#41: Jimmy Soni — The PayPal Mafia, Writing Books, and Internet Friends

Sup nerds, welcome to another episode of the Jason Levin Show. Today we have Jimmy Sonion. He is the author of 4 books, the most recent one being called The Founders. It is about the PayPal Mafia, which are the early members of PayPal: Elon, David Sacks, Peter Thiel, Reid Hoffman, and more. They are the most powerful, probably the most powerful people in Silicon Valley, prominent founders, VCs, etc. So I talked to Jimmy about the PayPal Mafia, how to start my own mafia, and then also writing books and making friends on the internet. I hope you enjoy today's episode. Please share it with a friend if you enjoy.

Are you cool if we hop into things?

Yeah, absolutely.

All right, sweet. So I kind of split things up into the book and PayPal Mafia, that kind of stuff. I'm pretty familiar and have some solid quotes from Zero to One to work with and then split it up from that into like personal and creative.

Cool.

All things writing. So I want to ask, read a quote that I think my friend sent me the other day. Of the 6 people who started PayPal, 4 had built bombs in high school. Why was PayPal so weird and why were they all like such crazy hackers.

Okay, let's unpack this one. You know, we're starting with the easy stuff.

I think that quote is from Peter's book, Zero to One, and I came across it during my research, obviously, and I kind of have two thoughts about it.

The first thought is he is only in that quote scratching the surface of the variety of interests that people in this group have, right? So the more you dig into the story, The wackier certain things get, I'll give you an example.

This was not in the book.

So this is not in my book, The Founders. It's just something I heard, but like it made the cutting room floor, but I thought it was really funny. So there's this engineer, David Gausebeck, who told me that one of the things they used to do during the early days of PayPal is they like, so it's late at night, like it's like 1 or 2 o'clock in the morning and the back of their office was this kind of parking area and there were there were brick walls on like two sides or three sides or something.

So they had like PVC pipe potato guns, like potato cannons, and they accelerated the speed of the potato cannon so much that they would take potatoes, like, like shoot them against the wall and they would like explode into like, you know, microscopic pieces.

And so like, I think that, that, you know, the more serious analysis of that quote and the potato gun story is You know, I heard someone say something the other day that was like, no one ordinary ever built anything interesting, right?

And I think, I don't know that you can like generalize that much, but if we're being honest with ourselves, most of the people that make headlines for creating big companies or creating interesting things have a little bit of weirdness to them. And you know, if you were looking at it more seriously, you would say to yourself, well, it actually, you kind of need to be like, like you, you need to have something in you that is willing to cut against convention. You need to have something in you that's willing to look at people like Visa or MasterCard or whatever your industry, you know, like, and say, you're wrong, I'm right.

And I don't know anything and I haven't been doing this for as long, but you're wrong and I'm right.

And so if you tap into what he's saying, there's a kind of anarchist quality to, not in a good way, not a bad way to startup founders. And we, here's what happens though. We only see the downsides of that, like, because the downsides are written about and they're written about, I think disproportionately, but you don't see the kind of curious, like things that make these people tick. And then those very same things are the things that lead to startup creation and success. And I'm doing a, I'm doing like a bad job describing it, but the idea of someone like knowing how to make a bomb, it's unlikely that these people actually ever really made bombs, like they'd be in prison, right? I mean, this is like, but the idea of you being a little bit set apart from the rest of society, a little bit willing to cut against convention, I found that over and over again and not just in the 6 people, but in like several hundred people, right?

Whether Yeah.

So that, that I, I think there's some truth to what he's saying. I, the other thing is, you know, like attracts like. So if the, if the people who created the company originally have these kinds of off-the-wall passions and interests, they're not gonna select against that. So when you're interviewing, you're also looking for people who have something interesting to say or who have some habit or hobby or passion or something that is unique to them, that's unique and sets them apart from other people. Like attracts like. So you have this thing of like maybe great startup founders are the people who like have this weird quality because it allows them to say that the world is wrong and they are right. And then they attract other people like that and build startups.

Yeah, I write content for startups and VC firms and I just fell in love with it as soon as I got in the industry. Like everyone is just weird and proud and You know, I start every newsletter with sup nerds, because everyone that I know in this industry is proud to be a nerd. And so like, you know, hacking away on some weird bomb, you know, that's not weird to me. Like that's, you know, it's weird to a lot of people, but like, that's just like something like a nerd would want to do. That's like a hacker kind of nerd thing to do. Like I 3D printed, you know, a model of Edward Snowden to like screw around. Like that's just, weird nerd thing to do. And I love it.

And I think, by the way, I think it's also one of the few areas of economic life that celebrates that kind of weirdness.

Like, it's actually like what we're joking about it, but it's actually one of the only places where I think some of the people certainly that I've interviewed that you work with, it's like one of the only places where they could be gainfully and powerfully employed, you know, like, like you really wouldn't find these people fitting in, you know, I don't know, at some other more traditional company, it'd be very hard because it just does— the rhythms of normal employment don't really suit some of these individuals. And Silicon Valley has allowed them to find a place to express their particular weirdness and their talents. And I mean, I think there's sort of pro and con debates about this, but in general, I think that we need more like of this, of people to talk about some of these weird quirky hobbies and things that they do.

It makes the world more interesting.

I completely agree. I, so I studied English in college and was gonna go that route and, and try to, you know, apply for some like, uh, pre-professor kind of thing. And I was just, you know, too out there, too weird. I, during classes I was always on my laptop working on side hustles and side projects or on Twitter. It was just like too different. And at some point, so I guess my backstory, I realized like, oh, how the hell am I gonna make money? As an English major. So learned how to code, you know, did a bootcamp, got the coding job, built up the writing on the side, and then the writing took off. But it was like, just, you don't fit in. I think a lot of my friends and a lot of very online people feel that way. It's like, we feel like when we're growing up, we don't fit in. We use the internet to meet people, to learn. And now, like, you know, some of my best friends are my internet friends that, Yeah, I hang out with all the time.

It's really funny that you say this because I have a bunch of these people. I'm very similar. I was an immigrant. I was super nerdy growing up. You know, I mean, every nerd box you could check. I was on the chess team. I like did well at math. Like every, every, like if there's a bingo board, I got bingo, you know?

But what was, what was interesting, like more, more, more interesting to me is this internet friends phenomenon because this is no joke.

I am closer with some of the people that I have never met in person than I am to some of the people who are my neighbors or people I've known my entire life.

And it's because you can more quickly find kinship with people who are like peculiar, you know, like I have friends, you know, like one great example is my friend who runs the Founders Podcast, David Senra.

David, like I have yet to like meet, truly meet anybody who's as obsessive about business writing as I am until I met David Senra where I'm like, all right, like you are a lot like me and you obsess over this stuff in the same way, right?

And he's just one example. I've never met David once in person. We communicate several times a week over texts and Twitter and various other things.

And it's, and my friendship with him, I would sort of grade as like, it was like an old friend entered my life through Twitter and now we're like best friends.

You know, it's like one of those relationships. I think that's like the internet friends phenomenon is super interesting to me. And I think Silicon Valley and startups are a place where you take that phenomenon and you kind of like, put it into a system that's designed to create companies and like companies emerge.

100%. Yeah, I'm writing a book right now about memes. So Memes Make Millions, all about meme marketing and whatnot. And, you know, I'm interviewing people that like, you know, I would have been friends with if we were in the same school. We were just goofy on the computer making memes and goofing around and on Twitter. And it's like, these are my kindred spirits and it's very cool. I, It's hard to write about the internet friendship phenomenon. I don't know if you've ever noticed that, like talking about the experiences of like doing that. It's not like saying a story, I went to a bar, you know, it's interesting from an outside perspective, but I'm playing around with it a lot because, you know, the one part of it that I would say that's, that at least again, like I'm generalizing here from my very narrow interactions.

So this is like admittedly like there's a ceiling on these conclusions, right? This isn't academic research. I'm just sort of talking with you. But one of the interesting things about it is if you think about where your friends come from, I have a 7-year-old daughter, she's about to be 8, and it's like a very good window into like, how do friendships form?

Like for most of human history, friendship was basically geographically limited, right?

You were friends with people because like you had the locker next to them or like you ended up as neighbors or maybe you were in the same class. Or like, you know, you sat at the same lunch table, you graduate to college, okay? Your friends are probably mostly in your dorm, right? So it's very, very—

it's like, it's entirely a lottery.

It's like, it's a geographic lottery and you could win and you have great friends or you lose, you don't have great friends.

What's great about the internet is at least my internet friends, it's purposeful friendship. If I notice something, I think you and I connected because we were like noticing interesting things about each other on Twitter or like work overlapped. It almost short circuits all of this sort of like accidental meeting up. And we know we're meeting with purpose.

We know we're connecting with purpose. So I actually like, in a weird way, I think over the long haul, like if you were to look a century into the future, I think internet friendships are going to be better than like real friendships. I mean, that's maybe controversial, but I'm— the people I meet now, I consider sort of like wedding and funeral friends, you know, where it's like, These internet friends, and I like, I don't want them to attend those things digitally. I'd like to attend in real life.

But these are people where I have so much in common and it is because of the internet and it's because the interest is what drew us together, not like having the locker next to Jason Levin.

Exactly. I feel that 100%. My wedding's coming up in 11 months and there will be a table full of Twitter friends. One of my Twitter friends will actually be a groomsman. That's amazing. Yeah, it's pretty incredible. Something I've also found, you know, hearkening back to mafia is there are different mafias on Twitter. You know, there's the obvious ones like Morning Brew Mafia where everyone has their coffee cup. There's the Workweek Mafia. Everyone has a yellow whatever. But then there's like also mafias where they're group chats of different creators in the background who are all supporting each other, engagement group chats. There's all sorts of mafias and something I'm thinking about right now is like, how do I build my mafia? Right. You know, and I'm slowly doing that with the newsletter and everything. I'm curious, how did the PayPal Mafia form and was it obvious for them during the time period that there would be something like a PayPal Mafia?

Yeah, so I'll answer the second one because it's easy, which is absolutely not. Well, I wouldn't, shouldn't say absolutely not. I mean, it's, you shouldn't be that definitive, but here's what I would say. If you were looking at where the state of the internet was from 1998 to 2002, when all of these people met, like Peter Thiel, Reid Hoffman, David Sacks, Elon Musk, no one could have said, oh, you know what's going to happen? They're all going to like get together, build like path-beating companies, like make a ton of money, stay in each other's lives in various ways, and underwrite the, like the next generation of Silicon Valley. Like that just would've been ridiculous. You know, no one could have crystal balled that. Information given what was happening in 1998 to 2002. Here's what I will say, and this is probably one of the lessons that, you know, you often, like, I often get asked the question, like, why was there a PayPal mafia and not like an Uber or not a Google mafia or a, you know, a Yahoo mafia or whatever? And a big part of it is that they worked under, we worked in very close quarters. It was very intense for 4 years and they emerged successful when so much of the internet in 2002 was like not, you know, I mean, the Nasdaq had lost sort of all its value. And you have these people who have taken an internet company public, sold it and have a success.

And then they are the ones that they don't— as one person who I interviewed put it, he said, we didn't have retirement money, but we had down payment money.

And so what we were able to do was like continue to build.

And then who do you naturally turn to when you're building your next thing?

You turn to the people in the cubicle, from the cubicle left, cubicle to the right.

And they invested in one another and that kind of grew. But I would say here's something really important to remember.

It was much more organic than the media often makes it seem. It wasn't like there was like a smoke-filled room and, you know, it wasn't, it wasn't like selecting the Pope. Like it was more like, I'll give you an example. When I was doing this research, I had like a ton of emails, like somebody shared just gigabytes of emails and I went through very, very meticulously looking at emails.

There was an email I found from Reid Hoffman to one of the people that's a part of the PayPal alumni group. And in the email, it's the most extraordinary document. It is a pitch, a 2-paragraph pitch for what became LinkedIn. And this is in like— this is in 2000, 2002. I think it's late 2002.

And I looked at it and I was like, my jaw dropped on the floor. I was like, this is like— this, this email is worth, you know, however much money. Like, this is an extraordinary thing.

But that, that isn't some grand plan.

When you read his description for what LinkedIn is, sure, parts of it are spot on, but it's not like anybody could see into the future and be like, oh, that's gonna be the one of the biggest social networks in the world.

It was more trial and error. It was more catch as catch can. And I think that's like, so to answer your second part of your question is it was not foreseeable that the quote unquote PayPal Mafia would become PayPal Mafia. But even though you can't foresee it, what can you learn from it? Number one, like high performance groups are really powerful. Two, there's real value in staying in touch and in contact and working with the same people over and over again. I would say number three, like recognize when concentrations of talent exist and know that like concentrations, you'll, you'll bake in those fumes, you know, you'll sort of get some, something from that that you might not have otherwise. I also think the other thing to appreciate is it can be somewhat random, like the initial group of people who helped to create the company PayPal, were alumni from Stanford and alumni from the University of Illinois at Urbana-Champaign.

That's because Max Levchin went to University of Illinois and a lot of the engineers followed from there.

And because Peter, Ken Howery, and a few others came from Stanford and they recruited friends from Stanford. Why were they able to recruit their friends?

Nobody else wanted to work for them.

They were a tiny company. They weren't a public company. And they, they, they had the virtue of having very good friends who are very smart and they built a company. So it's, it's not the kind of thing that you can scope out except to say that like there are people you meet in your life and they're so talented and you're like, I have to find a way to do something with them. And I will say that's the one thing I heard over and over again. Like I remember I interviewed this, this engineer, his name was Doug Mack.

This is a great story actually. Doug met Elon and at one point in the early X.com history, X.com for those who don't know is the half of PayPal that was Elon's.

Elon has this problem.

They try to overthrow him at earlyx.com, and Doug is given a choice. Do you stay with Elon or do you go with these other people who are now leaving the company?

And most of the company leaves. I mean, it's a really extraordinary moment. And Doug says, Doug told me, he said, you know, I decided to stay.

And my natural question, I was like, Doug, why'd you stay?

And he said, because I met Elon and I realized this guy would give his last dollar to succeed.

Like, I just knew it. You could tell. And he had already put in a lot of dollars.

And so I believed in him and I was going to stick with him. And I heard story after story like that.

When someone had met someone talented, they were like, I am hitching my star to that wagon.

So I think there are some principles that are, that are kind of things you can learn from the quote unquote PayPal Mafia story.

But in general, it's best to think about it as not a planned, like, like two-decade con on the world.

Of course, of course, that makes sense. So how did, how did you get fascinated by the idea and start writing the book?

Yeah, it, it's here.

I mean, the, the, the story is, in the real way it came about, is I had done a book before this one that was about Claude Shannon.

And Claude Shannon is this really interesting mathematician and engineer.

He's got sort of qualities of Feynman and qualities of Einstein, and he worked at Bell Labs.

Bell Labs is another place in the 20th century was, I mean, it was the Olympic dream team of tech talent.

It was unbelievable the things they did. We, we, like you and I are having this conversation because of communications networks that they built, satellites that they built, transistor. I mean, the transistor is basically the reason that we have like any of the tech that we're using right now.

I started to think about what are other like clusters, nodes of talent, and the PayPal Mafia is just like one that always came up. And no one had done a book about the creation of PayPal.

People had done books sort of about individuals in this group, or like, you know, like somebody, Ashley Vance had written the Elon biography, you know, Peter had written Zero to One, Reid Hoffman had written books like Blitzscaling and The Startup of You.

But no one, like, I found that no one had really gone back and was like, well, yeah, but you all started at this other company. It's called PayPal.

It's still around.

What happened there and then? And I, that's what started, is it just, there wasn't a book about this experience. And to me it was, it was like, like college or the military or some formative period in these people's lives. And these people were people that like, you know, have redefined the technological world.

So like there's probably something to learn from their first experiences. So that was what started the project and that's what became The Founders.

Got you. I bet in a few years, I don't know when, there'll be something like that about MrBeast and his mafia.

I'm 100%. Yeah, it's hard not to. The scale that he gets, that he's operated at. I think the other thing I love about his story is just how early he started. And like, I mean, that's like a story of compounding, right? Like it's— and to think that he was obsessed with YouTube before it was the platform that it was now. Like I— that, that whole story, I don't know as much about it. As I should, but the things I've heard, I, I'm totally blown away by.

It's incredible. I started making YouTube videos when I was probably 7 or 8. Wow. Maybe, maybe, yeah, 9, I wanna say. I don't know, sometime around then. And unlike MrBeast though, I did not have that stick with it behavior. Whether it was natural, you know, my parents were, fighting a lot, divorce, like going through that emotional. I also just, yeah, I, I just didn't have that. Um, and it's so interesting to see somebody like that who did. And you know, it's, it's beautiful. And I hope when I have kids one day, whatever they choose to do, like, you know, I, I, the, the power of compounding, you know, is just like, oh, it's crazy. Like if you start young, you know, like you, you could do a lot, you know?

Yeah. And I actually think it's, it's one of the things that as a parent, it's hard to get right.

Like, I can only do so much. You can only encourage people so much, right? And then, then there's kind of also like this challenge of like, you know, MrBeast probably also like didn't have the easiest childhood growing up because of the YouTube obsession. I mean, he, we see the success, but we don't see everything that came for it, right? And, uh, but I am 100% on board with you on the idea that starting early and staying with an obsession way past what is normal is, to me, like, it's the quality that defines my best friendships, my best projects, everything I'm interested in. I like obsessive people who, like, stick with their obsessions for 50 years, you know? Like, that's, like, my, that's my thing.

I just, I think you're right, it's hard to do that How does somebody do that?

Those questions are really interesting to me.

100%. I've been tweeting since I was probably 14, 15.

Wow.

Went back, found old tweets about girls, went back, old tweets about school, about Chipotle. Just really funny to be able to see that. And even tweets about like, hopefully I'll be able to, you know, grow business and not have to work in corporate kind of thing. It's right. Yeah, it's It's really cool. And yeah, I hope somebody who's younger and listening to this takes the inspiration and keeps running with it. I'm curious, what was it like sitting down with some of the PayPal Mafia? Like, A, how did you manage to get in contact with them? Just like tactical question about that. And then, you know, sitting, talking, like, what was that like?

Yeah, I can answer the questions in order roughly.

You know, as you could imagine, like the book, the book took a long time. It took 6 years. And the reason it took 6 years is because it took a long, long, long time to get access to everybody that I needed to talk to. These are very busy people. You know, my call might be sandwiched between like a prime minister and a CEO. Like, it's not the easiest thing in the world to get on their calendar.

I think there were a couple of things going in my favor. One is that I had done books before this one. So they sort of like when you walk in and you hand somebody a book, they know you're not like, this isn't your, you know, you're not in the Little League.

You sort of know what you're doing, right?

That was one thing. The second is that I, the person I started with was Peter Thiel and he made two intros to a couple of people. And then I never, I tried never to like go back to one of the people that had already made intros and make more intro asks, right?

Like I wasn't a burden. And so I just daisy-chained like I mean, hundreds of introductions of different people.

And my basic thesis was, you know, this story is 20 years old.

It's all sort of water under the bridge at this point. Someone's going to write this. Like, you may as well have it be somebody who's a little nerdy and likes computers and likes technology, right?

And then I think the other thing is I wasn't there for 5 minutes.

I wasn't there for the quick quote. I wasn't there to publish weird headlines.

I was there to write a book, like a book of history that's, pretty long and well-written, and I wanted to sit down and actually talk. And I think that's just not what, you know, it's like sort of not the usual pace of these things.

Usually they get somebody who's writing about them and it's like 2 seconds and whatever.

But for me, I knew that wasn't going to be sufficient for a book like this. And so tactically, it was just intro to intro. And then I would say a lot of cold emailing too, because the people who are not well known, I would just cold email dozens.

I mean, hundreds of people I cold emailed.

And you'd be surprised, like, I mean, I'm sure you found this to be true too. Like, it's amazing what people who, who will respond, right? And even the busiest people in the world, you can find a way to get to them if the ask is genuine. And I think that's the other part about it is I wasn't there, I wasn't there to like make PayPal look like some weird global conspiracy. I was telling the story of how the company was created and I wanted to give people a chance to share their stories and then I was gonna treat those stories with respect.

And so if you communicate that in different ways, like people definitely opened up and over time it actually got kind of crazy. Like, I would have people say no to me and then like a year later they would hear from their friends that like everybody else would talk to me and they'd be like, all right, I should talk to you, you know? And so that became kind of cool.

I would say you asked a question about how, what it was like to sit with them. It was, it was great. I mean, it was one of those experiences that I caught these people, I think, at the exact right time in their lives because they're not, you know, they're not retired. They're still doing things in the world. And so we were able to have really substantive conversations.

And at the same time, like, this experience was 20 years in the rearview mirror, so it was okay to talk about it.

100%. Cold email is, is how I've done everything.

Yeah. And you have to be really judicious, like cold emails and cold emailing is an art. It's like every—

if you saw the number of drafts I wrote for some emails to the people that I emailed, I mean, it was crazy. I would agonize over Every single word. And I know they wouldn't care, but I cared.

Oh yeah. I'm, I'm the same way. Uh, I love cold DMs. That's, they changed my life. Um, I actually, yeah, I got in contact with, uh, the guy who was the Bad Luck Brian meme.

Wow.

Um, yeah, which is like weird. Um, but need to, need to follow up on that interview. Um, curious, uh, on your, on your website it says you're a speechwriter as well.

Yeah.

Who do you write speeches? Who do you write speeches for? Is it, is it for you, for others?

Oh, it's, it's for others.

It's kind of the hustle that it's like the day job hustle and then the books are the side hustle, right? So I write for politicians, I write for CEOs, I write for university presidents, Hollywood actors, everybody.

Like, so an example would be like somebody needs to give a commencement speech, but like if you're a CEO, I mean, you know, your job is not to write a commencement speech.

You know, your job is to like go be a CEO. So you work with somebody like me to get the stories out of you. To tell your story well.

Yeah, let's say you're invited to give a wedding toast.

I had to do a wedding toast recently, you know, so it's like, okay, like you're a very busy person. This is not a good use of your time.

So you find somebody like me and you work with me, you know, in general, I would say that the goal of a speechwriter is to somewhat be invisible.

Like if I do my job well, nobody knows that it was written by me. They think it was written by the person speaking.

Exactly. Same with ghostwriting. You know, nobody knows half of these people's tweets are ghostwritten, which is crazy. How did you start writing speeches? Was it through like an agency of some sort, or was it just through relationships that you built?

Yeah, it was through relationships mostly. I was working in the D.C.

mayor's office and there was a big speech coming up called like the State of the State. It was like sort of the State of the Union, but for the city— sorry, the state of the city, the state of Washington. And I just put my hand up like they were just—

it was so clear everybody's like a little too busy.

And I was like, listen, like, I kind of know how to do this and I could try it. And that's— I tried that. And then I just kept building from there. And one thing kind of built on the next, built on the next.

And then you just sort of, you're, you know, I'm sure you found this, like your clients kind of tell other people about you, other people find you. And I would say at this point, like speeches are more limited, a more limited part of what I do.

I do a lot of op-eds and I do a lot of like talking points or like you need to say something that's quick. Or you have like a quarterly update to your employees and I'm writing that.

It's that kind of stuff. The speeches are, I mean, speeches are a big, big, long sort of thing. And to be honest, there's not that many that people give anymore anyway.

Interesting. I didn't realize op-eds were—

Oh yeah. Like almost all of them.

That makes sense. That's, that's so cool. I'm curious what, what's kind of your style of writing? Like me personally, Just when I start, wait, when I wake up, just coffee and start writing until lunch and then take a break and then nap or something in the afternoon and then write at night in the afternoon, uh, whenever, like my newsletter is weird. Like I don't set hours to do it. I just like sit down and start doing it or in between things. Um, curious what, what your, uh, preferences on that stuff and, and also how managing it as a father, cuz I'm nervous as hell about that.

Yeah. So I'll answer that in sort of sequence. So, because one shapes the other. So I get up super early in the morning and I do my writing that's for me first. So this morning's a good example, like 4:30 and between 4:30 and 9:30, I was working on book projects that I'm currently engaged in. And it was the, it's what I sort of think about as like distraction-free time. You know, the world basically like doesn't bother you from 4:30 to like, I don't know, around 8:30, right? And you can kind of like, nobody cares because nobody's texting, right? And, and so nothing, like, because nothing's urgent, you can actually get done like the important personal stuff.

And so I typically will just, I will try to cut the time between when I wake up and get started. And generally that time is sometime between 4 or 5 o'clock.

And like, that's like a good day for me is when I start then, because then I can just get that stuff out of the way.

And then switch to client work after, because then you just, you know, you're sort of like making your business work.

Right.

And so that's kind of how I split up the day. And I would say like, I don't know how your experience has been, but it does become a little bit like training a muscle.

Like the more you write, the better and easier it is to write more, you know?

And so for me at this point, like if someone said, if you said to me, hey, I need an op-ed by 3 PM about this subject. It's going to sound crazy, but I could do it. Like, it's really not that hard anymore. It's not great.

It's also a bit of a scary skill because you're like, wow, I could argue on any side of a topic no matter, you know, like, it's like a little weird, but it just gets easier over time. At this point, I've written hundreds of op-eds, right?

And so it's not that difficult. So, but my, my schedule and my kind of practice is like, just get up and get going because if you don't, then everything else every other little thing crowds the day, right? Like, it's astonishing how much time you can lose to like Amazon returns.

I mean, like, you're listening to random stuff that happens. You get an email about something and then you're distracted for 25 minutes.

The way to beat that for me, just do the important stuff as early as possible. Do it 7 days a week.

Like, I found that that works really well for me.

If I, if I don't break the chain, I—

it becomes like a default.

At this point, it's my default. My default is just get up, and go.

And there's not like a way that I have— there's no other way I have to think about it. It's not like I wake up and I'm like, I should really like take a day off.

I'm like, nah, just like get up and go. Like, this is the, you know, you asked a really important question, which is how do you do this as a dad? So it's even more important for me once I became a dad to like keep the insanely early schedule.

I didn't keep an insanely early schedule before I became a dad, but because my daughter gets up around like 6:30, 7-ish, and she really wants to go like right when she wakes up. I have to use the time in the morning productively because otherwise there's no time left and I'm too tired by the end of the day to do anything productive. And so I just get up like, and I, it's actually funny, I'll tell my friends, I'm like, I'm on borrowed time. My daughter, like Venice, my daughter's name is Venice. I'm like, Venice is gonna be awake. She's gonna be awake in 2 hours. I'm on borrowed time. I gotta go. And so I just, I don't do any phone calls.

I don't do any meetings. I don't do anything in that early morning time.

And then everything else after that is just whatever.

Nice. Nice. Yeah. I love waking up and just working on my own stuff first. I was telling a friend who was getting too busy ghostwriting to work on his own work. I was like, you gotta treat yourself like the best client.

Yeah. Are you—

and it's hard, by the way, it's super hard. Like I, it's also, I say all that and this schedule took a lot of like pain and, you know, reshuffling and stress and how does it work and how do you overcome the— all that stuff is real. But I think the abiding principle for me is if I do my stuff first, it, it actually, it's like almost like I won the day and then everything else is like going to be great.

But if I don't do my stuff when I'm doing client work, I'm always in the back of my head like, why did I do that? You know, I should have done my stuff and now I can't get it done. And now I have this excuse.

And then this email came in and this crisis happened.

I just don't want to deal with that.

Same. I feel that completely. So you're working on a new book.

I'm working on kind of two new projects that are book length.

And, you know, one of them is probably a little bit more at liberty to talk about than the other. But it was one of these situations where, like, I wrote a proposal that didn't sell for a long, long time, and then all of a sudden it sold.

And it was this story that's not— it doesn't have anything to do with tech.

I met this woman who had spent 36 years in prison for a crime she did not commit.

And I met her and she was the most amazing person because she kept fighting for her freedom year after year. And I was like, Judy, you should really write a book.

And Judy was like, well, I, I, I live in, I mean, I've spent 36 years in prison, Jeremy. I have no idea how to do what you're describing. And so I worked with her over the course of several years to try to sell this book.

And we just, we could not get a bite on it. And then Hachette bought it all of a sudden.

And so I've been working on that and then another tech book, but I'm going to save that one for the next time you and I talk.

Nice. Nice. How did you sell your first book? Like finding an Asian and stuff like that?

Cold emails.

So this is like, gets back to my first book was called Rome's Last Citizen.

I basically convinced my buddy Rob from college. I was like, we should write a book proposal.

And he was like, we don't know anything.

And I was like, doesn't matter. We're just going to write the proposal and then we'll see if we can get somebody to bite.

And we sent some cold emails and I actually sent one cold email to an agent that had gone to Duke where I went to school, and she responded and she decided to represent the project and then she sold it.

And so it was a classic, like, I eat my own dog food, like the cold email helped change my life too, because that was what led me to my agent and that's what led me to book contracts and doing that kind of work.

Nice, nice. I'm working right now with, her name's Ellen Fishbein, kind of indie publisher. They just published, um, uh, what's his name? Uh, Draper, Tim Draper's book. Oh, cool. So yeah, it's cool. Um, definitely want to explore, uh, yeah, the, the hardest part for me, like, as a teenager was how do you get an agent? Like, how the hell do you find this person? You know?

Yeah, it's, it matters less now, you know, look, you're, you're somebody that you have an audience, you have people who are paying attention to what you're doing, you have a way to distribute. And production costs for books are so low now that for my next projects, I'm not sure I'm gonna go with a traditional publisher.

Like, I'll be honest, like, I, I, it's nice, but there's, they don't, I mean, it's nice and there's some support and some editing, but I can find everything I need using independent sources or using, you know, hybrid publishers, that kind of stuff. And the economics are way better for authors in some ways if they don't go with a traditional publisher. Because unless you're getting a huge advance, like you're just sort of getting an advance against sales and the royalties are super low. So there's not, I mean, I've said this before, but like there's really nothing like stopping somebody from having a multi-million copy book where they make many, many, many more, many more millions of dollars than they would have if they had gone with like a Random House or whatever. And so I would like, I don't know, I'm, I'm somebody who's done every book I've done, I've done with a traditional publisher.

And my next, like the two projects after this one, I'm like, I'm not sure I'm gonna do that.

Like, I just don't like the royalty split. I don't wanna lose 85% of my sales to some publisher.

Got you. Yeah, I'm quite happy I'm going with her. But there's like that side of me, you know, where it's like, oh, I want the prestige of that, but I'm quite happy with how things going.

I think you'd be surprised how much It doesn't make a difference.

Yeah, it's probably one of those things where you think it feels good and then you get it and you're just like, ah, okay.

A book's a book. Can you name the publisher of the last book you read? Probably not, right? Like I couldn't. I'm reading 3 books right now for various projects. I couldn't tell you who published them.

That I'm not, by the way, I'm not saying like I've had really good relationships with my publishers and they've been good to me and they've like, they push my thinking and they've done some great things, but for a certain kind of book, What I don't want to happen is I don't want somebody who says, I have this great idea and they send out a bunch of letters to agents and agents send back a bunch of rejections. And then that person is like, no, I'm good.

I'm not gonna do it.

I would hope that that person says, in today's economy, I don't need an agent.

I could go do anything I want because there are all of these other publishing options, like what you're doing.

Like, and your book could, I mean, like your book could outsell many traditionally published books.

Like, yeah.

In fact, I have no, in fact, I have no doubt that it actually will. I'm like, Convinced that it will.

Nice. I appreciate it. I'm very happy with how the presales are going and having a lot of fun with it. Speaking of books, what have you been reading?

Let's see, what have I been reading? It's sort of like a movable feast at the moment because I'm like looking over to see what I'm reading. I have this book because I'm writing a book about somebody who spent time in prison. I'm reading—

my friend Chris Wilson wrote this great book called The Master Plan. Chris was incarcerated when he was 16.

He was granted his freedom in his 30s. He's an amazing story. He's like a huge artist now and he's built businesses and he's super successful, but nobody could have predicted that for his life when he started. And he wrote a book about it called The Master Plan, and it's insanely good. And then I'm reading this memoir called Educated, which is like a pretty famous memoir.

And it's because I've never actually, like, you know, I have to—

I've never written like a memoir before. So I want to find like, what is great memoir? Let's like figure out how to use those tools.

This is going to sound funny. I read very— I'm like a utilitarian reader. I'm like somebody who needs to read with a purpose. It's weird. Once I started writing, I kind of have a tough time just enjoying a book, right?

I have to like have a reason and hopefully I shake that habit because it's not actually a great habit. It means you can't find random things to enjoy.

But I am reading those two pretty closely. Like, and when I say reading, I mean, I'm reading them, but I'm also like marking them up. I'm like looking, I'm like flipping things around. I'm like studying where things are on the page. I'm like taking mental notes.

So it's more like reading in order to write a book as opposed to reading just for pleasure's sake.

Got you. Got you. Yeah, I definitely feel that.

Are you—

you're a paperback person still?

I am. I don't know why.

I mean, I think it's force of habit for one.

Two, I find that I've never really played with a Kindle for an extended period of time, like long enough to appreciate it maybe.

But I think I'm going to get into it soon. And I love audiobooks. I'm like an audiobook and a hardcover guy.

I think that's going to change.

I just like every one of my friends is like, why are you like, why do you have like mountains of books in your house? They're just taking up space. You just should switch to the Kindle.

There is also for my line of work, there's value in like if I have a thought about a book I read, being able to pull it off the shelf is a different experience than having to go into a Kindle archive.

I am, I could be wrong about that, but it just feels that way to me.

Yeah. I, I switched completely to Kindle because of an app called Readwise.

Oh yeah. Yeah.

Yeah. Just absolutely love it. And I import everything to my Notion. So it just like is all in one place. So I'm, I'm obsessed.

Obsessed. Okay.

Well, that's a strong recommendation.

I should do that, I think, because it might also actually make my research process easier.

Some habits you're just like, like, I'll give you an example.

Like my first thing I do in the morning when I'm in book mode is I read, I don't write, I read. Because I want to like get the brain going and give, you know, caffeine time to do its work.

That's such a, like a, it's so instinctive for me to like wake up, grab book, go sit, read.

It's like brushing your teeth. It's just like, I don't even know how to be any other way, you know? And so I think I'd have to change that if I were doing the Kindle and I would want to make sure that I wasn't like reading on my phone on the Kindle app because then I would just like bounce all over and go into texts and stuff.

Oh, 100%. I have the old Kindle where like, oh, can't even really go on the internet too much.

Yeah.

Um, just keep, I only like, I don't bring my phone in bed anymore and, or in the bedroom and just have the Kindle there. So it's, it's like no distractions. It's my peaceful time.

That's great. Yeah. Well, you sold me.

I'm gonna get a Kindle after we hang up. I'm gonna get one and, and play around with it. Nice.

I, I definitely recommend it. Um, Yeah, it's wonderful. That, that really covered all like the major questions I had. This was a lot of fun.

Yeah.

I guess if I, if I had to ask like one more question, one more question, kind of like book marketing and that kind of stuff, getting, getting the word out there, any like unconventional strategies or, you know, things that have worked really well for you.

Yeah, I would say there, let me offer two, one sort of a strategy, one's a tactic.

The strategy is, and you can appreciate this, I mean, I know you don't even need to be told this, but this is more for like people who are listening.

Your book launches the rest of your life.

You know, it, it's, people treat launch as like one day or one week or like I've gotta be on the bestseller list for this month or whatever. It's actually like if you write a great book and the book is relevant, just keep selling. Like, what's the downside of continuing to sell?

I still do book marketing for my Claude Shannon book. That book's been out for like 7 or 8 years, right?

I still get like sales and interest and people and whatever. And so I think that's like one thing to remember is like marketing is not— to me, book marketing is not like you do it once and then you're set.

It's IV. It's like an IV. It's just going to drip for the rest of time. Now, not everybody needs to do that. It depends on what your goals are for your book. But if you love what you created and you took a long time to make it, which books take a long-ass time compared to anything else, why not continue to sell it years after it's been out? I never got why authors are just like, nah, I'm good.

I'm gonna give up now. Right? Like, why?

Like, you can still pitch, you can still talk to people. There's still millions of people have not read The Founders. I'm not gonna stop. There's millions of people that should hear about it. That's one thing is like to think about Marketing is a long game. The second thing I would say is, you know, of the things I've done for book marketing, the one of the best was Reddit. Like, Reddit is an underrated and like truly underappreciated corner of the internet. And I, my AMAs there were amazing. People asked such good questions. They were really thoughtful.

They went and bought the book.

I noticed the sales spike. And people don't think of Reddit as like a place to go talk about books, but it's actually like one of the biggest book communities on the internet. And I can't recommend it enough. Like, it's like one of those places, like, it's an— it feels more obscure than it is, but the people there are really thoughtful and super nerdy and like really engaged with ideas. And not on everything, obviously, but like for books and for a specific kind of book, Reddit can, like, if you love Reddit, Reddit will love you back.

Yeah.

Yeah. I feel that I've gotten a bunch of newsletter subscribers from Reddit. Just doing an AMA about social media marketing, content writing, you know, working with startups, that kind of stuff. I gotta do that for the memes book actually. That's a great idea. Yeah. I didn't even think of that.

Oh, it's like, and it's also like Reddit's where memes are born. It's where they like take over the internet. Like, come on. I mean, that's the place.

Exactly. Cool. I think that was like all the main questions. I'd love to do this again sometime soon.

Yeah, absolutely.

And let me know.

And it'd be great to help with your launch.

And congrats on pushing on, like, not waiting for somebody to give you permission to do the memes book. You were just like, I'm going to do it.

Going to do it. Yeah, I actually, I set it up first on Amazon by myself. It got taken down because memes wasn't allowed to be in the title. I put it on Gumroad, got like 40 presales.

Oh wow.

Um, and then, you know, signed kind of the book deal with the indie publisher Ellen and, um, Altamira Studio. And so like, I, yeah, I'm so glad. And at first, even before the Amazon, sorry to go into the story of this, um, before the Amazon, I asked two friends if they wanted to co-write it with me. Um, they were too busy making memes and, you know, working on a project. And yeah, I'm very glad and I hope that a listener can also appreciate that and just go do the thing.

Go do the thing. Yeah. You don't have to wait anymore.

Exactly. All right.

Awesome, Jason.

Cool, man. This conversation. Yeah, this conversation's gonna go live on Sunday. I'm gonna do a couple posts around building your own mafia and yeah, we'll make sure to feature the book heavily.

Awesome.

I really appreciate it.

All right. Thank you.

All right. Have a good one, man.

Bye.