SPEAKER_02
I don't know the last time we've heard a founder pitching a traditional software business.
SPEAKER_02
Now, part of that is the meme that everyone's just an AI, everything's an AI company now, everyone puts AI in their deck. I think the issue, as we all know, is if you can code an app in a matter of minutes, and why do you need so many engineers? What's the value of the workflows that you've built? But we're seeing an application layer is people are going after systems of intelligence, they're going after systems of action, it's new types of spend, and we're going to continue to back those. All right, I'm really excited to be here with Kevin and Bennett from Astar. You guys, thanks for doing this with me. Thanks for having us. Thank you. I want to start with just the quick history on Astar, how the firm came to be, how you guys are working together, and then I want to go into seed investing. But can you give us the quick backstory on Astar?
SPEAKER_02
[SPEAKER_00] Well, we first met through Ramp, and that was at the seed stage. Eric and the team were out raising, and I participated as an angel. This is pre-Astar. And Bennett was at KOTU, and that's where we first interacted. And we started Astar five years ago now with our third partner, Gotham. And the idea was to build a new kind of venture capital firm that could focus on partnership with founders at the earliest stages and work closely with them as they continue to grow and mature. Five years in now, we just closed our third fund. We're at a billion of AUM, and the idea is to bring something different to the early stage market. So a year ago, I started this podcast basically a year ago, and one of my first guests was Josh Koppelman. And obviously, you know, founder of First Round, amazing seed stage firm. One of the things he was talking about was the venture arrogance score. That really stuck. And basically, what he was saying was, you know, bigger funds are super arrogant to think that they can have big returns, directionally speaking, because you own X percent of a company. How big can the companies be? What returns are you getting? And so on. That argument really resonated. It's funny now to me looking back, you know, 10, 11 months later, whatever it is, a lot has happened. There are more of these five to fifteen billion dollar funds than ever. The rounds are more expensive than ever. There's these three plus huge looming IPOs, which gives credence to the big fund. You know, some of these big funds are doing really well, actually. So anyway, there's this whole situation. I'd be curious your guys take on the landscape and being a smallish seed focused firm relative to this market moment.
SPEAKER_02
Well, look, you always have to play the hand you're dealt. And we live in this world of giants. Yes, it's true about Anthropic, SpaceX and OpenAI and these massive returning large capital necessity companies. But at the same time, you know, big funds, the thing that is right is big funds, big fees for those partnerships. And you know, we stayed small so we can be agile. It's kind of like the equivalent of when you're the CEO of a new startup and you don't take a salary.
SPEAKER_02
[SPEAKER_00] Do you think if the fees were like instead of 2-20, if it was capped and it couldn't go past a certain amount, like let's say after a billion, there were no more fees, you think VCs would behave way differently?
SPEAKER_02
[SPEAKER_00] Absolutely. Without a doubt. I've seen funds go from small to large and the behavior absolutely changes. No names, no name drops here, but it happens that way. And then, you know, there's so much in this really exciting upswing of the market. LPs want to get in and they're not going to be able to negotiate those fees down. If you think about it, the fees haven't changed as the asset classes change. Look at long only oriented funds in the public markets. They charge 1%. They charge 10% carry or hurdle. Yeah. At this point, these growth funds that are raising five, six, seven, eight, nine billion dollars, they're investing in what would have been public companies a decade ago. And they're essentially indexing the asset class. Why should you make 2-20 for that? We built Astar to be aligned with founders, which is that we want to partner early. We want to take risk. We want to work hand in hand with them. It's a different craft, but our incentives are aligned. We only win as they win, which is different than I think the prevailing view is of the bigger firms.
SPEAKER_02
[SPEAKER_00] Yeah. I mean, you do need to do well enough as a big firm. You need to cross some threshold that you can keep raising your funds. Yes.
SPEAKER_02
[SPEAKER_00] But you think about a five or ten billion dollar fund and you think about them playing seed. I was joking with you before we started that your guys fund is like 450 or whatever. And some of these funds, if they raised 8.3 versus 8.8, none of us would clock it, but that's a whole extra Astar. And then they can use that going into seed rounds and their incentives there are different. So I'm curious, maybe could you walk out what is their strategy? What is a ten billion dollar fund doing at seed and why are they doing it?
SPEAKER_02
[SPEAKER_00] I like any unit of measurement that is an Astar unit of measurement. Maybe it'll be adopted as a practice. We'll just all talk about Astars going forward. [SPEAKER_00] I think there's two facets. We used to joke at KOTU, there was two ways to make a billion dollars. And one way was the Benchmark way. Like you find incredible series A, you lead it, you partner, you have a generational public outcome and you earn your percentage of the company.
SPEAKER_00
[SPEAKER_01] That's hard and takes a long time. [SPEAKER_01] Or the Astar way. [SPEAKER_01] Or the Astar way. In addition to Benchmark.
SPEAKER_02
[SPEAKER_01] In addition. Or you put a billion dollars into a company and you double your money as it goes public in three years. And that also earns you a billion dollars to distribute carry. One is a lot easier than the other. And one way are you more repeatable. So I think incentives have shifted in a way that reflects the market reality. Seed specifically, and we see this with a lot of our sort of friends at multi-stage firms, it's option value. Let me build a basket of companies with a certain amount of ownership and see what pops. And if it pops, I could double and triple and quadruple down. I don't think founders want to be thought of as an option as part of a basket.
SPEAKER_00
I obviously want to believe that too. But can I give you the counter there? And I'm curious how you sort of manage it in the market. The counter is basically, look, I also don't want [SPEAKER_01] easier than the other. And one way are you more repeatable. So I think incentives have shifted in a way that reflects the market reality. Seed specifically, and we see this with a lot of our friends at multi-stage firms, it's option value. Let me build a basket of companies with a certain amount of ownership and see what pops. And if it pops, I could double and triple and quadruple down. I don't think founders want to be thought of as an option as part of a basket.
SPEAKER_00
I obviously want to believe that too. But can I give you the counter there? And I'm curious how you manage it in the market. The counter is, look, I also don't want to be thought of as an option, but 10 at 100 sounds a lot better than three at 30. And I have 7 million extra dollars to go hire a team, run my experiments, see where I'm at. And that is the discrepancy that's been created. So how do you navigate that as a seed specialist?
SPEAKER_00
[SPEAKER_01] You know, we're a boutique firm, so we can't be everywhere and we can't cover every scenario. And we find enough founders that are looking for a great partner to work with and to go through this battle. And we've been through it before. I've been involved in founding a couple companies from inception all the way through IPO and beyond. You know, we can't win them all.
SPEAKER_00
[SPEAKER_02] I would also say that the challenge of this era, and maybe I'm biased by this, is that the amount of capital in the market does mean that you don't have as much help in oversight. And I've seen more mistakes, rookie mistakes being made in this environment that just shouldn't have happened. It's funny, there's a class of thing that is very hard to sell in a fundraising process that are in the quadrant of true, false and easy to sell and hard to sell. There is this set of things like what you're talking about, help during the hard times, which I think is very hard. It's real, but it's very hard to communicate in around process in a market moment like this. I think when markets are hard, maybe that resonates more. But I think when markets are really frothy, in many ways it is right now, it's just tough. So it's an interesting time, I guess, as a seed specialist. We've seen this before, though, in 2021, that was the era where Tiger was offering every software company the lowest solution, highest valuation offer. Solo GPs were promising very little help, but they were hitting the highest price bids in series A. Most of those companies and most of those outcomes did not. I mean, the pitch was we'll be uninvolved.
SPEAKER_00
It's the sell was we won't talk to you. 100% and building a company is a marathon, not a sprint. I think a low dilution lead offer is relevant for founders. And when we compete and when we win on deals, we're not trying to get a value deal. We are also offering what we think is a low dilution competitive offer and support and partnership and things that founders, I think, should care about. You guys invest, you know, I know you start at seed, but you seed A and B. And so you're very in tune with all of those market stages. What have you seen over the last six or 12 months in terms of how these rounds are happening in succession, where valuations are going, how dilution is happening across them? What are the trends along those rounds?
SPEAKER_01
[SPEAKER_00] Well, I'd like to think that we're headed. We're not top ticking. We're not there yet, but we're headed to the mother of all bubbles. You know, a historic precedence. And if you think of the 80s and the personal computer and what came out of that era or the 90s and the internet and the 2000s and mobile, well, AI and the platform and the boom that we're seeing right now is immensely exciting. We have such a global audience to reach. And I think we're going to have a few years of this continuing to grow. But unfortunately, as in capitalism, it always ends badly. I don't mean end. I mean, we all know that after 2000, Amazon and Google and so on came out of the internet bubble. And now they're multi-trillion dollar companies. Netflix and PayPal and so on. It's an exciting time. But yes, capitalism is a pendulum. It's either too far one direction or too far the other.
SPEAKER_01
It's funny on the bubble topic, I have a friend at a growth stage firm, and he and I keep track of all of the signs that we might be in a bubble and things like how quickly are the rounds coming in rapid succession.
SPEAKER_01
[SPEAKER_02] Like what are the degenerate gambling behaviors we're seeing from people in and out of venture, what's happening with SPVs and you go through this list and you're there are a lot of the signs. The counter, which is a strong counter, is there's a lot of extremely interesting companies and there's a lot of companies getting to 100 million of revenue with happy customers and crazy new technology faster than ever. I'm guessing that you're probably feeling a mix of whoa, this looks like a bubble, but these companies look so interesting.
SPEAKER_01
[SPEAKER_02] I mean, look, we're optimists by nature. That's why we were venture capitalists. And I think in any platform shift, you're going to have some incredible companies that come out of this vintage. And in fact, they're probably going to be larger than anything we've ever seen. But you're also going to have a lot of companies that aren't going to go the distance. And I think we all see it in our portfolios, who's building durable revenue streams, who's building moats around their business versus what the labs are offering. And if we're doing our jobs correctly, we're going to find these handful of companies that matter and then have relevance, but there's going to be carnage in their wake and not every company is going to make it. And that's true in every prior cycle. I think the other thing I would say is what's changed since we started a-star seeds used to be 20 to 30 posts. They're now 40 to 50. A great series A used to be 100 posts. Now they're happening at 250. Series Bs used to happen with real traction at a few hundred million dollar valuation. They're 500 million, a billion. Everything has changed, particularly as large funds have gone earlier. And this will end absolutely fine for the best companies that will continue to grow and mature, but it will also be more challenging for founders that struggle to raise above their pref stack and don't go the distance.
SPEAKER_01
[SPEAKER_02] So you guys are investing at the earliest stages where you're basically just looking at teams. I mean, there's an idea, but there's probably not much [SPEAKER_02] They're now 40 to 50. A great Series A used to be 100 posts. Now they're happening at 250.
SPEAKER_02
Series Bs used to happen with real traction at a few hundred million dollar valuation. They're 500 million, a billion. Everything has changed, particularly as large funds have gone earlier.
SPEAKER_02
And this will end absolutely fine for the best companies that will continue to grow and mature, but it will also be more challenging for founders that struggle to raise above their pref stack and don't go the distance. So you guys are investing at the earliest stages where you're looking at teams. There's an idea, but there's probably not much of a product. The idea is probably squishy. And you've got this backdrop where this is both the most exciting time ever and a scary time in certain ways as an investor. So what are the founder attributes that you look for right now? And maybe if there's any contrast to what you looked at in the pre-AI cycle, I'd be interested in hearing that too.
SPEAKER_02
[SPEAKER_00] There's a curious movement around age as founders are getting younger. I guess they're not aging in reverse, but they're getting into— No, it's wild. I mean, you just look at a YC batch. You're seeing people in their teens and early 20s. I bet they have great data on that.
SPEAKER_02
[SPEAKER_00] Yeah, it's going young. Very young. And it's interesting because I see it as in the late seventies when Steve Jobs founded Apple and Bill Gates founded Microsoft, they were 19. And then you fast forward and there are some other examples along the way. Then you had Zuck and then you really had this accelerate. You had Peter Thiel and Luke Nozick devise Thiel Fellows in 2010. That was very prescient. [SPEAKER_00] Which has been incredibly successful. [SPEAKER_00] Yes. And it's a nonprofit. The results of the Thiel Fellows were unbelievable. [SPEAKER_00] It was very prescient of what was coming. And that is this lowering of the age and dropping out.
SPEAKER_02
[SPEAKER_01] But it wasn't quite this right before AI. It was never this before. I mean, there were always young founders building incredible businesses, but you and I have spoken about this. In this paradigm shift, who cares if you know how to build a SaaS product or sell a SaaS product or hire a traditional enterprise go to market team? This is new for everyone. We're all rewriting the rules as we build these companies in real time. And young founders are situated very well because they're the first adopters of this technology. So it's why you're seeing very large companies built by people under the age of 25 or 30 at an unprecedented rate. And for us in practice, that means more and more of our founders are skewing younger and younger. Just the other day, I was speaking to a founder going over some documents and he said he would run things by his lawyer. And I said, isn't your lawyer your mother? And he said sheepishly that he's a teenage founder. He's like, yes, she's a good lawyer, by the way.
SPEAKER_00
[SPEAKER_01] That's good. What else besides age? You were talking about durability and the world is changing. What other attributes, aside from just young founders having certain advantages now?
SPEAKER_00
We generally map talent, not markets. I think to be a seed stage investor, you have to be founder centric, but also recognize what's happening around you. The labs are not just infrastructure companies now. They are legitimate competitors at the application layer, which happens to be where most seed stage companies are building because that's where you raise a traditional round and launch a business. And obviously there's Cogen, which is the central battleground, but it's going to proliferate to every part of knowledge work and every part of the enterprise. We do try to think about where is there white space to build or where can you have enough of a runway to finally build differentiation?
SPEAKER_00
Yeah. Nobody is differentiated at seed. I think this whole idea is, what makes this different? Why couldn't your competitor do this? Every seed stage company can obviously be disrupted or built by an incumbent, but we need to figure out where there's at least enough white space, enough of a runway where you can start to achieve liftoff. [SPEAKER_02] When you say you map talent, what does that look like in practice? What does a day look like? Is it reaching out to interesting people in certain networks? Are you tracking people that you've already known? What does it actually tactically mean to map talent?
SPEAKER_00
It's a lot like mining, where you are in a vein of gold and you've found an area, but that exhaust and you've got to find new talent in new areas. I don't know if that's a good analogy, but things are constantly shifting, but the founders are always the same. They're always those that have had to overcome some kind of obstacles and still achieve at a very young age and be able to recognize the signs in the talent. We've gone through this big phase of IOI and all the coding competitions and things of that nature as a measurement for teens that are achieving on that side. So you're looking for these types of attributes, but the reality is—
SPEAKER_00
[SPEAKER_02] People who worked at Jane Street, I feel like has been another good one recently. [SPEAKER_02] Yes. [SPEAKER_02] Because there's been more interest from exchange for people to be in startups and obviously it's a very talented group.
SPEAKER_00
And this isn't some unique insight, but high quality people want to hang out with high quality people. So when you go to the top universities, when you go to the accelerator programs, when you go to companies like the most talent dense nodes, they work very closely together. So as you start to work with founders in those nodes, you naturally meet their friends who go on to start great companies. I also think as you see people leave companies, you see certain patterns. Certain companies breed better founders than others. Airbnb, Stripe, there are so many of these companies that are magical businesses. They worked and not to say there wasn't hardship in the early days, but when they took off, they really took off. So it doesn't necessarily breed as many founders that run through walls to start companies. Palantir is an example.
SPEAKER_00
[SPEAKER_01] Everyone's a mini CEO. Everyone had to build and launch a product and find product market fit. It's why I think Palantir has the highest per capita rate of unicorn founders of any company. And part of what we need to do is continue to find those areas where the next founders come out of. [SPEAKER_01] Yeah. I mean, we love those Palantir founders. They're fantastic. Companies are magical businesses. They worked and not to say there wasn't a hardship in the early days when they took off, they really took off. So it doesn't necessarily breed as many founders that run through walls to start companies. Palantir is an example.
SPEAKER_00
[SPEAKER_01] Everyone's a mini CEO. Everyone had to build and launch a product and find product market fit. It's why I think Palantir has the highest per capita rate of unicorn founders of any company. And part of what we need to do is continue to find those areas where the next founders come out of. [SPEAKER_01] Yeah. I mean, we love those Palantir founders. They're fantastic. You can't get enough. They're so good. Whatever they feed them over there is really working.
SPEAKER_00
[SPEAKER_01] I also think probably with Palantir, there's a certain non-consensus mindset implied simply by wanting to work at Palantir. And at least that was true at a certain time. Now it's maybe become a bit more, but I think people who worked at Palantir at a time before it was popular and, you know, on the contrary, even when it was something that you had to defend. Yeah. And that takes a certain mindset that is related to being a founder.
SPEAKER_00
[SPEAKER_01] One thing we didn't talk about, there's a whole new crop of founders that never existed, at least in my time of doing venture. It's the researchers. It's folks that are leaving labs or PhD programs that are raising massive funding. Which by the way, used to be a big anti-pattern of researchers. Absolutely. [SPEAKER_01] Yeah. That's hard. You're totally right. Researchers tend to have high intellect, but not as commercial. Academic, not commercial. But now obviously there's all these counter examples for maybe the first time. I'm sure there were examples in the past, but that's a whole new thing that people have to grapple with.
SPEAKER_00
It's very hard. It is. You know, I think that's where, when you're spending time with the founder and getting to know them, if they can really articulate what they're doing, you have to listen so carefully because every word, like a great founder will have every word very much meaning and intention about what they're going to build. Right. You're saying there can be cues with the language someone's using of where they're headed. Yes. And how they prepare and how they're thinking about the business. And that is much. Sequoia had backed my previous two companies and they were always sticklers on your presentation, how you presented and how you showed up at the same time.
SPEAKER_00
Do you guys find that meeting founders in around versus getting to know them before their fundraising is some huge difference? Do you have good examples of success with each? Do you prefer one over the other?
SPEAKER_00
[SPEAKER_02] So I think the Decagon team is a great example. I mean, you know, Kevin, why don't you talk about the history with Ashwin, but I think the prior history informed how we thought about this company. I had been an angel in a company that Ashwin had founded called Helia. Russell Kaplan and Daniel Berrios were in that too. Russell's now the president of Cognition and Daniel's over at Meta. Yeah. But you know, that company didn't make it, but stayed close and was always a big fan of that trio. And when Ashwin went off and met up with Jesse to start Decagon, it was a no brainer to get involved in the seed round there.
SPEAKER_00
[SPEAKER_02] The funny thing about Decagon, there wasn't really an idea. You know, they had this insight that— But you knew the team was great. [SPEAKER_02] We knew the team was great. We knew there was white space in building on top of the foundational models in a moment in time when no one had really commercialized different enterprise applications. And you had the history of the team to say, wait a second, we understand why their prior companies were a modest success, but why one plus one equaled more than two in this situation. And that's an easier bet to take in some ways when you have that history.
SPEAKER_00
[SPEAKER_02] The flip side is, you know, there are founders we meet during a process where we try and build as much rapport and relations as we can. We try and understand them as people, we try and understand the opportunity. And those have worked for us well, but it's a shotgun marriage. Totally. And you need to move faster many times with less information. Especially in a market right now that can, you know, sometimes you meet them, you have three days or something or less.
SPEAKER_00
[SPEAKER_02] Three days. So, you know, I would say at A-Star more than half of our seeds have been pseudo proprietary in nature. And that doesn't mean no other funds around it. That doesn't mean they're not meeting other folks. It just means you didn't start cold during the process. Exactly. We maybe were first to reach out to them. We had some informed knowledge. We had a dinner with them in the past. There was some relationship of relevance and some insight we had going in around who they were as a founder, what they wanted to do. [SPEAKER_02] Is it obvious to you off the cuff, which half of your investments are better?
SPEAKER_00
Yes. The half that we had some prior relationship or somewhat proprietary have disproportionately generated returns. We have done well with some of these shotgun marriages, but there's a higher volatility.
SPEAKER_00
One of the things that I think is interesting in seed is there aren't that many firms that stick around seed for a long time and are very successful. You know, I gave the example of First Round. You guys are obviously doing great. There's a couple others that have been around for long periods of time, but a lot of times people either leave seed or they stop doing what they're doing entirely or something else happens. Why is it that it's a less persistent part of the market than multi-stage in your guys' view?
SPEAKER_01
[SPEAKER_00] Well, I mean, seed is just incredibly hard. It's so challenging. It's investing in just people and no product and hardly even a roadmap or anything else. And so you just have a great deal of uncertainty day in and day out and then compound that with the current environment where we've had the multi-stages come in and want to get a toehold in seed and so, you know, just great money. When you say seed is hard, do you mean hard in the sense of high effort or hard in the sense of difficult to get a good result?
SPEAKER_01
Both. You work incredibly hard to build relationships with founders and earn the right to invest two, three, four, five million dollars in a company that by all odds will likely not work because most companies do not become billion dollar plus companies. And if it's not a billion dollar plus company, it has almost no relevance to the [SPEAKER_00] a great deal of uncertainty day in and day out and then compound that with the current environment where we've had the multi-stages come in and want to get a toehold in seed and so,
SPEAKER_01
just great money. When you say seed is hard, do you mean hard in the sense of high effort or hard in the sense of difficult to get a good result? Both. You work incredibly hard to build relationships with founders and earn the right to invest two, three, four, five million dollars in a company that by all odds will likely not work because most companies do not become billion dollar plus companies. And if it's not a billion dollar plus company, it has almost no relevance to the performance of your fund. It is genuinely hard to find these founders. It is genuinely a lot of work to convince them to partner with you. And it's even more work afterwards to support them in building a company. So I think what you have is two facets of this. You have historically seed firms that have been successful. They maybe do not continue to adapt to the environment. They don't refresh their networks. They don't continue to be aggressive as new types of founders and new technologies emerge. And they tend to fall by the wayside. And that's a crop of seed type funds and others that have been successful that have found that one or two or three amazing companies are there. They grow up, they graduate, they raise opportunity funds and growth funds. And what's left is a relatively small group of firms that still specialize at seed and look to work with the best founders and don't try and find value deals or diamonds in the rough, but compete to be the partner for the next generation of winners. And if you can't do that, seed is a bad asset class. Just to emphasize, venture capitalists should be much better managers of people too. You know, the generational change, handing things off. Very few firms make it on from there. They usually die with their original GP. What do you think is the big source of difficulty in generational transition? Do you think it's finding talent? Is it older partners letting go? Like where do you think most people get it wrong? I mean, my perception has always been finding talent, but I'm sure older founders or older GPs are holding on a bit long, but you've got to find that needle in the haystack out there of somebody that's going to be able to identify the next Google.
SPEAKER_01
[SPEAKER_00] It's also interesting because as funds grow and you start, you guys could very easily make a lot of investments in your seed companies that are performing well and start putting huge amounts of capital behind them. And then one day you could wake up and your growth fund was bigger than your seed fund. And now the incentives are to make right by as many of your dollars as possible. I think that explains where the focus goes. Are you inviting us to do series A's now? A hundred percent. Okay. A, B, C, whatever. Do it all. Do it all.
SPEAKER_01
I do think, and we're a little different than traditional seed fund. We do have a reserve heavy model. We do have more capital available for fall-ins than seed. I think if all you're writing is the first check in seed, it's exceptionally hard to drive returns. I mean, for our best companies, we've piled in every single round and out of a portfolio of 40 seed investments, we might have three, four, five companies that have the lion's share of our capital. It's concentration, but different than the way that a traditional growth fund would talk about it. Yes. You're saying seeds hit so infrequently that if you don't double down on the few that work, it's very hard to get good returns as a basket. I think that's absolutely true. And I don't think your fund is going to return the multiples. And we look at other of our peers who look at pro-rata and say, what's peanut butter pro-rata? Everywhere. You always want to support your founders, but as you look at the series A, the B, the C, the D, those fall-line decisions are actually, in many cases, more important than your initial investment.
SPEAKER_01
[SPEAKER_02] Well, what's interesting is I would argue that from a basket of seeds, I would guess that most of the time, it's actually very difficult to tell by the series A where you should be concentrating. But a lot of funds just do their pro-rata in the next round and that's that. But that really looks like peanut butter across all of it. I would think it's much easier to know where to put huge amounts of money, like a stage or two even later than that.
SPEAKER_01
Agree. I think in our case, we do agree to support our companies in the A. And so we'll always do the pro-rata in that round. Yeah. And then watch, but you're right, that inflection. But there's a different pool of concentration. Let's say you had a fund that was $100 and 40 of it's going into initial seeds and then there's 20 for those pro-ratas. I would think for the last chunk, that's probably a, I would guess done right, you're probably doing 10% of the fund into a few companies each. Is it that concentrated or?
SPEAKER_00
You know, this is interesting because Brian Singerman is creating this LP fund to find new managers to be able to concentrate and help them go all in. And that's, I think since 2005, that's what Founders Fund pioneered was breaking the old venture rules and putting this inordinate amount of money, like when they sold all their Spotify off at a $9 billion valuation and rolled it into Airbnb. [SPEAKER_02] That was pretty monumental. [SPEAKER_02] Which is interesting because that's more of a trader mindset, which you don't normally see in venture. But I mean, Spotify did well, but I guess that was a good trade because Airbnb was at what, two or something like that?
SPEAKER_00
[SPEAKER_02] Yes. Two and a half.
SPEAKER_00
[SPEAKER_02] Two and a half. So instead of getting a 5X, you got a 50X. Great. I think you need to know what great looks like to be successful. So for us, we have $450 million fund, more than 50% of the dollars come after seed. Most growth investors look at seed companies. They think they're completely uninteresting. It's a founder, it's a product, it's raw. Most seed investors look at growth companies and they say, these are all amazing. They have product market fit and revenue and scale. And the founder can actually string together two sentences. And that's historically why people create separate early and growth stage teams. I think to be really great as an early investor and to follow your founders as they mature, you need to know what great looks like at every level. And to your point, the series A may be a hard stage to do that. Obviously you as a practice now are picking that stage too, but it should get easier over time. But as things become more consensus, as you know,
SPEAKER_01
[SPEAKER_02] it's a product, it's raw. Most seed investors look at growth companies and they say, these are all amazing. Oh my God, they have product market fit and revenue and scale. And the founder can actually string together two sentences. And that's historically why people create separate [SPEAKER_00] early and growth stage teams. I think to be really great as an early investor and to follow your founders as they mature, you need to know what great looks like at every level. And to your point, the series B may be a hard stage to do that. Obviously you as a practice now are picking that
SPEAKER_01
[SPEAKER_02] stage too, but it should get easier over time. But as things become more consensus, as you know, they get more expensive, it's harder to buy ownership. So it's always that pendulum on where you want to be on the risk curve. The other side is when you do back the truck up and really go for it, ensuring that it is the money round. I think of in 06 or 07, we used to sit on the floor and project SpaceX launches that were
SPEAKER_01
[SPEAKER_00] going off. They'd launch them in the South Pacific somewhere and they would blow up every time. And that was the sucker's bet, to actually invest in those rounds as these things were blowing up. But as soon as they got one into orbit and that landed the contracts and that put forth the sequence of events, then that's that next phase of putting money in. And then certainly Starlink was the big unlock more recently. [SPEAKER_00] I mean, Founders Fund's SpaceX concentration is extremely impressive to do it over and over into that company. I guess the key is you got to have a SpaceX in the portfolio that's worth concentrating
SPEAKER_02
[SPEAKER_01] into for 15 years, but it's still pretty impressive to do it. A lot of people just wouldn't have the stomach for it. I'm curious about some of your opinions on, and obviously I know you spend most of your time trafficking in founders and talent, but I also know you guys have strong opinions about the market and where it's going. And I'd be curious to hear some of those. Bennett, maybe starting with you, we had talked a little bit about roll-ups and buying businesses that are older established companies and applying AI to them. And you've got a background doing growth as well. So you kind of have some familiarity with this. What's your view here?
SPEAKER_02
[SPEAKER_01] There are a few things that are going to be worse than for incumbent businesses and the venture capitalists that are participating in these, then work buying and transforming and dealing with the culture and the process changes. Like everyone thinks it's as easy as buying a business, deploying AI, improving free cash flow margins and earning a return. I mean, private equity firms have been
SPEAKER_02
[SPEAKER_00] doing roll-ups forever. It's incredibly, incredibly challenging to turn around an existing business. I think this is actually a great business for founders. It used to be that you have to raise capital, you had to buy an asset and you'd improve the asset and you would keep 20% of the profits. [SPEAKER_00] Now a founder can go and raise venture capital dollars, dilute 20%. So keep 80% of the profits
SPEAKER_02
and go buy a business. It is phenomenal for them. I think it is an exceptionally tough asset class that allows venture capitalists to raise lots of money. But I think it will be very hard to achieve real profits doing. By the way, on that point, as the venture capitalist, don't you need the thing to like appreciate a lot just to get back to even? Yes. If you gave somebody a billion dollars and then they went and they bought an asset for a billion dollars and you only own 20% of that thing, don't you now kind of have 200 million dollars? So that's... Am I not thinking right?
SPEAKER_02
No, the ironic element of this is the founder can't lose. The founder has literally bought into a business with embedded asset value that they now own a large percentage of. But unless these companies appreciate dramatically in value, the venture capitalist owns a relatively small percentage. Now people are doing convoluted structures where there's a holdco and an opco and there's carry and there's waterfalls. But no one has actually proven a way that you can monetize this in any way that resembles venture-like returns. Yeah. The other dimension of it, in this private venture capital, private equity play is simply that venture capitalists are very good at watching the top line. They want things to blast off and they're not so precise. And this is all about the top line, but the bottom line, more importantly, and venture capitalists don't pay as much attention to that with their companies. So it just doesn't feel like the right culture fit for this sort of stuff.
SPEAKER_02
Are there any forms of roll-ups or structures that you are bullish on? Like when you look around the different types that are happening, is there any form where you're all right, if I had to buy one, that's the one I'd buy?
SPEAKER_02
[SPEAKER_01] I think there is something to be said for looking at services-oriented professions that have largely recurring, if not truly recurring revenue sources, and looking at how you could replace people with technology. Because if AI has been very good at one thing, it's looking at traditional pockets of labor spend and automating it. So I think there's a reason why accounting roll-ups are interesting for people. There's a reason why HOA roll-ups are interesting for people. I think ITSM as well for that reason. It all deals with tickets and deflection, replacing call center people.
SPEAKER_02
[SPEAKER_00] That feels like a very interesting area, but I would argue 90% of the value created is going to be buying the asset for the right multiple, which once again, venture capitalists are historically very bad at. You're not going to be doing any roll-ups. We will not be doing any roll-ups today, Star. [SPEAKER_00] I mean, the other side, there are always great teams where they're exceptional teams in using technology and Bending Spoons comes to mind as we just sold Eventbrite to Bending Spoons. And that's an incredible operation of how they integrate all these assets and what they're doing in Milan is remarkable.
SPEAKER_02
[SPEAKER_00] What about within AI? What are you guys most excited about? Where are you anxious? [SPEAKER_00] You know, maybe to frame up a common meme right now that software is extremely difficult because the labs are sort of expanding and everything's being workflows are being replaced by agents and the workflows I need that are important, the labs are going to own. And so we can't take that position. I mean, we have to want to back these independent companies and the labs, they need to have a very audacious appetite and keep the growth up. But we'll still keep backing the application layer all around where we see the right barriers, the right teams and so on.
SPEAKER_02
[SPEAKER_00] And there's a distinction obviously between application layer AI companies and more traditional [SPEAKER_00] because the labs are just expanding and everything's being, workflows are being replaced by agents and the workflows I need that are important, the labs are going to own. And so,
SPEAKER_00
[SPEAKER_02] we can't take that position. I mean, we have to, we want to back these [SPEAKER_02] independent companies and the labs like they need to, they need to have a very audacious [SPEAKER_02] appetite and keep the growth up. But we'll still keep backing the application [SPEAKER_02] layer all around where we see the right barriers, the right teams and so on. And there's a distinction obviously between application layer AI companies and more traditional incumbent software. I don't know the last time we've heard a founder pitching a traditional software business. Now, part of that is the meme that everyone's
SPEAKER_00
[SPEAKER_01] everything's an AI company now. Everyone puts AI in their deck. But I think systems of [SPEAKER_01] records are still very sticky for a reason. I think the issue, as we all know, is if you can vibe code [SPEAKER_01] an app in a matter of minutes and why do you need so many engineers? What's the value of the workflows [SPEAKER_01] that you've built? But we're seeing on the application layers, people are going after systems of intelligence. They're going after systems of action. It's new types of spend. [SPEAKER_01] And we're going to continue to back those. I would say in terms of the public markets,
SPEAKER_00
I mean, there is a reason software is having significant drawdowns, but the best companies should be able to navigate this. Kevin mentioned early on that
SPEAKER_01
[SPEAKER_00] we were investors in RIP. I would say they are a great example of an incumbent pre-GPT company
SPEAKER_00
that has now become an AI business and agents are driving top line and margins. The best teams are going to adapt. So I think you're fine if you're in an incumbent software
SPEAKER_02
[SPEAKER_01] business as long as you have a team that is going to re-architect everything from the ground up. [SPEAKER_01] What about hardware and hard tech? I know you've been incubating a company that is [SPEAKER_01] software-enabled hardware. And I assume you guys have been investing in it. How do you guys [SPEAKER_01] think about non-software, potentially even non-AI, but at least hard tech, [SPEAKER_00] hardware companies? It's again, we want to go where the talent is and we're being drawn to these [SPEAKER_00] various hardware companies for the reason of, they're being
SPEAKER_02
[SPEAKER_00] really impressive people. It's happening across the board. There's a revolution there.
SPEAKER_01
You know, we certainly don't want to get caught in the same traps that have been
SPEAKER_02
[SPEAKER_01] difficult for hardware in the past, but hardware gives you, it puts you out in [SPEAKER_01] the real world. Like before in software, we were trapped inside of a jar and hardware and robotics and so on is an exciting new world for us. [SPEAKER_01] There's some good defense if you have some sensors and things out in the world, at least [SPEAKER_01] someone can't just come along and vibe code that. [SPEAKER_00] I think that's exactly true. I think we just haven't hit the ChatGPT moment for robotics. So I [SPEAKER_00] think AI for the physical world should be as large, if not larger than what we've seen for
SPEAKER_02
[SPEAKER_00] the knowledge world. The challenge is right now we haven't seen as much commercial [SPEAKER_00] applications. We care to receive investors. We're backing robotics companies. We're backing [SPEAKER_00] companies working on sensors and edge AI, but we do think a number of robotics companies have raised at huge valuation, very little commercial promise. So we think a lot of this is still to come. Are there types of companies that you are excited about, but given your fund size, you just can't engage in, you know, I'm thinking of Neo labs or heavy robotics projects or things that don't start with a five to ten million dollar seed round?
SPEAKER_02
[SPEAKER_01] Yeah, those are tough to see and have them go by us. But with that said, we've been able to invest in a lot of scrappy verticalized [SPEAKER_01] robots. So we're in a company wanting robotics, it's data set data center cabling in robotics. [SPEAKER_01] That is a very specific task that's very high value. And that differs from [SPEAKER_01] going after a full horizontal market. Or we backed a research team out of Stanford called [SPEAKER_01] Simway, which was focused on market research, which went on to raise a hundred million after the seed
SPEAKER_00
[SPEAKER_01] round, but at the time only needed a little money to prove out and commercialize their research. [SPEAKER_01] Those are the rare exceptions, in normal cases, they skip the seed round, [SPEAKER_01] despite how hard we try to convince them of the value of it. And they raise ten, fifty, [SPEAKER_02] a hundred million dollars. And by the way, that is where a lot of the multi-stage dollars are going [SPEAKER_02] and at seed and that we can't really do those rounds. Yep. Makes sense. So you guys have this new fund [SPEAKER_02] now, any changes coming for Astro overall, or is it just more of the same bigger, better, faster?
SPEAKER_00
[SPEAKER_02] I think it's more of the same. There's inflation in round size, [SPEAKER_02] there's a larger volume of founders that are flocking to start companies than ever. And I think we just [SPEAKER_02] need to be playing the game in the field. We need to be meeting founders where they are moving [SPEAKER_02] quickly and leading seed rounds. And hopefully we could be a bigger and better partner over time [SPEAKER_02] as our fund size has grown modestly. But we started Astro with a three hundred million dollar fund five years ago.
SPEAKER_01
[SPEAKER_02] Our new fund is not that much larger. I think we look to a lot of our peers who've stayed [SPEAKER_02] focused, who've become experts at their craft. And that's what we look to emulate and what we'll [SPEAKER_02] continue to do. And we can also extend out. We've shown to be very patient and we're [SPEAKER_02] not just trying to put capital to work and we kind of wait patiently for those right companies, [SPEAKER_02] even if it takes a little longer to deploy. [SPEAKER_02] And you guys are moving into this building, right? [SPEAKER_02] We are. [SPEAKER_02] We want our founders to keep moving up before, when they raise their future rounds.
SPEAKER_01
[SPEAKER_02] You guys fund them, send them over here. It's beautiful. [SPEAKER_02] We could put a fire pole. [SPEAKER_02] I love that. I think we dig a little hole somewhere. I don't know if you're above or below, [SPEAKER_00] but we're a little staircase.
SPEAKER_00
We're of course below. [SPEAKER_02] Okay. It doesn't have to. [SPEAKER_02] It's a seed thing. [SPEAKER_02] Exactly. That's right. All right. Well, thank you guys. This is super fun. I appreciate [SPEAKER_02] you both making time for it. [SPEAKER_02] Thank you, Jeff. [SPEAKER_02] Thank you. Thank you. Yeah. Nobody is differentiated seed. I think this whole idea is like, what makes this different? Why couldn't your competitor do this? Every seed stage company can obviously be disrupted or built by an incumbent, but we need to figure out where there's at least enough white space, enough of a runway. You can start to achieve liftoff.
SPEAKER_02
When you say you map talent, what does that look like in practice? Like, what does like a day look like? You know, is it just sort of reaching out to interesting people in certain networks? Are you tracking people that you've already known? Like, what does it actually tactically mean to map talent? You know, it's a lot like a, you know, mining, uh, you know, where you are in a vein of like gold and you've found, you know, an area, but that exhaust and you've got to find new talent in
SPEAKER_00
new areas. I don't know if that's a good analogy mining, but you know, like things are constantly switching, but you know, the founders are always the same. They're always, you know, those that have had to overcome some kind of obstacles and still achieve at a very young age
SPEAKER_02
and be able to recognize, uh, the signs, you know, in, in the talents, you know, we've gone through this big phase of IOI and all the coding competitions and things of that nature as a, you know, as a measurement for, you know, like teens that are achieving on that side. So you're looking for, you know, these types of, you know, these types of attributes, but the reality is- People who worked at like Jane Street, I feel like has been like another good one recently. Yes. Because there's been more interest from exchange for people to be in startups and obviously it's a very talented group.
SPEAKER_00
And this isn't like some unique insight, but high quality people want to hang out with high quality people. So when you go to the top universities, when you go to the accelerator programs, when you go to companies, like the most talent dense nodes work very closely together. So as you start to work with founders in those nodes, you naturally meet their friends who go on to start great companies. I also think as you see people leave companies, you see certain patterns, certain companies breed better founders than others. Airbnb, Stripe, there's so many of these companies are magical businesses. They worked and not to say there wasn't a hardship in the early days
SPEAKER_00
when they took off, they really took off. So it doesn't necessarily breed as many founders that like
SPEAKER_01
run through walls to start companies. Palantir is an example. Everyone's a mini CEO. Everyone had to build and launch a product and find product market fit. It's why I think Palantir has the highest like per capita rate of unicorn founders of any company. And part of what we need to do is continue to find those areas where the next founders come out of. Yeah. I mean, we love those Palantir founders. They're fantastic. You can't get enough. Like they're so good. Like whatever they feed them over there is like really working. I also think probably with Palantir, there's a certain non-consensus mindset implied simply by
SPEAKER_01
wanting to work at Palantir. And at least that was true at a certain time. You know, now it's maybe become a bit more, but I think people who worked at Palantir and Anderil at a time before it was popular and, you know, on the contrary, even it was sort of something that you had to like defend. Yeah. And that takes a certain mindset that is like kind of related to being a founder. One thing we didn't talk about, there's a whole new crop of founders that never existed, at least in my time of doing venture. It's the researchers. It's folks that are leaving labs or PhD programs that are raising massive quantum. Which by the way, used to be a big anti-pattern
SPEAKER_01
of like researchers. Absolutely. Yeah. That's hard. You're totally right. Researchers tend to be, to have high intellect, but not as commercial. Academic, not commercial. But now obviously there's all these counter examples for like maybe the first time. I'm sure there were examples in the past, but that's a whole new thing that people have to grapple with.
SPEAKER_00
It's very hard. It is. You know, I think that's where, when you're spending time with the founder and getting to know them, if they can really articulate what they're doing, you know, you have to listen so carefully because every word, like a great founder will have every word very much meaning, you know, have great meaning and intention about what they're going to build. Right. You're saying like there can be cues with the language someone's using of like where they're headed at. Yes. And how they prepare and how they're thinking about the business. And that is much. Sequoia had backed my previous two companies and they were always sticklers on,
SPEAKER_00
you know, your presentation, how you presented and how you showed up at the same time. Do you guys find that meeting founders in around versus getting to know them before their fundraising is some huge difference? Do you have good examples of success with each? Do you prefer one over the other? So I think the Decagon team is a great example. I mean, you know,
SPEAKER_02
Kevin, why don't you talk about the history with Ashwin, but I think the prior history informed how we thought about this company. I had been an angel in a company that Ashwin had founded called Helia. Russell Kaplan and Daniel Berrios were in that too. Russell's now the president of Cognition and Daniel's over at Meta. Yeah. But, you know, that company didn't make it, but stayed close and was always a big fan of that trio. And when Ashwin went off to and met up with Jesse to start Decagon, it was kind of a no brainer to get involved in the seed round there. The funny thing about Decagon, there wasn't really an idea. You know, they had this insight
SPEAKER_02
that- But you knew the team was great. We knew the team was great. We knew there was white space and building on top of the foundational models in a moment in time when no one had really, you know, commercialized different enterprise applications. And you had the history of the team to say, wait a second, we understand why their prior companies were a modest success, but why one plus one equaled more than two in this situation. And that's an easier bet to take in some ways when you have that history. The flip side is, you know, there are founders we meet during a process where we, you know, we try
SPEAKER_02
and build as much of rapport and relations as we can. We try and understand that as people, we try and understand the opportunity. And those have worked for us well, but you, it's a shotgun marriage. Totally. And you need to move faster many times with less information. Especially in a market like right now that can, you know, sometimes you meet them, you have three days or something like that or less. Three days. So, you know, I would say at A-Star more than half of our seeds have been pseudo proprietary in nature. And that doesn't mean no other funds around it. That doesn't mean they're not meeting other folks. It just means you didn't start cold during the process.
SPEAKER_02
Exactly. We maybe were first to reach out to them. We had some informed knowledge. We had a dinner with them in the past. There was some relationship of relevance and some insight we had going in around their, you know, who they were as a founder, what they wanted to do. Is it obvious to you off the cuff, which half of your investments are better?
SPEAKER_00
Yes. The half that we had some prior relationship or somewhat proprietary have disproportionately generated returns that we have done well with some of these shotgun marriages, but there's a, I would say, higher volatility. One of the things that I think is sort of interesting in seed is there aren't that many firms that stick around seed for a long time and are very successful. You know, I gave the example of first round. You guys are obviously doing great. There's a couple others that have been around for long periods of time, but a lot of times people either leave seed or, you know, they kind of stop doing what they're doing entirely or something else happens.
SPEAKER_00
Why is it that it's a less persistent sort of part of the market than multi-stage in your guys' view? Well, I mean, seed is just incredibly hard. It's so challenging. It's investing in, you know, just people and no product and no, you know, hardly even a roadmap or anything else. And so you just have a great deal of uncertainty day in and day out and then compound that with the current environment where we've had, you know, the multi-stages come in and want to get a toehold in seed and so, you know,
SPEAKER_01
just great money. When you say seed is hard, do you mean hard in the sense of high effort or hard in the sense of difficult to get a good result? Both. You work incredibly hard to build relationships with founders and earn the right to invest two, three, four, five million dollars in a company that
SPEAKER_00
by all odds will likely not work because most companies do not become billion dollar plus companies. And if it's not a billion dollar plus company, it has almost no relevance to the
SPEAKER_01
performance of your fund. It is genuinely hard to find these founders. It is genuinely a lot of work to convince them to partner with you. And it's even more work afterwards to support them in building a company. So I think what you have is two facets of this. You have historically seed firms that have been successful. They maybe do not continue to adapt to the environment. They don't refresh their networks. They don't continue to be aggressive as new types of founders and new technologies emerge. And they tend to fall by the wayside. And that's a crop of seed type funds and others that have been
SPEAKER_01
successful that have found that one or two or three amazing companies are there. They grow up, they graduate, they raise opportunity funds and growth funds. And what's left is a relatively small group of firms that still specialize at seed and look to work with the best founders and don't try and find value deals or diamonds in the rough, but compete to be the partner for the next generation of winners. And if you can't do that, seed is a bad asset class. Just to emphasize, venture capitalists should be much better managers of people too. You know, the generational change, handing things off. Yeah. You know, very, very few firms kind of make it make it on from there. They
SPEAKER_01
usually like die with their original GP. What do you think is like the big source of difficulty in generational transition? Do you think it's finding talent? Is it older partners letting go? Like where do you think most people get it wrong? I mean, my perception has always been finding talent, but I'm sure maybe older founders or older GPs are holding on, you know, a bit long, but it is, you know, you've got to find that needle in the haystack out there of somebody that's going
SPEAKER_00
to be able to identify the next Google. It's also interesting because as funds grow and you start, you know, you guys could very easily make a lot of investments in your seed companies that are performing well and start putting huge amounts of capital behind them. And then one day you could wake up and your growth fund was bigger than your seed fund. And now the incentives are to make right by as
SPEAKER_01
many of your dollars as possible. I think that sort of explains where the focus goes. Are you inviting us to do series A's now? A hundred percent. Okay. A, B, C, whatever. Do it all. Do it all. I do think, and we're a little different than traditional seed fund. We do have a reserve heavy
SPEAKER_02
model. We do have more capital available for fall-ins than seed. I think if you, all you're writing is the first check in seed, it's exceptionally hard to drive returns. I mean, for our best companies, we've piled in every single round and out of a portfolio of 40 seed investments, we might have three, four, five companies that have the lion's share of our capital. It's concentration, but different than the way that a traditional growth fund would talk about it. Yes. You're saying seeds hit so infrequently that if you don't double down on the few that work, it's very hard to get good returns as a basket. I think that's absolutely true. And I don't think your fund is
SPEAKER_02
going to return the multiples. And we look at other of our peers who look at pro-rata and say, what's peanut butter pro-rata? Right. Everywhere. You always want to support your founders, but as you look at the series A, the B, the C, the D, that those fall-line decisions are actually, in many cases, more important than your initial investment. Well, what's interesting is I would argue that, you know, from a basket of seeds, I would guess that most of the time, it's actually very difficult to tell by the series A where you should be concentrating. But a lot of funds just do their pro-rata in the next round and that's that. But that really looks kind of just like,
SPEAKER_02
you know, a peanut butter across all of it. I would think it's much easier to know where to put huge amounts of money, like a stage or two even later than that. Agree. I think in our case,
SPEAKER_01
we do agree to support our companies in the A. And so we'll always do the pro-rata in that round. Yeah. And then watch, but you're right, like that inflection. But there's a different pool of concentration. Like let's say you had, you know, a fund that was $100 and 40 of it's going into initial seeds and then there's 20 for those pro-ratas. I would think for the last chunk, that's probably like a, I would guess done right, you're probably doing just,
SPEAKER_00
you know, 10% of the fund into a few companies each kind of thing. Is it that concentrated or? You know, this is interesting because Brian Singerman is creating this LP fund to find new managers to be able to concentrate and help them like go all in. And that's, you know, I think since 2005, that's what Founders Fund kind of pioneered was like breaking the old venture rules and putting this inordinate amount of money, like when they sold all their Spotify off at a $9 billion valuation
SPEAKER_02
and rolled it into Airbnb. Right. That was pretty monumental. Which is interesting because that's more of a trader mindset, which you don't normally see in venture. But it was, I mean, Spotify did well, but I guess that was a good trade because Airbnb was at what, two or something like that? Yes. Two and a half. Yeah. Two and a half. So instead of getting a 5X, you got a 50X. Great. I think you need to know what great looks like to be successful. So for us, we have $450 million fund, more than 50% of the dollars come after seed. Most growth investors look at seed companies. They think they're like completely uninteresting. It's a founder,
SPEAKER_02
it's a product, it's raw. Like most seed investors look at growth companies and they say, these are all amazing. Oh my God, they have product market fit and revenue and scale. And the founder can actually string together two sentences. And that's historically why people create separate
SPEAKER_00
early and growth stage teams. I think to be really great as an early investor and to follow
SPEAKER_02
your founders as they mature, you need to know what great looks like at every level. And to your point, the series eight may be a hard stage to do that. Obviously you as a practice now are picking that stage too, but it should get easier over time. But as things become more consensus, as you know, they get more expensive, it's harder to buy ownership. So it's always that pendulum on where you want to be on the risk curve. The other side is like when you do back the truck up and you know, really go for it, you know, ensuring that it is the money round. Like I kind of think of in like 06 or 07, we used to sit on the floor and project, uh, SpaceX launches over like that were
SPEAKER_00
going off, you know, they'd launch them in the, in the South Pacific somewhere and they would blow up every time. And, you know, like that was the sucker's bet is to actually invest in those rounds as these things were blowing up. But as soon as you know, they got one into orbit and that landed the contracts and that put forth the sequence of events, then, you know, that's that next phase of putting money in. And then certainly Starlink was the big unlock more recently. I mean, founders fund SpaceX concentration is extremely impressive to do it over and over into that company. I guess the key is you got to have a SpaceX in the portfolio that's worth concentrating
SPEAKER_01
into for 15 years, but it's still pretty impressive to do it. A lot of people, you know, just wouldn't have the stomach for it. I'm curious about some of your guys opinions on, and obviously I know you spend most of your time trafficking in founders and talent, but I also know you guys have strong opinions about the market and where it's going. And I'd be curious to hear some of those. Bennett, maybe starting with you, we, we had, um, we had talked a little bit about like, you know, roll ups and sort of buying businesses that are sort of, you know, older established companies and applying AI to them. And you've, you know, got a background doing growth as well.
SPEAKER_01
So you kind of have some more familiarity with this. Like what, what's your view here? There are a few things that are going to be worse than for incumbent businesses and the venture capitalists that are participating in these, then work buying and transforming and dealing with the culture and the process changes. Like everyone thinks it's as easy as buying a business, deploying AI, improving free cashflow margins and earning a return. I mean, private equity firms have been
SPEAKER_00
doing roll ups forever. It's incredibly, incredibly challenging to turn around an existing business. I think this is actually a great business for founders. It used to be that you have to raise capital, you had to buy an asset and you'd improve the asset and you would keep 20% of the profits. Now a founder can go and raise venture capital dollars, dilute 20%. So keep 80% of the profits
SPEAKER_02
and go buy a business. It is phenomenal for them. I think it is an exceptionally tough asset class that allows venture capitalists to raise lots of money. But I think it will be very hard to achieve real profits doing. By the way, on that point, as the venture capitalist, don't you need the thing to like appreciate a lot just to get back to even? Yes. If you gave somebody a billion dollars and then they went and they bought an asset for a billion dollars and you only own 20% of that thing, don't you now kind of have 200 million dollars? So that's... Am I not thinking right?
SPEAKER_02
No, the ironic element of this is like the founder can't lose. The founder has literally bought into a business with embedded asset value that they now own a large percentage of. But unless these companies appreciate dramatically in value, the venture capitalist owns a relatively small percentage. Now people are doing convoluted structures where there's a holdco and an opco and there's carry and there's waterfalls. But no one has actually proven a way that you can monetize this in any way that resembles venture-like returns. Yeah. The other dimension of it, you know, in this like private venture capital, private equity play is simply that like venture capitalists
SPEAKER_02
are very good at watching the top line. Like they want things to like blast off and they're not so precise. And, you know, this is all about the top line, but the bottom line, more importantly, and, you know, venture capitalists don't pay as much attention to that, you know, with their companies. So it just doesn't feel like the right culture fit for this sort of stuff. Are there any forms of roll-ups or structures that you are bullish on? Like when you look around the different types that are happening, is there any form where you're like, all right,
SPEAKER_01
if I had to buy one, that's the one I'd buy? I think there is something to be said for looking at his services oriented professions that have largely recurring, if not truly recurring revenue sources, and looking at how you could replace people with technology. Because if AI has been very good at one thing, it's looking at traditional pockets of labor spend and automating it. So I think there's a reason why I think accounting roll-ups are interesting for people. There's a reason why HOA roll-ups are interesting for people. I think ITSM as well for that reason. It all deals with tickets and deflection, replacing call center people.
SPEAKER_00
That feels like a very interesting area, but I would argue 90% of the value created is going to be buying the asset for the right multiple, which once again, venture capitalists are historically very bad at. You're not going to be doing any roll-ups. We will not be doing any roll-ups today, Star. I mean, the other side, there are always great teams where they're exceptional teams in using technology and Bending Spoons comes to mind as we just sold Eventbrite to Bending Spoons. And that's an incredible operation of how they integrate all these assets and what they're doing in Milan is remarkable.
SPEAKER_00
What about within AI? What are you guys most excited about? Where are you anxious? You know, maybe to frame up sort of like a common meme right now that software is extremely difficult because the labs are sort of just expanding and everything's being, you know, workflows are being
SPEAKER_02
replaced by agents and the workflows I need that are important, the labs are going to own. And so, you know, we can't take that position. I mean, we have to, you know, we want to back these independent companies and the labs like they need to, you know, they need to have a very audacious appetite and keep the growth up. But, you know, we'll still keep, you know, backing the application layer all around where we see the right barriers, the right teams and so on.
SPEAKER_00
And there's a distinction obviously between application layer AI companies and more traditional incumbent, you know, software. I don't know the last time we've heard a founder pitching a traditional software business. Now, part of that is the meme that everyone's just an,
SPEAKER_01
everything's an AI company now. Everyone puts AI in their deck. But, you know, I think systems of records are still very sticky for a reason. I think the issue, as we all know, is if you can vibe code an app in a matter of minutes and why do you need so many engineers? What's the value of the workflows that you've built? But we're seeing on the application layers, people are going after
SPEAKER_00
systems of intelligence. They're going after systems of action. It's new types of spend.
SPEAKER_01
And we're going to continue to back those. I would say in terms of the public markets,
SPEAKER_00
I mean, there is a reason software is having significant drawdowns, but the best companies should be able to navigate this. Kevin mentioned early on that, like, we were investors in RIP. I would say they are a great example of an incumbent pre-JAT-GPT company that has now become an AI business and agents are driving top line and margins. The best teams are going to adapt. So I think you're fine if you're in an incumbent software
SPEAKER_01
business as long as you have a team that is going to re-architect everything from the ground up. What about hardware and hard tech? I know you've been incubating a company that is sort of like software-enabled hardware, I think. And I assume you guys have been investing in it. How do you guys think about like non-software, potentially even non-AI, but at least sort of like hard tech,
SPEAKER_00
hardware companies? It's again, like we want to go where the talent is and we're being drawn to these you know, various hardware companies for the reason of, you know, they're being, you know, really, really impressive people. It's happening kind of across the board. There's a revolution there.
SPEAKER_01
You know, we certainly don't want to get caught in the same traps that have been difficult for hardware in the past, but yeah, hardware gives you, you know, it puts you out in the real world. Like before in software, you know, we were like kind of trapped like a brain inside of a jar and hardware and robotics and so on is an exciting new world for us. There's some good defense if you have some like sensors and things out in the world, at least someone can't just come along and vibe code that.
SPEAKER_00
I think that's exactly true. I think we just haven't hit the chat GPT moment for robotics. So I think, I mean, AI for the physical world should be as large, if not larger than what we've seen for the knowledge world. The challenge is right now we haven't seen as much of the commercial applications. We don't care to receive investors. We're backing robotics companies. We're backing companies working on sensors and edge AI, but we do think about a number of robotics companies have
SPEAKER_02
raised at huge valuation, very little commercial promise. So we think a lot of this is still to come. Are there types of companies that you are excited about, but given your fund size, you just like can't engage in, you know, I'm thinking of like Neo labs or, you know, heavy robotics projects or things like that, that don't, you know, start with it's five to $10 million seed round?
SPEAKER_01
Yeah. You know, alas, those are tough, you know, to see and, and have them go by us. But, you know, with that said, I mean, we're in, we've been able to invest in a lot of, um, scrappy verticalized robots. So we're in a, in a company wanting robotics, it's data set data center cabling in, in robotics. That, um, is a very specific task that's very high value. And, and that differs from, you know, going after a full horizontal market. Um, or we backed a research team out of Stanford, uh, called Simway, which was focused on market research, which went on to raise a hundred million after the seed
SPEAKER_01
round, but at the time only needed a little bit of money to prove out and commercialize their research. Those are the rare exceptions, as you know, in normal cases, they skip the little seed round, despite how hard we try to convince them of the value of it. And they raised 10, 50,
SPEAKER_02
a hundred million dollars. And by the way, that is where a lot of the multi-stage dollars are going and seed and that we can't really do those rounds. Yep. Makes sense. So you guys have this new fund now, any changes coming for a star overall, or it's just more of the same bigger, better, faster? I think it's more of the same. I mean, there's, as you know, there's inflation round size, there's a larger volume of founders that are flocking to start companies than ever. And I think we just need to be playing the game in the field. We need to be meeting founders where they are moving
SPEAKER_02
quickly and leading seed rounds. And hopefully we could be a bigger and better partner over time as our fund size has grown modestly. But we started a star with a $300 million fund five years ago. Our new fund is not that much larger. Like, I think we look to a lot of our peers who've stayed focused, who've become experts at their craft. And that's what we look to emulate and what we'll continue to do. And we can also, I mean, extend out. I mean, we've shown to be very patient and we're not just trying to put capital to work and we kind of wait patiently for those right companies, even if it takes a little longer to deploy.
SPEAKER_02
And you guys are moving into this building, right? We are. We are. We want our founders to keep moving up before, when they raise their future rounds. You guys fund them, send them over here. It's beautiful. We could put a fire pole. I love that. I think we dig a little hole somewhere. I don't know if you're above or below,
SPEAKER_00
but we're a little staircase. We're of course below.
SPEAKER_02
Okay. It doesn't have to. It's a seed thing. Yeah, exactly. That's right. All right. Well, thank you guys. This is super fun. I appreciate you both making time for it. Thank you, Jeff. Thank you.
SPEAKER_00
Thank you.