How I Invest with David Weisburd
00:01:25 · Jack Selby, David Weisburd
[00:01:25] S1: It doesn't directly answer your question, but [00:01:28] S0: Jack, you were one of the first 10 employees at PayPal. You worked with Peter Thiel for more than twenty years, but I wanna start in the PayPal days. PayPal Mafia has produced... Seems like every year, there... There's one more additional person that that becomes impressive from the list, Elon Musk, Peter Thiel, Max Levchin, Reid Hoffman, David Sacks, Roelof Botha, Steve Chen, who founded YouTube, Luke Nosek, Keith Rabois, on and on. Do you think that's second of order effect of just being such a prolific project early on in in Silicon Valley, or were these people really that exceptional? [00:02:05] S1: I think it was a function of a couple things. So we we had a good outcome. We ended up selling the company to eBay for, I think, around $1,500,000,000, which I know in today's times feels like [00:02:17] S0: That's a seed round.
00:02:17 · David Weisburd, Jack Selby
[00:02:17] S0: That's a seed round. [00:02:18] S1: That's chump change. But back then in 2002, that was seemingly a real number. But the majority of our time during PayPal was actually after the dot com crash. And so it was it was a really difficult process, but at the same time, was also relatively short. So from when we started the company to when the business sold to eBay, it was less than four years. So quite short, especially by today's standards. So I think for a lot of the folks, they kind of got a taste, and they really enjoyed that success, but they wanted more. And then on top of that, the average age of our executive team, like, where we went on the IPO roadshow, I think it was 26. So we got a taste. We're all still very young, but wanted more, I think, be the most succinct way I could put it. [00:03:04] S0: A lot of people today, it's almost an overused term at this point, talent magnet. How did PayPal recruit this kind of gang of characters that ended up building some of the greatest companies in Silicon Valley?
00:03:04 · David Weisburd, Jack Selby
[00:03:04] S0: A lot of people today, it's almost an overused term at this point, talent magnet. How did PayPal recruit this kind of gang of characters that ended up building some of the greatest companies in Silicon Valley? [00:03:16] S1: Peter's approach to hiring was very much kind of a best athlete approach. And so we weren't looking for someone who was necessarily, say, an expert in payments because we kinda stumbled into, you know, the ultimate product for PayPal, you know, emailing payments. I mean, our original product was beaming money between PalmPilots, and that's what we spent most of our entire series a round that we raised from Nokia because we were literally beaming money between PalmPilots and most importantly, trying to figure out how to encrypt that infrared beam between the two Palm Pilots. So it wasn't as if we were hiring for specific aspects of how the business looked at the time. We're just really looking for kind of the the best athlete, smartest people we could bring onto the team, and I think Peter did a really good job of that. [00:03:56] S0: And what was the trade off there outside of the domain expertise? Was there also cultural trade off in terms of if it's the best athlete, it doesn't necessarily have to be a culture fit?
00:03:56 · David Weisburd, Jack Selby
[00:03:56] S0: And what was the trade off there outside of the domain expertise? Was there also cultural trade off in terms of if it's the best athlete, it doesn't necessarily have to be a culture fit? [00:04:05] S1: The culture just kinda coalesced naturally, organically. I ended up running the international operations. I was 25 years old. I mean, I didn't know anything about running international payments or international operations for a payments company. So like most of us on the team, on the executive team, we just kinda made it up as we went along. And so... And the culture just kinda coalesced. And if you fast forward today, like, we did a twenty year post IPO reunion party at Peter's house in LA a couple years ago, and, basically, everyone showed up. It was really cool. We had, like, 400 plus people there, and so we're all still really friendly and get along quite well, which is, which is pretty amazing. [00:04:37] S0: There's a lot of turmoil around the company in terms of a lot of fraud and just these big issues that you had to solve. It was obviously a very stressful time. Did that help define your career in terms of that's where you started and there was, like, a second order effect? I'm still trying to double click on why everybody became so successful.
00:04:37 · David Weisburd, Jack Selby
[00:04:37] S0: There's a lot of turmoil around the company in terms of a lot of fraud and just these big issues that you had to solve. It was obviously a very stressful time. Did that help define your career in terms of that's where you started and there was, like, a second order effect? I'm still trying to double click on why everybody became so successful. [00:04:56] S1: There was always a lot of stress. I mean, the analogy I would give you, if you're working at a successful startup, it's like you get on the treadmill, and it just goes faster and faster and faster. And if it starts slowing down, that's a problem. And so it was just a fire drill at all times. Like, on the fraud side, you mentioned, like, Max Levchin, world class in helping figure out how to prevent all these attacks from these Russian mobster, Mafia types that were trying to infiltrate our system and steal money out of the PayPal, overall network. And that was just one of many, many, many issues that we were dealing with nonstop. But that was just... That was the kind of the normal business affairs on a day to day basis. So I think that probably forged us to be, I don't know. Maybe we... That left us stronger because of it, but it was a constant fire drill. [00:05:38] S0: Oftentimes, think about there's this meme now that you wanna find founders that have childhood trauma. So I wonder whether there's such a thing as an adult... Adulthood trauma that that leads to success.
00:05:38 · David Weisburd, Jack Selby
[00:05:38] S0: Oftentimes, think about there's this meme now that you wanna find founders that have childhood trauma. So I wonder whether there's such a thing as an adult... Adulthood trauma that that leads to success. [00:05:49] S1: I mean, we certainly had a lot of turnover. We had to certainly had to let some of the senior staff go because they just ended up not being cultural fits or they just were underperformers. But for the most part, the team that was with us from the earliest days, that was the team that we basically left with when we sold the the company to eBay. So it was... Again, to Peter Thiel's he's a very, very, very skilled guy, and arguably his best skill for at least from the PayPal days was as a hiring manager. [00:06:11] S0: And you have the track record of being with Peter Thiel, I think, longer than any other human being in the world, close to twenty years. What did you learn from Peter Thiel that a lot of people don't know?