MI273: The Incredible Story of PayPal w/ Jimmy Soni

23:15The important thing about the internship is to some degree that he interned at a bank. The more interesting thing is that he meets this mentor, Dr. Peter Nicholson, who I had the great fortune to interview. So I spent a lot of time talking to Dr. Nicholson. And Dr. Nicholson is this person, he's got a wide range of interests. He was in Canadian politics. He was a PhD. So he had a scientific training. and he kind of like Elon cold calls him. And so, when Elon and his brother are new in Canada, they don't know anyone. And so, all they do is just like they talked about in some other setting, they talked about like we just cold call anybody we could just to like get meetings.

23:48Dr. Nicholson for some reason is like, okay, I'll take a meeting with you. And so, they have lunch with him. And he said, he's like, look, right away, you could tell these brothers were sort of very impressive. And he had this internship that he was trying to fill. So, look, I got a spot on the team. Elon takes that spot. And he ends up working at Scotiabank. for a while. And it's interesting because the thing you describe is like, even then, Dr. Nicholson said, like, number one, he was very, very precocious. Like he could sort of, you know, he was thinking about problems in a way that was far beyond his years.

24:16The other is that he had a huge appetite for risk. And so, he proposes this idea that's very risky for the bank, but could be very lucrative. And the bank pooh-poohs it. And Elon's lesson from that is, as he puts it in the book, very colorfully, he puts in the book, like, banks don't take any risks. They're not innovative. And his line in the book, I think I'm paraphrasing, but he says something like, if this is how they operate, then anybody can come in and beat them because they don't know what they're doing, right? And so that lesson or that nugget stays with him. And it's the reason that the idea of x.com is appealing to him, the idea of doing something in financial services with the internet, because what he sees is an opportunity to essentially cut out a lot of the friction and cut out a lot of middlemen within finance.

24:54Yeah, so Elon's always been such a big dreamer before SpaceX and Tesla, he was in the financial industry. And yeah, it was really interesting learning about that part of his journey. And then I guess let's merge together the two stories between X.com, which was Elon's financial industry company that he wanted to, that he did create, and then Cofinity. And kind of talk about how they were two different, completely different business models and then how they eventually came to compete with each other. Yeah, it's the craziest story, right? Right. Like it's like you, it's like one of these things, like the more I dug into it, the more I was like, this is like, I mean, it's, you know, what is it sort of fact is stranger than fiction.

25:36Here's what happens, the condensed version. Elon pursues X.com. What he wants X.com to be is the one financial services superstore, the only place you need to go if you need to do anything financial. Max and Peter, after several pivots, like you described, what they land on is this idea that we want to email money. We want to like make emailing money work because nobody had really made it work seamlessly. And what happens is x.com emailing money is just a part of a big portfolio of projects. Both of these companies, they kind of launch around the same time. They launch the emailing money components around the same time.

26:10And both of them take off. And a big part of the reason they take off is because they're basically giving money away, $10 and$20 bonuses to people who open up new accounts. And so you can sort of predict what happens. If somebody walked up to you in the street and handed you$10, you would like, okay, great. Thank you. That's essentially the internet equivalent of what they're doing. And they take root both companies, X.com and Givinity on a platform called eBay, a new-ish auction platform at the time. They were a public company, but still relatively new. eBay had not figured out how to reconcile payments.

26:38And so the idea of like a seamless way to email money was really appealing. And so what happens is that both of these platforms are like becoming successful. And you have on one side, a ferociously competitive person named Elon Musk. And on the other side, you have two ferociously competitive people named Peter Thiel and Max Lefgen. And they start to essentially like fight for dominance on eBay. And I don't think if you asked any of them, like in January of 1999, if you said to them, hey, did you know that by December of 1999, you're going to be competing against this other company? And that company is three blocks down the street from you in Palo Alto.

27:10And you guys are just going to spend money like crazy to try to beat each other. All of them would say you're crazy, but that's exactly what happened. And so the story of these two companies and of these people's lives from roughly October of 1999 through March of 2000 is this unbelievable, very personal, sometimes vicious competition over market share on eBay. In January and February of 2000, they start to realize like, look, we're just going to spend each other into oblivion. And there's a very complicated series of negotiations. And the companies have what I describe in the book, and I think it's a fair description as like a shotgun wedding that's concluded in March of 2000.

27:45So they essentially go from trying to kill each other to like being locked together. And they all join as one company. What was also super funny to learn about in the book is how Max Levchin thought that Elon's idea of X.com, he was like, he's going to drown in regulatory hurdles. And then Elon was like, their idea is stupid because at first, Cofinity was the Palm Pilot idea. And they wanted people to be able to, I guess, transfer money via Palm Pilots. And the email thing came way later. That was an afterthought. And it was funny reading that Max even wanted to scrap that idea at first, the Palm Pilots.

28:19So that was very interesting. It's actually like one of the... I'm glad you picked up on that because it's one of the things... I've sort of two thoughts about it. The first is if you think about where PayPal ended up, it's actually a bit of a disappointment to both groups of founders. Elon wants to like run finance, like defeat all the banks. PayPal did not do that. Max wants to make Palm Pilot money beaming into a thing because Palm Pilots were the rage in Silicon Valley and people thought they would be the iPhone, right? We sort of have our version of that. It's the iPhone and mobile phones generally, but that's what he thought was going to take off.

28:49Neither company really succeeds at its ultimate vision, which is kind of funny. The more interesting and kind of thing that I think I had the benefit of 20 years of passage of time so they can say this now. I'm not sure they felt it in the moment. Actually, I think they felt it in the moment. I asked each of them, you know, so tell me like, what did you really think about this person that you're competing with? And they weren't being interviewed together. I interviewed Elon separately and Max separately. And Elon said, you know, it was interesting because I had never really come up against people who could compete with me, like meaning as quickly, worked as much, like worked as hard, were as driven to win.

29:21He said, but these Confinity guys, I mean, he said, man, they can move. And he actually did this great line. He says, if you can keep up with me, whoa, respect. And it was like delivered in this kind of funny way. Max, when I asked him about Elon, he said, you know, when we met him, like he's like, his line in the book is like, he's completely crazy, but he's also really smart and I really like smart people. And so there was, you couldn't call it an admiration at that point. The admiration I think comes later, but there was at least a healthy respect that the people down the street were just as competitive and smart.

29:53And I will say, like, I think it is hard for people like this to find people who are as competitive and smart, which tells you something about both groups of founders. And I just loved all of the, I guess, the struggles, learning about everything they did along the way. And I learned so much about the startup industry too. Maybe that's just a Silicon Valley thing, but the sleeping bags under the desks, the 48 hour nights and just like full days, they basically lived at the office. And so we'll get into a bit of the culture later, but I am interested for our listeners to kind of learn more about the story, tie the knots together.

30:28These companies were fighting to the death and then eventually they do merge together, but they still didn't really want to. So talk a little bit about the decision why they ended up merging. Yeah, it was complicated to be sure. Elon really did not want the merger to go forward. Several people within the executive team on both sides were pretty skeptical. They thought they were trying to achieve fundamentally different visions. So you could like, it's all understandable. You could sort of see why they're like, I don't want to merge with these people. But what happens, and this is, I think, partially the credit goes to Peter Thiel.

31:02Peter could sort of see the writing on the wall in two ways. One is Confinity was just going to run out of money. Confinity had far less capital than X.com. And the other piece of this is that the markets at this point were starting to teeter. So, if people who didn't live this period, and I was a kid during this period, but what I learned in my research and interviewing people, from 1994 to 1999, if you attach a.com to anything, you could become successful. And they're like, this is the era of like Super Bowl ads, big parties in Silicon Valley. I mean, this is like the era of excess. And in early 2000 is when that excess starts to crumble.

31:38And there's a kind of in the year 2000, it's like basically the NASDAQ loses 86 % of its value. All of these dot coms go under. In early 2000, both Elon and Peter see that that is like, that's going to happen. There's just no way to sustain some of the valuations. A lot of these companies like did not have any kind of business model. Even if you did things like sort of discounted cash flow, you just didn't see how it would all, the math would work. That led Peter to believe that if they did not merge, they could not close a new round of funding and that the company Confinity would ultimately go under.

32:11So he really pushed his board to try to get the best deal possible for the merger, because originally it was supposed to be an acquisition and it ended up being a 50-50 merger. But in everything I just described, you could imagine like they didn't, this wasn't well plan. This wasn't like a year of due diligence. And this was like a few weeks and slapping these companies together. And as one executive put it, he said, you know, we never really solved the 2X problem. We had two CEOs, we had two of everybody. And the goal was to just to get the merger done as opposed to make it smooth. And so the next three or four months were pretty chaotic.

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36:01That's theinvestorspodcast.com slash tip-finance. All right, back to the show. And so then eventually when they did merge together, you mentioned they faced the financial troubles with the dot-com crash. And so what were some of the other challenges they faced when they merged these two once competing companies together, lots of strong personalities and people with honestly different visions. What were some of the hurdles that they faced? Well, I think within weeks of the merger, they oust their CEO. So the entire employee group and senior executive group essentially threatens to resign en masse.

36:42So there's a CEO who is ousted. He is replaced by Elon Musk, a CEO. Within two and a half, three months, the three months of Elon being CEO, the employees again threatened to resign in mass. And they oust him in a kind of now famous moment where he's on his honeymoon. And they say that it's either him or us. And the board says, well, we're going with the employees. And so that's like problem, you know, sort of issue one, issue two, you could go down the list. There's also fraud. So part of what happens is that it's not particularly, you know, in my descriptions of it from other people, it's not really that hard to build an emailing money system.

37:18What's hard is making sure you don't lose your shirt while you're building an emailing money system. And so they have just like endless amounts of fraud. They're sort of minor fraud. Like if you think about like college students creating, you know, Elvis dot Presley at hotmail.com and using it to get 10 bucks and like siphoning that away. That's relatively minor. The more complicated stuff was when people were creating phony transactions to the tune of hundreds and sometimes thousands of dollars and using the PayPal platform as a way to defraud eBay sellers or to just defraud like the companies in general.

37:47And so you have that, you have regulatory challenges. PayPal is new. There's never really been a ubiquitous digital payment system. So all of a sudden, what happens if somebody pays for terrorism or pays for weapons or pays for illegal drugs, right? Suddenly PayPal is intersecting with the government and the government's not particularly thrilled about that sort of behavior. And then finally, you have the merger, as you described, of two very different cultures, two very different teams. And it's really like they double the team size. There's this great line in a kind of concluding chapter of the book where Luke Nosek says, you know, a merger is really hiring 50 people sight unseen.

38:25At least that was his experience at the time. And so they have to figure out like, OK, we have two people doing the same job. How do we actually mesh this stuff? The last thing I'll say, Confinity created a product called PayPal. PayPal was taking off. But Elon and some members of the X.com team were still wedded to the idea that X.com was going to be the brand. So even at the level of the brand, there's like no agreement. So imagine the summer of 2000, everything I just described is happening and the bottom is falling out in the stock market. So this is just like controlled chaos for this, these series of months.

38:59Yeah. And they went through a lot of CEOs, like you mentioned. And I liked reading and hearing how you told the story about it was Elon wasn't mad. He was mad, I think. But then eventually he kind of came around to it because at the end of the day, he had such a large stake in the company. I think he just wanted it to do well. And if the people weren't going to perform well, if he was there, he was like, I'll move on to other things, which he did. And so it was just interesting learning about the culture. And even before that, the previous CEO where he got outed too, he was very, I guess, it seemed like he took it well the way you wrote it.

39:35You know, I think it's always sort of, you have to, what I tried to do, and I hope I did in the book, is not present one side story. So I interviewed all the people who were involved in this drama or these sort of two dramas. And I tried to, for the, like, I didn't, I'm not in a position, I wasn't at the company. So what I wanted to do is just present the facts as both sides saw them, right? So take the Elon example. There's a version of the facts that the people who ousted him have. And I present those, the challenges about the brand, the challenges about money, feeling like emailing money was going to be way more successful than a financial services superstore.

40:08And more importantly, feeling like they didn't have time because they were running out of money to do the financial services superstore. They had to stick with the successful product. Then I present Elon's side, and there's an architectural disagreement as well, a technical disagreement about what platform to build on. Then I present Elon's side of the arguments, right? Sort of here's how he is thinking about all of this. And I sort of leave it to the reader to like, if you want to judge, you shouldn't judge. But if you want to judge, you can judge based on the facts, right? Here are emails, here are records, here's sort of what we know about the company.

40:35And I tried in each case to at least like give each side a fair hearing and not be to have my thumb on the scale either way. But I think one of the things that you pointed out, and it's very surprising, is in the aftermath of being ousted as CEO, Elon is very gracious. He's angry, but he is gracious to the people who ousted him. And he continues to serve on the board. And he does not burn the company down in the press. And he doesn't sort of do funny business. He is upset that he's not the leader. But he is not upset to such a degree that he's like, I'm going to tear PayPal down. You know? And there's a rational reason for that.

41:12He had a huge amount of equity and he wanted the company to be successful. There's also this part that's often missed, which is he recruited a bunch of people who worked at the company. He wasn't going to ruin their careers either. And it's this really interesting moment because even the people who ousted him will say he behaved very well in the aftermath of that ousting. And so well that, and it's sort of how I conclude his portion of the story, that when he launches SpaceX, some of the first people to support him financially when they raise big rounds of funding are the people who ousted him at PayPal.

41:40They didn't lose faith in his entrepreneurial ability. They didn't think he was the right leader for that moment in PayPal's history, but they didn't say, oh, this person's a bad person or a bad entrepreneur. and I think that's one interesting thing is you can be an amazing visionary and have these great ideas and execute them but that doesn't always make you a great leader and I liked how you did expand on some stories where people didn't particularly like the way he led and because he just wanted people to work as hard as he did and see things the way he did sometimes and so it was interesting just reading all those different sides of the story.

42:16Yeah. And I think it's as true today. You see this sort of maniacal urgency at Twitter, right? His words, not mine. I think it's really... I mean, I'll be honest. I think it's hard for people to truly grasp just how hard he works. People sort of take shots at him for different things. The one thing I don't think that you could fairly criticize him for is being a slouch. And that sounds funny, except that what I heard from engineers who worked with him at x.com is always a version of the following. And by the way, this happened multiple times. They would say to me, you know, it was the hardest I've ever worked.

42:53But part of what was inspiring is that the CEO was there at two o 'clock in the morning working with us. And it wasn't somebody that was just sort of a suit who came in and didn't know how to code. Like we were solving engineering problems together. And he was sleeping there all night and he was working just as hard. And I think it's an important theme in his career, which is he'll put a lot of pressure on people, but he will put more pressure on himself. Yeah, I really like that characterization. And I want to get into the culture a little bit more because both Cofinity and X.com seem to have a very unique culture from their vetting process where they often would quiz each other in these puzzles, logic games just for fun.

43:35And so it was really cool learning more about their story and their culture. So can you give our listeners a sense of what the culture was like at cofinity and x.com, which eventually became PayPal? Yeah, it was, you know, you could imagine that given the companies that came out of this group, like YouTube, you know, et cetera, et cetera, like these world beating companies and SpaceX and all of these things, like you're sort of raw material as you start with a lot of very smart people and very driven people. And so one specific aspect of the culture that I tried to focus on, because it came up again and again in my interviews, is puzzle solving.

44:11And they had this process where they would interview people. This is not unique to PayPal, by the way, but they took it to extremes, which I'll describe in a second. They, when interviewing candidates, they would toss these sort of complicated math and logic puzzles at them. This is particularly true on engineering, but honestly, they did this to the folks who interviewed on the business side too. And it was, and the description, you know, there are some people who hated this practice, still do. The description that was given to me by Max Levchin was interesting. He said, you know, a lot of these puzzles or problems, it's actually about being an efficient problem solver.

44:40At a startup, you don't have weeks and weeks and weeks to work on something. You actually have to find the sort of shortest distance between two points. And if you're looking at a puzzle or one of these sort of trick questions or some word problem or some logic puzzle, if you're looking at it the right way, there's usually a little hack. There's like a little trick. And if you get it, That's how I know that you're not going to spend ages on a problem when there's a short solution because the only thing you have as a startup is time. And the only thing you have as an advantage is that you can do more in less time, meaning you have speed, right?

45:11It's like a big point of leverage for Silicon Valley startups that they can do things more quickly than a big competitor. And so the base version of that is these sort of logic games. The reason I said that PayPal took it one step further is it wasn't just an interview practice. I had this thing happen during the middle of my reporting and research on this. somebody shared a bunch of email from that era. And I had the weekly company newsletters like going back like four years, like for the four years that I was writing about. And every week, they would put a new puzzle like in the weekly company newsletter.

45:38And the only thing you got, if you got it right, was you got a shout out the next week with the right answer. And you wouldn't believe like the number of people who are trying to solve this just for bragging rights, right? Nothing more. And so, it sort of shows you two things. One, this is like a puzzle or problem solving culture. And the other, these people are very competitive and competitive when there's nothing on the line, like other than your name in like the weekly company newsletter. And you mentioned in the book how him and Peter would just sit there and do this. And it's just, they just liked it.

46:09They're cut from a different cloth. And that was, again, just so cool to learn about their stories and more about their personalities and just what make them so different. Maybe that's what makes them so successful. And that's kind of what I wanted to ask you next is because you've spent so much time both researching and then being in person with them and interviewing them. Was there anything common in their personality, their traits that you think just really made them so successful, not once, but multiple times? Yeah. And I think, you know, as with the other question where I attached a disclaimer, one of the important disclaimers to this one is they're not all the same person.

46:48There's a temptation in Silicon Valley or in writing about Silicon Valley or thinking about it to think like everybody is Elon, they're really not. Like these are very different personalities, right? And I interviewed hundreds of people. So, it wasn't just like sort of these three people giving me all the facts. Here are some common characteristics that stood out to me. And some other things might stand out to other readers. One is there is a kind of, call it like a broad-minded curiosity. So, one of the things that happened as I got to know these people is I discovered not just like how well-read they were in technology and like in their particular business, but how well read they were just across the board, like the novels they read, the movies they watched.

47:26Like I was just, I was honestly, maybe I shouldn't have been surprised, but I was pretty surprised that like Elon in our interview was like quoting and citing the Bible as casually as he was, right? Or that Max Levchin had this kind of obsession with Kurosawa's Seven Samurai, or that, you know, David Sachs was a film buff. And I suppose that's like, maybe that was to be expected, but it surprised me. So, there's a kind of broad-mindedness. They read very widely. They've learned a lot. And they learned a lot, I would say, between the age of sort of zero and 20, right? Like it was like a real curiosity and it was a broad-minded curiosity.

47:55That's one. The second is there is a desire to win. Like the one thing about the description I gave earlier between the sort of competition between Confinity and x.com is both sides really, really, really, really, really wanted to win. It was a big deal to them to not lose. And I think like, Like if you look at each of the companies and ventures they've been involved in, like there's a real premium placed on like actually trying to win and be successful and a competitiveness that is just sort of there. It's like a fire that kind of burns in your conversations with them too. Like it's just like, there's like a twitchiness, like it's like, okay, we have to win.

48:31The last thing I would say, and this is kind of a kind of additional comment on the puzzle solving. You know, it was important to the people in this group to try to like find answers, like to try to find the right answers to things and to do so like somewhat efficiently, but to really like enjoy the company of other people who were interested in that same thing. So like, here's a great example of this. There are people in this group who at that during that era were like examining life extension, right? Which is sort of fashionable now, but wasn't really fashionable then. There are people who are interested in like, there are people who drop out of high school.

49:09There are people who, if they showed up, their clothes were disheveled, you know, but they were very smart, but their clothes were disheveled. There are people who were socially maybe not the most gracious or like didn't have social graces, but they were razor smart. What I would call this, this basket of things is like an embrace of weirdness. Like part of what this group does so well is that it is a place where you, if you came in, like Elon did and said, I want to make mankind a multi-planetary civilization. That was like, okay, like it's like within the realm of the possible, right? And so, there are all these things that I would say like are at the fringes in maybe other parts of society or other parts of economic life that are wholly embraced within this group.

49:49And I don't think that's an accident because I think what you see later is a lot of things emerge technologically and otherwise, where someone had to push on a crazy idea and push on it maybe a little farther than other people would go, and it bears fruit. And so that embrace or tolerance of weirdness is actually a very important thing. And I'll add a comment to that. Something that I observed when reading the book was it seemed like they were very direct, both with each other, but then they also were receptive and open to that directness, whether it was a criticism, a comment, or some way that they could make the product better or what they were doing.

50:29They didn't shut people down like, no, I'm smarter. And so I think that also contributed to their success at PayPal and then eventually in life going on to do other things. I think that just made things go by quicker. Yeah, you nailed it on the head. There is a directness and an honesty and a kind of bracing quality within this group that I think would make, and it would make me uncomfortable, I think it would make most people uncomfortable because it's massive intellects kind of in collision with each other. But you're right that what they managed to do, and you know, there's a few moments in the book where I kind of have them expound on this or I find quotes where they expound on it.

51:05But Max Lepchin in particular says, you know, it wasn't that we were, that meetings were almost harmonious. Like it wasn't actually that we all got along well. We just like, we wanted to be direct. We wanted to be honest. And what he says, it's interesting. He says, you know, there are environments I've worked in after where the criticism was happening behind the back. And those are actually worse environments. What was interesting about PayPal, not always, obviously, there are some things that were just personal. But what happened in many cases that I saw is that when people were shouting at each other, they were actually shouting at each other about the product and making the product better.

51:39They weren't shouting at each other because they didn't like each other. They were trying to figure out what the right answer was. That truth-seeking is a big part, a key ingredient to the company's success. Yeah, I wholeheartedly agree. I think that was such one of my biggest takeaways from the book. And the last thing that I want to ask you for today is if you could write a sequel to this book or just focus maybe on a post-PayPal story of someone, who would it be about, what would it be about, and why? Oh, wow. No, I've never really thought about it. Here's what I would say. I think sequels have a place, right?

52:13But I think one of the things that I take away from this group is that newness has a very strong appeal. So, I wouldn't be the person that would do the sequel because it's like, I don't, you know, you sort of don't want to like part of what you learn in studying these people is like how much a new thing matters. Like this is like obviously popularly titled or popularly becomes zero to one. This is the title of Peter's book. The idea of going from nothing to something and something is new. It's not just a sort of vague improvement on what was there before. So, I probably wouldn't do a sequel. But if I had to, I think, you know, knowing what I know about what's been written, oh boy, it's a great question.

52:51What I think I would focus on is, you know, it'd be almost impossible to do it. Like it'd be so hard to do it. But there's a school that is at SpaceX called Odd Astra. And my understanding of it, again, just from reading what's been written, is that Elon essentially wanted to have his children educated in a specific kind of environment. And what's been written is that he essentially built a school for his children and then for the children of SpaceX employees. And it's called Odd Astra. And look, there's like a million other things he's done. But to me, as somebody who's a dad, I'm like, what is going on in that school?

53:25I want to know everything, right? And I want to like find out like, what are they learning? How are they learning? What's who are the teachers? How do they choose what to teach? I would really be interested in that. Sort of this like, it'd be a short book and the book's not over yet. But I'd be really interested to know, like if there's a school and buried in the SpaceX campus, like what the heck is happening at that school? It'd be so cool to learn about. That's a one story that they put on the spot. That's the place I'd want to go. You should definitely do that. I'm so intrigued. Yeah, what are they teaching them at this school?

53:55But that is fascinating. I would definitely support that book. Well, maybe I'll pursue it when I have a sufficient break. And maybe when Elon's life calms down a bit, I'll reach out to him and see if he's interested. Well, I really appreciate you taking the time to come on today and discuss this amazing story with us. For the listeners who want to pick up the book and learn more about you, where can they go? Yeah, the book, you know, it's sort of that cliche, like the book is available everywhere. Books are sold, but you should probably just buy it on Amazon because then you can get the audio version if you prefer that or the Kindle version or the hardcover.

54:29And for me, I'm on Twitter. I'm not the most active person on Twitter, but I'm JimmyASony at Twitter. And then I'm just JimmySony.com. And I love hearing from readers. To me, the best part of doing this is hearing what people notice. Even what you noticed about the book is interesting to me. And so, I welcome the chance to interact with readers. It'd be great. And thank you so much for having me. Well, thank you again so much for coming on. I'll make sure to link all of those in the show notes. Thank you very much.

55:25and we'll help you understand what's going on in the markets in just a few minutes. So with that all said, I will see you again next time. Thank you for listening to TIP. Make sure to subscribe to We Study Billionaires by the Investors Podcast Network. Every Wednesday, we teach you about Bitcoin, and every Saturday, we study billionaires and the financial markets. 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 Investors Podcast Network.

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