TIP417: THE INCREDIBLE STORY OF THE PAYPAL MAFIA

W/ JIMMY SONI

27 January 2022

Trey Lockerbie sits down with author Jimmy Soni, to discuss his new book The Founders – the story of Paypal and the entrepreneurs who shaped Silicon Valley. The original team at Paypal has become known as the “Paypal mafia,” because nearly all of them went on to found other multi-billion dollar companies. For example, Elon Musk went on to found Tesla and SpaceX. Peter Thiel went on to found Palantir. Reid Hoffman went on to found LinkedIn and there’s more! Max Levchin with Affirm and others. David Sacks founded Yammer. How on earth did all of these founders get lightning to strike more than once? It all originated with Paypal. This is a story widely understood, but hardly explored in depth. 

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IN THIS EPISODE, YOU’LL LEARN:

  • Members of the Paypal mafia and their origin stories.
  • How Paypal came to be.
  • The many trials that Paypal endured.
  • The culture at Paypal and how it developed.
  • Jimmy’s main takeaways having personally interviewed each billionaire and years of additional research.
  • And a whole lot more!

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Trey Lockerbie (00:00:03):
Today’s episode is a fun one where I sit down with author, Jimmy Soni, to discuss his new book, The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley. The original team at PayPal has become known as the PayPal Mafia, because nearly all of them went on to found other multi-billion-dollar companies. For example, Elon Musk went on to found Tesla and SpaceX. Peter Thiel went on to found Palintir. Reid Hoffman went on to found LinkedIn. Max Levchin with Affirm. And others, David Sacks founded Yammer. I mean, the list goes on. How on earth did all of these founders get lightning to strike more than once? It all originated with PayPal. This is a story widely understood, but hardly explored in depth.

Trey Lockerbie (00:00:46):
In this episode, we discuss members of the PayPal Mafia and their origin stories, how PayPal came to be, the many trials that PayPal endured, the culture at PayPal and how it developed, Jimmy’s main takeaways having personally interviewed each billionaire and years of additional research, and a whole lot more. This is the kind of story that would make a great movie. You’ll be able to see quickly and clearly that Jimmy has done an immense amount of research and provide some amazing insights. I hope you enjoy it. Here’s my conversation with Jimmy Soni.

Intro (00:01:21):
You are listening to The Investor’s Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected.

Trey Lockerbie (00:01:41):
Hi, everybody. Like I said at the top of the show, I’m here with Jimmy Soni, the author of The Founders. Jimmy, welcome to the show.

Jimmy Soni (00:01:48):
Thank you so much for having me.

Trey Lockerbie (00:01:50):
I find the story of the PayPal Mafia just endlessly fascinating because at this point, it has all this almost myth and lure around it where it’s like The Avengers story. All these folks have gone off and just created more and more billion-dollar companies. And there have to have been something in the water that they were drinking in the PayPal office or something at some point. So I would love to, first of all, take a step back for those who aren’t familiar and just describe who the PayPal Mafia is. And then I want to lead into what made you want to write a book about them.

Jimmy Soni (00:02:27):
The Avengers is a good metaphor. I haven’t used that, but I think I might borrow it. I’ve always been using the 1990s Chicago Bulls. This is last dance with Silicon Valley where you have all these amazing people who come together at one time. So just to give your listeners some background, I suspect that most of the people who listen to you are familiar with the names of the alumni, certainly the better known alumni from PayPal. It includes people like Elon Musk and Peter Thiel and Max Levchin and Reid Hoffman, David Sacks, Keith Rabois, among many, many, many others. There are also folks, the CEO of ancestry.com is a PayPal alum. Some of the senior-most people at Facebook. Several high level people in government are ex-PayPal.

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Jimmy Soni (00:03:16):
The founder of kiva.org, a social enterprise is an ex-PayPal alum. And there was this interesting thing that I had worked on. I had done a biography of a mathematician named Claude Shannon, and he worked at a place called Bell Labs. And Bell Labs in the 20th century, they put the Bulls dynasty to shame. They invent the transistor, they invent touchstone dialing, the laser, they win six Nobel Prizes. It was just an incredible powerhouse of talent. And I just started thinking about other clusters. Not individual stories of success, but what are places in American life, particularly technology, where you had groups of people come together. I looked at General Magic, which is one example. There’s a great documentary about General Magic. I looked at Fairchild Semiconductor, Xerox PARC, and I fast forwarded that history to PayPal.

Jimmy Soni (00:04:04):
And I’d walk in as the person who maybe asked one too many questions about why there wasn’t a more comprehensive look at that period in these people’s lives, meaning, you get a lot of coverage, understandably of Elon and Tesla, or of Max and Affirm or of any of these other things. But why hadn’t anyone gone back and tried to excavate this 20-year-old story. And then that was what interested me. I thought to myself, it’s one thing to ask them questions about what they’re doing today, but what made them who they are, what were their defining experiences? And among those defining experiences was their creation of PayPal during the height of both the dotcom boom and in the middle of the dotcom bust. And so it was this really intense experience and I wanted to understand it. That was the motivation, I wanted to know what happened.

Trey Lockerbie (00:04:58):
And before we get into the background a little bit more, paint a picture about the research that went into this, because it was over a number of years. You seem to have had amazing access, for example, you say in the book how you had a three-hour plus interview with Elon and he was rummaging around in the attic to come up with memories of this time, which I just love that visual. But talk to us about what went into the research for the book.

Jimmy Soni (00:05:24):
Yeah. And just for the spirit of true fact-checking, his line about it was that I was making him rummage in the attic. He wasn’t actually rummaging in the attic, but he felt like he was because here he was well into his Tesla and SpaceX years and this guy shows up and has questions about 1997 and 1998 and 1999, which is probably something that nobody asks him about these days. I’m not a tech writer or journalist, I’m a historical, most of my books have been historical narratives and I like that sort of work. I came at this as an outsider. To give you a sense of the process, I just daisy-chained one interview to the next to the next. I did 275 interviews over the course of five years. I was given access to a lot of, let’s call them mementos, memorabilia, old emails, old notes, people kept their PayPal t-shirts.

Jimmy Soni (00:06:16):
So I had a lot of access to that kind of stuff. And then I benefited from the work of the internet archive, which folks who have time to spend there on the internet need to go down rabbit holes. You can look at old versions of webpages, old versions of anything that was online. And so I started out, I didn’t think this would be that intense a project, but I was at best, an uninformed person asking questions. So in order to get more informed, I had to go back and really pay attention to what they had done and said over the years, let’s say, the late 1980s through 2005. It’s going to be funny to talk about this, I just went on YouTube and I went on Vimeo, and I went on the C-SPAN archives and I would find every scrap or nugget I could find where someone had spoken about the company.

Jimmy Soni (00:07:08):
I went and just looked at every mention of PayPal for basically a period of 20 years and I started to piece together a picture of what I thought had happened. And then, the virtue of this book as opposed to my others is the subjects are alive. So I had the ability to email them and say, “Hey, I’d like to do this, but it’d be useful to have some of the context, some of the colors, some of the stories I don’t have access to.” And I will say to a person, everyone was very gracious. These are people who have no time, I mean, no time. I don’t know how some of these people do what they do. And they made time for this.

Jimmy Soni (00:07:41):
And I think it was a walk down memory lane. I had multiple discussions with Reid Hoffman and this is a person, I don’t know how he manages the schedule he has, but he made time for lengthy substantive chats about business strategy and about his approach to business at that time and why he made the decisions he made. And on down the line. I would also say that part of my, and this is important, part of my conceit with the book was, your listeners know the bold face names that built some of these companies. There are all these people who never got attention. They never got recognition, in some cases, by the way, because they didn’t want it. It was not something they sought. But they made really substantive contributions to the company.

Jimmy Soni (00:08:19):
So I spoke to all these folks who, in many cases during my interviews, they would say, “No one’s ever actually interviewed me about PayPal.” And I was astonished. But they had some of the best stories. And so I interviewed board members, I interviewed people who worked there for a few weeks, I interviewed customer service agents, on down. Because I do think that sometimes we have a tendency to think that what really happens is in the boardroom, but it’s not. The real substance of a company, particularly an internet product company, is in these little fine grain decisions that happen day to day. And I just wanted to get a texture for what that was like.

Jimmy Soni (00:08:52):
It was a long process, but I had fun. I will say, every conversation taught me something new. If I heard the same thing 200 times, I would not have had 275 conversations. Every single person I spoke with revealed some new element or angle. And some of these are some of the most enjoyable conversations I think I’ve ever had.

Trey Lockerbie (00:09:14):
Yeah. I want to talk, especially about the culture there, because that also seems to be something very unique. But before we get too far into that, I want to set the stage for people. You just mentioned that some people weren’t getting the credit they’re due. This first person is not that. But speaking subjectively, Max Levchin is not a name that often comes up for me. So he’s a well known guy, he’s very successful, again, post PayPal, even more so. But he’s not a founder that is often in the headline. So I wanted to talk first about Max and what influence he had specifically at PayPal.

Jimmy Soni (00:09:51):
Yeah. And you picked up around him. Chapter one of the book is Max’s story. I saw him as someone who people ought to know more about him, I also just found his story endlessly fascinating and interesting and he’s just an interesting guy. He is a Jewish refugee who comes to the United States when he is a teenager, and had already fallen in love with computers when he lived in the Soviet Union, continued that love in the United States and ends up going to college at the University of Illinois Champaign-Urbana, which at the time that he arrives is just a buzz with all things internet because Marc Andreessen built the Mosaic browser then went and built Netscape and had become a huge success, and he’s on the covers of magazines.

Jimmy Soni (00:10:36):
And what Max and all his collegiate friends are thinking is, “Well, yeah, he was in that dorm and in that quad and he was taking that class and he was doing all the same things we were doing.” He set the course for what you could do in internet business at that time. So you have Max Levchin go to University of Illinois Champaign-Urbana, he built several startups that don’t work out, just some comic effect in some cases. And then he finds his way to Palo Alto and links up with a young investor who no one knows, named Peter Thiel. A few people told me, they said, “The story of PayPal properly told is the story of Max Levchin.”

Jimmy Soni (00:11:15):
And I don’t know that I would go that far, because I think it’s actually the story of several hundred people, but there’s a reason I wanted to have him kick off the story because there is something fundamental about the University of Illinois and that experience. And I would also say there’s something about his cryptography background and his interest in mobile security that lays the foundation for the kind of company PayPal becomes. I think the other piece of it is, just to be honest, I always felt like I was the B student talking to the A students whenever I was talking to Max or Peter or Elon because these people, they’re several IQ points ahead of many of us and myself, for sure. He’s just razor-smart.

Jimmy Soni (00:11:55):
Some people have testified to him having a near photographic memory, and I saw that vividly. He would remember things and I would find a piece of paper that had the exact detail. And I think of him as somebody who’s an engineer’s engineer, and that’s how many other engineers described him. The other engineers I interviewed described him with real admiration, in part because he was not an executive, he was an engineer. And in fact, he, like many of the people who are at the top of the story, actually don’t enjoy managing people, they like building things. And I found his story just really interesting.

Jimmy Soni (00:12:24):
And it was helpful to also understand where some of the genesis of the early days of the company comes from, because it’s really from Max and the Confinity. On the Confinity side, this other half, his half of the company, he’s really the genesis of a lot of early thinking around mobile security and what becomes mobile payments.

Trey Lockerbie (00:12:44):
Yeah. That relationship with Peter Thiel that you really put a lot of color around in the book is so fascinating because you’re describing them sitting in bookstores, pitching puzzles to each other for fun. This is how they spend their free time. These are not normal people. You know what I mean?

Jimmy Soni (00:12:59):
No, they are not.

Trey Lockerbie (00:13:00):
This is not a normal friendship.

Jimmy Soni (00:13:03):
Yeah. It’s worth going into that. The way I write it is, it’s a particular kind of person who turns math into sport. And what they would do is they would try to best each other with puzzles. They were both ace chess players. They enjoyed pushing the limits of their minds. And it’s interesting, I think back, I’m like, I don’t know that I’ve ever gotten together with my friends and decided to solve puzzles, but I guess that’s what you do if you’re Peter Thiel and Max Levchin because their early get-togethers were these elaborate sussing out process. Max would toss a puzzle to Peter, Peter would toss a puzzle back at Max, and they would spend hours doing this, hours, just trading these bits of logic games and numbers games. And it is.

Jimmy Soni (00:13:48):
I don’t think they know that it is different from how the rest of us operate in the world, but I do think that there’s something about it that is very particular to a specific subset of this group of founders, that there’s a real passion for math and logic games.

Trey Lockerbie (00:14:04):
Yeah. You can tell they have this insatiable appetite for knowledge and just expanding their mind. It’s a good segue to Peter Thiel, who a lot of people do know. But similar to someone like Elon Musk, let’s say, he’s become mostly known for his post PayPal activities. So being the first outside investor in Facebook, for example, founding Palantir, a billion-dollar company, taking down Gawker, which maybe people are less familiar with, but I find it a fascinating story. What were some of the events that led Peter to meet Max and decide to found PayPal? You describe Peter as an investor, which I also thought was interesting, because obviously he came out of school, became an attorney. Where did he get all this money to start investing in these startups?

Jimmy Soni (00:14:45):
It’s interesting. I do think that like a lot of the folks who are at the heart of the story, their contemporary activities suck all the oxygen out of the room. The way I write it is, space travel is more interesting to write about than late 1990s payment service. And so it’s easier to focus on these things they’ve done in my book. It’s 1997, 1998. He had what he described to me and he’s described in other places as a midlife crisis, but he was 25. So like a quarter life crisis. And he had actually been turned down for a Supreme Court clerkship. And he’s spoken about this, this isn’t new news. He had been turned down for a Supreme Court clerkship and it was, as he puts it, the most devastating event. And it was, “Oh my God, is my life over?”

Jimmy Soni (00:15:28):
But it actually leads to him pivoting and becoming a global macro investor. He moves back to California, where he had grown up for part of his childhood, and he begins, as everyone does, this mania for all things internet. Anything with a dotcom is getting money and all of a sudden it’s in public, and there’s this real gold rush, and he wants in. And he is passionate about technology. He went to Stanford, so he’s got [inaudible 00:15:55] to the area, and he starts to meet people. He goes to different things and he connects with different people. And this is how they met. Peter is teaching this very small class at Stanford around currency investing based on his experience doing some of that, and Max Levchin is looking for air conditioning because his Palo Alto apartment doesn’t have any and it’s especially hot summer.

Jimmy Soni (00:16:17):
So what he does is he floats around Stanford’s campus, he’ll find little notices for classes that are being taught that are open or relatively open, and he would go and sit in the back of those classrooms just to get some brief relief from the heat. He goes to this class that Peter Thiel is teaching, and he’s heard Peter’s name before through a friend, Luke Nosek. Peter had invested in Luke’s startup. Max says, “Okay, I know his name, he’s teaching a class. Worst case, I get air conditioning. Best case, I get to talk to the guy.” He goes to the class, it’s a small class, so he can’t just hide in the back just to benefit from the air conditioning.

Jimmy Soni (00:16:54):
And the way Max described it is he said, “This isn’t a computer scientist, but this is definitely a nerd.” And he said, “If I’m ever going to do anything in the financial world, I really should talk to this guy.” And Max also was looking for investors for startup ideas. And so he goes up to him and introduces himself. And basically what Peter says is, “Great to meet you. You want to start a company, we should meet.” And they agreed to have breakfast at Hobee’s. No one could have planned that, there was no grand introduction. It was Max looking for air conditioning, happening upon this class, going to it, and then introducing himself.

Jimmy Soni (00:17:31):
And they meet for breakfast, and that that’s the beginning of a very long business relationship, friendship. And I think it’s one of the great underexplored partnerships in business. I know your passion for Warren Buffett and Charlie Munger. And there’s a way in which these business partnerships are actually almost in some ways more interesting than sometimes the solo stories. And I do think of the Max and Peter partnership as among the more interesting in the history of, I would say, in the history of American business, because they each do something the other can’t, they’re both smart enough to push the other person. But there’s a very interesting friend dynamic as well that’s at the heart of it. But that’s how they meet and that’s what starts… Peter decides that he’s going to invest in Max. He gives him $100,000 loan and thus the earliest iteration of PayPal is born.

Trey Lockerbie (00:18:26):
All right. To continue setting the stage, now enters Elon Musk. It’s very hard to even contemplate this, but Elon’s first success even predates PayPal. And he could have even effectively retired before meeting Peter Thiel and co. Let’s touch on Zip2 and what set Elon up for this opportunity to even meet Peter in the first place.

Jimmy Soni (00:18:47):
It’s a great story, and I think, again, we have this challenge of he is who he is today. Today he’s hosting SNL and it’s hard to imagine a time when he was just someone getting started. And he applied and accepted into a Stanford graduate program in material science and engineering. And it’s a prestigious program. And all rational thought would suggest you get into Stanford grad school, you go. But the internet boom is happening right around him. And he has been writing code for a long time. He was an avid video game player, avid video game engineer. He feels like, “Look, I’ve got the skills to do this.” You’ve got people creating companies like Yahoo and Amazon and they’re no more talented than he is. So he comes to the Bay Area and along with his brother and a gentleman named Greg Corey, they launch Zip2. And Zip2 goes through several different iterations.

Jimmy Soni (00:19:36):
It’s originally called Global Link Information Network. A bit of a mouthful, but they adjust the name, they adjust the company’s ambitions. And it’s a wild ride, it happens very briefly, but the company does sell for a little north of $300 million to Compact Computer. And it’s a substantial exit. Substantial enough, that as you pointed out, he could have sat on a beach for the rest of his days and been quite happy, but he decides that he wants to do another startup. And he had been interested in the financial services’ sector and that’s where he turns his attention. Zip2, I think, it was formative. I think for any of us, our experiences between the age of, let’s say, 20 and 25, whether that’s first job, military service, a startup, a band, whatever it is, it’s going to leave an imprint. Zip2 left a powerful imprint.

Jimmy Soni (00:20:25):
It taught Elon about what it means to build a company and to create something from scratch. Now, he had done some smaller entrepreneurial ventures in college. I found this old ad for a Musk Computer Consulting that was buried in the archives of some student newspaper. So he wasn’t a total neophyte, but this was his first funded venture back company and it’s a success. However, Elon always thought of the success as a bit qualified. It was a financial success, but he had always imagined that the internet was going to be this revolutionary thing. And that he felt Zip2’s ambitions and its wings had been clipped by its investors.

Jimmy Soni (00:21:02):
So there was a sense, in my discussions with him where he said, look, he actually the internet as he thought it would be a nervous system for humanity. And he said, “And I had built technology, but I hadn’t seen it flourish.” And so there was this sense of like business unfinished, there’s real opportunity still, the internet boom is not over, so there’s some financial interest in doing this. And he had had some incipient ideas around how the internet could change finance forever. And by the way, just to give context for your listeners, we’re talking dial-up modems, inconsistent internet. You pick up the phone in your house and the download cuts off. A lot of us suffered through those years.

Jimmy Soni (00:21:40):
He believes that the internet should be used to reconfigure finance from the roots up and he thinks he’s the person to do it. And he goes and takes the vast majority of his Zip2, exit and puts it into his next venture.

Trey Lockerbie (00:21:54):
Yeah. That point right there, I found fascinating because obviously he didn’t have to do that. He could have raised more money. And what was interesting to me is just, it gives you an idea of how Elon thinks. But he wanted to show people not only, I think, his conviction, but he used it as a marketing ploy to enroll people into the business and get good key hires by saying, “Hey, I’ve got my own money, 13 million into this thing.”

Jimmy Soni (00:22:19):
It is something that comes up time and again. He really believes in putting skin in the game. And he had described this to me, but also has described it in other settings. The things he told me, I’d always see how consistent they were with things he’d said in other places. And he’s a very big believer in investing your own funds in the thing you’re going to do. Now, there’s also some benefits here. You get to control more of the company if you put your own funding in. I had read somewhere that there were some tax benefits, but I think that was actually a marginal part of the decision-making. My sense is that when he believes in something, he knows he wants to put his own capital in. And this is the first time in his life when he has this kind of capital to allocate to something.

Jimmy Soni (00:22:56):
Now, his employees, had this really funny interaction with Ed Ho, who is a Zip2 employee who Elon recruited to work at X.com and Ed was like, “That’s nuts.” That was his description. He was like, “That’s crazy. 13 million of your own dollars when you don’t have that much.” He was like, “That’s risk. Oh my gosh.” But there was also a sense of admiration. Ed describes that he would call people, engineers, in a white hot market for engineering, recruiting, and he’d say, “Oh yeah, yeah. The founder is betting his fortune on this. So you know it’s going to work because he’s burned the boats.” And there is that daring dude, the risk-taking, the quality of betting everything you have that is a part of who he is.

Jimmy Soni (00:23:36):
And again, I think there are more practical reasons, but this is funny to say out loud, I’m not sure there’s anything that I’ve worked on where I would take 90% of what I own and bet it all on this one particular thing. Call it whatever you’d like, that is a style in which he operates, it’s a way he operates, and it evokes surprise, admiration, scorn, total fear and terror, but it is how he does business. I find it remarkable for the following reason, when he came to the United States, he had very little. He and his brother were living, they don’t have money. They’re showering at the YMCA, they are living and working in the same space. So he is not someone who had anything to fall back on, which is why that risk, it’s even bigger, if you think about where he started just years before this, building Zip2. It’s astonishing. And it’s why even his employees were just so amazed.

Trey Lockerbie (00:24:35):
A lot of conviction and a lot of irreverence for money, it seems. And one thing just to give people more context on this, he walked away from that Zip2 deal with a little north of 20 millions. So putting in 13, I mean, that’s a good chunk of net worth that he had at the time. And then, to think that his checking account went from $5,000 to 21 million with just this check arriving in the mail. And then to turn around and bet on it. And he’s, again, in his early 20s. This just shows you a lot, I think, about how he just thinks and operates and I just find it fascinating.

Trey Lockerbie (00:25:09):
So he now goes on to start X.com. He’s putting this large amount of capital into it. Maybe not a lot of people are aware of this, but X.com actually merges with what is called Confinity at the time, Peter Thiel’s company. How did the merger come about? What was the main benefit? And then talk to us a little bit about how it almost collapsed.

Jimmy Soni (00:25:29):
There’s a great pre-history here. It’s the reason that I wanted to do this project, because I think we all live with PayPal today. We know PayPal. Fewer people know that PayPal is the byproduct of two companies that came together. One was called X.com, that was created by Elon and three other co-founders, and one was called Confinity, was called Field Length and it became Confinity. PayPal was a product that Confinity created. X.com and Confinity arrive around the same time, they launch around the same time. And Elon’s ambition for X.com is, “We’re going to offer everything financial that you could imagine. If you want insurance, if you want a mortgage, if you want a line of credit, if you want a checkbook, if you want a savings account, a checking account, a brokerage, we’re going to do it all. Oh, and we’ve got this feature that allows you to email money.”

Jimmy Soni (00:26:15):
So if I, Jimmy, wanted to send Trey 20 bucks, I can send you 20 bucks. And that’s super easy. That product arrives at the same time that Confinity launches a product called PayPal. Now, what PayPal was supposed to be was, if Trey had a Palm Pilot and I had a Palm Pilot, we were at lunch and I paid for your lunch, if you wanted to zap me $10, you could do it through the infrared port on the Palm Pilot. As a backup, because what are the odds that you and I both have Palm Pilots and the infrared port worked that day, et cetera, they created an email money feature that was, again, a backup to the Palm Pilot feature. The backup Palm Pilot feature called PayPal and X.com’s emailing money technology take off. And they take off at the exact same time on the auction website, eBay, which is, I suspect, most familiar to many of your users.

Jimmy Soni (00:27:02):
EBay users had this problem, there was no standardized payment process. It was like if I bought something from you, I had my choice. I could mail you a check, cash, money order, Western Union, whatever, and I could email you money using a series of different services. The two services that take off are X.com and PayPal. They take off for a variety of reasons, not least of which is they’re giving bonuses if you join the service and refer other people, it’s a classic referral incentive model. At some point, leaders on both sides of these companies recognize, “Look, we’re just going to spend each other into oblivion.” There is this week’s long war where X.com and Confinity are really duking it out and they’re staying up late and they’re trying to one up each other. And it’s classic, they’re just trying to fight and claw for market share.

Jimmy Soni (00:27:47):
Despite different visions, there’s this, what I describe in the book as a shotgun wedding. They’re fused together, these two companies, to unite their user bases so that they can say credibly to investors, “Hey, there’s only one game in town now. We have the most users, we’ve beat everyone else and we’ve got the volume and the volume is going to win.” But that doesn’t mean that a merger is going to be happy. These companies merge and there’s a lot of drama and tension, and people don’t know who’s going to work with who, there’s duplication of executives. The joke I wrote in the book is, there’s two people who handle finance and both their names are David.

Jimmy Soni (00:28:21):
And so you have this merger, but the reason they merge fundamentally is the idea that if you have the biggest set of users, you’ll own the market, and if you’re going to raise capital, we have a compelling story to tell. And in March of 2000, the joint entities raise $100 million round, which again, sounds like peanuts today compared to what you read in the news, but at the time, a nine-figure round of financing in the year 2000 was a really big deal. And they close it just days before the markets start to collapse in 2000. And internet starts to go bust, takes the wider economy with them. And it’s a really fortuitous turn of events, but that’s the brief history of the pre-PayPal pre-union, which is Elon as a company whose vision is really, the vision is big.

Jimmy Soni (00:29:05):
And I think that’s something for listeners to remember, he doesn’t think small, he’s not interested in winning the person to person payments score, he wants to change the financial system. And when he spoke to me about it, as he put it, he said something like, “When I talk about these things, it’s like me saying the sky is blue. It just seems obvious to me.” His view was, banks and governments have been writing bad code on old mainframes on COBOL and these old programming languages. Given that the technology has improved so much, why haven’t we improved the underlying infrastructure of finance? And it’s costing users money, there’s all these people in the middle taking a fee here, a fee there, what if we just got rid of all of that and all of your finances were in one place that was called X.com?”

Jimmy Soni (00:29:49):
And it’s a surpassing vision, it’s very big and it’s consistent with some things we’re seeing in the world today, but to think about that in 1999 or 2000, it’s visionary in the best sense, I think. And so that’s the pre-history. And then these two companies come together and as you might imagine, it’s a lot of horsepower to have in one room at that given time, especially with the markets tanking.

Trey Lockerbie (00:30:16):
Yeah. And on that last note there, I’ve heard Peter talk about this and perhaps in hindsight, it’s easy to talk about in hindsight. But I tend to assign Peter and his financial aptitude responsibility for having the foresight to close that capital when they did, because Max has even put it in the book, Peter, his horsepower was coming around the financial side of things. He wasn’t the engineer in the room, but he understood markets and he understood, I think, the bubble territory that the tech boom was entering into. And I think we probably owe Peter a lot of credit. That might have been one of his biggest impacts, I think, for the company.

Jimmy Soni (00:30:54):
Yeah. I think that’s right. To be fair, there’s a lot of signs of crazy at the time. Evaluations are out of control. It’s not just Peter. Elon gives an interview actually to his alumni magazine where he talks about how … he’s speaking at the ripe old age of whatever, 27, 28, and he’s saying, “There’s a reckoning coming effectively, something is going to happen and you got to be ready for it.” And so it’s not just Peter. But what Peter does do that multiple people in the story told me that he does deserve credit is, he was insistent that they turn promises into checks, that they turn commitments into real like, get the wire transfers done. Because he felt that the economy was on the precipice. He wasn’t the only one, there were others, but he was insistent that the company finish closing the actual round as opposed to waiting.

Jimmy Soni (00:31:42):
There were people on the team who wanted to wait, who wanted to hold out for more money or a higher valuation, but he was convinced that things were about to go sideways, and he was right. And I think it’s a little … you can’t go back and say, well, he was Nostradamus and all that, because it could have gone any number of ways. But I heard from the people at the front lines of that financing round, talked about how they had never seen him that insistent. And that did say something. And it wasn’t abstract, it was Peter who would call and say, “We’ve got to get this done. It’s all dependent on this.”

Jimmy Soni (00:32:13):
And I had multiple people then say to me that in hindsight, that round closing enabled the company to continue to exist through a very hard period, because if they hadn’t closed that round, the money in Silicon Valley dried up and you weren’t going to close a nine bigger round in late 2000 for an internet company that’s losing money.

Trey Lockerbie (00:32:35):
So not only did they go through a very hard time economically with the external forces at play, PayPal was what you call “startup under siege” from the very beginning. So talk to us about some of the other challenges that the company was facing in those early days.

Jimmy Soni (00:32:52):
It’s remarkable that they managed to make it work. I look back and I think when I started, I knew there were challenges, but I didn’t realize just how many things they faced. Domestic fraudsters, foreign fraudsters, drama within the team, inquiries from the Secret Service, the Better Business Bureau, concerns about his use for everything from drugs to money laundering, chargebacks, fractured relationships with credit card associations, banks that didn’t want to have anything to do with PayPal. You name it. They had copycat products built by their own investors. PayPal is not the only payment system that’s on the block. It’s, everybody wants to get into payments because it’s hot and because the internet is hot. And so it’s not one challenge, it’s challenges from all sides.

Jimmy Soni (00:33:39):
And I think the biggest challenge, the one that I think probably I gave most attention to and I think probably was the biggest risk is, the company was just losing money. At one point they’re burning $12.5 million per month, they’ve got maybe four to five months of runway left. And their investors have said, “You’re not getting another $100 million round.” But that was a once in a lifetime go, let’s say, once in a dotcom bust kind of go. And that is the biggest thing, is that the company is just burning through the funds it had already raised, and you have this image of a burning platform and the company is a topic. But they faced every challenge you could face.

Jimmy Soni (00:34:18):
And I would also say, none of these people are seasoned operators. They were not who they are today. They don’t command audiences. These are people making it up as they go along. So it’s not like there’s some wise and Obi-Wan figure telling them exactly where they need to go, this is just figuring it out as you’re going along.

Trey Lockerbie (00:34:36):
I love this idea of all this horsepower in one room, because the management team we’re talking about, you paint them as being highly dysfunctional. So they were going through all these external impacts on the company, but they also had this disorganization happening internally. What were some of the best examples of the quarrel that was happening within the management team, and how did they end up pulling through and working together? Obviously, people came and went is what we’ll talk about, but what were some of the biggest moments of them butting heads?

Jimmy Soni (00:35:06):
I don’t know that it was dysfunctional, it might have been. There are parts that certainly were. I would say that it was disharmonious. There was a lot of, call it spirited debates. Let’s say it’s spirited debate among these very big personalities with huge IQs. And I think any room that has Peter Thiel, Elon Musk, Max Levchin, David Sacks, and Reid Hoffman in one room, there’s many others who are at their level if not surpass them, but just those people having disagreements, your disagreements, they’re not going to be mild, you’re bringing some real heft to those discussions and debates. And it was interesting because I actually come to the conclusion that the intensity of the debates is part of PayPal’s secret sauce from that era.

Jimmy Soni (00:35:55):
And Max Levchin has a few great lines about this that are in the book. And he said, “It’s actually dangerous if people are saying critical things, but saying it behind each other’s backs. We just said the critical things to each other’s faces and it made the company better.” Now, that doesn’t always make for probably the nicest place to work, the friendliest environment, but I noticed this really interest thing when I was interviewing people, let’s say not the bold face names. I remember interviewing a few people and I might say something and they were very quick to critique something I said if I said something wrong, meaning they had no shyness about even calling out when I was incorrect about something. And it was bracing. It was this bracing quality of like, “Well, you’re wrong. Here’s why you’re wrong. I’m going to tell you the truth.”

Jimmy Soni (00:36:39):
And what these people tried to get me to understand is, this is not personal, it’s about the ideas, it’s about rigor, around the ideas, and around the analysis, and around how you think about business. It is not, “I don’t like Trey.” It’s like, “Trey said something, and I’m going to tell you why you’re wrong.” But imagine doing that with people who have photographic memories, are chess champions. There’s this story, it might be apocryphal, that Elon read every book in his childhood library and started reading the Encyclopaedia Britannica because he ran out of books. So even if that story is partially true, you have people at that level who are having those kinds of bronchus debates. So I don’t know that I would describe it as dysfunctional, because it was functional, they got the job done. I would say it was disharmonious but productively disharmonious.

Jimmy Soni (00:37:24):
And actually, Jeremy Stoppelman, who is the founder of Yelp, who was another PayPal alumnus, he gave me some really interesting thoughts about how that level of honesty is actually hard to achieve, that it matters that you are that honest, because it’s actually out of respect for the other person. You respect that person a lot and you want to improve, you want to help them improve. Will they always get it right? No. Were there obviously some factions and things that were created? Sure. But I actually think the powerful lesson from it is, do we have people in our lives who are willing to do that for us? Who in our lives cares about us or cares about the quality of what we’re doing enough to just call us out when we’re dead wrong and to not sugarcoat?

Jimmy Soni (00:38:03):
Again, I’m not sure that everybody would characterize it that way, but I was looking for what these people might have taken from it. And from my perspective, that’s what they took from it is, boy, it’s important if you care to be that honest and it means management meetings aren’t always going to be fun, but you’re going to try to fight for the right ideas.

Trey Lockerbie (00:38:19):
So as I mentioned, some people were moving in and out. What I mean by that is, Peter Thiel was running the company, then he steps down and says, “Hey, the company’s gotten too big.” Elon Musk is running the company, then he steps down and says, “The company is too big.” At some point, Reid Hoffman, who’s been sitting here in the wings this whole conversation enters the picture. He’s been sitting on the board of PayPal for a while and he comes in as COO. Talk to us about the impact that that had on PayPal.

Jimmy Soni (00:38:46):
If there weren’t enough bold face names in the story already, you have Reid Hoffman who today is famous for various things. His founding of LinkedIn, his service on the Microsoft board, the various books he’s written, podcasts, his engagement with various nonprofit and political causes he’s a part of. Back in 1998, 1999, he is the not quite thrilled co-founder of a startup called SocialNet and it isn’t working. And it’s an early social network before social networks became cool, and he’s deciding what to do next. And he speaks to a college friend, Peter Thiel, and they go … Part of what’s happening is they’re going through these long walks around the Dish loop trail near Stanford. And he’s having this interesting engagement where he’s downloading everything that’s happening. He’s giving him the rundown of, “Here’s what startup life is like.”

Jimmy Soni (00:39:42):
And Peter says to Reid, “Hey, you’re figuring out what to do next, we are running like a hot mess, you should come in and help us organize this thing and package it all up for a sale.” And Reid says, “I didn’t necessarily want to do this.” But what Peter said to him is, “Just come in, you’ll work for a little while and then you can leave and we’ll be good.” That turned into a longer stretch. It was, let’s see, he joins in January of 2000 as COO, so roughly two and a half, three years of service there. He becomes what I would think of as an emissary. He’s a diplomat. He’s the person that they send into rooms when there are sensitive issues, when there are fires going. And he goes and figures out how to get people to come to some decision, come to some conclusion, figure out how to negotiate with the company.

Jimmy Soni (00:40:33):
He’s an interesting character because he’s hugely empathetic. I had multiple employees talk to me about how Reid was among the people there who really cared about people and really cared about how they got along, but he’s also no slouch. This is somebody who has a razor-sharp mind, grew up playing strategy board games, loves strategy, was a great strategist himself. And he helps navigate the company in and out of things like its tussles with eBay. So one of my favorite moments is, he’s working with his counterpart of eBay to keep eBay from shutting PayPal down. His role is emissary in chief and firefighter in chief. I think Peter’s called him the firefighter in chief in different instances.

Jimmy Soni (00:41:13):
But if there’s a significant thing happening in the government, you turn to Reid. He is someone who has the ability to go and see the other person’s point of view and find a way to bring them into the fold. Again, which is not a quality all of these people have necessarily, but I think that’s Reid’s great contribution. I would say the other piece of it is, he already had a startup experience at SocialNet and had to do all of these things that neither Peter nor Max had to do, like deal with investors and deal with even some of the product decisions. So there’s a way in which he’s not older than these folks, but he’s had this one extra experience. So it’s almost like he’s an elder statesman, but not really elder.

Jimmy Soni (00:41:52):
Peter, when he was reflecting with me, he said, “One of the tough things is that all of a sudden, Reid my friend became Reid my employee.” Those aren’t his exact words, but he did reflect on the fact that sometimes there can be an adjustment if you’re doing business now with someone who was your friend, that you actually can reconfigure the relationship a bit. And I found that interesting, but at the same time, they were sparring partners intellectually, tey knew the other person had the same chops and Reid becomes this ace diplomat. You send him into any situation and help find a way in and out.

Trey Lockerbie (00:42:24):
Well, they certainly needed it, it sounds like. So that brings up another point I really want to explore, digging in on the secret sauce. And that seems to be this culture that they had. These guys, as you put it earlier, they’re engineers mostly, they’re not managers, and somehow, they managed a ton of people to become very productive. And I think partly from what I took away in the book is this lead by example sort of approach. And it was reminding me of the Shackleton effect, so to speak. So for those who aren’t familiar, or if you are familiar, bear with me, but 1907, Ernest Shackleton puts up this ad about going to the Antarctic.

Trey Lockerbie (00:43:04):
And the ad says, “Men wanted for hazardous journey, small wages, bitter cold, long months of complete darkness. Safe return doubtful.” And you would think, who would want to sign up for this expedition? And yet, according to myth, there were 5,000 people that showed up according to the myth. So I don’t know if that story is true, but to me, it’s a good anecdote for what maybe happened here at PayPal because it seems like these guys were running this machine in the trenches with everybody else. They were sleeping under their desk, they were working days on end, working into long hours of the night. Part of that is just startup culture, it’s been chalked up to nowadays.

Trey Lockerbie (00:43:44):
Part of me wonders if that was a moment in time, if startups still operate that way or could get away with that 20 years later. What’s your take on the culture that they actually developed there and how effective it was?

Jimmy Soni (00:43:58):
You hit a lot of the right notes and I would offer a few insights. I’ll try to get as close to answering that question. The question in the introduction is, what was in the water? What made this place tick? I’ll offer one assessment that I’m not sure readers maybe expect, but it’s worth sharing. We’ve spent a lot of time talking about the folks who are at the very top of the organization, and I would say at the top in some ways of technological life today, the folks everyone knows. One of the most interesting people I interviewed, one of the most compelling and dynamic was a woman named Amy Roe Clement. I didn’t write this explicitly, but I think like all cars need oil, all cars with an internal combustion engine need oil to make sure that the engine doesn’t seize up, PayPal needed Amy Roe Clement.

Jimmy Soni (00:44:45):
She was a hugely important, hugely inspiring leader. And part of what she did was actually interface with almost every part of the organization and find a way to make sure that everyone connected to the other person. She was on the product team, she was a Lieutenant of David SacKs, who was the head of product. She had joined X.com, had interviewed with Elon, was really motivated by his vision, was deciding between grad school and startup life and chose startup life. And she’s somebody I had described as, if you had a problem with the product, you went to Amy, and if you had a problem with the people, you went to Amy. She was this person who made the organization with all of these hothouse personalities really work. And she had a co-conspirator and a head of design named Sky Lee, who did some of the same sort of thing.

Jimmy Soni (00:45:32):
They kept the place on an even keel. They kept the organization moving forward in spite of all of these convulsions. And part of it is, we think of the story as a few people, it’s a lot of people. And there are all these people in the organization who are keeping it going, keeping the momentum moving forward, taking visionary ideas and saying, “This is good, this is bad, we’re going to do this, and here’s how we resource and support that.” Part of it is, I’ll tell a story. Someone mentioned this to me, and I won’t say who it is, but it was a great story, and he said it with some endearment in his voice. He said, “I was once out to lunch with Max.” And his wife, the person who was telling the story, his wife was with him. And they sat down and Max had a book, and it was a book about physics.

Jimmy Soni (00:46:14):
The wife said to Max, “What are you reading?” And he goes, “Oh, this is my physicist of the moment.” And at some point, Max goes to the bathroom and this person, the wife leans over to him and says, “Who has a physicist of the moment?” But to be candid, PayPal was the place where people had physicists of the moment. Every week in the company newsletter, they’d put a puzzle out for the organization to solve. And people were crazy about trying to be the fastest, the first, sending in the right answer. There were all night video gaming sessions. I remember one person, “Sometimes people would just come in and throw out a puzzle, see who could solve it first. And there was a quality of, if you were the best, you’d know how to solve it.”

Jimmy Soni (00:46:55):
It was a high bar for intellect. So I do think that’s a part of the culture. And look, maybe you can’t repeat that, maybe that’s just something that’s peculiar to the time or peculiar to the fact that it’s people like Elon and Peter and Max doing the recruiting. But I had this funny experience, Trey, when I was doing the interviews, every person, not every person, many people would point to someone and say, “That person is a genius.” And it was very rare that two people ever said the same name. So it was this really interesting thing. I had Max Levchin tell me, “Russell Simmons is a genius.” And then I had so and so. Actually, Sarah and Max said “Sanjay Bhargava is the genius.” She said something to the effect of, “Watching Sanjay Bhargava navigate the financial system is like watching a conductor conduct a symphony.”

Jimmy Soni (00:47:39):
And I had experience after experience where someone who I was interviewing would say, “Oh my goodness, you really need to talk to Joe Smith because Joe is a genius.” And it turned out that this just happened over and over again. I kept hearing this phrase, this word, and this kind of praise. It wasn’t that they all pointed to Max and said, “Boy, Max is really a genius.” It was that they would point to someone who I had never heard of and say, “This person is brilliant.” I do think there was a high bar for intellect. The last thing I would say, and this is going to be a little counterintuitive, they had enemies and they were running out of money. There was pressure, a huge amount of external pressure.

Jimmy Soni (00:48:19):
I interviewed this gentleman and he said to me, “The value of having fights that you’re fighting that are external is that you minimize the number of fights you have that are internal.” So he said, “One of the things that never happened in PayPal, we never really thought about titles. Yeah, there was a little bit of that and there was a little bit at the margins, but we had so many enemies externally and so many things we were trying to do and it was so hard and the money was running out and everything was crazy, we didn’t have time to fight over who was the VP of marketing and who was the chief marketing officer. There were fights that took a backseat because the fights we were fighting were so in our face.”

Jimmy Soni (00:48:53):
It doesn’t mean that there weren’t internal divisions and ranker, all of that was there, there was some politicking as there is in all organizations, but Skye Lee and George Ishii, “Really, nothing brings a team …” This is Skye Lee’s line, she said, “Nothing brings a team together like having a mortal enemy.” And so there’s a way in which actually external pressure was a part of the culture too. And you don’t want to make too much of it, but how many companies today spend so much time focused on themselves because there’s not this gripping fear from the outside world of who they’re fighting. PayPal had a good reason to be afraid. Fraudsters were defrauding them in the millions. Credit card companies were on the march and were really concerned about PayPal.

Jimmy Soni (00:49:36):
The market was drying up, and eBay wanted to crush PayPal. And so externally they were facing these difficulties. And in a way, it shaped a culture of a group of people who they always feel like they’re a little bit on edge, like, “Oh my God, the world’s …” They’re sort of all chicken little. And again, I don’t want to make too much of that, but it was repeated to me enough times that I do think of it as a part of the culture.

Trey Lockerbie (00:49:59):
All right. So having put in a number of years now, researching Reid Hoffman, Elon Musk, Peter Thiel, Max Levchin, David Sacks, goes on and on, and again, just baffling. What were some of your biggest revelations or takeaways after researching these billionaires and founders and culture that they’ve developed? What were some of the biggest surprises or takeaways?

Jimmy Soni (00:50:23):
I’ll start with, again, something a little unexpected. In my interview and my correspondence with Amy Clement, she said that one of her big takeaways was that a company takes many different kinds of personalities. So the way I would reframe that or think about it is, I’m not sure this team would’ve succeeded if there were 200 people like Elon Musk. I’m not sure this team would’ve succeeded if there were 200 people like Peter Thiel, and on and on. I do think the interesting thing about this company is, it needed every one of these people, both the names you recognize and the names people will, well, hopefully learn when they read the book. It’s this peculiar thing of, there are particular kinds of personalities and you don’t want uniformity in those personalities, you don’t want a team that’s all diplomats.

Jimmy Soni (00:51:06):
You do need someone like David Sacks. And the description of David Sacks from multiple employees was, “He pushed us. He was there as a propellant. He would make us think about the product more rigorously. And it was tough because he was very smart and he suffered no fools and he would call people to account.” But you need that in an organization. At the same time, you need somebody who when they interface with government, isn’t going to necessarily push. They’re going to find a way to push and pull and be diplomatic. You need somebody like Sanjay Bhargava who his contribution is the creation of this technology random deposit, which allows you to authenticate bank accounts.

Jimmy Soni (00:51:44):
And if he hadn’t spent 22 years or whatever, the two decades in the trenches of the financial system, it’s possible PayPal wouldn’t have had the knowledge or the thought process to do that sort of work. Her lesson was, it takes all of these different personalities. And I think it’s a useful thing to think about. This is a company that warehoused all of those people, and it’s not a cult of personality around any one of them. Apple is a little different. The Apple story is always told through the eyes of Steve Jobs. Amazon is always told through the eyes of Jeff Bezos. This is not that. And I think there is something powerful here about the mixture of these people.

Jimmy Soni (00:52:19):
Again, it’s not always harmonious, but it is interesting to think about it if you’re building and assembling a team. I think my second big takeaway is, everyone in this story that I interviewed had a very quirky love of learning. And again, I suspect the people who listen to you have this probably more than others, but it’s the who has a physicist of the moment, it’s the passion for space. Elon’s passion for space starts when he’s a teenager. and he’s talking to his mentor at a bank about space and about what it could mean to go to space. It’s volumes of books that are traded, it’s the team reads Cryptonomicon right and Neil Stevenson. There’s a desire to learn and a desire to learn and to push one’s thinking that I think is something to be emulated and admirable.

Jimmy Soni (00:53:07):
And honestly, when you talk to them, you’re like, they don’t just learn in a utilitarian way, there’s a genuine love of new things. Max Levchin once said his idea of a vacation is a book of math puzzles at the beach. And I think there’s something about this idea of pushing your mind that all of these people shared, and I think it’s something that we can all find in our own ways. And I would also add, it’s not that they had one particular passion, it’s not like they were studying just X or Y or Z. It’s a broad-based love of learning that I found in person after person that I interviewed.

Jimmy Soni (00:53:42):
I think the other thing I take away is, I found that there was this line in the book that someone had said, I’ll attribute it to Max, and it was, “As hire As, Bs hire Cs. So the first B you hire takes the company down.” Let’s go to the charitable assessment of that. The less, get rid of your B player’s assessment. Which is, we should want to find places that are populated with these kinds of people for ourselves. You should want to find a company or an entity or a group of friends or an organization where someone is saying to you, “I need you to bring your A game. I need you to step it up. I need you to be better.”

Jimmy Soni (00:54:21):
It was a remarkable place to work because it demanded that you bring your best. And I think that maybe that has something to do with the wealth that’s been created and the people and the companies and all that. I suspect that it does. Now, the question is whether it’s nature or nurture. Did these people get selected for this or did they learn this while they were there? I think it’s a bit of both. It’s interesting to see the development of say an engineer like Jeremy Stoppelman, who arrived a little later in the story, but he’s there and he’s shaped in this way. And could he have been the Jeremy Stoppelman who founded Yelp in some other place? Sure. Certainly. But I think there’s something very particular about this place that pushed him, and that all of these people pushed each other in that way.

Jimmy Soni (00:55:02):
I’m sure there are people, in fact, I know there are people who had negative experiences related to that, but the majority, certainly plurality, but actually the majority of people said, “I have been looking for a team like that the rest of my career, and the best moments were when I found teams like that.” And it’s this curious mix of innovation and embracing honesty, and also external pressure, and a whole heterodox group of people. They’re all over the place, they come from all corners. I think that’s one of the big takeaways. And most I would say the most self-aware people in the story acknowledge they were super lucky.

Jimmy Soni (00:55:37):
And it’s not that they didn’t work hard and it’s not that they didn’t win fights against this and that and design the right product and all the rest. One of the people I interviewed at length was a board member who saw this story from the beginning to the end. His name is John Malloy. And if there is an Obi-Wan figure in this story, it’s John Malloy. And he said, “We tend to spin these narratives, the idea that there was a pre-destiny or that this was going to happen.” And he said, “It’s not true. There’s a lot of luck that’s baked into these stories.” And the way you know that it’s more accurate than not is, there are so many startups from that era that aren’t around today.

Jimmy Soni (00:56:17):
Any one of these people at another startup would’ve had an experience where they failed instead of succeeded. And one of the things that Peter said, and I’m not sure he would ascribe things to luck, I think he’s taken strong anti-luck positions in the past, in the sense that that word, for him, I think is not quite accurate. But he said, “What people took in this experience was that startups were hard, but doable. It wasn’t that it was easy and we succeeded, it’s like it was hard and we succeeded.” Which meant it gave people a certain cast of mind as they did future things. That’s a lot.

Jimmy Soni (00:56:49):
And there’s endless other tiny little lessons and things baked into the process. But for me, it made me rethink whether I have the right people in my life saying, “I need you to be better. I need you to do more. I want you to bring your A game.” If there’s one big thing I discovered is that, it’s that those people are rare and it’s hard to get to that level of honesty.

Trey Lockerbie (00:57:14):
Yeah. Warren Buffett has this metaphor about studying value investors. And he describes this gymnasium, I think, full of monkeys flipping quarters. And if you do that, you’ll see that the average comes at 50%. It’s like, what if you found out that, I’m paraphrasing here terribly, but what if you found out that the 10% that flipped the most quarters all came from the same town, lived in the same, ate the same food, whatever it might be. And what you’re talking about, I agree with, getting lucky, having the right people in the room. But there is this element of something else, I think. And you describe it very early on in the book about what’s in the water, as you said, because it’s not like lightning struck once for these guys.

Trey Lockerbie (00:57:59):
And it would be enough for these guys to get together and build this multi-billion-dollar company. That’s a once in a lifetime achievement, and for very few people. But then to go on and create Palintir and Tesla and SpaceX and LinkedIn and on and on and on. It reminds me a little bit of the recent Beatles … This might be a generic proxy, but it reminds me of this recent Beatles’ documentary where they’re just in a room together for quite a while. And you think about what made them a great band, but they all went on to do individual music that was all pretty great. Some of my favorite were George Harrison’s records and stuff.

Trey Lockerbie (00:58:35):
It certainly shaped these founders to go on and found other billion-dollar companies. And I think that is just truly remarkable. And I hope someone takes your book and makes a movie about it. Because certainly, if they could make a movie about Zuckerberg, they can make a movie about these four or five founders all in the same room.

Jimmy Soni (00:58:54):
Yeah. And again, they’re not done, by the way. The crazy thing about this book is, I can’t actually do the afterlife without another 500 pages. I did 1998 to 2002. But if you think about the fact that most of these people are in their late 40s and early 50s, and there are the startups that get coverage. But one of the startups that a founder from this group is creating is a startup called Terraformation. Terraformation’s ambition is to reforest three billion acres of forest ecosystem. There are people in this group who are building all kinds of technologies, big and small. So they’re not done. That’s the other astonishing thing, is they’re so far from finished. I take your point, and in some ways, your point is a pushback, which is, you can’t ignore what they’ve done in the afterlife, in the aftermath of PayPal.

Jimmy Soni (00:59:47):
Here was my challenge. The aftermath got so much attention, I had to duck it a little bit just to focus on the PayPal years. Because I felt like they got short lived and nobody really went back and did a deep dive. These folks learned how to build a company, they did it when they were, many of them, relatively young. And in many cases, they did invest with one another, they backed each other’s ventures. Some of their earliest money into each of these startups comes from another person in this particular network. But it’s also, this was a formative experience that showed that you could build a technology company from scratch and be successful. And it gave them a template for doing it over and over and over again, in different sectors of American life as well.

Jimmy Soni (01:00:28):
And they’re not done. And is there going to be another 10 or 20, 30 years of this kind of creation and ambition. You’re tapping into something, which is, this created a framework for them. It created a way of thinking about the world.

Trey Lockerbie (01:00:42):
Yeah. And it didn’t change Elon’s approach to money because I think he took his earnings and put half into Tesla and half into SpaceX and was broke again for a long time. What a story. The book is fantastic, really well done. Jimmy, before I let you go, I want to make sure you have the opportunity to hand off to our audience where they can learn more about you and the book and any other resources you want to share.

Jimmy Soni (01:01:05):
I really appreciate that and I appreciate your close read of it. And I think you are somebody who has a lot of business context. So this was a really fun conversation because we can compare these things to others, what are called seniors, like the Beatles or the Bulls, or that sort of … So I appreciated the chance to talk about this at some length. I have a website, jimmysoni.com. I’m infrequently on Twitter @jimmyasoni. The book is called The Founders, I hope people will check. It out debuts on 2-22-22. And it was a lot of fun to do and I think I hopefully captured some of the lightning in a bottle that was there. I’m just jimmyasoni on Twitter.

Trey Lockerbie (01:01:42):
Fantastic. Well, Jimmy, best of luck with the book. I highly encourage everyone to check it out, and let’s do this again sometime soon. I really appreciate it.

Jimmy Soni (01:01:48):
Great. I appreciate it. And thank you.

Trey Lockerbie (01:01:51):
All right. Everybody, I hope you enjoyed that one as much as I did. Jimmy and I originally connected on Twitter. You can find me there as well, @treylockerbie. If you want to be a billionaire someday, the best place to start is theinvestorspodcast.com. Be sure to check out all of the amazing resources we have for you there. And don’t forget to follow us and maybe even leave a review, we’d greatly appreciate it. And with that, we will see you again next time.

Outro (01:02:13):
Thank you for listening to TIP. Make sure to subscribe to Millennial Investing, by The Investor’s Podcast Network and learn how to achieve financial independence. To access our show notes, transcripts or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only. Before making any decision, consult a professional. This show is copyrighted by The Investor’s Podcast Network. Written permission must be granted before syndication or rebroadcasting.

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