got it. At Brian_Johnson.
1:47:34
I'll put that in the show notes as well.
1:47:36
Uh any any parting thoughts or comments?
1:47:38
No, Tim, I just love this.
1:47:40
You know, we've we've had fantastic conversations, you know, over time, so this is fun to actually do this formally and you know, I really enjoy the friendship. Likewise, man.
1:47:49
And this is it's I'm so glad that I was able to uh to try to give people a view into these conversations that we have.
1:47:57
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.
1:48:18
And so I I really believe that you're a force for good, so thank you for spreading um confidence in in in the world and I think you're you're trying to really leave sort of sort of a dent in the universe and an impact, so. Thank you, my friend. I appreciate that a lot.
1:48:37
So to be continued everybody. I hope you enjoyed this. This was a blast for me.
1:48:43
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.
1:48:47
Let us know what you think.
1:48:49
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.
1:48:56
You can find the show notes for this episode and every other episode by going to fourhourworkweek all spelled out fourhourworkweek.
1:49:04
com/podcast and until next time, thank you for listening.
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