Skip to content
The Twenty Minute VCThe Twenty Minute VC

Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943

Brian Singerman is a Partner @ Founders Fund, one of the best-performing funds of the last two decades. Among their portfolio, they have the likes of Airbnb, Facebook, Stripe, Anduril, and many more generational-defining companies. As for Brian, he has led investments in the likes of Affirm, Oscar Health, Wish, Asana, Oculus, and Postmates to name a few. Brian also sits on the board or is an observer to The Long Term Stock Exchange, Solugen, Cloud9, Modern Health, and of course, Anduril. Prior to Founders Fund, Brian spent a very successful 4 years as an engineer and executive at Google. ------------------------------- Timestamps: 0:00 How Brian got into the world of venture 1:16 Do you agree with the buy low and sell high principle? 2:55 Does early stage venture need to worry about Macro economics? 4:30 Company valuations and funding prospects 6:48 Did you deploy too fast in 2020-2021? 7:56 Lessons from the last few years 11:18 How do you advise your founders today? 13:22 How much does market matter? 15:24 Are winners obvious early? 16:07 Reserves and cross fund investing 17:31 What gets easier and what’s get harder? 21:58 What makes Founders Fund special? 26:20 Do boards add value? 27:23 How to plan strategy with a founder 28:45 What have you been wrong? 31:22 Advice to fund managers 36:55 How to backchannel when hiring 39:04 How to advise young investors 41:11 Most successful investment ever 42:15 Dollar to fame ratio 43:06 Biggest personal strength and weakness 44:02 Did becoming a father impact your mindset? 45:10 Best board member you’ve worked with 47:07 What makes Anduril so good? --------------------------------- In Today’s Episode with Brian Singerman We Discuss: 1.) From Google to Befriending Sean Parker to Founders Fund: How Brian’s friendship with Sean Parker led to his joining Founders Fund over 15 years ago? What does Brian believe makes Founders Fund such a unique fund? What does Brian know now that he wishes he had known when he started in venture? 2.) The Landscape Today: Where Are We Now? Why does Brian believe there is a huge price mismatch between private vs public companies? How does this impact the pace with which Founders Fund invest? Why does Brian not feel any pressure to invest in this environment? What are the 10 hypergrowth companies that Brian is looking to invest in today? What advice does Brian give to young investors today who are concerned at their first market correction and questioning if they are actually any good at this? 3.) Brian Singerman: The Investor: How does Brian reflect on his own investing style? What is he world-class at? What is he bad at? Why does Brian think boards are a waste of time? What is better than a board? Why does Brian not ever think about reserves? How does Brian answer LPs concerns when they cite them on the topic of cross-fund investing? What does Brian believe is the secret to venture capital? What elements make those at Founders Fund thrive? What characteristics make those that do not work out, fail? 4.) Founders Fund: The Firm: How does Founders Fund structure and optimize its decision-making process today? How does Founders Fund approach the hiring process for all new team members? What one question do they need to be able to clearly answer with all team members joining? How do Founders Fund approach the reference checking process for all new hires? What questions do they find most revealing of the true talent of the candidate? What are the single biggest hiring mistakes Brian has made? What did he learn from them? --------------------------------- Subscribe to the Podcast: https://www.thetwentyminutevc.com/brian-singerman/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Brian Singerman on Twitter: https://twitter.com/briansin Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok --------------------------------- #VentureCapital #FoundersFund #BrianSingerman #HarryStebbings #20VC #Venturecapitalist #Anduril

Harry StebbingshostBrian Singermanguest
Oct 31, 202249mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:16

    How Brian got into the world of venture

    1. HS

      Bryan, I'm excited for this. I always love our chats. So first, thank you so much for joining me once again today, Bryan.

    2. BS

      No problem, Harry.

    3. HS

      Listen, I wanna start, for those that maybe missed our first show-

    4. BS

      (pinging)

    5. HS

      ... just with some context. How did you make your way into the world of venture and how did you come to be a GP at Founders Fund in a, in a short one to two minutes? (laughs)

    6. BS

      Man, it's been a long time now. It was... I started at Founders Fund almost 15 years ago. Um, I was at Google. I was an engineer and an engineering manager, and started doing startup investing on the side there in 2006, 2007, investing in a whole bunch of Y Combinator companies when Y Combinator was still brand new. Um, decided to make that my full time thing in '07. Was trying to figure out what to do. "Do I raise my own fund? Do I do something else?" And that's when I met, uh, Sean Parker, and we became friends, and he said, "Hey, why don't you check out what we're doing at Founders Fund?" And I came in, and that's when, uh, we were considering, uh, uh, little investments in a company called SpaceX and, you know, said, "This is what I wanna do." So I joined up.

    7. HS

      I love that, and what an entry point with the SpaceX investment. (laughs) I- I- I wanna dive straight in on investing mechanics, to be quite honest,

  2. 1:162:55

    Do you agree with the buy low and sell high principle?

    1. HS

      Bryan. I- I had Keith on the show, uh, not too long ago, uh, and he vigorously kind of debated or disagreed with an idea, which is, uh, buy low, sell high. Um, I often-

    2. BS

      (laughs)

    3. HS

      ... get it now from LPs, and they say, "Ah, this is the time, Harry, where you can buy low and sell high." Do you agree with that principle? And can you give me an example of either way where it's- it's worked for you?

    4. BS

      Yeah. I don't know. Ven- venture, to me, is just very different from normal investing. Um, I don't claim to know anything about macroeconomics, and I don't f- follow it all that much. Th- at the end of the day, venture is a game where you make an investment and you're not gonna see any payoff from it for, you know, a decade. Right? Like, and so, i- that's going to span a whole bunch of different macro economies, so this concept of buy low, sell high, like, using regular stock market phrases in venture, to me, just doesn't make any sense. Um, you have to invest... Y- y- you have to just invest in really good companies. Now, you can't pay ridiculous prices, because that limits your upside, right? So venture capital is a game of upside maximization, um, and the higher price you pay for something, that- it's gonna limit your upside, uh, potential on that. So you can't just go an re- invest at ridiculous price, you know, ridiculous tw- end of 2021 prices in things. Um, however, you know, either the company is going to do really, really well, um, over time, in which case you'll be able to sell it high (laughs) or sell it higher, or it won't, in which case it won't matter to you at

  3. 2:554:30

    Does early stage venture need to worry about Macro economics?

    1. BS

      all.

    2. HS

      Do you agree with the thesis or notion that early stage investors, because of b- by very nature of liquidity being ten years out and the long nature of our business, that we don't need to pay attention to macroeconomics and macro markets because it is so far away from where we are in the insertion point?

    3. BS

      No, I think it's good to pay attention to it, because it... Like, you know, for instance, right now, we're at a point in time and, you know, we're- we're talking in September 2022, or I guess October 2022. (laughs)

    4. HS

      (laughs)

    5. BS

      We can leave it at that. Um, and there's such a huge price mismatch between, uh, let's say a company's last round of financing and what the macro is, that it's really difficult to in- invest right now, simply because private companies lag public markets, in terms of pricing, by quite a bit. Um, because private companies dont have a, you know, new price associated with their companies unless they raise another round of financing, many great companies are opting to just not raise money now and try to ride it out. Right? And so I don't think it makes any sense to not pay attention to macro. You have to pay attention to it. I just don't believe anybody can actually predict it. Right? My partner, Peter Thiel, is brilliant macroeconomist and probably the best in the business at this, and he can't even predict this. Right?

    6. HS

      (laughs)

    7. BS

      Like, predicting macro is extremely hard. So I think you pay attention to it, I think you let it impact your investing, but I don't think you try and predict it or sweat it too much, because there's nothing you can do.

    8. HS

      In terms of where we go from here, I see

  4. 4:306:48

    Company valuations and funding prospects

    1. HS

      this as, like, three stages. There's, like, structured rounds coming now, you know, increased late prefs, you name it, um, and then down rounds and then recaps. Would you agree with that kind of stage of process of how we're gonna see this shake into the ecosystem?

    2. BS

      Sure. I mean, you're already seeing a whole bunch of companies go out of business, um, or companies trying to just raise bridges, um, to- to- to get them through this. Or the best companies just simply say, like, "Yeah, we can, you know, let some people go and- and ride this out." Or not even l- you know, some of the best companies don't even have to let people go, um, and just ride it out. Right? And so it's tough to do a deal, um, in this climate, because you don't wanna just be doing these deals. Like, doing recaps while theoretically playing into your buy low, sell high, you know, it does al- have a lot of negative impact on- on companies. Right? And so sometimes they just can't ever get out of that. And again, with venture being about upside maximization, t- are you really just looking for, like, a good deal or do you just want to invest in the best companies? And I would argue it's all the latter.

    3. HS

      So I totally agree with you. Um, you saying about kind of it's hard just to get a deal done, is that not a prime opportunity for someone like Founders Fund, and the notion of, you know, be- be greedy when others are fearful, and keeping that in mind?

    4. BS

      It depends. I mean, w- if you- if you find one of the be- y- we only wanna invest in the best companies, right? And so if one of the best companies... If we s- see something as a best company, you know, that's an amazing company, and we can actually get a reasonable price on it, absolutely.... we're going to invest. But if even the best companies want, you know, end of 2021, beginning of 2022 prices, where other comps in their market have gone down by 80%, then we're just, we're also just not gonna play that game. Like, we don't have any pressure to invest capital. Um, you know, we've done very well by our LPs. They trust us with their money and we feel zero pressure to invest capital. We can just wait. And there's always going to be, you know, you know, hopefully, right, (laughs) in the world, there's always gonna be really, really, really good companies regardless of the macro cycle. Um, and so, (laughs) I, we can just, we can just wait until prices actually catch up, and then we can invest in great companies at great prices.

  5. 6:487:56

    Did you deploy too fast in 2020-2021?

    1. BS

    2. HS

      Can I ask, when you look back at '21 and '20, on reflection, do you think you deployed too fast?

    3. BS

      Um, yes. In '21... That said, like, you know, we had great... We had our best year ever in 2021, right? Just because we kind of got... Our, our strategy has always been to distribute shares/capital right when we can in companies, simply because we don't think we know the public markets better than anybody else. Um, what we do better than anybody else is private company investments. And so why would I do anything else? And so, you know, you had to make decisions in 2021 on whether... You known had a bunch of companies go public, it was kind of a crazy year for venture capital, and you had to make a decision on whether you held, held those or distributed. And we've just always had a history of distributing these shares at lockup, just because, you know, we, we, we don't know more about the private, about public company investing than anybody else. And so we tend to not hold those.

  6. 7:5611:18

    Lessons from the last few years

    1. HS

      If you think about the last few years, I, I have two big lessons. One is, you know, bluntly, I should have been more strategic about taking cash off the table. And, uh, and two, I think I should have been less focused on what the next round investor would want because you can't predict how that changes over time, as it-

    2. BS

      Sure.

    3. HS

      ... has done recently. Are there any kind of lessons or key observations you're telling the team, younger ones in the team, that you think through from the last few years?

    4. BS

      Sure. I mean, for me, I, I have not... We've had so many discussions about this and about what the last couple of years means, and did we go too fast in 2021? And of course we did, but I still... You can always predict the past, (laughs) and predicting the future is much harder. And to me, I've never been able to be convinced that we should be doing anything other than investing in the best founders or best companies possible at the best prices possible. I, I, I, I, I don't really know what we could have done, what to do differently. And right now, I've personally slowed down investing a ton simply because you cannot get a good price on the best companies. Um, okay? So I'll slow down. But I don't know any other way of doing venture capital and regardless of any lessons or anything else, I have not found anybody who can change my mind that this is just about investing in the best companies possible, or putting the most money into the best companies possible at the best price possible.

    5. HS

      The weird thing I find is we see, oh, I'm almost, especially at the early stage, seeing this price infl- well, price, um, inversion element, where you see the migration of later-stage capital down earlier and earlier stage. And so actually for obviously the best pedigreed founders, the price is actually higher than ever, 'cause you've got an increased-

    6. BS

      Sure.

    7. HS

      ... supply of capital going in. I think we're gonna see that for your... Does that, how do you think about that then? Because it ha-

    8. BS

      I mean, that, it, it's why we haven't deployed much capital in the last six months. (laughs) You know, we deployed one, one... You know, my, my typical strategy is to try and deploy just a huge check, um, into the best companies. And I've deployed, I have d- you know, d- we did a $200 million check, um, this year into Anderl, right? And that's a, you know, that for us is like, yes, no-brainer to plow a large check into, um, at this time, but there's been nothing else. Um, even though I've seen great companies, we just can't get... They're not interested in (laughs) raising yet, you know, October 2022 prices, right? And so I would love to invest in them and we'll, we'll see. There's probably going to be some that it'll be like, "All right, all right, we get it. We'll raise a little more capital right now. You know, we won't raise a lot more capital, because we don't want to take that dilution, but we'll raise a little bit more capital now just to, you know, shore up the balance sheet and do it at a reasonable price." And those, we're gonna be all over. But so far in 2022, the only f- the only big check I've done is Anderl.

    9. HS

      Can I ask, if you were to draw up a list of like one, two, three names of companies that you would love to deploy capital to, but haven't-

    10. BS

      Yeah. (laughs)

    11. HS

      ... where, where should those be?

    12. BS

      No, I'm not, I'm not gonna, I'm not gonna do that, 'cause I'm actively trying to-

    13. HS

      (laughs)

    14. BS

      ... do those right now and I don't want to... Yeah.

    15. HS

      I, I was literally, I literally had this conversation with you today.

    16. BS

      But, but I will, but I will say that, yes, there are actively companies that I'm trying to deploy (laughs) a large amount of capital to. It's just always just a matter of can you come to the, to the right turns with the,

  7. 11:1813:22

    How do you advise your founders today?

    1. BS

      with the team?

    2. HS

      How do you advise your founders today?

    3. BS

      Um...

    4. HS

      When you're worried about fu-

    5. BS

      In which, in which case?

    6. HS

      They're, they're-

    7. BS

      Like, you know, for founders that are, you know, profitable?

    8. HS

      For-

    9. BS

      I mean, (laughs) you know...

    10. HS

      Founders that are saying, "Hey, fundraising markets have changed. We've got 18 months left. Is it gonna get better? Is it gonna get worse? Should we raise more now?"

    11. BS

      Well, I, I don't... I, as you can probably... My answer is, I do not know. I don't try and predict macro economy, period. Um, I don't. I, I, I, I only play games that I know that I can win at, right? Which is why I don't do pub- I, I don't buy any public stocks ever. Right? Like, and I don't try and predict, you know, be one of those VCs who sits there and like says, "Oh, the funding environment's gonna be bad for a long time," or, "It's gonna get better." Like, who kn- I, nobody knows. And so...... you only do what you can for right now, and you assume that right now is how it's going to be. Um, and so if you're a company that needs to raise some money, like I advise doing it at a reasonable price that doesn't kill the company or some companies are going to have to shut down. (laughs) And this is just the reality of this business, is you get into these cycles, and I've seen this before, I've been doing this for a long time, where, yeah, some- a lot of companies are just gonna shut down, and that just is how it is.

    12. HS

      Brian, do you know what I love? You're so different to every other VC with the pontifications and the "ah" ...

    13. BS

      I, I don't, I don't, I don't pontificate. I invest... Uh, here's what I do. I invest in... Or I have a really, or I, what I think is a pretty good knack of picking the best founders, doing things that have a potential to be very outsized, and I have no fear of backing in the tru- uh, you know, backing the truck and plowing a whole bunch of money into those companies. That's what I do. I don't sit here and try and tell you about macro. I don't d- there... I don't know how to run a company, right? Like, that's not what I do either. I'm not... I would be a terrible CEO. Um, all I can do is spot really good founders in outsize markets doing things that have true moats,

  8. 13:2215:24

    How much does market matter?

    1. BS

      and I'm pretty good at that.

    2. HS

      So, I, I lost money for the first time earlier this year, and my takeaway was actually that no matter how world-class the founder, no how- no matt- no matter how brilliant the team is, if they're in a market which is just inherently fucked, challenging, vulnerable, no team can get out of it if it's, it's sometimes so hard. Uh, uh, like-

    3. BS

      Sure. That happens. (laughs)

    4. HS

      ... how much, how much does market play a role in your mindset then, given your ability and knack to pick founders?

    5. BS

      Oh, pretty good. I'm pre- uh, a, a lot. I mean, it's... You've gotta be... You know, it's... If you have a re- really, really, really good company in a tiny market, it's still not gonna make a... move the needle on a multi-billion dollar venture fund, right? It's gotta be both. It's gotta be really, really good company in really big market, um, to move the needle on, on funds of this size. And so, you know, thinking through the market and thinking through that definitely plays some role. I mean, founder quality is still 80 to 90% of my investment thesis, right? But the market ca-

    6. HS

      Would you say that Airbnb was a big market?

    7. BS

      We... Of course. I mean, if you <|agent|><|en|>

    8. HS

      No, but it

    9. NA

      If you do it.

    10. HS

      ... at the, like early stages, like sh- like s-

    11. BS

      Of, of, of c- of c- of course. If you could see that this was, like, taking over in terms of, like, how people were thinking about staying at hotels versus staying somewhere else, um, especially we had a huge advantage living in San Francisco at the time, because the hotels here are just like terrible and the hotels are in such terrible locations in San Fran- I don't even know how people come visit San Francisco, right? Like, it's the hotels are just in such terrible locations that you just have to stay in an Airbnb here, because you don't wanna stay downtown, in downtown San Francisco. Um-

    12. HS

      I rem- I remember one time at the Cliff and I was like, "Hoo, hoo, this is busted."

    13. BS

      Yeah. A- and, yeah, no, it's just like it's, it's... And, and so, no, we could... We, we definitely saw at the time that the network e- the network effect on Airbnb was at, at the time was huge, and, yeah, the market was, um... It wa- it was clear that they could penetrate into the travel (laughs) market or even the lodging market, which I guarantee you, Harry, is huge.

    14. HS

      Uh, th- that, that

  9. 15:2416:07

    Are winners obvious early?

    1. HS

      I totally get. (laughs) Uh, do you think your winners are obvious early?

    2. BS

      Oh, it depends on which stage we invest in. Like, do I think our winners are obvious at the seed stage? No. Do I think that we invest... Do we plan a better dart board than most people, because we can see founder quality better and get into those deals with the best founders? Yeah. Um, I think they're pretty good. But do we... No, I don't think anybody can see that something is gonna be... Or they can, they can say, they've got their thesis and I... you know, whatever. But (laughs) like I don't think you can predict $100 billion companies at the seed stage. That's silly. But you can predict, "Hey, this company has a way, way, way, way, way better shot at being a big company than most." And that's what you're doing at this... at the

  10. 16:0717:31

    Reserves and cross fund investing

    1. BS

      early stage.

    2. HS

      You said about kind of loving to do the, uh, uh, larger checks, kind of one a year, say your $200 million check like you mentioned earlier. Does... In terms of, like, reserves, does that mean you kind of put the check in and that's your position? Or do you want to

  11. 17:3121:58

    What gets easier and what’s get harder?

    1. HS

    2. BS

      ... the, the getting in part has a huge amount to do with brand. And founders wanna be associated with winners. And so that part does breed success. Now, does it help with the seeing stuff? No. And that's why I'm so- always so obsessed with are we seeing, you know, the right companies. Like, in brand can be noise, um, and detrimental for the seeing part, for the diligence, you know, for the, for the, um, you know, seeing companies part. But the, uh, for the sourcing... But I'm obsessed with making sure that we've got, you know, a broad range of people sending us deals.

    3. HS

      I totally agree. Oh, and w- if you go one level beyond, uh, the seeing, people often are quite binary around, "It's a picking game," and "No, the best deals are the picked ones." So-

    4. BS

      Oh, no. I, I don't know which... The, the, the, the, the seeing, picking, and getting in part are equally as important to me. Um, you have to be top level. The best firms all know this. Like, you have to be top tier at all, at all three of those things. And, you know, even if you can pick, y- you know, good luck winning a deal over, you know, us or whatever, if we're, if we're there at the same time. Right? Like, you've gotta be very... You've gotta be top tier at seeing, picking, and getting in. They're all equally as important. And I'm just... The part that's just harder and harder over the years as you do this longer and, quite frankly, get older, um, is the seeing. Um, you've gotta keep your networks fresh. You've gotta, like, make sure that (sighs) you're somehow still connected. Right? 'Cause your networks get stale, and we know that. You know, adapt or die in this game. Right? Like, you can't just rely on, like, the PayPal mafia forever. Um, you've gotta just, you know, keep adapting. And so, keeping our networks fresh, interesting ways of doing sourcing is... I'm obsessed with that stuff. I think we are, you know, I think we're pretty good at... We're, we're fine at picking. And I think success breeds even more success at the getting in.

    5. HS

      Yeah.

    6. BS

      Um, but the, the seeing part is just really hard.

    7. HS

      Can I ask, when you, when you sit around the table with, with other partners today. If it's lunchtime at Founders Fund and you're saying, "Ah, this is our main challenge. This is our main challenge."

    8. BS

      Sourcing.

    9. HS

      What are you... Sourcing.

    10. BS

      Uh, well, right now, it's a little bit different. Our main challenge right now is there's just a huge price mismatch between the public and private markets. And so...

    11. HS

      But, so-

    12. BS

      I'm, you know, saying there's, there's not much you can do about that. But a, a... And I don't think we can act- There's not much we can control about that. Right? 'Cause that's a lot macro-related, and I never try and control macro.

    13. HS

      Yeah.

    14. BS

      Um, of the part that we can control, and this is literally (laughs) what I ta- what I obsess about at the lunch table, is the sourcing part. Like, how are we keeping good... How are we making sure that we at least talk to founders of awesome companies that are out there?

    15. HS

      Where does that conversation go? Like, you s- aga- You see other funds, you know, creating products like accelerators, incubators, scout networks. Uh, where does your conversation go?

    16. BS

      Yeah. I mean, look, we've done that too. I mean, I don't think that goes to any one strategy. Right? The way that we do things at Founders Fund is everybody runs their own strategy based on what they are the best at. I don't know how to run a company, so I'm not gonna go start a company. But Trey is excellent at starting companies. Keith is excellent at starting companies. So, great. So, Trey and Keith go and start companies. Um, right? And yeah, hopefully, one of the reasons they do that is they have an awesome company and both, you know, Anderl and OpenStor are fantastic. Right? But one of the reason... But another reason is to keep their networks fresh. Uh, 'cause they're gonna have a lot of people working for them that are eventually gonna go start companies. And hopefully, you get an Anderl mafia and an OpenStor mafia or whatever. Right? Like, absolutely, that's part...

  12. 21:5826:20

    What makes Founders Fund special?

    1. BS

      Uh, that, that, that's part of it.

    2. HS

      Can I ask, uh, I was listening to a podcast, uh, the other night about Benchmark's journey. And they were talking about actually a really challenging time for Benchmark and I can't remember when it was exactly. I was just going over, like, in my head and from the outside, Founders Fund has just been this continuous progression of success. I'm sure internally there are moments when there's like a year or two where it's actually harder. Can you take me to one of those years or two? And, and why?

    3. BS

      Well, I don't know. I mean, I think one of the reasons that we're successful is that we... You know, as a firm, we have no dogmas or we try and have no dogma. Or we have... try and have no "Oh, this is how you do it." I think, honestly, I think we are just better at adapt or die than other people. Like, we're better at realizing that even the things we say... said last year or the things, honestly, that I'm saying on this show, they might be total bullshit. Right? Like, you have to change it. Right? Um, if, if the world changes, you change. And we're really, really, really, really good at not having specific set views that are set in stone here. Which is why... You know, one of the things I think we've done really, really well is our hiring. We've been able to focus our hiring on people that come in that have a unique, truly unique angle or moat, if you will, that makes them, you know, specifically special. Whether it's in the sourcing, picking, connections, getting in, anything. Right? If it's a unique strategy that is differentiated from the current partners that are here, we are interested in hiring that person. And that's really paid off. Like, our focus on not hiring clones, our focus on not hiring just people who are generically good, our focus on just hiring people who have unique, you know, strategies and strengths that can pay off is what we've been really good at. You know, we just hired Sam, um, our newest partner, Sam Alon, right? Like, this... Sam has a phenomenal unique story. Like, usually, when I'm in these interviews and I'm interviewing candidates and I, I specifically say, I'm like, "Okay, what is the thing that you're better at than anybody else?" And I... Honestly, I don't care what that is. I just want somebody to have something. Right? Um, Sam's answer is just phenomenal.There's not many people who understand (laughs) high growth tech and actual s-, you know, sales and enterprise sales in high growth tech better than Sam. And that's just, it, it is what it is. And so he has such a unique skillset that most people don't have, that it made him a no-brainer to hire. And to answer your question of why we've been successful, um, you know, throughout our, you know, approaching two decades now of existence, is that. It's ma- It's being able to see, just like we can see unique moats in companies, we see unique moats in people, and just hire those people.

    4. HS

      Can I ask, with traditional firms, when they bring in partners like Sam, they have a lot of structure around them, a lot of mentorship, they kind of sit with you in boards and they kind of learn craft of venture beside you. Founders Fund's obviously a lot less structured than, like, traditional firms.

    5. BS

      (laughs)

    6. HS

      H- how do you think about providing those same, kind of, positive educational guardrails to someone like Sam? You know?

    7. BS

      Oh, we, we, me and Sam strategize all the time. Like, you know, I, again, I don't try and ... I could never do what Sam does. Right? So I don't try and, like, tell him, "Oh, here's how you should do this." But we strategize about (clears throat) angles that he could be playing in order to see, pick, and get into the best deals all the time. And those are some of our most fun conversations, when we're just, like, strategizing about how to leverage his strengths, which he is the best in the world at understanding actual sales of high growth tech companies. And again, for founders listening, like, they know this. Right? He is a guy that you want to talk to, because nobody knows this better than him, and he needs to then leverage that into seeing the best high growth, you know, companies that can utilize his skills and then grow into other things from there. Remember, I'm a gamer. You know, true and true. Right? Like, I, I, I just focus on, what are my strengths, what are my, you know, the c- the current things that I have that nobody else has? How do I exploit those, how do I leverage those in a way that nobody else can catch up with? And

  13. 26:2027:23

    Do boards add value?

    1. BS

      that's what I talk about with Sam all the time too.

    2. HS

      Brian, do you think boards add value?

    3. BS

      (laughs) I n- I, I can't stand boards. Um.

    4. HS

      Uh-huh.

    5. BS

      Private company boards, like, I would much rather do strategy dinners with founders, and they know that. My strengths is not corporate governance or financials or... I, I'm really bad at that kind of stuff, Harry. Like, I, I... It just is what it is. I, I'm not, I'm not good at corporate governance and financials. I am pretty good at strategy. And so the founders that want to work with me are typically the ones who, like, instead of needing to have me in a boardroom, where I don't... You know, it's not my strength. Right? They would rather just be like, "Oh, hey. Every, every month, every other month, we're gonna grab dinner and strategize." I'm like, "Great." That's, that's the part of this job that I love. Like, you know, we've been pretty successful, and after doing this for 15 years, you, you s- you start to think, like, "Okay, well, what am I doing this for?" And the main reason, the thing that I love about this job still is

  14. 27:2328:45

    How to plan strategy with a founder

    1. BS

      strategy dinners with top founders.

    2. HS

      What makes-

    3. BS

      I just love that.

    4. HS

      What makes the best strategy dinners with top founders, and what makes a strategy dinner where you thrive?

    5. BS

      Where it's very clear what the s- the, the moat is, it's very clear what the unique, you know, thing that this company has that nobody else has is, and then we can really talk about leveraging that into the next level and beyond. That's what I love. I love focusing... I, I'm very open to, you know... And a lot of people can say this, but I don't think they're good at it. Like, I think at Founders Fund, we are simply just really good at being open to the fact that there are multiple different strengths, moats, uniquenessn- (laughs) you know, things about people that other people can't see. A lot of, a lot of firms are looking for tracked founders, or like, you know, they have a good sense of what they're looking for. I'm like, "I have no idea what I'm looking for. Surprise me with something that is truly unique, and I'm in." Right? They... Regardless of what it is. Um, and so, I love that. When you're dealing with a company, a founder in a company that know what their strengths are and are very honest about what their weaknesses are, and we can talk about leveraging the strengths of the company, um, into a much more dominant situation, that is Strategy Gaming 101. Um,

  15. 28:4531:22

    What have you been wrong?

    1. BS

      and that's what I love.

    2. HS

      Can I ask if you ever thought there was a moat, and actually you overemphasized it, thought it was stronger than it was, and it didn't pan out the way you thought it was?

    3. BS

      Of course. Yeah, yeah, yeah. You know, like, you're not going for... This is such a generic thing to say, but you're not going for, like, having all, you know... No way in venture, especially when you do these, like, massive bets, are you gonna have every single one of these be right, nor do you need that. Right? You're, you're trying to maximize your upside. You're not trying to minimize your downside. This is why I've never understood these, like, "Oh, we're gonna do a round with 3X participating preferred, and a round with a whole bunch of structure." I mean, like, I get that from a... If I'm a debt guy or I'm a bank guy, like, yeah, that's exactly what you want. If I'm a upside venture guy, it's like, that's just totally irrelevant. Like, why do I care if I, like, get 2X my money back in a downside scenario? It's like the same thing as going into zero. And so I just maximize only for, for, for upside. And so of course I'm gonna be wrong. Um, I'm wrong all the time. It's, you know, I've always said... This is what I say to founders too. Right? There's never... Somebody who needs perfect information before making a decision is going to be terrible at this job. Um, you do n- you never have perfect information, um, in this job, ever. If you need it in order to do a deal, don't do this job. And so because of that, you're going to be wrong, so all you can really do is follow your gut, whether you're me or whether you're a founder. And then when you're, when you are wrong, not if, but when you are wrong, you refine your gut. You're like, "Ah, what did I, what happened there? Okay, well..."You know, probably won't fall into that same trap another time, right? You know, for instance, for, for me, meeting a founder in person is just critical. I was terrible at this job during COVID, right? Like, when you couldn't meet founders in person, I, I'm just terrible at this job without being able to meet founders in person. Um, and so I needed to not do a lot of investing when the only way you could meet founders was over Zoom. Now that that's over, and now that people are meeting back in person, great. This job is, you know, I can do this job again. (laughs) But that's kind of a recognition of, you know, what you're good at, honing your skills, realizing something went wrong, and not trying to make the same mistake twice. But still trusting yourself and trusting your gut enough, because you are never going to have perfect information. If you get shell-shocked in this business, you're not gonna be successful, because you'll never make an upside investment. There's gonna be hair on every single deal, right? Like there's never,

  16. 31:2236:55

    Advice to fund managers

    1. BS

      never is any deal gonna be perfect.

    2. HS

      I totally agree with you. You said there about kind of the, uh, the importance of upside and how actually if you get one X back, but 0.5 X back doesn't make a difference. On paper-

    3. BS

      Doesn't make any diff- I don't really care if I get one X back, two X back, three X back on a speci- on a, on a company. I care about getting, you know, multiples of a fund back. (laughs) I don't c- like, you know, there's no difference between a ... I mean, honestly, our f- our funds are multi-billion dollars, right? Like, if we have a $10 million check, there's no real difference between that going to zero or that going to 30 million. I mean, there's just no difference between those numbers.

    4. HS

      Does that not make it, uh, I mean, given the size of your fund size, does that not make it incredibly hard? I mean, you can do-

    5. BS

      Yes.

    6. HS

      ... a hundred million dollar check

    7. NA

      and make 50-

    8. BS

      It makes it incredibly hard. If I'm, if I'm talking to new managers, the advice that I always give them is ... And this is counterintuitive, but it's the right answer. Raise as small of a fund as you can in order to just crush it, because then you can write your ticket for a number of funds. It is much harder to get returns on larger funds than it is on smaller funds. It just, just is. And so, you know, until you really, you know ... I, I, I would say until you know that you can write a 30%, 25 to 30% of fund size check, you know, raise whatever fund size you can in order to, like, be comfortable writing a 25 to 30% of fund size check, right? Like, if you're not comfortable writing a, more than a five million dollar check, do not raise more than a $25 million fund. Just go crush a $25 million fund, right? And maybe raise more frequently. Um, for me, this fund size is important because remember what I do. I like ... Where I'm best is at writing these two, three, $400 million checks. And so, you know, if I'm using my own ... Practicing what I o- preach, it's like, if I'm comfortable writing a, let's say for the c- most, the biggest check I'm comfortable writing is a $500 million check. You know, it's probably roughly that. Then I should raise a two and a half billion dollar fund. But not many people can say that they're truly comfortable writing a $500 million check in venture.

    9. HS

      Can I, I, sorry, I sound really immature and naive here, but $500 million is a, that's a lot of money. Do you go whoof when you are writing that check? Like do you feel-

    10. BS

      I mean, I wish I'd written 500 ... We, I wish we had written a $500 million check into Airbnb at the, you know, one and a half billion dollar round instead of a, whatever, $150 million check. I d- d- again, you're gonna make ... Put the most money possible into the best companies possible at the best price possible. That's venture capital. There's nothing else in it. There's no, like, "Oh, have a bunch of Monday morning partner meetings in order to be successful." There's no like, "Oh," ex- uh, i- most money in, best companies possible, best price possible.

    11. HS

      And loss ratios matter a lot.

    12. BS

      Loss ratios don't matter. Losing, I can't, uh, you know, you don't wanna lose a $500 million check, right? 'Cause it's gonna be then ridiculously hard for you to, um, (laughs) to return that, to return multiples on that fund. Whereas like if you lo- even in a fund that size, if you lose a five million dollar check, it doesn't really matter at all. But no, you don't want to lose a $500 million check and I ... That's why I reserve those for ... You know, I wrote a $200 million check into Andero this year because I, you know, Andero is going to be an extremely valuable company. I am, there's ... Yes, quite sure of that. We are not gonna lose that $200 million check. That $200 million will turn into, you know, two billion.

    13. HS

      Have you always been this style of investing, Brian?

    14. BS

      That's the only way of investing that I know how to do, and I think it's one of my unique moats and unique angles is that m- I'm good at this type of investing. And I'm honest with myself on what I'm good at and what I am not good at. And I'm good at this kind of stuff and I'm not good at other things in this, in this space, which is why we, I tr- we try and partner with people who are totally different from us, right? Like, I don't know how to start a company. Great. I, do I love having Keith and Trey as partners? 100%, right? (laughs) They're great at it. Um, you know, I don't know how to do financial analysis on companies. Do I love having Napoleon as a partner? Absolutely. I know nothing about macro, right? Do I love having Peter Thiel as a partner? Absolutely, right? I mean, you, you try and ... You don't try and hire clones of yourself. You try and work with people who have their own unique strengths that are the best in the world at something.

    15. HS

      Is there any part in this that where you feel you're missing that skill set? You mentioned, uh, the financial analysis with Napoleon. You mentioned the macro with, with, uh, Peter. Are there any way you're like, "Ah, we really miss a pop sales person"?

    16. BS

      Oh, I'm sure, uh, w- well look, I didn't know what we were missing. Like, I didn't know how much we were missing a Sam until we met Sam. But I'm just very open to there being, you know, a, somebody who's really good at something that I never even considered. Both on the com- this is, again, this is the same thing that I do on the company side is on the team side, right? I'm looking for companies that have a unique moa- I'm open to anything. I'm the most sector agnostic person you can possibly imagine. Um, and ...You know, I'm open to any company that has a unique moat and a huge market wi- run by a great founder. I'm open to hiring anybody at Founders Fund that has a truly unique angle that I never even... that I didn't even necessarily know I was looking for. So, when you ask me a specific, "Oh, are there like a specific hole?" I'm sure there's an infinite number of holes (laughs) that we have at Founders Fund, right? Like, and I'm open to, you know, seeing whatever they are, right? I didn't know we had a hole until we met

  17. 36:5539:04

    How to backchannel when hiring

    1. BS

      Sam, and then I realized, "Oh, man. This is gonna hu- fill a huge hole." (laughs)

    2. HS

      You know what I find really hard about hiring and pre-seed investing in particular, is trust. And trust, I think, is built over time in many interactions, in many different situations. And both with pre-seed and with hiring, you're often thrown a meeting and, "Hi, Brian. Uh, lovely to meet you. Uh, I can sell really well. I, you know, believe it or not, I'm good at marketing myself." (laughs) Um, but that may not be true. You know, we both know people, you know, who m- may not be as good as they seem or are not... are much better than they seem. How do you think about that? Because I find that really hard and I don't have an answer for that.

    3. BS

      Oh, I mean, we, you know, just like, you have c- multiple conversations with people, like backchanneling is still important. And I like the b- the, the, the type of backchanneling that I like is where they can't tell what you want to hear. Right? It's all... It's, it's quite easy to backchannel, um, and do diligence on something when, you know, the human being that you're doing diligence with like kinda knows what you wanna hear. And they're just like inclined to tell you what you wanna hear because no downside to them. Right? So, the stuff that I like the best is when you ask questions that the other person doesn't know that you... what the answer should be. And so (laughs) or what you're looking for. Um, and so that's how we kinda backchannel all of these candidates to try and figure out like, well, is Sam truly an expert at, you know, high-growth tech enterprise sales? Right? And so we try and figure that out. And of course, like, you know, we've been wrong sometimes on that front too, but that's okay. Right? We're really good at adapt or die. We don't just sit there and be like, "Oh, we made a mistake, so let's never do this again."

    4. HS

      Have you made mistakes on hiring?

    5. BS

      Of course. I, I've made a mistak- you know, on investing, on hiring, it's the same thing to me, right? Like, everything. I'm, I make tons of mistakes. Again, you do not have perfect information in this business. If you are the type of person that is gonna do work, work, work, work, work, work, work, work, work, work, and make sure it's perfect before you invest, or make sure it's perfect before you hire, you are

  18. 39:0441:11

    How to advise young investors

    1. BS

      just not gonna do well in this business, period.

    2. HS

      How do you, how do you advise your younger members of the team who saw their books last year blown up, and they thought they were fantastic investors, and now everyone's looking a little bit less confident? As, as a, like, you know, patriarch leader, how do you sit them down and, and-

    3. BS

      We have had this conversation. The, the, this, this is... This has happened with many emerging teams. It's like if you get shell-shocked in this business... Like, you want a little bit of shell-shock 'cause you don't wanna just deploy capital willy-nilly. But if you get so shell-shocked that you can't do another deal, you're not gonna last either. So, you know, we see some... Anybody we hire, anybody that comes, you know, on board here, we see something, and they know what this is usually. We... This is part of our discussion. Um, some unique angle that they have. And yeah, maybe stuff is blowing up, but you get shell-shocked, you may as well leave.

    4. HS

      For those that do, uh, th- like... Y- shell-shocked, you may as well leave. For those that do well, you've seen partners rise through the ranks very, very efficiently and well. Are there commonalities in what makes them rise through the ranks versus the shell-shocked but fall?

    5. BS

      Yeah. I mean, in this bi-... Again, the, the, the investors that are waiting around for pure, perfect information are not going to last. However, so therefore, and, you know, there's all this debate. There's... I, I see a lot of chatter on the internet like, "Oh, there's no... This whole concept of gut in investing is nonsense." I'm like, "What are you talking about?" Like, when do you ever have perfect information? Like, you can't just like analyze a business plan and know, "Oh, this is going to work." That's like total nonsense. Right? And so the, the, the, the team members that we have, yeah, take the punch in the gut from these companies and learn from it, and do... maybe make some refinements on your strategy. But unless you can keep leaning into your strengths, just leave.

    6. HS

      (laughs)

    7. BS

      Right? If you're too shell-shocked to like leverage, you know, what made you special, then you're just not gonna last in this business at all.

    8. HS

      That, I... Listen, I, I totally agree with you. I just, I just love the way that you put things so bluntly, Brian (laughs) , to be honest. Um, I-

    9. BS

      But yeah, it doesn't... It's... To, to, to me, it's just we're, we're n-

    10. HS

      It's refreshing.

    11. BS

      Yeah.

  19. 41:1142:15

    Most successful investment ever

    1. BS

    2. HS

      It's refreshing. Uh, can I ask, what was your most successful investment ever, Brian, to date?

    3. BS

      Oh, I don't know. I mean, we, we, you know, we've had a, we've had a bunch of these things. Um, in terms of like a returns, uh, tons of stuff. Dencentrix, Affirm, you know, Airbnb. We'll see what h- you know, Stripe. I mean, uh, we, we, we, we've had, we've had a lot. I mean-

    4. HS

      Uh-

    5. BS

      ... and then there's SpaceX, right? And I, I'm not gonna talk about like me personal, but from a Founders Fund perspective, we've had a... We've been fortunate to have a lot of successful investments. And again, just as part of our just the w- we don't have hubris about knowing the public markets better than anybody else, but the fact that we were able to distribute, you know, end of 2021, when a lot of people kind of held, was worked out in our favor this time.

    6. HS

      It is interesting though, 'cause you have this kind of, uh, a bit more lone wolf style partner approach internally, than most do. Um-

    7. BS

      Yeah.

    8. HS

      ... but, but yeah. But then i- to the external world-

    9. BS

      Because, because, because we all have our unique strengths, right?

    10. HS

      Sure, but then to the-

    11. BS

      And we trust our AI-

    12. HS

      But then to the external world,

  20. 42:1543:06

    Dollar to fame ratio

    1. HS

      there's no star culture. Do you see what I mean? It, it's interesting.

    2. BS

      Yeah. I mean, I, I try and... My life strategy is to maximize my dollars-to-fame ratio. Like, I want to m- make a lot of returns for myself and LPs, and have the minimal amount of...... fame possible, right? (laughs) Like, you have to do some things to kinda get your name out there and I get it for ... But we don't have like a need to be the star thing. I just want to make the returns.

    3. HS

      I thought you just liked talking to me, Brian. Now I'm-

    4. BS

      No. (laughs)

    5. HS

      ... asking you that. No. Uh, listen, I totally get you. I would, uh ... Someone once told me you wanna be the most famous person in the bri- private jet center, and no one know you in McDonald's. And I thought that was well put. Um, but, uh-

    6. BS

      I guess that's one way of looking at it, yeah.

    7. HS

      (laughs) But I wanna move into a quick fire round, Brian. So I say a short statement

  21. 43:0644:02

    Biggest personal strength and weakness

    1. HS

      and you give me your immediate thoughts. Does that sound okay?

    2. BS

      Sure.

    3. HS

      Ready? Okay, so what's your biggest strength and what's your biggest weakness?

    4. BS

      Uh, my biggest strength is I am truly, truly open to anything. Um, I have no dogmas about how the world should be, how the world will be, how the world is. I'm open to unique angles of any type.

    5. HS

      And weakness?

    6. BS

      I mean, I, I guess it's a weakness. I don't put skill points into things that I know that I am weak at, which could, you know, be kind of a strength, but it's also a weakness. In that, I remain weak at what I'm weak at for very, very, very (laughs) long periods of time. Maybe that's more of a life weakness than it is a, you know-

    7. HS

      Well, no, it's a strategic choice.

    8. BS

      ... job weakness. But it's a life weakness, right? Because there's always things in life where you kinda need to get better at them where you are weak that you can't just hire a team member to supplement. And

  22. 44:0245:10

    Did becoming a father impact your mindset?

    1. BS

      I'm just remain weak at those things, and that's not a ... That's a w- that's a weakness.

    2. HS

      D- D- Did becoming a father impact your mindset? Investing or-

    3. BS

      Sure.

    4. HS

      How so?

    5. BS

      In ... Well, two things, right? I used to be able to do this job with, you know, every night I was having dinner with a different founder or, uh, you know, I was, you know, doing stuff at odd hours, and you know, doing all kinds of stuff, right? And now, post having two kids, that's just a lot harder. So I guess there's, there's the mindset and then there's the physical. (laughs) And, you know, I'm with my kids for dinner every night, right? Like, and so it's harder and harder to do, uh, strategy dinners, uh, with, with, with, with founders. Um, and in terms of a mindset of knowing that I need to get better at certain things that I'm not good at, well, you need to do that with your kids, right? 'Cause, you know, you don't wanna ... There's lots of things you can outsource in life, but child-raising is not something you want to entirely outsource, right? Like, you need ... You wanna spend time with your kids, and I do. And so, I suck at a lot of those things. And needing to get better at those things is, is hard for somebody who's always put

  23. 45:1047:07

    Best board member you’ve worked with

    1. BS

      skill points into things that they were already good at.

    2. HS

      Who's the best board member you've sat on a board with and why?

    3. BS

      Usually, the best board members ... Board members, not, not necessarily investors. Right? But the best board members are ones who (clears throat) , really know the s- the sector that the company is, and know people in that sector really well such that they can easily connect, um, said company with other people that might be relevant to them. Right? Like, that's not the same as the best strategizer, right? These people could be very stale on strategy, but they're the, they're the best, the board, best board members ... You do want board members who are good at governance, Rolodex, financials. Right? That's not me. Um, and so, you know, the best board members I've seen are ones where it's like they're just so good at that specific, for that specific company, you know? That ... And I don't, so I don't think there's any investor per se. Right? I think that the best board members are like the specific ones, the outside ones that you find that really are truly door openers for your company.

    4. HS

      I totally get you. Who's the person that when they send you a deal, you jump on it? You're like, "Oh, shit."

    5. BS

      (laughs) Brian.

    6. HS

      "Excellent."

    7. BS

      Gary Stebbings.

    8. HS

      (laughs) Now you're a charmer, Brian. That is, uh-

    9. BS

      No, I, I, I, I try and make sure that my network is al- Like, when somebody who I think is talented sends me a company, I ... Highest priority to do that meeting. Just because, again, the part of this ... I think we're ... If this, if venture capitalists see the right deals, pick the right deals, get into the right deals. I'm not too worried about my picking and getting in skills, um, and I'm very worried about my seeing skills. Especially as I get older and my network's getting more stale. So for, for people who send me stuff that I think are awesome, I will drop ... I, I'll, I'll take

  24. 47:0749:31

    What makes Anduril so good?

    1. BS

      that meeting.

    2. HS

      I, I totally get you. Uh, tell me, final one. You managed it before, but Anduril, what, what in the moat in particular ... I'm intrigued. You mentioned moats a lot. What got you confident that Anduril's moat was just so compelling that you wanted to put $200 million in?

    3. BS

      I, I don't even know where to begin on that. We put more than ... We put $400 million in that company total now. This is just our most recent one was $200 million. It's an example of cross-fund. I don't think any of our investors are upset about the fact that Anduril is in, uh, multiple funds. Um, but the moats are, uh, extensive on Anduril, right? Like, the, they, they're in a space that hasn't had true new tech, you know, l- entrepreneurship in decades. Right? Your most valuable companies in the space are Lockheed, Boeing, Raytheon. These are companies that have been doing cost plus models in defense forever, um, and have had no real true, you know, ingenuity. You take the Anduril team, the, the team who like ... A team who, uh, is seasoned, who knows what they are doing, has great government relations. Pair it with a person as brilliant as Palmer Luckey in terms of product (laughs) , um, tech and product brilliance to be quite frank, right? And you've got something truly special. Pair it with a space that until recently was considered, "Oh, you can't do that in Silicon Valley." Now it's not post, you know, Ukraine and post a couple of other things. But before, it was like, you know, "Oh, you can't work on defense. That's not a c- that's not a, a proper thing to work on. You should work on chat instead." Um, and so you take a team that was will- that has the culture of working on things that nobody else is, was willing to work on, with a top tier tech, top tier product, top tier government relations, and top tier execution team. I, there, there's nothing like that, period. I mean, we've, we've seen the tons of defense, defense based defense tech is an area that I'm bullish on. But there's nothing like Anduril. It's just, there's no other team like Anduril because they came around and they came together in a, at a time where you just couldn't ... Nobody else could possibly pull off what they were doing. So they got the best people who wanted to do that.

    4. HS

      Brian, I absolutely love our chats, always. I can't thank you enough for, for being so entertaining-

    5. BS

      Thanks.

    6. HS

      ... and for also answering my very prime questions. Um, I really appreciate it as always. So, thank you.

    7. BS

      No problem, Harry. Thank you.

Episode duration: 49:31

Install uListen for AI-powered chat & search across the full episode — Get Full Transcript

Transcript of episode Mo29D0Q0TJw

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome