#130 You Have One Life - David Senra on finding his life's work, trial & error, the necessity of talking risks, mortality, balancing his entrepreneurial endeavours and family life and what can be learned from reading hundreds of biographies.

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today I am talking with David Senra. I am really excited to chat with you today, David. I've been listening and binge listening to a bunch of Founders Podcast, which you created. I think you started in 2018.

I love the podcast so much because in my opinion, it sort of is better than the original books because it's sort of through this modern lens of thinking about the internet, thinking about creativity, entrepreneurship, all that. Have enjoyed a bunch of the episodes, especially Ed Thorp, David Ogilvy, Henry Ford, a bunch of those. Definitely recommend people check it out. But excited to dive into your personal story too. And it's interesting, I think we both started some creative things in 2018 and have sort of oriented around the long term. So excited to dive into that.

Welcome to the podcast, David.

[02:05] David Senra: Thanks for having me and thanks for listening. I appreciate it. I put a lot of my life energy into making Founders, so it always feels good when people get value from it.

[02:11] Paul: I love it. What were some of the stories and scripts you grew up with around who you were supposed to be, what you were aiming towards as you thought about adulthood, becoming, uh, grown up, as we say.

[02:27] David Senra: I heard— so I was listening to a few of your episodes, and I especially like the one with David Perel, and I heard that question. I was like, man, if Paul asked me that, like, I don't have a good answer. So it's kind of weird where you feel like somebody is obsessed with history so much that, like, I'm dedicating, you know, my life's work to documenting the history of entrepreneurship, doesn't think about his childhood and his past too much. So there's all, you know, there's probably a lot of, like, psychological reasons there. What I would say is that I just read this fantastic book for the second time, and it's called The New New Thing: A Silicon Valley Story. And it's about this guy named Jim Clark, who's actually the first person in history to found 3 separate billion-dollar technology companies.

And he grew up, you know, his dad left. He grew up unbelievably poor in, like, a small rural town in Texas. And he has a line in his, in that biography. It's written by Michael Lewis, one of my favorite writers. And when I read that line, I was like, yeah, that's how I felt when I was a kid too. He said, I thought the world was shit and I was sitting in the middle of it.

So all I knew was that this, like, I did not like— I saw essentially, like, I didn't really have that many positive examples. I just saw a lot of negative examples. And so the way I would think about it is like, okay, we don't have a lot of money. Nobody in my family is educated. Like, I was the first person in my family to graduate high school, you know, to this day. Like, my parents never mentioned the word college to me once.

Like, they never, like, they never asked, are you gonna go to college? You should do this. They just did never even cross their mind. And so the, the big, I think the most important thing that happened was something I didn't even choose. And that's something that I learned from Jeff Bezos, who I've become a little obsessed with, like his thinking. So much that I've like read every book I can find about him.

I just read his shareholder letters for the third time. I just released an episode on that, which I think is anybody creating on the internet, you know, we're not, me and you are not trying to build businesses as large as Amazon, but I think there's a lot of lessons in there from somebody that really wrote the blueprint on how to run a successful business using the internet. But he said our passions don't choose— we don't choose our passions, our passions choose us. So the one main thing that sticks out from my childhood other than, you know, me saying, hey, I'm not gonna— I'm gonna be— I'm like, I'll do whatever I can to learn as much and make sure I can make enough money that I can like buy my independence and control my time, is that I was just obsessed with reading from the time I was Like, I can, I've never, I can't remember a time before I, like, before I learned how to read.

And once I learned how to read, I just read obsessively.

[04:56] Paul: What were some of the books you were drawn to as a kid? Were there ones you came back to over and over again?

[05:02] David Senra: They didn't even have to be books. Like, my mom passed away a few years ago from breast cancer rather at a young age. But one of the things that she talked about, because I don't have any, like, recollection from my childhood because You know, I don't— there's like 1 or 2 pictures of me. There's no video. You know, my dad got in some trouble, so he had to take a vacation for a little bit. So he wasn't like— I can't ask him.

And one of the things that my mom said is just like I would read the back of cereal boxes. I'd walk in any room. It doesn't matter what it is. If there's like a poster on the wall, anything, I would just go up to the wall and just like, I'd go into every room and just read whatever's there. It could be a book, it could be a newspaper, it could be whatever. It could be something hanging on the wall.

I remember I got into these, these like kids novels. I think they were called like Encyclopedia Brown or something like that. I think I read those books. And so another thing is like when I find something, I would like read them all. I do this now for the podcast, right? It's like if I, when you mentioned liking David Ogilvy, I found David Ogilvy because I was obsessed with Warren Buffett.

I read everything I could find about Warren Buffett, read all of his shareholder letters. And in Warren Buffett shareholder letters, He's like, David Ogilvy is a genius. I'm like, who the hell is David Ogilvy? And why is Warren Buffett, who I think is a genius, calling this guy a genius? So then what happened is I just read— I think I've read 5 books on David Ogilvy so far. I think I've made 5 or 6 podcasts on him.

So anyways, I read all the Encyclopedia Brown books. I read like Goosebumps. Do you remember Goosebumps?

[06:28] Paul: Yeah, it sounds like we had a similar reading docket as a kid. I was reading Goosebumps, Encyclopedia Brown.

[06:37] David Senra: Yeah, I think, I think it's that R.L. Stine, I think is. And he would just, it's like over and over and over again. I think they were like scary books too, if I remember. But just literally anything I could get my hands on. And to me, that was like, oh, you don't have anybody around you.

It's like my parents weren't educated. Like I just said, they never graduated high school. I think my dad has like an 8th grade education. Their parents, were, you know, dumb. I mean, there's no way I could say that. Like, there wasn't anybody in my extended family that I could look to.

It's like, oh, that's like somebody I can emulate. So therefore you have to turn to, you know, outside examples. And for me, I found those outside examples in books, and that just continues, you know, 30-something years later.

[07:22] Paul: So you did go to college. I think you went to UCF. Yeah. What was your mindset as you were approaching college? Were you pretty driven in high school? How were you thinking about life?

[07:36] David Senra: So yeah, I didn't— so this is another thing that's really interesting, right? Is I think the older I got, the more benefit that, like, I started having the ability to learn from the examples of other people. In fact, I'm just reading this book right now and I can't put it down. It's called like, Tell Me Where I'll Die So I Don't Go There. And it's just a collection of really, it's like, The reader is having a one-sided conversation with Charlie Munger and Warren Buffett. That's how the book is written.

And it's like 275 pages. And the guy named Peter Beveland who put the book together, he just took, you know, not only like do they have all the shareholder letters, all the speeches, think about how many speeches they gave, you know, year after year at their annual meeting. So the transcripts of that. So essentially he's like, hey, I got in the habit of writing memos to myself. And he wrote memos to himself as if he was having this imaginary conversation with Warren Buffett and Charlie Munger. 'Cause he liked that, right?

And he's like, oh, this is good. I should put this in a book. And I'm obsessed with this book. It's actually just jumped to the top of my queue. It's going to be the next episode of Founders. And so Warren and Charlie say over and over again that they never had— like, most people don't have the ability to learn from other people and they don't have the ability to learn from history.

And if you could master those two things, like, you're going to have an advantage over 90, you know, 95% of the people. And so I didn't know how much I read compared to other people. I also didn't know how much I worked compared to other people. I just thought, okay, I remember my dad sitting me down when I was 15. You know, you get your driver's license in the United States at 16. He's like, listen, I don't have any money for you.

You don't have to pay rent here, but if you want things, like I grew up in Florida, you could start working at 15 years old then. He's like, you gotta get a job. And once I got a job at a car wash, and once I got, I remember getting my first paycheck and I was like, holy shit, I made $100. It was like, you know, maybe $100. and you're on the hot Florida sun. Like, it's terrible.

Like, it's terrible work. But I was so excited. I was like, I made $100. How can I do this more? So I'm going to answer your question about how I went to college. But because essentially I started working full-time at 15, what I would do is even before I had a job, I realized it's like, man, there's some subjects I don't like.

Like, I remember geometry. I was like, man, geometry's like, that's— I don't know anything about that. That's kind of weird. And so what you could do is if you elected to go to summer school, most people went to summer school because they like failed and they had to make it up. But if you had good grades, right, or you weren't failing, at least you could go to summer school and in 6 weeks you can get the same credit that would take, you know, a full semester. So what I would do is I would just go to school year round electively, right?

And I would take as many classes as possible. So by the time I got to junior year in high school, and I'm, uh, younger, I'm like a year younger than my grade, so I graduated at high school at 17. But anyways, by the time I got to junior year, I only had, instead of having 6 classes, I had 4. And so they, my high school, I went to this this public high school, they had this thing called OJT called on-the-job training. And I realized that's my ticket to like make a ton of money where you could go to the first 4 classes and then you don't, you go to work and you earn credit for the other 2 classes. So I was working essentially like 35 to 40 hours and going to high school.

And so as a result, and then when you work at a car wash, I got promoted and everything else and I became a detailer and that was actually really instructive and accidental lesson that I learned that was really important in life is like, I, I've never worked for like a set salary, right? Where it's like, if you detail, it's like you sell the, if you sell the actual service, you get a commission from that. If you do the service, you commission from that, you get hourly rate, you get tips. And so I was making, you know, $400 or $500 a week in high school. This is back in like the late '90s, early 2000s.

[11:11] Paul: That's great.

[11:11] David Senra: So, so much so that I could buy like my own brand new car, like I paid for myself. So anyways, when high school, when college came, to answer your question, is it's like, okay, I looked around I had no positive role models. I was like, well, I— who are the rich people, right? There's no such thing as like entrepreneurship industry like there is now. And so I'd watch TV shows when I was a kid. I'm like, oh, all the rich people.

Like, there's two ways to get rich in the United States. It's like— and I'm talking about young kid— I was like, you'd be a doctor or an attorney, right? All the— like, the TV shows, like, oh, the doctor's rich, the attorney's rich, or a judge. Because I like The Fresh Prince of Bel-Air. And I was like, dude, I could be like, like Philip Banks.

[11:48] Paul: That's wild. Have, have you come across Rob Henderson's writing on this? Because he came to similar— he has this essay where he talks about how he learned about education and success from The Fresh Prince of Bel-Air. You guys should definitely have a convo about this at some point.

[12:03] David Senra: I heard him talk about it, I think, on Jim O'Shaughnessy's podcast Infinite Loops with my friend Trung Phan. Trung is actually one that put me on to Rob Henderson. That's my first, like, exposure to him. but anyway, so I, I had this idea. I was like, okay, uh, like I'm only gonna go to college, um, just so I can go to law school, right? I was interested in business.

I had already started a business part-time by detailing my own, like that was my first business, right? Realizing, hey, what I'm doing here instead of it, you know, let's say you do something that costs $150, $200, I might make like $50 of that and the rest goes to the business. Like I'll just do this on myself and get all the money, right? And so what I would do is, um, The original idea was like, okay, I'm going to just go to college. I have to work full-time. Like, so it's same situation I was doing high school.

I was working and building businesses back then. So like, I look back, I just had this conversation. Who was I talking to? I can't remember who I was talking to about this, but I was like, man, I think like the 21-year-old version of me would think I'm so soft, like, like the amount, because I just can't believe what my schedule is like. And I didn't know any better. I just really had a goal and tried to get there as fast as possible.

So instead of taking 12 credit hours, 2 semesters, I'd take 15 credit hours, 3 semesters in college and work full time. So the time I woke up at 7 in the morning and I was busy either working or going to school from 7 in the morning till 10 at night. And I did that for a while. That is not sustainable. If you look at pictures of me during that time, I just looked like shit. I wasn't getting any sun.

I had gained the freshman 15. My eyes were sunk in my head, but I had no safety net. So I was just so driven to not be a loser. And then by that time I was like, being an attorney is a terrible idea. Like, I'm obsessed with entrepreneurship. I'm just going to do that.

[13:54] Paul: I'm so grateful you decided not to go to law school. I do wonder how many people are in law school that could channel genius through creative work.

[14:03] David Senra: I know a lot of time there. I know a lot of attorneys that are friends of mine. They all hate it.

[14:08] Paul: Yeah. So what, what year did you graduate and what did you do right after college?

[14:15] David Senra: So let's see what year I graduated high school in 2002, graduated college in, I think, 2006. So I was working. So this is something that I talk about on the podcast all the time. In fact, there's a line I say on the podcast that's always thrown back to me because you never know what's going to resonate when you put it out there. But it's so interesting how Regardless of, you know, what I like to look for is like themes across people where they didn't know each other. Maybe they were alive at different points in history.

They worked in different industries, in many cases different parts of the world. But you see a lot of things reappear. And one thing that, that pops out is like the importance of doing the very best job with the opportunities right in front of you. Because by doing the best job with the job that's right in front of you, it's going to unlock an opportunity in the future that you can't possibly like predict. So you think of like Andrew Carnegie, and I have a situation like this where like Andrew Carnegie starts out, you know, his family's poor immigrants from Scotland. He couldn't go to school after I think he was like 11 or 12 years old.

Starts working in a factory at 13, does the very best job at that, gets promoted at that factory. Right. Then does a very good job with that. He's like 14, 15, gets to go from working in a factory, you know, throwing up, you know, the smells. And this is like, you know, like in the Industrial Revolution. To like, the smells are so bad.

He's got this great line in his autobiography where he's just like, well, they put me in, in part where I had to like soak things in fats of oil and the smell was so bad that I would throw up. He's like, no big deal. That just means I have more room for dinner, right? So eventually he gets promoted out to work in an office and he's just like running errands and stuff. But in the office is a major technological revolution of his day, which is the telegraph. So in his spare time, he's doing the best job as a messenger, but he's also picking up telegraph skills.

That telegraph skills has him to be hired by, uh, an executive in the railroad company, another major technology of his day. Then he learns railroads. And so essentially you could trace Andrew Carnegie's career. He winds up building, uh, the Carnegie Steel Company, which is the first, gets recapitalized, it ends up becoming the first billion-dollar company in the world that ever existed. And that all starts from him doing a really good job when he was 13. So I'm working at the car wash.

Um, I think I was a senior in high school. Might have been right before my— the summer before I went to college. I can't remember. But my brother's friend Jake would come in and I'd clean his car for him. And I had known Jake forever. Like, you know, same thing.

It's like not a lot of education. He winds up like his family— like he winds up being adopted. Last time I had seen him, he was like selling things door to door, right? Then he comes in and he's like driving like a Mustang. I'm like, oh, this is like, last time I saw you were in like a Cavalier. This is interesting.

Then he comes in and he's driving like a 3 Series BMW. I was like, oh, okay. This is all happening over, let's say 9 months or 12 months, something like that. Then he comes in with an M3 and then he comes in with a Lamborghini. I'm like, dude, what are you, Jake, what the hell are you doing? Like, what are you doing?

And so this is in Orlando, Florida. And he had started a company that there's not, at that time, there wasn't many industries in Orlando. Tourism, obviously Disney, and like real estate. I mean, there's just not that many industries there. And so he had started selling vacations, like timeshare vacations. Timeshares are like, I don't even know how you describe it.

Like you buy partial ownership in a vacation property. Turns out very lucrative. Maybe not a good deal for the customers, but really lucrative for the developer and the salespeople. And so he's like, hey, come work with me. And so I got a job. like, you know, no interview.

I just knew the guy and I was selling vacations over the phone. Um, and then I did that for a while and, you know, on commission you can make a lot of money. You learn sales. That's a valuable thing to do. But then he's like, hey, I need your help. Um, because like he, his back office, he's like this, this, he was probably like 25 at the time.

So anyways, he's like, hey, I need your help, uh, to organize like think of like everything you need, like logistics, fulfillment, processing, database, building databases. There's no cloud computing at this point. So essentially, like, I started doing this for him. He introduced me to other, a bunch of other people. I started building these things out for other people, getting partial ownerships in businesses and essentially just like taking what I learned here and expanding it. So that's what I was doing throughout college, right?

And I did that for like 5 or 6 years. You make, I made a good amount of money, enough to, I got to the point where, um, between all the different things I was working on, all I had, like, maybe I own like 16% of one business and 50% of another, but, and then managing a bunch of other people. I didn't realize how important it is to design a business that's in line with your natural drift, which is what Charlie Munger says. 'Cause I'm an introvert and I was managing way too many people. And that just is not something that I learned through trial and error. This is stuff I don't want to do.

So long story short, or else it's going to go for— the story's going to go on for hours. It's like I saved up a lot of money. I've always been that way because I was, you know, I had no safety net and I got to the point where I was like, I don't want to do this anymore. I want to actually enjoy what I'm doing, not do things just for money. And so I saved up enough money where it's like I have, you know, a large buffer. Let's say I have, 8 to 10 years where I could go not making any money, um, till I'm completely broke again.

And so then I moved back down to South Florida, which is where I grew up, and just started looking for other businesses that I actually truly enjoyed and something that was way more in line. One, I wanted something more tech, like tech, tech, uh, that was heavily, uh, more heavily, uh, utilized technology, and one where I didn't have to manage a ton of people.

[20:00] Paul: And what were some of the— what were some of the experiments there? I imagine there were other experiments before you landed on going all in on podcasting.

[20:10] David Senra: Oh, yeah. Like, that's the— there's this great guy that builds in public, this great entrepreneur that's really popular on Twitter. His name's Peter Lovells.

[20:19] Paul: Yeah, he's—

[20:20] David Senra: are you familiar with it? Yeah.

[20:21] Paul: And I used his Nomad List to kind of guide where to live for multiple years.

[20:27] David Senra: Yeah. And what I love about him, he's like, yeah, like Nomad List is very successful. His job board's successful. He's got like the new, the new AI avatar thing and all these other projects. But he randomly posts every few months. He's like, yeah, you guys see these businesses that may make millions of dollars now, but you didn't see the 80 or 50 other projects.

And that is— I've never read a biography, you know, I study history's greatest entrepreneurs for a living. I never read a biography where somebody's like, hey, I have this idea, I started it, everything went well, end of my life. That, that doesn't exist. It's always, hey, I want to do something, I can't really, I don't know, I don't have the means to, or I don't know how the knowledge to, and then just have to constantly learn along the way and then keep persevering through the inevitable, like, ups and downs. So, um, about, like, I would say, like, a year or two earlier in this, I had The first thing that got me interested in technology was there's this founder of this company that was really popular in the mid to late 2000s called Digg, and his name is Kevin Rose. And he had this show called Digg Nation, which is—

[21:30] Paul: I used to watch that.

[21:32] David Senra: Yeah. Like, would you— it's not really a podcast. I don't even know. It's like an internet show. Like, I don't know how to describe— I guess today it would be considered like a podcast, right? Because like the video and audio is kind of like melded together.

Me and you were talking about this before we started recording. And so I was just like, he opened my mind, my eyes up to all these, like, just interesting ways to build businesses and using obviously internet and software. And then like a year or two earlier in that, maybe 3 years earlier in that when I was in college, I read Tim Ferriss' 4-Hour Workweek. And so I was just obsessed with this idea of like, hey, having a small but really effective and really profitable business. And utilizing, like having, like approaching the building of a business from completely different— I just went to business school, right? Like I had a degree in, in business management.

I was in the pilot entrepreneurship program, literally the first year, the first class I was in that. Um, and yet these people were talking about building businesses in such a unique and interesting way. And so that's what I started doing. So I started trying to build like different things, uh, around software. Like we tried to build a CRM because we started reading about the Basecamp guys. We're like, wow, like, could you imagine that?

And so again, this is, I guess, a main theme that you and I should touch on is Stephen King puts this the best way, is that imitation precedes creation. And so when people, like, when you want to do something, what's going to happen is you're going to study people that do it. You're going to start imitating them. That's the first step in learning. As you get further down the path, you're going to add your own unique ideas and unique twists to what you had previously imitated. And the combination of that is actually something unique, right?

And that's, that's my own journey with founders. Um, so I was build— we were trying to build different software programs. I was really into, um, uh, this time, and this is another thing I, I made a mistake of, of chasing trends. Let's say 2015, 2016, uh, chatbots were really popular. So I had this idea of like, um, uh, of automating personal finance through this chatbot. Where it would essentially, like, there's a bunch of different products like Wealthfront, Digit, this is years ago, I'm sorry, so I'm forgetting some of the names where essentially like you have a chatbot that, that will walk through, walk people through how to automate their personal finances and you're utilizing new, like you're doing customer acquisition for a lot of fintech companies, right?

And then I had, I designed this, this thing, this is what I was working on right when I decided to go all in on On Founders, I started Founders in 2016, but I was, didn't think it was gonna be like a real thing. I was just obsessed with the podcasts. And so I started making them and I wasn't making any money on it, but, uh, I'd release 'em and I'd get like weird messages. Like there's an intensity around Founders that is very bizarre for people to understand. You just said like people discover it and they don't just listen to one or two. They like listen to a ton.

And even at the very beginning, like I remember I got a review, one of the first reviews, it was like, this guy's like, hey, I don't ever leave reviews, pay attention to this. And it was like 2,000 words. And I was like, what the hell is going on here? So I was doing it for a while, just intermittently, no consistent upload schedule, just like whenever I found it, I'd go months without making an episode. And so I had made this thing where, um, at the time the I was building chatbots on Twilio and Twilio was still a private company. Can't believe I didn't invest in that company.

That was a big mistake. Um, I even went to TwilioCon in like 2012. So like I was there early and just never thought, hey, you should probably buy the stock when it IPOs, you idiot. Um, anyways, they had the, I saw this thing where they're like, the FTC has this bounty where it's like, if you can help stop robocalls, they do like a $50,000 award or whatever. And I started reading about like this guy named, the guy that won the thing called Nomo Romo or Nomo Robo or something like that. But he was just like amazing business just off of this like one specific problem he's trying to solve.

So I figured out a way to, uh, essentially identify the true origination points of verbal calls using the payment network. And that was like a, one of these businesses, you know, high technology leverage, not a lot of people profitable, but I didn't give a shit about it. It was just like, you know, I knew I was in trouble because when I wasn't working, I wasn't thinking about it. Never popped into my mind. And that's a bad spot for an entrepreneur to be in, in my opinion. Um, and so that's when I was like, man, I'm so sick of doing things just because they make money.

Yeah, they're, they might be like clever hacks or they might be, they're interesting, like maybe at the beginning, but there's no longevity. And I just had this instinctual idea where it's just like, I want to find my life's work. I want to find something that when I find it, my exit strategy is death, right? Like, I want to do Founders till I'm dead. And I was like, I was like, I like this thing. I just did a Paul Graham essay.

I spent a few weeks reading all of Paul Graham's essays, which, if you're in this position, I think is a really good use of your time to read them. And on episode 275 of Founders, I talk about this like I was— I remember it like it was yesterday. Um, I had already started the podcast. This is in 2008. You could see, 2018, you could see when this was because I start uploading Founders and I never stop on a weekly basis. So that's literally happened the week before.

So I'm, I'm, uh, I'm up in bed late at night. I think my wife's already sleeping and I'm reading Paul Graham's essay, How to Do What You Love. And, and that's really a lot of his essays. I feel is like that message, like it's like, how are you gonna find something that you love to do?

[27:09] Paul: Yeah.

[27:11] David Senra: And I just snapped and I was like, you know what? Like, I'm going to take a big risk here. You know, I have a wife and a kid, my daughter right now. I have two kids. At that time I had one. I was like, I have a wife and a daughter.

I'm going to close, stop doing every other project besides the podcast. And I know right now that I love this so much that I'm willing to do it until I go through my last dollar that I have in my bank account. And my belief is that If I'm 100% focused on it and I give everything to it, I'll figure out a way for it to make money. Right? And worst case scenario, I get to the point where I go down to my last dollar, uh, I'll get a job and I'll just do this shit at night. Like, I'm just not gonna quit.

And that, that realization happened in 2018. It took till 2020 for it to pay my bills. And then now in the last, you know, 133 days, 135 days when I made it a public podcast, not a subscription-based podcast. And then when I partnered up with Patrick O'Shaughnessy of Invest Like the Best and his podcast network, you know, the growth is like 50x.

[28:19] Paul: I love this so much. It's, it's also interesting. I think I read that essay around the same time in 2018. I quit my job in 2017. I was freelancing as a consultant, but I didn't love it. And I was so afraid of creating another job for myself that I just sort of secretly stopped working and just started writing.

And I came up with this mantra for myself, write most days. And I can see now that directly led to my book. Um, and I sort of had this hunch that things would be okay, but I couldn't prove it. Right. And you sound like a crazy person if you start telling people you're going to make it when you've barely done anything and you're just starting. What, what was the story you were telling other people at the beginning then?

Like, did— was your wife on board in terms of supporting you and kind of seeing it?

[29:16] David Senra: So what was the story I was telling other people? I think I have a benefit where I don't think about other people, and I don't mean my wife, obviously. I think of my wife and kids, but I just believe so much in like what I'm doing for founders. I heard what you and David Perrot were talking about and he quoted something that I've talked about a bunch on the podcast and it's about what, what, what Steve Jobs said where he's like, listen, I want every person in the world to have an Apple device to be able to do, to be able to do that. We not only have to make great products and a great company, we had to be a great marketing company, right? And so you wouldn't believe how much time Steve Jobs spent on marketing at the beginning when he's returning around Apple.

He, every Wednesday they'd have this like long 3-hour-long meeting. There was not a billboard in Missouri that would go out without Steve Jobs personally approving it. So he was showing with his actions, with his time, how he spent his time, what was important to him. And so I felt so passionate about what I was doing and the fact that I thought it was so valuable that I thought if you, something was wrong with you, if you wouldn't like founders. Like I still feel that today. Jay-Z has a great line in one of his songs.

He is like, oh, it says a lot about you if you're not feeling us. He's talking about like his music. Like if you don't like it, that's, that's indictment on you. And so my wife, no, she's like, Stephen King talks about this in his autobiography where he's just like, I had no idea. I'd never read Stephen King's books before I read his autobiography, but I didn't know how much he struggled. He was like, his daughter was sick.

He was so poor, he couldn't afford medicine for his daughter. Yeah. Couldn't afford medicine for his daughter. Living in a trailer. Couldn't afford a phone. Like, phone service.

Could not afford that. you know, just having these, like, visions that, oh my God, I'm going to be stuck. I think he was like a teacher. I haven't read the book in a while, but what he talks about is like, when you see an author write a book and they thank their spouse at the beginning of the book, he's like, I know exactly what that means because he talks about the love, like the unconditional support he got from his wife. And, you know, she was rewarded for it. Now he sold, what, 300 million books or whatever, what kind of stuff.

So that's the relationship I've always had. Like, my wife's like, she just, she, She's probably the second— she's the person that believes the second— the person that believes the most about me, like behind me, you know, I just thought like, oh no, I like if I put everything into this, like I will make this work. And so, yeah, she was like stressed, like, you know, she knew like my savings was going dwindling, you know, but she just thought that it was good and she thought that, you know, once people discovered that they would like it.

[31:55] Paul: That's beautiful. Yeah, I'm equally as lucky. My wife, Angie, she gave me a wedding gift with a quote about The Pathless Path on it. And that basically became the title of my book. And it seems so obvious now, but like, the soul of the book is her support for me and belief in me, because at the beginning, like, You only need a couple people to believe in you. It sounds like that review, that 2,000-word review, I had a couple things like that happen to me when I was like, oh, people, I found some of the others.

Um, I wanted to ask you about the paywall. So you, you talk a lot about it now as like, oh, that was a mistake. I should have been public. But was there a certain element that kind of wanted to like protect your creative? Work and keep it smaller on purpose?

[32:54] David Senra: No, no.

[32:56] Paul: So that was just a mistake. Not at all.

[32:58] David Senra: It was, it was a giant mistake because, um, well, first of all, I had like, I start the podcast, right? And first of all, it's not an interview podcast, so I can't grow through like, if you can like think about that, uh, like you interview David Perel, he tweets about it, he's got 200,000 something, you know, maybe even more, uh, followers on Twitter. A percentage of the people that listen are now going to be converted to fans of yours, right? I don't have guests. I'm an introvert.

[33:23] Paul: Henry Ford's not retweeting.

[33:26] David Senra: No, Henry Ford's not retweeting. Most of the people I cover are dead, for God's sake. But I'm also introverted. I didn't have any social media presence. I just had this idea, like, I'm really obsessed with podcasts. I was obsessed with audio, talk radio before there's anything such like— when I graduated college, podcasting didn't exist.

We could talk about this later. I just, I just talked, I gave a career day talk at my daughter's school and I don't think, I don't think the teachers liked it very much because I essentially like, I show up there. Let me just, we'll go back to, don't let me forget.

[33:55] Paul: Yeah, I want to hear this.

[33:57] David Senra: This is funny. And this is also just like, you know, one of my favorite founders is Yvon Chouinard, founder of Patagonia. And he says the greatest thing, he's like, if you understand the entrepreneur, study the juvenile delinquent. The juvenile delinquent is saying with his actions, this sucks, I'm going to go do my own thing. And so the one thing I love about hanging out with so many founders is like they don't really pay attention to rules too much. You know, it's like our social, like, you shouldn't say that or you shouldn't do that.

You know, they tend to deviate from that. And I find those people interesting. And so I show up to Career Day. I think this is last year. So my daughter was in 4th grade. How old is she?

She'd be 9 now. She's 10. But so she was 9 when this happened. And she asked me, she goes, Dad, you have an interesting job. Will you come and and give a speech or talk to critics? Yeah, of course.

And so I show up and first of all, the teacher's like, okay, we didn't get an email from you. Like, did you bring a thumb drive? I'm like, for what? And they're like, oh, for your PowerPoint. Like, don't you have a PowerPoint presentation for the kids? I go, I would never subject a 9-year-old to that.

I didn't know I was the only person. I didn't know that I was supposed to have a PowerPoint presentation. And so if you listen to my podcast, it's not like I'm not reading from script. It's like, this is the stuff that's in my mind. So it comes out and I was like, oh no, I would never make Like, I remember being 9 or 10. You're going to sit through— what are you— so I go, no, no, I was like, I'm just going to talk to them directly.

So I essentially— they give you 30 minutes. I use like 2. And I was like, listen, the biggest thing that's important is like most likely the job that you're doing hasn't been invented yet. The biggest thing is like focus on like learn how to learn, follow your natural interests. Do not listen to your teachers. Do not listen to your parents about what you should be interested in.

The only person that could decide your path in life is you. And so use all your time, read as much as possible, listen to podcasts, you, you use YouTube, whatever. And so that was like the synopsis of my talk. And then I go, okay, for the rest of the time, ask me questions. What do you wanna talk about? And they loved it.

She came home and she's like, uh, she's like, uh, all my friends thought your talk was the best. I go, well, who came after me? And it was like, bless her heart, but it was like, uh, one of the moms was like a, uh, a real estate attorney and she gave like a PowerPoint presentation. Oh, God, they're 9. They're 9. Yeah, they're like, come on.

So yeah, that's, that's— I don't know how, why that— what did you ask before that that made me think of protecting your creative? Oh, okay. So I had, so I had no idea how to make money as a podcast back then. I contacted a couple like—

[36:32] Paul: I don't think most people did either, by the way.

[36:34] David Senra: So yeah, like the ones that were doing it were all ad-based. And, but when you, when you contact now, like I think Spotify is trying to fix this, AdSwizz, there's a bunch of other ways to essentially like what there's companies that what YouTube did for video advertising is they're trying to do for, for, for podcasts, right? Where it's like, you know, if you only have 1,000 subscribers, you could still access the network on YouTube. That didn't exist back then. And so when you would contact them, they're like, yeah, yeah, uh, we'll sell ads for your show. You would need like at least like I think 50,000 downloads an episode or something like that.

And I was like, oh my God, like how the— like, I'll never get there. Like, that's, that's such a large number back then, you know? And so I was like, okay, well, I got to figure out other ways to make money. Like, how could I do this? And so I actually got the idea for the business model from a socialist podcast. And this socialist podcast—

[37:24] Paul: ideas are ideas—

[37:25] David Senra: that still exists to this day. It's called Chapo Trap House. And they, they didn't have any ads. And what they would do is like they would make one episode, they'd give every other episode away for free. And if you wanna listen to every episode, you'd pay like $5 a month. And they use Patreon and Patreon's API is public.

So you can go to this, to this day, you can go to this, this website called Graftreon. So it's instead of Patreon, it's Graftreon. And you could see all the, like all the publicly available data from Patreon's API, like how big some of these subscription businesses can get. And I think at the time Chapo Trap House had like 25, let's say they had 20,000 subscribers.

[38:05] Paul: That's $100,000 a month. I just pulled it up. They have 38,000 now.

[38:09] David Senra: Now they have—

[38:09] Paul: Yeah. $164,000 a month.

[38:11] David Senra: Yes, exactly. So, um, what, what's interesting about that, so for the longest time when I was building a subscription podcast, my, when you open a new tab, it would open to Graphtron. And so what was interesting is like you could see that the market was expanding. So at the time, the most, the highest number of, um, subscribers for any podcast was like 20,000. Then it got to 25, then it got to 35, and now it's gotten up to like 47, 48. Like, it just— the market keeps getting bigger and bigger and bigger.

Um, and so I was like, okay, well, I'm just gonna copy that, uh, like that model. And I think I would try— I experimented with a bunch of different pricing models, whatever the case is, and then I settled on, for the long term, I think it was like let's, let's call it $100 a year, you know? And that worked to the point where it, what I eventually went to, I copied what Sam Harris was doing where it's like you can listen to the first like half or the first like 30 minutes and then if you want to pay, if you wanna listen to the whole one, you can subscribe. That's actually an idea in the book Masters of Doom, which is one of my favorite books about the, the business model behind the video game Doom, which is where they would give away the first 15 levels. And then if you want the next 30, you chart, you would pay, um, for them.

There's a story in that book that I think your audience will find interesting where, um, this is in the '90s, it's 6, the entire company is 6 dudes living in a house together eating pizza. Their only expenses is rent in the house that serves as their office, the copious amounts of pizza that they're eating and their computers. And once they released Doom in this model, they were, uh, their company was making $100,000. It, the, the company was making, uh, bringing in $100,000 every day. At like, you know, 90% margins or whatever. So imagine, and then it went even bigger and bigger and they raised money and all this other stuff.

Or, uh, I don't know if I think they raised money, but anyways, um, so that idea was working cuz it's not a new idea, it's just an idea approach, uh, applied to podcasting. People did it with shareware, with business applications in the '80s. They did video games in the '90s. It's like, oh, this is a main theme. Like, history doesn't repeat, human nature does. And so if you have a business model like that, that works, that, that's working for other forms of media or entertainment or even educational entertainment, it'd probably work for you.

I got, I got to the point where it was like a very respectable business. Nothing wrong with that business, but I had met so many people where they're like, like I started to talk to listeners and a lot of these people were very impressive listeners. And they're like, you're doing this wrong. Um, your podcast should be more well-known. If you don't put a paywall on it, first of all, people will spend a lot of money in ads because your audience is very valuable, but it'll help more people because like there's, you know, people— I've had stories of people literally, um, there's a guy homeless living in a car in, uh, I can't remember if this was Nigeria or Kenya, but anyways, I got this message. He's like, David, I used to listen to all your free episodes.

Uh, every day while I live in my car. Eventually he founds a company, raises money, founds a company. He emails me, he's like, hey, now I can afford the subscription. Right? And it's just like, whoa, what the hell is happening here? I obviously told him, I was like, here, take your money back.

You'll get it for free. Like, that's ridiculous. Like, that's a, that's an inspiring story to me. Um, so anyways, there's a few integral, like really important people along the way that just pull me to the side and they're like, reconsider what you're doing. Make your podcast free, just make it ad-based. I promise you it'll work out.

So like, uh, my friends David and Ben from the Acquired podcast, right? Uh, one of the most successful technology and business, uh, podcasts. This is months, months before I, I did this deal with Patrick from Invest Like the Best. Yeah. Um, and they're like, hey, like they, they were very, like, they were very kind where they're like, let's get on Zoom. They went through, they showed me everything.

They're like, this is how many downloads we have. And they showed me something that's really important. They're like, this is our public downloads. They also had a private feed. They're like, listen, for every one person that'll pay for a podcast, there's 100 that would listen if you just made it free. They showed me their downloads.

They showed me this is how much we sell. We, this is who, like who our advertisers are. This is how much money we make in ads. All this stuff. They're like, just do exactly what you're doing. but make it open.

Like you have a great, like your audience is very valuable. You have a great product. Just do this. Um, so, uh, and interrupt whenever you want 'cause I can take the story a number of different ways. And then I got another, there's just one other person that was, that played a role too. And, um, so, you know, Human Lab Podcast, obviously one of the biggest podcasts in the world.

So the co-founder of the Human Lab Podcast is this guy named Rob, and I get this crazy DM from him. In fact, I'm going to visit him next week. Um, and he's like, listen, I've never DM'd another podcaster in my life. He's like, I found your podcast. I'm obsessed with it. It's really good.

I'd love to talk to you about ways to grow your podcast. Like I could just essentially, because they got to, you know, they have millions of people in their audience now. Right. And so they're like, essentially like, hey, I just, I don't do this. I'd love to talk to you. The first time we talked, we talked for like 2 hours.

And same, same story. It was just like, it's really valuable. And he told me something that really like, like hit me, like made me like, I was like, damn, I don't want to be described this way. He's on the phone with his friend. So the good, the thing about entrepreneurs and founders is all their friends are going to be entrepreneurs and founders for the main part. It's like, we're so weird and unique and well, it's because we're crazy.

[43:46] Paul: We need to hang out with fellow, um, Unusual Minds, I think, as you put it, Unusual Brains. I think that's what you said to Jim O'Shaughnessy. I love that.

[43:55] David Senra: Yeah. Um, and so he's on the phone with his friend that's also a founder, and his friend is telling him about all this, all these things that Jeff Bezos said. And Rob's like, how do you know this? And the guy's like, oh, you gotta listen to Founders, but the guy makes it really hard to share his stuff. So let me buy you a gift subscription. So he, Rob, so this guy buys Rob a gift subscription.

Founders is still private at this point. Rob starts listening. Same thing when people discover it, they, they hit one and they just go like, they go down this huge rabbit hole. You know, it's just like almost 300 episodes now. And every single episode is about somebody that was so successful, so good at their job that somebody wrote a book about them. That's like weird, right?

Very bizarre. Um, and so Rob, within the first week, he buys like 6 or 7 other gift subscriptions. So, I'm like, wait a minute, this guy hears about my podcast word of mouth, listens, then spends $600 or $700 on a podcast in a week. And that's like very, there's some people that have literally spent thousands of dollars buying gift subscriptions. That means they bought 20, 30, you know, like it's crazy. Um, and so anyways, Rob's like, your best weapon is your best, like, tool it is in this like fight for attention, right?

We, we live in the age of infinite, uh, like there's infinite things that you could pay attention to. You're asking people to pay attention to you. You, they should pay attention to your podcast because he felt, he felt it was valuable. But he's like, you're, you put your best asset behind a, you hide it. Like you're going into battle for, with like your arms tied behind your back. Um, and so at that point, and I'll wrap up the story real quick, 'Cause I, again, I do a monologue, so I could literally talk for hours and I could talk for hours about the business of podcasting 'cause I'm obsessed with that.

I think about it every day. So I had previously, there's this guy named Sam Hinkie. Sam Hinkie is the former general manager of 76ers. That's where he became famous. After he left the 76ers, he moved to Silicon Valley. He's now an investor.

He found my podcast unbelievably early. You know, I think I only had like, I don't know, 1,500, 2,000 subscribers, something like that. I don't know, something like that. and he's like, sent me a message. He's like, I love what you're doing. Like, I'd love, you know, I'd love to talk to you, whatever.

Months, months go by, didn't hear from him again. Then I hear from him again. He's like, I've listened to you speak for 100 hours. You're unusual. I want to talk to you. And now we've become good friends.

Now we become really good friends. But anyway, Sam is relentless because his network is ridiculous. Um, and so he hooked, like, he, he essentially like spread my podcast to so many people. Uh, like Blake Robbins, the investor at Benchmark now. Uh, he's the one that put me in touch with Patrick from Invest Like the Best. And so this is all occurring when Founders is still relatively little, like it's really unknown.

[46:41] Paul: Yeah.

[46:42] David Senra: And then, um, and I'm in, um, I'm traveling at the time. I'm in California. Um, I was actually, I flew to California to meet a really impressive founder who was also a big fan of Founders. His name is Alexis Rivas. Alexis Rivas. He found this company.

He founded this company called Cover, which is essentially like building houses in a factory. This dude's— he got an alien brain. Like, he's a very impressive person. And he had sent me a message saying, hey, I love your, love your podcast. I'm having this event at my company, you know, would you come out? And I live in Miami and he's in LA.

He was so impressive. I just jumped on a plane. I was like, I went to LA for 48 hours just to meet him. And while I'm there, I like, I'm in the backseat of my car or my friend's car who, one of my oldest friends lived in California, so I met up with him when I wasn't hanging out with Alexis. And I'm like, why is my Twitter going so crazy? Like, what the fuck is happening?

And it turned out that I had been a fan of Invest Like the Best and Patrick O'Shaughnessy for, yeah, I've listened to his podcast forever. I think he's an excellent interviewer. And it turns out Patrick sends this tweet and he's just like, I never find new podcasts to listen to. Uh, David Senra's Founders Podcast is excellent. Listen to this episode. It was episode 217 of Estate Lawter.

I was like, what the fuck? What is happening in my life right now? Like, this is so weird. Like, I, dude, I've heard your voice. Like, why are you talking about me? That one tweet got me hundreds of new subscribers paid.

Patrick's got like a, you know, if, if Patrick says this is valuable, Yeah, it's valuable. So I screenshot that and I sent it to Sam. I'm hoping I remember this correctly because I knew Sam and Patrick were friends. Sam immediately puts me in a group chat. He's like, you two should know each other, right? And so me and Patrick wind up just talking again.

He's obsessed with entrepreneurship. He's, he's, he's an investor that thinks like a founder. He reads all the time. He's very curious. We just have the same— we love podcasts. We have the same, like, you know, interest.

So we just— there's no business relationship. We're just like two podcasters that are interested in the same stuff. We start We're talking and, you know, we develop a friendship and just like, just to talk, you know, because Patrick likes collecting, he calls them maniacs. Like he just, he just invested in, made a big investment in this company called Tegus. And he introduced me to the founder of Tegus, this guy named Michael Elnick. Michael Elnick is a maniac.

I don't like, I wouldn't bet against that guy. He's just completely maniacally obsessed with building his company. And so anyways, we wound up being friends. And Patrick had told me this, he said this on this episode I did with Patrick in August of this year. And he's like, dude, he's like, I can't tell you how many people told me to listen to Founders. And he's like, what?

And he's like, there'd be entrepreneurs, there'd be other investors, people he respects. These are high quality people. And they're like, okay, listen to this, this Founders. He's like, oh, okay, yeah, that's fine. The first time he's like, okay. Second time he's like, yeah, okay.

He's like, by the fifth time, he's like, I had no choice. Like, why are all these people in my network saying, listen to this show? And he starts to listen to it, wind up becoming, uh, like a fan of the show. I think on the episode I had talked to, when we did together. I think by that point he had listened to like 30 or 40 episodes. And so anyways, I had all these conversations, these conversations with guys from Huberman Lab, the guys from Acquired, fans of the show.

And I'm like, I'm doing this wrong. I need to admit my mistake.

[50:08] Paul: This was last year, 2021.

[50:10] David Senra: No, this was like July of this year.

[50:15] Paul: Wow. And so I think this ties into something you say, which is that like, I loved this so much because it perfectly captured how I feel too. The type of people that understand the scale of the internet and the type that knows he doesn't understand the scale of the internet.

[50:30] David Senra: There's, there's two types of people in the world, people that don't understand the scale of the internet and people that know they don't understand the scale of the internet. In other words, no one understands the scale of the internet.

[50:40] Paul: No one, like, I know I don't know, like the stuff that like this past year, this past, I'll give you an example and then I'll let you go. But, um, the, I basically wrote for free about work for several years. And when I launched my book last year, I had 5,000 email subscribers. So a year later, I still have less than 10,000 email subscribers, but I've sold 10,000 books.

[51:04] David Senra: I saw that. That's incredible. But it's incredible.

[51:08] Paul: And it sort of breaks my mind because I'm like, that's more people than actually follow me. Right. So, and I have no idea what's like coming next. I'm in the second category. I still don't understand how the internet works, but I think a similar thing is happening to you now.

[51:25] David Senra: It's you, you follow and we, uh, like we can talk about this too, which I think is really important. Um, like I'm just naturally interested and obsessed with this. And I just trusted that I'm not unique. Like, do you ever read the writing of Tim Urban on Wait But Why?

[51:40] Paul: Of course. Yeah.

[51:41] David Senra: Okay. So he— I love what he said. He's like, when I sit down to write, he goes, I just picture there's 100,000 Timms. And that's the biggest thing. It's just like, yes, like you can love your life and feel you're special. Like there's, there's been Davids and Pauls that are alive today.

They're just like me and you that our same personality type has existed since, since humans have existed, right? They will exist long after me and you are gone. And so my idea is like, the reason that I say the most interesting people are the most interested, if you literally pursue things you're genuine into. Naval says this, the best way to pick a career, pursue your genuine intellectual interest, not a trend, right? I just love to read. I love entrepreneurship.

I like reading biographies and I like podcasts. Like those are all my interests. Just so happens Founders literally just sits at the, the intersection of all those. And so my idea was like, if I just do this, and put this out there, I, there's other people that like the same stuff I like. And if no one else, and there's also an issue of like product differentiation, like you don't want to just cop, if like, if there's somebody else doing already what you're doing, you've gotta figure out a way to put like your own spin on it. Right.

Um, and so if I just trusted that, if I do that, like I know there's a bunch of other people, like how I, my, my idea was like, okay, like how many people, when I thought about even some subscriptions, I was like, well, how many people are interested in entrepreneurship? Connected to the internet and speak English. And even if you just look at business owners across the world that fit that, it's like, you know, hundreds of millions of people, hundreds of millions. I go, I just need to get tens of thousands and I have a wonderful business. And that was a paid subscriber. Now, you know, there's way more people that listen to it because it's free and it's like, just keeps growing.

So, uh, going back to just circling this around, like how we got to this point and like we can continue about like some ideas. That I think both you and I are utilizing in like, as we continue to do our work, um, and we can talk about like, obviously the importance of time. Like people are way too big of a rush. They think like, oh, it didn't work for the first 6 months, dude. Like it took a year.

[53:37] Paul: It's never going to work in the first 6 months. Sometimes it does.

[53:40] David Senra: And like, you're not good enough. You're not good enough.

[53:44] Paul: It's that too. I mean, you can get lucky quick, but often those people have these stories in the back, which I love to bring out in this podcast of Oh, they didn't just succeed in 6 months. They were doing this random thing 8 years ago and 10 years ago. And you do such a good job of that in your podcast too.

[54:03] David Senra: Thank you. Even if you look at Andrew Huberman, right, where it's like, oh my God, no one's seen, like, we haven't seen a podcast grow this fast, this, this quickly in a long time. Right. But he's been obsessed and a domain expert for decades. He was pre— that's prep for what he's doing now. He just didn't realize how, what's the best way to, to give this gift to the world of like the way that he could share his very unique set of knowledge just happens to be podcasting is a perfect medium for 'em, right?

Um, so all this was going on, I was like, man, I'm just gonna fight. Like, I trust that if, if I, I, I heavily targeted to entrepreneurs and investors, that's who, like really entrepreneurs, right? I, I trust that if you're an entrepreneur or somebody wants to try to do something, you know, unique or difficult or, you know, dangerous or creative, and you can search the podcast directories and you can either listen to a podcast like Founders or a podcast that's not like it, I think if it's free, as if it's just a matter of what button that person pushes, I think if I just give it enough time, I'll get the audience I deserve just because I know how much effort and time and, and, and work I put into this. I, I literally work on it 7— I haven't taken a day off since 2018 cuz I read every day.

[55:08] Paul: Well, I also call this like, I call this design for liking work.

[55:12] David Senra: Mm-hmm.

[55:13] Paul: Cuz if you design for liking work and you actually have work you want to keep doing, Ambition, I sort of think, is just a question of how fast you want to go, right? Because you're going to do this until you're old. Like with my newsletter, it's like, well, I'm going to keep writing this for 20 years, so I don't care about the growth hack in the next 2 months because it doesn't matter. The long game will win.

[55:37] David Senra: Have you had Billy Oppenheimer on your show?

[55:39] Paul: We— I just took a walk with Billy yesterday.

[55:43] David Senra: Okay. He's really good at thinking about this because I love the thread he—

[55:48] Paul: I need to do an interview with him because he is, he's so smart.

[55:52] David Senra: Yeah, I talked to him too. And, um, I, for people to know, Billy Oppenheimer is, uh, one of Ryan Holiday's research assistants and he's got this great thread on Twitter that talks about Ryan's approach to work. He's just like, I'm doing this for, like, he's not obsessed with like logging into ConvertKit and figuring out like what's our open rate or what's our growth rate. He's like, I'm going to do the best job I can. I'm doing it for long term and therefore like the score will take care of itself. And that's very like, I'm going to try to influence it as much as possible.

I'm going to make sure like I, like the quality is always high and then I'm actually showing up and doing the work, but I'm not going to stress over like, I just know it'll work out and it's already continuing to work out. So going back to the story real quick. And so I was like, I'm going to fight. I want to compete on a level playing field. I want more people to hear this because I know, I genuinely know, and I've heard from so many people that it like literally will make your life and work better and it's made my life and work better. And so I was like, okay, well I'm gonna launch an ad, an ad supported model of Founders.

And I was thinking, how am I gonna do this? And then I just called Patrick and I was like, dude, and you know, he'd been a fan of Founders and I was like, I'm gonna make an ad-supported version of Founders. He's like, oh, that's interesting. And I go, I think it should be on your podcast network. And he is like, oh, that was really interesting. And so anyways, we worked something out in like one phone call, like very simple.

'Cause he was just, uh, like we knew each other and he had already known what the product was like. And then from there, the biggest thing that ever happened was him putting his force behind it. Me going on his show and him saying, hey, like, this is real. Just like all these people in the past that helped me along the way, like saying that when you put a personal endorsement on something, right? Yeah. Like, and you have, especially like, this is why audiences can be so valuable because if your audience like and likes and trusts you and admires you and you're saying, hey, this is good, right?

They will at least Try it. Doesn't mean they're like, they're gonna love it as much as you do, but it changes. If somebody, if like, uh, this happened in multiple cases, like Sam Hinkies goes and says, hey, Founders is worth your time, it's valuable, right? That person that admires Sam and goes and listens to it is gonna have a different experience than if that person discovered it on their own. Uh, the founder of Mad Happy, um, co-founder of Mad Happy sent me a message. He discovered Founders because this guy named Blake Robbins, who's very respected, said, I endorse— he said something on Twitter.

He's like, Founders Podcast is excellent. I highly recommend. And the founder of Mad Happy was like, if Blake says it's good, it's good. So that you can't overestimate how important that was, where it's like you have Patrick not only putting me on his show, he's got one of the most valuable shows in the world for the business community, right? For in terms of investors and entrepreneurs and him saying, not only do we have a good episode, I think, but, um, and him saying, no, no, this is Like, you need to listen to David's stuff. It's valuable.

Um, and so right there, you know, that happened. I think that episode came out August 30th. I haven't— I feel like I've been shot out of a rocket, like a shot out of a cannon, and I haven't stopped since then. Um, because all the opportunities that one thing opened up.

[59:06] Paul: What is the craziest opportunity that's emerged since then?

[59:10] David Senra: So the, the conversa— some of the conversations I get to have and the people I get to meet are just like, it's unbelievable. Um, I can, some of this, a lot of stuff I can't say. And actually I'm gonna be gone for like, I'm leaving next week and I'm gonna have some crazy experiences as a result of this. Um, what, what I would say is that if you like, people will respect your work if they know how much time and effort you put into it. And so for me it's like, well, like how many people in the world have read almost 300 biographies of entrepreneurs? I don't know, like there, Charlie Munger has read, you know, hundreds of biographies.

Marc Andreessen has read hundreds of biographies. Warren Buffett has read hundreds of biographies. So there are more, there are people alive right now that have read more biographies of entrepreneurs than I have, right? None of, but none of the, it's not like those people also have a podcast dedicated just to documenting what they learned from doing this. Um, and so what I would say is like Ryan Holiday's got a great post about this. He had this, he recommended like 25 different biographies and he goes, listen, if you, the, the most successful people in the world, if if you look at their bookshelves, they read biographies.

They read other things too, but they all read biographies. And he says some of the most valuable, valuable reading you can do. And I believe that as well. And that's also what I've realized, like when you read biographies about people, they also read biographies of other people. Um, and so what I would say is like, I can't say names or weird things that happen to me because some of the, a lot of that's private, but it's just like you have a unique experience and you've demonstrated the ability to take it to an extreme where people, like some of the most successful people in the world, are attracted to that. And the people that are in the audience for founders are, you know, they know that they can, that the world is malleable, right?

So like, let me give you an example. I'll give you an example that I can talk about. And what I mean by that is like the people in my audience are like, oh, I like David's work, I know I can reach out and get in touch with them, like, depending on, you know, who that person is. And so I got this, I kept getting this weird, like, like, Twitter DM, email, LinkedIn DM. I'm like, what is going on here? They kept saying like they're, uh, they wanted me to hire me to give us, to give a talk, right?

I thought it was like BS. Um, and then eventually like it was like, I didn't know, it was like this broker guy. But anyways, the, the CEO of, um, a private investment company, uh, the company's been around for 93 years and they have $250 billion of assets under management. Eventually the bro— I, I sta— I didn't ever reply to the broker, but his assistant got in touch with me and it was like, oh, it's legit. Like I checked out her LinkedIn and everything and they're like, our CEO of our company's obsessed with your show. Uh, you know, he's listened to like 40 episodes.

He wants you, he's wanting to know if you want to come and speak at this small company offsite we're doing where it's just going to be the CEO and like 40 of the, like the managing partners of this investment firm. And they're like, we'll pay you, you know, whatever. And we'll take care of travel. And so I was like, let's set up like a talk because like one, I like, I never even thought about doing this. So we end up having a Zoom with the CEO. We get along, we have, we've read the same books, like the guy's got crazy energy and charisma.

I was like, oh yes, I'm, I'm gonna do that. So like, that's an experience, like that's weird. But he knew that because it's like those kind of people, those kind of founders, those investors, those CEOs, like they know that the world is malleable. So, you know, I can get invited or have access to unique experiences because the people in the audience know that, you know, they can influence that. And if they're also, if it's a unique experience to me, like, why wouldn't I do that?

[01:02:55] Paul: I'd love to dive into Ed Thorpe a bit. So he's somebody you mention a lot because you admire, and it sounds like you aspire to just build a complete life, right? Be a good father, be a good partner, also succeed in business. And I was definitely inspired by Ed Thorpe as well. How do you, how do you balance like your interest in that with with the harsh reality that a lot of people, like, I love the, the, I downloaded the book of Larry Miller from the Utah Jazz, where it's like, this guy didn't live a great life. His wife is writing.

But how do you balance like your personal curiosity with people like Ed Thorpe and the harsh reality that a lot of entrepreneurs, though I do think this is changing in the current generation of entrepreneurs, Um, but past ones really didn't have that balance with family and other things.

[01:03:50] David Senra: I think there's a certain personality type that like overall happiness is kind of beside the point.

[01:03:58] Paul: Yeah.

[01:03:58] David Senra: Um, because they become so lost in their work and so obsessed with what they're doing that that is what it is. It's like kids be damned, spouses be damned, health be damned. You know, like that is what they're going after. And what's scary to me is I just had this conversation with my wife because she knows I've been completely obsessed. And she said something like, come back to us. Where it's like, I may be physically here, but she could tell that I'm so obsessed with, with, with Founders.

I am completely and utterly obsessed with what I'm doing. And I'm also pre— I have the personality type where I'm predisposed. Like, if I did not have a wife and kid or kids, I'm pretty sure I just wake— my eyes are open and I'm working, and then my eyes closed and I'm not. Um, like, I, I have to— the reason Ed Thorpe resonates so much with me is because this is like, I'm not like that naturally, and so therefore I need to have guardrails on myself, or I could find myself in a position— not Larry Miller, because I'm not gonna— like, I take care of my health, you know. Larry Miller was like really obese, and like, you see when you— when people Google Larry Miller, Utah Jazz, you're going to see him in like wheelchair and like the, you know, on the court or everything.

Um, and so I need the— first of all, I'm intentionally developing the skill to learn from the experiences of others, right? It's so arrogant for me to think that all— I consider every single person I've covered on the podcast smarter than me. And so it's so arrogant for me to think that this person that is so far more driven, smarter, more successful than me, and yet still fell prey to this mistake, it'd be arrogant to think that I'm not prone to making that same mistake over and over again. And so Ed Thorp shows me is like the balance. Like even right now I've been thinking, I was like, I need to have, I need to have more fun, right? Because essentially, like, for people that don't know Ed Thorp's story, he's out of every single person that I've studied on the podcast, he's probably the only one that I consider is like closest to mastering life.

Like he, he pursued his work that was, that was intellectually stimulating to him, but also made him wealthy beyond, you know, you could imagine. Once he had more money that he could spend, he didn't give up more time to make more money. He's like, this doesn't make any sense. Like, why would I do that? Like, I already, I can't spend all the money I already have. So he found work that he genuinely enjoyed, that stimulated his mind, that made him wealthy.

Right. And I think making enough money to buy your freedom is like the first step of wealth. And you can decide how much you need after that. But I think that's the first thing we all have to achieve, right? Because control over your time is super important. Ben Franklin, you know, says what's time like?

Time is literally the stuff life is made up of. Like, don't squander it. Like, pay attention to it and like make the best use of it. So work that you, that you love, that can buy your freedom. He was a good father, good husband, took care of his health. He's still alive to this day.

You can go, you can go on YouTube and put in Tim Ferriss, Ed Thorp, and you'll see that guy's giving interviews at 90. He looks like he's like 65, right? Did you see it?

[01:06:59] Paul: So crazy.

[01:07:00] David Senra: I want to—

[01:07:03] Paul: that's such a good metric. I just want to look 60 when I'm 90.

[01:07:07] David Senra: But, and like, he's still, his brain is still there and everything else. And then he treated life like the adventure it was. Like, that dude built the first wearable computer with Claude Shannon. He was the one that invented the easiest way to count cards, to count cards on blackjack to give you an edge. Writes a book called Beat the Dealer, I think in the 1960s, that sells millions of copies. He's doing this like part-time.

Winds up going to dinner with a 38-year-old Warren Buffett and leaving dinner and turning to his wife and saying, hey, that guy's going to be the richest person in the world one day. Like he just had— winds up being the first LP in Citadel, the hedge fund that, you know, like traveled over the world, like built this beautiful life. You know, it's just like you get to the end of this book, it's like, I want that. I want that. And I think for people especially entrepreneurs, the more likely outcome is you're obsessed, you build a fantastic company, you get rich as hell, and then you get to the end of your life like, damn, I wish I was better to my wife, or I wish I was better to my kids, or I wish I, you know, saw more of the world. You're kind of like myopically focused on your business.

And I understand that because I'm telling you, if I don't put up these guardrails, I'm gonna be that way too. Yeah. And so that's why Ed Thorpe's so important to me.

[01:08:19] Paul: Are there any specific experiments you're thinking about doing? Like, this is interesting for me. Last year, at the start of 2022, I decided, okay, I am going to inject play and fun into my life. I actually took like DJ lessons and started doing— I think I thought I had them somewhere. I started doing yo-yo because they were like these childhood things. And it felt silly, but I had such like deep joy in the flow of like doing those things because they were just for the sake of themselves.

So I was still able to like channel my nerdy curiosity while still detaching from that. Um, any experiments you're thinking about?

[01:09:03] David Senra: I don't do any experiments. So like I have had this thought recently, I was like, I need to have more fun. Um, some of the things I do for fun though, are kind of related to work where, um, I meet a ton of founders because of the podcast. And so like, I love— there's nothing more than I like going out. Like Jay-Z has this line in his book that's fantastic. He's like, I love sharp people.

There's nothing that makes me more attracted to a person than intelligence. That's like a paraphrase, right? And so I like to have like long one-on-one or maybe, you know, maybe 2 or 3. I don't like doing group dinners, but like, you know, I— this other day I just met my friend Truman, I met through the podcast. He's like this young kid, he's like 22, um, already sold his first company, had been listening to Founders Forever. It basically, I, I got to have a super long dinner with him.

I see the new pro, uh, he's got some new ideas that he's working on. But, uh, we wind up like, it got to the end of the night, it's like, where's everybody going? And we didn't know we'd been at dinner for 3 and a half hours.

[01:10:02] Paul: I love that.

[01:10:02] David Senra: You know what I mean? Like that, like, so that's a part of like the flow state, the like autotelic, you just use the word the sake of itself. Like autotelic means like an activity that you do for the sake of itself. So like, that's fun. But like, I need more, I need to inject more things that are not just founders related. 'Cause like we're talking about entrepreneurship all the time.

Like I have to have, I'm not bound. That's the one thing I'm not, I'm making a mistake on where it's just like, I'm still, I still spend a lot of time with my family. I do have one trick and it's, I hate to say it's even a trick, but like I found that it's easier to spread my work over 7-day weeks than like 5-day weeks and take days off. And so what I mean by that is like, if you, if you only work 8 hours a day, right? But you do it 7 days a week. That means like every day I have 8 hours for sleep, 8 hours for work, and then I have 8 hours to do all the other stuff.

That's a lot of time. 8 hours to go watch my daughter play volleyball, 8 hours to go meet with a friend, 8 hours to go play basketball, 8 hours to whatever, you know? My problem is, is like I try to set that up and like, I'm like, where'd the time go? Well, you didn't just work 8 hours today. You did other stuff, you know? So I'm not— the answer to your question is like, I need to make improvement in this.

So I don't have— all I know is like the pace that I'm at right now is not going to be always sustainable. And I think I say this on the podcast all the time, it's like the most important thing for business success, once you find a business that's working, is just giving it time and not interrupting the compounding because time carries most of the weight. So eventually I'll get to this part where I'm, you know, making more time for fun.

[01:11:42] Paul: Yeah, I did this episode with Sean McCabe a few years ago, and he was in a similar situation working 7 days a week, and he implemented an every 7th week off policy. And I actually implemented this in 2021 because I felt like I had a lot of just low-grade stuff that was just hanging around and I just wanted to like ship more stuff. So I started taking every 7th week off and I literally would do nothing and just wander. Um, and I started to realize I got more done and the best ideas would emerge from my book and those weeks off of like wandering and bike riding.

[01:12:21] David Senra: Um, David Ogilvy said the same thing where he's like, I believe working really hard, but I believe in the power of sabbaticals that he thought like your subconscious starts to to like the ideas that emerge that like your subconscious comes up with only appears when you're doing nothing else. So when I would take time off, like my— me and my wife, we had this trip planned for the anniversary, like I'll be reading, but not nearly, you know what I mean? Like, so my job, I think if I had a different job, I would take more time off. But to me, reading doesn't— goes back to what you mentioned earlier. Also something Naval says, like find work that feels like play. So like, I know on the plane there I'll be reading, on the plane back I'll be reading.

I'm sure on like some of the days, like, 'cause I can just download a, uh, a Kindle edition of a phone or Kindle edition of a book onto my phone and like I've read entire books that way. Um, I, I don't think I, I, if I, if my job wasn't reading, I would definitely take time off.

[01:13:15] Paul: Yeah, I, I found this the same thing with reading. I wanted to dive into Ogilvy, so Somebody I've read a lot about is Marvin Bower, and Ogilvy mentions Marvin Bower. Marvin Bower, not the founder of McKinsey, but somebody that helped popularize McKinsey. And I'm, I'm, I've been fascinated with this era of like the 1950s, 1960s. There's these people like Ogilvy, Marvin Bower, who seem to be very good at injecting principles into companies. And you just don't see that same like obsessiveness and thoughtfulness about cultures today?

Like, what do you think it was about that era? Was it just that there was just so much emergent growth and new opportunity?

[01:14:01] David Senra: Well, so I think like all the stuff that we enjoy in America came from post the economic boom that came in America after post-World War II. And so, yeah, I do think not only is like I do think you still have the obsessiveness today, like, you know, again, my main thesis is like humans more or less are all the same over the year, all over the world, and more or less are the same in time. Like, I don't think human nature changes at all. I don't think it'll ever change. And so you still have these people. I mean, I know some really like crazily dedicated and just completely obsessive founders, a ton of them.

I've had dinner with them. I've gone to visit them. Like, they're on a different level. What I, what I think is The reason, like, it's, it's so pronounced, especially in Ogilvy's case, is because the reason I think people should study Ogilvy is because, like, he's one of the most gifted communicators that I've ever come across. Like, his writing— he is the, by far, the best writer that I've ever read in terms of, like, a book for the podcast, you know? Like, the clarity of thought and just, like, how much time and effort he put— it's just incredible.

Um, and then he also— what he would do is, like, he'd keep people like Marvin Bower around him. While you were talking, I just searched my Readwise. And so like there's a quote, uh, I just put in Marvin Bower from Readwise because I knew the name and it's from The King of Madison Avenue, David Ogilvy and the Making of Modern Advertising. And this is what he said. He goes, it is said that if you sent an engraved wedding invitation to my friend Marvin Bower, the great man of McKinsey, he will return it to you with revisions. And he goes, one such opportunity arose.

It was hilarious. It's like one such opportunity arose when Ogilvy drafted his statement of purposes for the agency, starting with earn and increase profit every year. And then he sent it to Bower for comment. Marvin gave me holy hell. He said that any service business that gave a higher priority to profits than serving its clients deserved to fail. And so that idea that Marvin is expressing, you know, in a, maybe like a, you know, a very direct way is your customers are more, you put your, the interest of your customers ahead of the interest of your business.

And that actually what Jeff Bezos makes the point is like, if you obsess over customers, the long-term interest, one of the key innovations that I think people that pay attention to what Jeff is actually trying to teach us, uh, was really important. It's like people think that shit, the long-term interest of a shareholder and long-term interest of a customer diverge. And Jeff is like, no, over time, like they're in perfect alignment. And so that's why Jeff repeats over and over again, obsess over customers. So my point being is like Marvin Bower is telling Ogilvy the same lesson that Jeff Bezos is now telling this generation of entrepreneurs. It's like customers first, not you, not the money you're gonna make.

You know, if you serve— my, one of my favorite quotes you've heard me say before, Henry Ford, money comes naturally, uh, comes naturally as a result of service. Marvin Bower is saying the same thing. He's like, if you serve your customers, the profits will take care of themselves.

[01:17:11] Paul: Who is your path role model? In terms of what you're trying to do? Do you— maybe somebody who's on your podcast and then maybe somebody, somebody else, or could be a group of people that you're trying to emulate?

[01:17:28] David Senra: I think what it is is like I'm just reading— like the way I think about reading biographies is very similar to like athletes watching game tape, right? Except instead of watching game tape, I have to read the book. And but it's a life story as opposed to just a career. and I'm taking little pieces from a bunch of different people and trying to just— I think you're, you're going to— you have to first of all spend a lot of time like really understanding who the hell you are. Like, what is important to you? Like, when you're sitting there by yourself, when you're— the inner monologue you have, like, you cannot like cheat that person.

Like, what are you naturally interested? What do you want your time to be? And one trick for this, uh, is what Charlie Munger says. He's like, I get to what I like by avoiding what I dislike. He's big on inversion, right? Invert, invert, invert.

And so what I think of is like when I'm reading these stories, it's like, okay, what do I want my life to be? And I see, I think very first and foremost is like, I think about all the things I don't want my life to be. I told that story earlier. It's like I was introverted and yet I had to manage a bunch of people. Like that drains me, you know? So I was like, how can I have like a very impactful and very valuable business, but using the tools that we have in this age of infinite leverage that we, that we, that we live in.

It's like when there was 500, like I do the same amount of work, like the business I've chosen in podcasting is like it leverages built into the product where it's like if one person listens, I do the same amount of work, or if a million people listen, I do the same amount of work. And so I just take different things where it's just like, okay, I am obsessed with the fact that the optimal size of a company is decreasing. That trend is continuing to increase. You can just see like if you compare market cap and headcount, you know, across very valuable businesses in American business history, you clearly see that it's getting smaller and smaller and smaller, right?

And I, and so I was like, okay, well, and then on some of the extremes where I collect these examples of what is like a one-person, what's the most impact you could possibly have on the world if it was just like a one-person business? Or what if like 3 people? Or what if 5? But I would never say, hey, what about 5,000? That's just not something that's interesting, interested to me. So I think it's just a combination of, you know, the personality traits that I pick up in the books and then I just try to like use, utilize for myself.

Like you mentioned Ogilvy. One thing I learned from Ogilvy is like the power of a he's a masterful communicator. And that is an unfair advantage in life because humans learn primarily, in my opinion, through two ways: storytelling stories and distilling ideas down to their essence. Maxims, aphorisms. Go read the unpublished David Ogilvy. It is, it was a gift given to him when he was, I think he turned 70.

It was 50 years, 40 or 50 years of internal memos and letters that he wrote. That was not supposed to be published. And you see the letters and the way he communicates as he's building his very valuable advertising agency. Eventually they bound it together, give him as a gift, and then they decided to publish it and make it available for everybody else. And so like learning from him is like, how do I take, like when I'm reading a book and you'll hear this on the podcast, it's like, I'm not just like reading the words, like, okay, like I'm really trying to just like, what is the idea behind this? And what, how can I simplify this story that's over, you know, maybe in 2 or 3 or 4 chapters down to like, what is actually important to us?

What, like, you're not gonna remember 4 chapters of a book, but you'll remember a story, but you'll remember a line. Like, I repeat these, these maxims from the history of entrepreneurship all the time. Like, excellence is the capacity to take pain. By endurance we conquer. Actions express priority. You know, these things that, uh, you're not advertising to a standing army, you're advertising to a moving parade.

That's David Ogilvy's maxim. These ideas. That's how you like hook these ideas into somebody's brain so then they can carry it with them and use it, you know, many years down the path. So I'm trying to really, that's why I mentioned earlier, it's like if I find somebody I like, I read, you know, every single book I can find about them over time. What has happened now, like let me just mention the people that I've done this with, it's like I have a good idea and you're going to start to see this with AI because my friend Max Olson, Um, he's the one, he's been working in AI for a while, but he's also the guy that, um, printed the book of Berkshire's, um, uh, shareholder letters. And so you can go to BuffettBot.com and he used all of Warren's writing and now you can have a conversation, right?

Quote unquote with Warren Buffett. So anyways, what I'm doing is like the reason I read all these books on Warren Buffett, Charlie Munger, Edwin Land, Steve Jobs, David Ogilvy. Um, you know, I'm sure there's more. Uh, read a couple on Coco Chanel, whatever. I, I try to have a sense of who they are, and therefore when I see something in my life, I try to ask them, you know, it's like they're sitting on my shoulder. It's like, what would Steve Jobs tell me to do right now?

Or what would David Ogilvy say to do right now? And we just talked about the fact I'm not having enough fun. Ogilvy treated life like an adventure. And so like, that's another big thing this year where I have a bunch of trips planned. Where it's like, I'm going to treat it like an adventure. That dude had fun.

[01:22:47] Paul: Yeah, it's— he has this quote, try to make working at Ogilvy and Mather fun. When people aren't having any fun, they seldom produce good advertising. Kill grimness with laughter. I love that. I picked up the book based on your podcast.

[01:23:04] David Senra: The Unpublished? Which one?

[01:23:05] Paul: Yeah, I don't know which one that's from.

[01:23:08] David Senra: Okay.

[01:23:09] Paul: It's just in my Ogilvy notes.

[01:23:10] David Senra: Yeah. Yeah, he's just, just the way he communicates. I envy that. And then also the clarity of thought where I, I, I crave simplicity. I think most humans crave simplicity, but I can't stop adding complexity to my life. And so when I do shit like that, I hear Steve Jobs who says, you know, like, the further away you get from one, the more complexity you add in.

Like, focus is saying no. You got to say no to 10,000 things. Now, I think in today's day and age, we have to say no to 10 million things. And so that's like when I'm like, man, I envy his clarity of thought. I want to do the work necessary so I can at least approach my whatever my version of that is. And so that's something I think about a lot where it's just like, okay, I want to be really, really good.

Well, I want to be world class at what I do for a living, but I don't. And but if that's not going to be all my waking hours, then the only way to be world class at what I'm doing is to pick one thing and not deviate, not focus on anything else, because I want other areas of my life not to suffer.

[01:24:08] Paul: So one thing a lot of people listening and following my stuff are thinking about is like leaving their jobs. And through your podcast, I kept hearing over and over again the same thing about work. George Lucas, Henry Ford, um, couple others about quitting, right?

[01:24:26] David Senra: Yeah.

[01:24:27] Paul: Jeff Bezos, this, I have to find out what, uh, what can you tell people about like the opportunity of taking a leap, right? I think another quote you say is, the only risk in the world is not taking any.

[01:24:45] David Senra: You're going to fucking die. You have one life and you are going to die. Are you really gonna spend your one life doing something that you hate for half of your waking hours? George Lucas says, he goes, people are in cages without doors. He's like, they just won't take the risk. And people are like, oh, it's easy for George Lucas to say he's worth $5 billion.

He had no money when he did that. So the problem is, like, you're presented this opportunity. You're usually not in the best position in your life where you have to seize that opportunity. And George, I'm glad you mentioned the George Lucas thing because it's like, if you listen to or if you read that book called George Lucas: A Life, I think it's by Brian J. Jones, the author. What's remarkable is because I knew George Lucas from Star Wars, I did not know the struggles that he had to go through.

The fact that he was in deep debt, that he refused to even compromise with the way he was building. People offered him money, right, to compromise, make this movie a certain way, or cut this part out, and he just absolutely refused. Or take this job just to pay the bills. And so that's the important part about reading biographies. I'm not saying quit right today. Maybe you know your situation better than I do.

Maybe you can't. But the reason I always remind people is like, you're going to die. That you think is risky or scary is nothing compared to the end of your existence. And so Steve Jobs said that. He's like, every morning before I go to work, I ask myself, if this is my last day on earth, would I want to do what I'm about to do right now? At any time where no was— when I said no too many days in a row, I know I needed to make a change.

He also does this great talk that's the commencement address at Stanford, where he's like, when he got the cancer diagnosis, they said, hey, go home, You know, this is the first cancer diagnosis. He winds up dying, I think, like 10 years later, like 7 years later. But at this point, the first diagnosis is like, go home, get your affairs in order. You got a couple of months. And he's like, when you're— when you know, when you're told, hey, you got a couple of months, like everything that you think is important— embarrassment, risk, having to take a part-time job to actually do what you want to do, or whatever it is— like all that falls away in the face of death. Another example that really pushed me over the edge when, when I was reading Paul Graham's essay too, is like what I had learned from Jeff Bezos in The Everything Store, the biography of Jeff Bezos.

He talks about like, you know, people thought he was crazy. He's like, Jeff has been a genius since he was a kid. You know, he's like valedictorian of high school. Like they knew he was bright when he was like a young kid. At 30 years old, he's working for a billionaire hedge fund guy named David Shaw, and he's got a really high-paying job. He's got a beautiful apartment in Manhattan.

And he's like, I think I'm gonna quit this job so I can start a bookstore on the internet. This is 1996. People are like, what the hell are you talking about, dude? Like, why would you do that? And he has— this is the way I make my decisions now and really pushed me on my edge of like trying to do the podcast full-time is, um, he calls it the regret minimization framework where he's just like, I try to picture— he's like, at 30 years old, what's important to me? Status, money, the opinions of other people, this giant bonus check I might get for next quarter.

And he's like, but I know if like, if you're, if you're in your 80s and you're on your deathbed, sir, and you're going back and you're having your own like a conversation with yourself, you're not going to be thinking, oh man, I missed, uh, you know, I shouldn't have quit that job because I missed out on my quarterly bonus. What would ha— what's more likely is like, I had the opportunity 50 years ago when I was 30 years old in the prime of my life to play a role in what I thought there was this giant technological revolution called the internet. And I didn't risk it because I was worried about missing my bonus. He's like, your 80-year-old self wouldn't even remember that, but you would remember. It's like, hey, I believed deeply in this powerful new, uh, opportunity I have. If, if my 80-year-old self said, hey, at least you tried and failed, I'd be cool with that.

That. That's not gonna be a regret. But there'd be a giant regret. It's like, you had— you saw it, you saw it, and you didn't do it. And now I'm on my deathbed and it's too late. You don't want to go— so that's why he calls it regret minimization framework, because it's like, you're going to get to a point in your life where there is no more time.

And so try to optimize your decision-making to have the least amount of regrets, uh, later on in life. I feel that way about podcasting. People think I'm fucking crazy. They literally, uh— do you know John Coogan?

[01:29:11] Paul: Uh, don't think so. No.

[01:29:13] David Senra: John Coogan makes excellent— he's a two-time Y Combinator founder. He's the founder of Soylent and this company called Lucy. He's also my favorite educational YouTuber. He makes excellent videos on tech businesses and the history of like Silicon Valley and artificial intelligence. He's a great storyteller. And he just had a tweet that went viral the other day because turns out he just, uh, his he became an, uh, EIR, entrepreneur in residence for Founders Fund.

And me and him had become friends through the podcast for the last few months. I just had this like super long dinner with him a couple weeks ago. So I text him, I was like, dude, like what's going on with this? And so we went up talking for a while because we both share like the, the power of, like we're both obsessed with learning. And then he puts out his form of learning and his research in these beautiful videos. I do the same to the podcast, right?

And he even said this, he goes, there's people that know both of us that tell me that like David's way too obsessed with podcasts. But the reason I bring that up now is because one, I think that's great because that means I still see an opportunity that is obvious to me that people don't see. But the other thing is it's like, well, the way Jeff Bezos felt about the internet, I feel about podcasts. I feel like we're at the very beginning of a giant technological revolution. I feel if you're gonna build, uh, if you're gonna create educational content for the most successful people in the world, uh, which is what I'm trying to do, which is what Patrick from Invest Like the Best is trying to do. We both believe that that medium that those people are gonna choose is gonna be on, it's gonna be podcast, it's gonna be on-demand audio.

It's going to turn all the times when your eyes are busy into a classroom. And entrepreneurs, investors are learning machines. They're obsessed with learning, and now they can learn from history-based entrepreneurs when they're washing dishes, walking their dog on, you know, commuting as opposed to like sitting around and having to watch like immersive video or whatever the case is. So when I see stuff like that, it's like, I know 80-year-old David, if he didn't have that decision in 2018, he's like, really? You had one shot to work at something you're passionate about, something that you would do for free. Not only would I do for free, I paid to do.

I paid to do it every month. I paid to do it. That's how much I love it. And you fucking didn't do it. Why? Because you're worried about what other people thought?

Are you worried you weren't going to make it? You had— are you worried you had to get a part-time job? That's pathetic, David. That's pathetic. Thanks a lot, buddy. Now I'm sitting on my deathbed and I lived this shitty life, this one opportunity, because your 30-year-old version of yourself didn't jump.

Jump, motherfucker.

[01:31:42] Paul: I love it. That is probably a good place to end. I'm inspired. I've actually written a similar letter of— I've I've done the inversion experiment. I've written the worst case scenario 20 years from now. And then I sort of work backwards and say, okay, what am I doing now that might end up there?

And then just get rid of those because aiming in the positive direction is still hard. There's so many unknowns, uncertain scale of the internet, but yeah, I love that experiment.

[01:32:14] David Senra: I agree completely. I actually think you learn more from seeing examples of what not to do and just avoiding mistakes. It's like, it goes back to what Charlie Munger, Warren Buffett says. It's like, we were just consistently not dumb. We're not trying to be brilliant, but it's so hard for humans to be consistently not dumb over a long period of time. And if you just see how like the common follies of humankind, and I'm going to talk about this in the podcast I'm working on this week for that I'm making about them is just like, you know, avoid the common things, avoid the drugs, avoid, you know, too much leverage.

They talk about debt, Avoid jobs that you hate. Like, these are things that humans do over and over again. Why wouldn't you think that you're— that's gonna happen to you too?