Please welcome Primary General Partner Jason Schuman. I'm a little shorter than the other people apparently. How's everybody doing? The speaker for this next fireside chat probably requires no introduction, but he's the only Barry's Boot Camp instructor from the PayPal Mafia, was early at LinkedIn, and is the former COO of Square. He co-founded Opendoor and was the first institutional capital into businesses like DoorDash, Affirm, and Faire. I met him following a cold Twitter DM the week before he announced his return to Coastal Adventures. I'm excited to welcome to the stage Mr. Keith Rabois. Interviewing him is going to be my friend, senior editor at Forbes, Alex Konrad.
It's such a pleasure to be here with you, Keith, in your favorite tech ecosystem of New York, right? It's four of my five, last four of five most recent investments are in New York. So do you spend a lot of time here these days?
I've been here most of the summer actually.
Okay. What about Miami? Is this a place that you still are as famously bullish about as your Twitter persona would suggest?
I live in Miami, really excited. The fifth investment is in Miami. It's going to be a great company. It's going to reinvent education. It's not announced yet, but we're really excited about it. We, Delian, had the stat recently that 11% of all seed investments in the United States are in Miami, which is great. That's up from like basically zero when I moved there. So I think we'll get it to 20% and then we're off to the races. The stats you should be looking at if you care about the future of tech are what fraction of seed investments, where are they happening? Obviously Series C, D, E, you know, there are companies founded five, ten, fifteen years ago, so it's kind of irrelevant. But I look carefully at seed and Series A companies, and we've had great success both at Founders Fund and now at Khosla with Miami.
When you have been coming to New York to look at investments, sounds like you've made several recently, are there certain ecosystems where you feel like New York is particularly strong right now and competitive with Miami or San Francisco?
Well, as you know, I'm really a founder-driven investor. I don't really have a hypothesis or thesis. I'm just looking for founders that resonate with me. But financial services, innovation of financial services, seems to have a concentration here. Two of the five investments are financial services investments.
Got it. And so these days, you're obviously a Midas List investor, a provocative tour on social media sometimes, also increasingly seemingly a political fundraiser, pundit, who knows. Does all these different hats you wear, is that where deals come in? Or like, where does the highest quality startup find Keith these days?
Well, one of the most difficult parts of venture is you never really know where you're going to find the coolest, most interesting thing. And it's really hard to disentangle with Ns of one or two, like your most successful investments per year, per five years, per decade. What do you learn from an N of one? Not that much. So, you know, for example, we found the founders of Ramp through playing Delian, playing video games. I'm not sure I should be spending all my time playing video games. That said, the common denominator, most good investments I've made come through someone on the cap table. I want to be the first institutional investor, but they might have an angel investor, they might have a co-founder that worked at one of the companies I've been involved with before. They sometimes have a seed fund that directly introduces me, which is great. I can lead the Series A, but I'd prefer to be ahead of the seed funds too. But fundamentally, it's usually through a person, not through some speaking event, but they do occur, not through some social media presence, although I do respond to DMs as Jason talked about.
Do you like being contrarian and disagreeing with people in general?
Well, the problem is the world's broken. Like, if you believe the world's great and the US is on the right track, you know, sort of like raise your hand. The problem is the ether is just filled with stupid people and stupid ideas. So I had this dumb idea myself, really dumb idea, like ten plus years ago, I'm going to go correct the Internet. It's the biggest fool's errand ever because there's an infinite number of bad ideas and bad people out there. But it does occasionally have impact, which is encouraging. It's a little bit like you play golf. Golf is really, really difficult, but you hit one ball perfectly and you see the arc and you're like, oh my God, I play golf another five years because it feels so good. So occasionally you correct something on the Internet and it makes a difference in some real person's lives and they come up to you and they tell you about it. It's like, I was going to do X, but then I read this and I realized that was a bad idea. So it propels you forever. But it is, you know, difficult and painful. That said, if you have a platform, like I have a reasonable number of followers, at least on Twitter, and I would feel like I, in the Jeff Bezos sense, I'd regret my life if I didn't post. If I had an audience and I didn't use it for good. So I feel like I don't want to wake up 30 years and think that I could have shaped some opinion, some policy, something, and not leverage the ability to communicate.
Do you think that, but is it sort of like calculated marketing, for example, to be such a vocal supporter of the Miami scene? Do you want to kind of corner that market?
That's less a political argument than an ecosystem. Like, to create a tech ecosystem, you need a lot of different ingredients. It's like cooking a complicated dish. You need angel investors, you need founders, you need Series A investors, you need a bunch of different skills within a company. You need engineers, designers, blah, blah, blah, business ops people, sales people. And so it's really hard to start an ecosystem. You have to play a little bit like Noah's Ark and literally put a little bit of two and two and two and two and two on the boat and get everybody to Miami. So proselytizing is important, but letting people know that there's these opportunities, that you don't have to sit and suffer in the Bay Area. Like, you don't have to wake up every day and get assaulted or, you know, see fentanyl right in front of you or, like, you know, be abused and all this stuff. Like, there are healthy, vibrant places to live and you have choices. So communicating that does matter, but you ultimately need an ecosystem. I remember one of the things that started this Miami movement was in October 2018, I had dinner with a very successful CEO and he asked me this question. He said, how many people does it take to move somewhere else to create a whole new Silicon Valley? Is it 100, a thousand, or 10,000? I was like, I don't know. But when I announced I was moving to Miami, he texted me, forgot about this dinner, and he texted me and said, oh my God, you're actually moving. And I was like, yeah, I decided to run that experiment you mentioned at dinner. We're going to find out, is it 100, a thousand, or 10,000?
I guess I'm just thinking like a lot of investors seem to want to keep neutral on a lot of topics to avoid alienating folks. And like, if you end up doing most of your deals in New York this year while also saying Miami is the best place to be a tech founder, does that create any tension in the narrative or sort of?
Well, my best New York investment has a major office in Miami. Kareem from Ramp lives in Miami. Zach Frankel, who's also the only other external board member, lives in Miami. We do three or four board meetings in Miami. So if Ramp is going to be, it's pretty hard to be a better company than Ramp, period, with no caveats. So if Miami and New York work well for Ramp, they should work pretty well for everybody here.
I feel like New York is going to claim Ramp and fight you on that one.
I don't mind. Whatever, wherever, you know, wherever they want to do board meetings, I'm happy. But fundamentally, I think you're going to see more of this. Obviously, Wall Street and finance has had this New York-Miami corridor for decades, and I think in tech this is new. So Ramp has an office in Miami, has an office here. Opendoor, the company I run as CEO now, has an office in New York. We were founded in Miami, but certain center of gravity for engineering, particularly, is going to be in New York.
So, I've obviously written a lot about your career over the years, including going back to Coastal events. And when I did that, I spoke to a lot of your founders. And, you know, this won't be news to you, but a lot of your founders will say, oh, Keith is so different in person than he is if you only know him from social media or the Internet. You know, such a nice guy in person. Is that a conscious choice to be what some people might consider an asshole on the Internet versus a person?
The founders you interview are not the stupid people I was referring to in society. Like, I have a very, the normal, the distribution of the founders I work with is very non-normal intentionally. Like, they're the, you know, top ten basis points on some dimensions. And so they're super smart, super ambitious, they don't take days off, their work ethic's off the charts, they think for themselves, they don't believe in group think at all by definition to be that successful. And so obviously, you know, my interaction with them is very different than standard person off the street who doesn't usually follow things, you know, derivatively takes their views from other people, likes to impress other people versus think for themselves. So it's a very just different population. Secondly, I think that, you know, the nuances of 140 or now 280 characters, whatever it is, are obviously lost on complicated topics. Almost no conversation with a top-tier founder is in 140 characters. It's usually an hour dialogue, particularly on complicated issues. It's like a give and take and a debate. Sometimes a debate, sometimes actually learn things. Like, for example, there's a company I'm involved in that you know about, was one of the founders you interviewed, that has a complicated topic that I was pretty opposed to the idea of what they wanted to do and it sort of tried to slow it down a bit. And then after we dug in, both the CEO and I dug in pretty deeply yesterday, in like three minutes we figured out that it actually is a pretty good answer, that what they wanted to do, but not necessarily for the reasons they were proposing it. But as you dive really deeply, but that was a constructive conversation across his team and me over weeks.
I guess I'm just, you know, you now work again with Vinod Khosla, and it feels like you guys both can't resist just arguing with anyone who provokes you. Whether it's Marc Andreessen provoking Vinod about AI safety, or it's like John Rando 999 tweeting about Trump to you. Why do you guys engage with people all the time on, you know, like, is it helping you as an investor? Is it just you being your full self? Like, why?
