00:01:21 · Brian Singerman, Molly O'Shea
[00:01:21] S0: We were talking about how old I am, and I'm not that old, Molly. I'm not a 100 and [00:01:30] S1: something. We're off to a really good start. Most people know you from Founders Fund. Bit of a legend there, I know. Grace from Vanderbilt, she invited me out to one of their conferences that they were doing. I think it was like in the fall or winter or something like that. She was like, hey, like, would love for you to come. You could interview Brian Sigerman on stage. You interested in that? Was like, Hell yeah. And then I think turns out I had to be in some foreign country. [00:02:01] S0: You're a woman of the world, Molly. [00:02:02] S1: So sorry. But here we are today in your music factory. [00:02:06] S0: Music studio, but sure. [00:02:09] S1: So I want to talk about, I mean, this is like the most crazy time ever. And most of the companies that are headlining are ones that you were an early investor in. So I want to talk through those from SpaceX, Palantir, Andoril, etcetera. But before we do that, I got some amazing questions from Max Levchin. [00:02:28] S0: Oh boy. [00:02:29] S1: I don't think you're ready for these. [00:02:31] S0: I really am not. Anything that Max is going to bring up, I'm really not ready for, but I'll do my best. [00:02:35] S1: They're very good. [00:02:36] S0: I will get him back though. [00:02:37] S1: We're going to get into all the investing stuff, so stay tuned, but to start, are you ready? [00:02:44] S0: I'm ready. [00:02:46] S1: When and how did you get into tabletop gaming?
00:02:46 · Molly O'Shea, Brian Singerman
[00:02:46] S1: When and how did you get into tabletop gaming? [00:02:49] S0: Oh, that's a great one. I've been into tabletop gaming forever. I'm a gamer, that's what I do that drives my investment strategy and drives everything else. I am a strategy gamer, I love it, it's what I love. I got into tabletop gaming, not even just video gaming, probably like age six, seven, and I would go to these local meetups near my house where people were playing anything from Monopoly to Acquire to any of the old games, and I just got really super into it. [00:03:19] S1: Who are your favorites? [00:03:21] S0: I've been competitive, like nation competitive, global competitive in a couple of different games. I don't know if I'd call it love, or if I just get kind of obsessed with one of these games at a time. I was like the Settlers of Catan US Champion, but this is in like nineteen ninety five-ninety six, before anybody was playing, before anybody had ever even heard of the game, was the first year the game came out. I probably was world top 10 in a game called Ascension, and I was definitely top 10 in a game called Terraforming Mars, a game called Kalis, I suck at poker, though. [00:04:01] S1: You suck at poker? [00:04:02] S0: I do suck at poker. [00:04:03] S1: How did you pick out each of those games? How does this all start?
00:04:03 · Molly O'Shea, Brian Singerman
[00:04:03] S1: How did you pick out each of those games? How does this all start? [00:04:07] S0: I don't know, think you play one of these, and then you start being like, Oh, that's interesting. Especially once they became online or computer versions of these, you could just play them so much that you could actually get good at them. Don't think you could. Back in 1995, it was pretty impossible to get really, really, really good at something like Settlers. The people who are good now would have it's night and day, and I would not be able to compete at all right now, but once online gaming took off in a really big way, you were able play enough of these things that you got really good, much to my wife's chagrin. I would play these things. To get that competitive at these things, you have to play them. [00:04:50] S1: 20 fourseven. [00:04:51] S0: Not 20 fourseven, but you've got to play them ten hours a day. [00:04:54] S1: You can't have family. [00:04:55] S0: Yeah, right. Ever since I've had a family, I have not been able to do this. But before then, yeah, it was really fun. [00:05:04] S1: Have you gotten into chess or Go or anything like [00:05:06] S0: I'm bad at chess. Anything that's got such I like strategy stuff. Anything where the tactical component is equally as important, if not more important than the strategic component, I'm going to be terrible at. I do not like tactics and this and that, I like strategy.
00:05:06 · Brian Singerman, Molly O'Shea
[00:05:06] S0: I'm bad at chess. Anything that's got such I like strategy stuff. Anything where the tactical component is equally as important, if not more important than the strategic component, I'm going to be terrible at. I do not like tactics and this and that, I like strategy. [00:05:25] S1: I want to break into the strategy component of this too, because this does bleed into your investment thesis and how you're looking at companies, I would believe. What are the main strategies that you go after? What are the competitive forces and how do you look at maneuvers? [00:05:39] S0: I don't look at maneuvers. When I was doing the venture investing thing, 98% plus of my decision was based on the strength of the founder. When I have a conversation with that founder, do I believe that they would just crush at what they are doing? Do I believe that they are the best in the world at something novel? It's still what I'm looking for right now, even though I'm not doing direct investing, but do I think that they are the best in the world at something, whatever that is, and do I think they can leverage that to build one of the world's greatest companies? [00:06:11] S1: Let's bring it back to 2007. You were talking with Sean Parker, he told you about Founders Fund, you were running an angel fund at the time, and was it SpaceX that piqued your interest of joining? What was it like back then?
00:06:11 · Molly O'Shea, Brian Singerman
[00:06:11] S1: Let's bring it back to 2007. You were talking with Sean Parker, he told you about Founders Fund, you were running an angel fund at the time, and was it SpaceX that piqued your interest of joining? What was it like back then? [00:06:25] S0: It was amazing back then. Was running my own fund. I was still at Google. I was going to leave Google, raise another fund, raise a bigger fund, became friends with Sean. And then he said, Hey, why don't you come take a look at what we're doing at Founders Fund? So I went there, just kind of hung out, met the guys. I didn't know who the other guys were, didn't know who Peter was, started and hanging out. That's when they were starting to look at a ridiculous company called SpaceX. And it was just so unbelievably cool. And there was just absolutely no other way that I was going be able to do that, just angel investing. And so I'm like, Oh yeah, this is the kind of stuff I want to focus on. And so I joined Founders Fund in early 'eight. [00:07:07] S1: That's crazy. How did you get to know Sean? [00:07:10] S0: I think I met Sean because I was either helping talk to one of the companies he was involved in. And I met him through, I believe I met Joe Green first, was his co founder at Causes. And then I met Sean through Joe. Everything, Silicon Valley networking, you never know exactly where it happened, but yeah, we became friends and there you go.
00:07:10 · Brian Singerman, Molly O'Shea
[00:07:10] S0: I think I met Sean because I was either helping talk to one of the companies he was involved in. And I met him through, I believe I met Joe Green first, was his co founder at Causes. And then I met Sean through Joe. Everything, Silicon Valley networking, you never know exactly where it happened, but yeah, we became friends and there you go. [00:07:34] S1: That's a good segue because another one of Max's questions, and I don't know if there's like backstory to this question, if there's something deeper to this, but if there is, I want to know all about [00:07:45] S0: it. Okay. [00:07:46] S1: Silicon Valley is a collection of characters. Who are the most interesting ones, whether they're in your portfolio or otherwise?