PayPal: Max Levchin (Part 1 of 2)

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Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. I'm Guy Raz and on the show today, how Max Levchin took an idea nobody cared about and transformed it into PayPal. A brand that embodied startup culture with its rapid rise, hairpin turns, and world famous founders. There are just a few companies in tech whose overall impact went a lot further than just the products they produced. Hewlett-Packard is a classic example. It's not that computers or printers they made that matter, but the fact that David Packard and Bill Hewlett were pioneers who laid the foundation for what is now known as Silicon Valley. Atari is another one. Sure, Nolan Bushnell's video games and consoles were cool, but what matters more is how Atari ushered in the video game revolution that's now a massive force in global entertainment. And then there's a company called PayPal. Yes, it may be convenient to pay someone using PayPal, but its products aren't nearly as important as the legacy that came out of it. The group of people who helped launch PayPal back in the late 1990s would go on to either found or fund companies including YouTube, Tesla, Facebook, Yelp, Flickr, LinkedIn, Mozilla, Palantir, and many more. You may have heard the phrase PayPal mafia, a term popularized by Fortune magazine in an article that came out in 2007. The PayPal story is full of public drama and private intrigue, and not surprisingly has focused on its three best known founders, Peter Thiel, Reid Hoffman, and Elon Musk. But the guy who actually had the earliest idea for PayPal is Max Levchin. Max is a gifted computer scientist and coder who founded his first companies as a student at the University of Illinois. In 1998, he launched a tiny cryptography company with Peter Thiel that would evolve into PayPal. Max would eventually go on to help start several other companies, including Affirm, a payment platform that lets you pay for things in installments. Max's story is so rich, so full of anecdotes of the now famous founders he once worked with, and so full of lessons for anyone hoping to launch anything of value that as the two of us were talking, I kept wondering how we were going to keep it all to a single episode. So, we decided not to try. Instead, we're going to tell Max's story in two parts. In this episode, part one, you'll hear about his early years, the launch and growth of PayPal, and its eventual sale to eBay. And next week, part two, everything Max did after PayPal, including the company he's most involved with today, Affirm. Max Levchin was born in the mid 1970s in Ukraine when it was still under Soviet rule. As a Jewish family, the older generation of the Levchin clan faced a lot of hardship.

And from what I understand when you were growing up, your mom was also a physicist, right?

So your mom worked for the state and was a scientist and your dad was a...

And did you speak Russian at home or did you speak a Ukrainian dialect?

Was your family at all religious? Did you have any Jewish identity or did they sort of stay away from it because you could be persecuted in the Soviet Union if you practiced religion or Judaism, right?

So I've read that as a kid in Ukraine, you were already getting into computers, right? Like you were already learning about programming, right?

Soviet Union collapses in 1991, officially in Ukraine would become an independent state. And today we're seeing the long tale of that story. Your parents decide to immigrate to the United States. First of all, what were they going to do when they got to the US? What was their plan?

You're physics royalty.

Wow. So you were let out and you land in Chicago in 1991. So what did your parents do for a living when they got there?

And did they speak English?

You were a 16-year-old kid. Did you speak English?

Wow. All right. So you could integrate into the school system and your brother. You're a junior high school basically. And was it hard for you when you got to school?

All right. So you get to school and you are determined from the day you get there to what? To become a software engineer when you graduate or to start your own software company or both? From what I've read, it sounds like you kind of knew what you wanted to do when you got there. Is that true?

I mean this was kind of a heady time at the University of Illinois. And I think Netscape was, Mark Andre came out of there, right? And so it wasn't MIT, it wasn't Stanford, but it was not far behind in terms of the innovators that would come out of there. But it's still the mid-90s, right? Early internet days. But you probably had access to see or be exposed to technology that maybe ordinary people weren't exposed to yet, even as a computer science student.

While you were in college, you already started to connect with other students to found businesses, right? So I think a lot of the immediate reaction to two things, the launch of Mosaic and kind of the like, oh my god, this is different and important and everything will change now. Plus, wow, Mark and five other people just up and left campus and went to Palo Alto, California, which seemed like going to Mars to start a company. And that construct was so cool and so inexplicably desirable. I ran into these people who were kind of hanging around the same computer science circles. And they're like, 'Hey, we're going to go start a company. You should join us because you're one of these guys who doesn't sleep, doesn't eat, just writes code.' And I was like, 'That sounds great. I don't really know what we're going to do.' And yeah, we don't know either, but we're just going to go start a company. Doesn't matter what it's going to do. And what we kept on trying to do is answer the question, okay, so the world today looks like this. Now add web. So advertising exists on TV. It exists when you drive Highway 57 from Chicago to Champaign. What happens to advertising when everyone has a web browser? We should build a company around that.

And I know you started a number of companies around this period. Which didn't quite work. But what were some of the ideas that you came up with?

When we come back in just a moment, how Max moves out to Silicon Valley, meets an up-and-coming small-time investor named Peter Thiel, and starts a brand new business that initially goes absolutely nowhere. Stay with us. I'm Guy Raz and you're listening to How I Built This.

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Hey, welcome back to How I Built This. I'm Guy Raz. So, it's 1997 and Max Levchin has just graduated from the University of Illinois with a bachelor's degree in computer science. He's already walked away from a few businesses that he couldn't raise money for. And now his former co-founders are telling him to go west. My co-founders number one and two up and left for Palo Alto because they knew you had to go there because that's where the action was. We failed to raise money. Silicon Valley was chock full of venture capitalists that were interested in giving money to people like us. And so they said, 'You know what? This college thing is overrated. We can drop out and go.' And because these two guys, Scott and Luke, moved to Palo Alto, I knew and we kept in touch and I had gotten a non-stop stream of, 'Oh my god, it's Mecca for startups here and you're rotting away in Champaign-Urbana. Get out here as soon as you can.' This is Luke Nosek and Scott Banister, right? Yep. They'd come back into your life. In 1998, you moved out there to hang out with them. Yep. Exactly. 469 Grant Avenue, apartment Q. I was crashing on Scott's floor and Luke was in apartment P across the hallway. And when you got there, what did you do? I sort of, because I was hanging out with Scott, I promptly became his brainstorming partner. I knew programming and I thought myself a pretty great software engineer, but I knew that most of my failures as a startup CEO, CTO, whatever I thought I was, was because I would build things that I thought were good and easy to use and then I would show them to someone like the classified software and people like, 'This is really great but I have no idea how to make it work. It's so complicated.' So I decided that my next sort of development phase in life would be to go hang out with people who are really good at product design. And Scott happens to be just a genius product designer type thinker. And so I sort of attached myself to him and would just roam around wherever he would go and say, 'All right, I have a product idea.' And he would tell me, 'All right, tell me a product idea.' And I'd tell him and he'd rip it apart and show me why it's a stupid idea and all the things that are wrong with it. And it was my crash course education in product design. So you were kind of trying to come up with different ideas. And I guess in August of 98, a fateful and certainly fortunate encounter, we went to a lecture at Stanford by Peter Thiel. We know who Peter Thiel is today. He was a...

So you were kind of trying to come up with different ideas. And I guess in August of 98, a fateful and certainly fortunate encounter. We went to a lecture at Stanford by Peter Thiel. We know who Peter Thiel is today. He was a...

Yeah. Comparatively what it would be today. Why did you go to that lecture? What was the lecture? And you were not a student at Stanford, but I think it took place on the campus.

What did he talk about?

Did you, from everything I've read about you, you were a little bit awkward. Maybe you still are today a little bit. Which is okay. Except that hasn't changed. No, no shame there. But you did have to summon the courage to go talk to him. By the way, was it a packed lecture hall? Was it like hundreds of people?

And what did you talk to him about? Just do you remember? Did you say, 'I liked your lecture.' Or

Which is very indicative of how Peter Teal generally does things that Peter Teal does. So next day you guys meet for breakfast. Where was it?

Yeah. All right. All right. So, you go for breakfast at Hobie's legendary Silicon Valley Diner Cafe. And you're like 22, 23, he's probably close to 30. So, he's like, you're probably thinking, 'Wow, this guy knows where it's at.' He says, 'What are your ideas?' And what did you tell him?

But I think in any case, you at this time do get some funding from friends and family. And I think you managed to hire your friend from the University of Illinois, Luke Nosek, right? to come out and help you.

And did you get office space? Did you rent a place and put computers in and get a fast T1 line in and start clamoring at the keys on your computer.

And at some point I think pretty soon after Peter Teal, he became the CEO of this company that you started. Did you ask him to be the CEO or did he sort of say, you know, I should probably be the face of this thing because I'm a little bit better at presenting.

So Peter is a CEO and you are presumably the head of technology and you're trying to develop this crypto software that will encrypt data between Palm Pilots. But at some point clearly this shifted to a completely different business. So tell me about how you came to the realization that maybe that wasn't the right thing to focus on.

And if you want to hear his story, you should go back and check out that episode. He went on to found LinkedIn. Was he kind of just hanging out as a friend or did Peter bring him on as an employee of this company?

And so you begin to kind of pivot into this idea that maybe you should focus on encrypting money transfers. Is it a year before you make that pivot or is it faster?

And you changed the name to PayPal at that point.

All right. At that time and this is 1999, your PayPal, it's not yet PayPal that we would know of as PayPal. It's still the concept is still like if I were just meeting you at a party somewhere and I was not a tech person, I'd say, all right, well, what are you working on? Explain this thing. How's it going to work? What from the consumer perspective, what would you have said in 1999? [laughter]

Of course. And yes, I frequently would get called out like, 'What are you talking about? I have cash in my pocket. Do you not have cash in your pocket?' [laughter]

And the promissory note would be tied to your bank account.

Oh wow. Okay. I like that. That's cool.

Yeah. No, I like it. I like it because you know what? I like it because I know that there are still people out there probably owe me at least a hundred bucks who like I'll pay you back next week. You'd pay for somebody's movie or something. I'll hit you up later. But I don't remember. And I'm sure I owe people like a hundred, two hundred bucks, too. So, that would have been great.

And presumably the business model would be around taking a fee. Yeah. Every time the money got transferred. Okay. But at that time, there were other products out there. There was something called Digicash, I think, right? So there were companies that were focused on ways to transact and send money back and forth in an encrypted way. So, didn't they already solve the problem that you were trying to solve?

So how are you guys going to solve that problem? How are you going to make this? You were going to basically make it so easy that you could just beam a digital promissory note to someone else at the dinner table and then that would be it. They connect to their computer and then it would connect to their bank account and then they would get the money deposited in their account.

This is maybe why you have not most likely used the PayPal on your Palm Pilot. The simplest user interface always wins.

So November '99, PayPal sort of begins operations. What as a consumer at that time, what did that mean? Was it a website or was it still focused on doing it through Palm Pilots?

So initially the idea was it was peer-to-peer like I send you money, you send me money, promise I know. And by the way, I imagine that we know e-commerce really took a long time for e-commerce to take off for people to trust it, seven or eight years. So it still when you launched it, it must have been a tiny number of people who were like yep, I mean it must have been really like early adopters who were confident and felt secure with this.

When we come back, how in the space of a year, PayPal goes from 17 users to hundreds of thousands. And how in the space of 3 years, it goes through a merger, a management shakeup, an acquisition, and an IPO. Stay with us. I'm Guy Raz and you're listening to How I Built This.

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Hey, welcome back to How I Built This. I'm Guy Raz.

So, it's 1999 and Max and his partners have built a new peer-to-peer payment system soon to be called PayPal. And almost right away, the service starts to attract one very important user group, people who use eBay.

And I think we should be clear here, which is you'd mostly created this thing to be used on Palm Pilots, right? I mean,

I mean, I think that ended up being adopted by like 100,000 users in January of 2000.

And I think by March of that year, something like a million people were using PayPal. So, how did it grow so quickly? I mean, this is not a time where there's social media marketing, right? Were you advertising or was it just people discovering it?

I know you were focused on the technical side, but you were probably clued into all parts of the business. How did you guys convince the credit card companies and the banks to cooperate?

But one of the biggest challenges you guys faced at the beginning once you launched was fraud, right? I mean, the company was losing millions of dollars a month from fraudsters who were trying to figure out how to outwit the system.

All right. So, as you start to see more and more people adopt this thing, I don't quite understand this part of the story, but there was another competing company that was founded around the same time called X.com, by Elon Musk. We all know who he is. And he was trying to do a similar kind of thing. I know this because Jeremy Stoppelman, who went on to found Yelp and we'll get to that later, and Jeremy's been on the show in the past, he was working with Elon. And to him, PayPal was the enemy. It was a battle to the death. But the two companies merge in March of 2000. How did that marriage happen? What do you remember about that?

You guys are mortal enemies. And all of a sudden you become X.com and PayPal are the same company. Did you remember just thinking, 'Wait a minute, this is crazy'? Do you remember how you felt about that?

I remember it kind of feeling initially very awkward and then not feeling very awkward very quickly. Was there relief about that? In a sense, instead of competing against people like Elon and his team, you were now all kind of harnessing your collective power?

When the two companies merged, how do you... this is around mid-2000. Do you remember how many employees total now this merged company had?

Okay. So, you knew everyone. And then pretty soon after the merger, Elon becomes the CEO and you're in the number two position as CTO. So, how did you find working with him at the time?

Did you... I mean, you were younger, you're younger than Elon and Peter. Were you comfortable with him kind of running the show? From everything I've read about, and there's a new book about PayPal, he really kind of saw this as X.com was the senior partner in this relationship and he was the boss.

I mean, clearly there were tensions growing within PayPal. Peter was out of the picture kind of. You were still there. And October of 2000, Elon Musk becomes the CEO. By the end of that calendar year, the board ousted him. They fired him. What do you remember about that? I mean, it was not a personal thing. Maybe it was, but from what I understand, it was really just a fundamental difference in how to operate the company.

What I'm curious, Max, what was your lifestyle like during that time? I mean, it seems like it was such an intense period. I've read about how you would sleep in your office under your desk or in a sleeping bag. Did you do that often or was it off and on again?

Tell me a little bit about... I think one of the benefits of early success but also downsides is you get quoted when you're young. I have some of that myself. So I've read quotes or articles about this time at PayPal and it sounds, I don't want to caricature, but it sounds like a little bit of a frat culture. I know that you did not want frat boys. But there was a confrontational style and an expectation to just fully live this thing all the time. Or is that not accurate?

How did PayPal survive the dot com crash of 2001?

Wow. So you guys had cash on hand because Peter had raised that money which enabled you to survive it.

All right. So now Elon is out. It's 2001. Peter Thiel is CEO again. And PayPal is growing. You're doing fine despite the collapsing tech world around you. It felt okay within PayPal. There was no nervousness or panic.

The company went public in February of 2002 and I think on day one, the shares were up like 55%. It was an amazing debut on the NASDAQ. When it went public, you were a CTO, Peter was a CEO. Did you envision your future? You were still 26, 27. Did you think that this was the beginning of the end for you? Like you were now sort of mentally moving on to something else, or did you still see PayPal as your career?

All right. We know that eBay would acquire you just a few months after you went public. But what you just said is also just unbelievable, which is eBay was trying to shut you down. Explain that. Why?

So they could have completely crushed your model. They could have said you can only use Billpoint on eBay.

I think at the time they were very concerned that if PayPal were to get turned off, commerce would slow down and eBay would make a lot less money. So even after you went public, you depended on eBay. You needed to keep them happy, but you also knew they didn't like you. Presumably you had to start thinking about diversifying your revenue streams because you were so dependent on eBay, and you're a public company, and your share price would have tanked if eBay kicked you off. So what were you guys doing to prepare for that possibility? That was the great unspoken or maybe spoken concern in the PayPal halls.

Yeah.

What an incredible opportunity that you had at such a young age to experience that kind of uncertainty and volatility because that was going to serve you well as you advanced in your life and career. But it's almost like a business school class, except the consequences are a little different. You're not going to get a bad grade. You're going to lose all your money.

In 2002, when eBay announced that it was acquiring PayPal, you were part of the leadership team. Was that surprising when they came and said, 'Hey, maybe we should just acquire you'?

Yeah. They paid $1.5 billion to acquire PayPal. They acquired it in October of 2002. You're 27. You walk away with on paper something reportedly about $30 million. You're set.

But I read that there's an article written in the Times about you in 2007. And you've been quoted in that article saying that the year eBay purchased PayPal was the worst year of your life.

Indeed.

What? And I'm not asking this with a sense of judgment. I'm just curious. Can you explain how that became the worst year of your life?

Why didn't you go, I mean, a lot of the folks that you worked with went into investing. Peter Thiel famously. Did you try that at all?

You were quoted at the time, and I'm sorry to read this quote to you because again if I was quoted when I was 27 I probably said some stupid things I would be embarrassed, but you said to the Times 'I took this perverse pleasure in seeing if I could make someone cry' which does sound a little bit mean.

And you think that came from this place of like 'I need to be doing this. Why am I not doing this?'

And that is where we're going to leave Max Levchin's story for now. Next week, we'll be back with part two of our conversation where we'll hear about all the things that Max built since PayPal.

Hey, thanks so much for listening to the show this week. If you want to hear every episode one week early, check out Amazon Music. If you want to listen one week early and ad free, subscribe to Wondery Plus in Apple Podcasts or on the Wondery app. Please do follow us on your podcast app so you always have the latest episode downloaded. Another way to support our show is by filling out a survey at wondery.com/survey. If you want to contact the team, our email address is hibtid.wondery.com. If you want to follow us on Twitter, our account is @howibuiltthis. Mine is @guyraz. On Instagram, I'm @guy.raz. This episode was produced by Alex Chung with music composed by Ramine Arablouie. It was edited by Neva Grant with research help from Clare Murroima. Our production staff also includes JC Howard, Casey Herman, Josh Lash, Liz Mezer, Carrie Thompson, Sam Pollson, Katherine Cipher, Elaine Coats, John Isabella, Chris Msini, and Carla Estz. I'm Guy Raz and you've been listening to How I Built This.