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David
Last time when we spoke, you told me about the strongest signal that you see for a new company. What is that signal?
Ken
The signal for us has especially in recent times, been key executives that leave large private companies to join early stage startups. If the head of engineering at Apple is leaving for a startup and has been there 17 years, we want to know about that company. And because we have the relationship with that executive, we we oftentimes get introduced to them by the management team and start understanding what that early stage startup is doing and get a very good look inside where other investors mainly haven't even heard about the company. And I think the best example of that was in 2019. We were approached by an executive to help him liquidate $35 million worth of strike. We asked him, well, why are you.
Andrew
Selling and why are you selling this much?
Ken
He goes, well, I'm leaving the company. I'm joining something pretty exciting called OpenAI. And at the time people had not really heard of OpenAI yet. It was a completely new concept. We did some work on it and actually started getting to know what OpenAI was all about.
Andrew
And ChatGPT had we not had that.
Ken
Signal from the executive, I mean VCs weren't even really heavily involved at that point. There was very little knowledge of this company. And due to the fact that we were able to build a relationship over a many month period, we started to understand that OpenAI and ChatGPT was going to be a very, very big thing. And the only reason why people would go there and le such a successful startup as Stripe would be that they figured this opportunity was much larger and had much more upside than staying where they were.
David
You mentioned that a Sequoia or Andreessen Horowitz may not be as strong of a signal. Why is that?
Ken
The large VC funds are managing 10, 20, $30 billion. So to say that you're leading around with say a $5 million check, when you're writing many multiples of those $5 million checks across your portfolio sometimes isn't a strong signal because the VC firms themselves are so over capitalized. If that bet doesn't work out, it generally does not affect their returns. It's really kind of a drop in the bucket for them. But it's a lot riskier for an individual who has a very large amount of equity and stock options in a startup to go leave to go to a Series A. And that to us means real risk taking.
Andrew
Right?
Ken
The risk that a VC is taking by leading a $5 million Series A or putting in a $5 million check or a $10 million check into a Series A is much, much less than a key executive who owns 100 million of equity in a very established corn. In many cases, to go to a company with $100 million valuation, that's pre revenue. Right. That executive is taking real calculated career risk on that move. They know something even the VCs don't know.
David
And there's not only the career risk of leaving one company and putting all of your career baskets into an untested company. There's also the fact that oftentimes at these large companies, you get refreshed in your equity pools, oftentimes every year, sometimes every couple years. So they're giving up this future equity.
Ken
When we look back historically, those moves have meant a lot more to us than who's actually leading the round. In fact, many of these executives are leaving to go to these companies before there's even a lead in a significant round. And what we found is those with the engineering background and those that are highly technical people that actually know the technology better than any VC ever will because they're internal and need to understand that the next wave of what they're doing.
David
You alluded to it. There's so much capital in venture capital today chasing, you know, a few really good deals. How do you know that you're not being adversely selected in terms of the companies that you invest in in addition.
Ken
To tracking fundamentals and metrics and what's really going on underneath the hood? I mean, we just invested in an AI chip startup which is pre revenue. Right. But our leading indicator on that one is key engineer from Apple that was there 17 years, just joined one of the key engineers from SpaceX that was managing 30 engineers at SpaceX. One of the head of design engineering just joined the company and also a key executive from lom.
Andrew
Now, they haven't even raised their Series.
Ken
B yet, but with that kind of firepower on the executive team already, we're thinking this is an opportunity that we really need to dig into. And now it's just understanding what the revenue traction is, what the commercialization is from a product perspective. We think they're, you know, they're way ahead. And that's a very strong signal there.
David
You're a thematic investor. Tell me about one or two themes that you're excited about for 2025.
Ken
We're thematic, but we also have to be pragmatic that we don't know, you know, the technologies that are out there today. I don't think that we could have guessed three years ago that Perplexity was going to be a nine billion dollar company. Right. And that's why the signaling that we keep talking about is so important. Because the true technology execs at these companies and the people that are actually building these products are the ones that we want to follow right now. We think AI chatbot agents are going to be a huge business. And that's where you're seeing executives from OpenAI Anthropic leading to these chap, leading to these chatbot startups. And they get it exactly right. Which they're about 80% there. Being able to actually duplicate what a human does in a certain task. We think that that's going to be a massive, massive business for corporations to reduce costs and increase efficiency. So we're very, very focused on that. We're also given the new administration focus a lot on defense tech. And we think that that business is just going from a true transformation where you have the old guard of the Lockheed Martins, the General Dynamics, those types of companies which had old technologies like the F35, which is basically already on the chopping block by the new Doge administration and now is really leaning into technologies on the battlefield that are being developed by very innovative startups. I mean, Andrew is obviously the blue chip name in that space, but SHIELD AI is doing very interesting things and other even earlier stage startups than that that are bringing technologies that we didn't even know know two to three years ago. So we're paying attention to these broad thematic themes. But you know, it all comes down especially in early stage investing, to the people, the team and their track record and what they've built at other organizations as the true litmus test of whether we're really interested or not.
David
We've seen a complete 180 in terms of venture fronts investing into defense tech over the last one, really two years. But in the last year, dramatic change in activity in terms of the institutional secondary market. Who is accessing the Elon companies or these kind of companies? Who is that is out there in the market buying these shares?
Andrew
It's a wide mix, but I would say it's obviously the large institutional investors. It's the VCs, it's the hedge funds that are getting.
David
So you have VCs going to you and saying, I want to buy on the open market, more exposure to my name.
Andrew
That's right. Once they get into a company, they come to us and say, look, we're trying to size up and we're trying to build a bigger position in this company. And we've done that multiple times this year. I think that they also are cognizant of the fact that they use us for liquidity and the other parts of their portfolio. So one of the biggest issues that VCs are having is DPI, right? So as much money as they're putting into these new LLM companies, all the AI startups, the military logistics companies like Anduril and the robotics companies, are also trying to exit a lot of legacy things that they invested in from2017 to 2021 and, and trying to get DPI for their investors, right? So their investors are saying, look, this is great that you're putting a lot of money to work in AI. And, and names like CO2 have deployed and raised a billion dollars just to focus on AI recently. But they're also looking at the rest of their portfolio and saying, well, what happened to that hot fintech company you were talking about in 2019 and that hot SaaS name that you did in 2020, what happened to those? Because all of a sudden nobody's talking about those, right? So they're kind of forgotten zombies. Many the companies have slowed their growth. They had to cut, burn during the tech crisis and a lot of VCs feel a little bit stuck, right? So a lot of our job has become help us get DPI on this part of our portfolio and then hopefully we can recycle that cash into other AI opportunities or things that we're looking towards the future on. So it's. But it's really become lopsided in that regard. Cash is not the problem for VCs right now, or fresh cash that they've raised ideas is not a problem. There's a ton of companies to invest in right now, but it's really liquidity in the rest of the portfolio. So when you're talking to an endowment and they're saying, give me fresh new money, they're saying, well, we have none yet. And obviously VC is a big part of the problem, but the biggest part of the problem is private equity. So there's a massive liquidity problem right now. It's creating really a bottleneck in the industry. But in terms of innovation and the pace of innovation, it's faster than I've ever seen it. It is really, truly astonishing what's going on and what companies are developing and, and how it's affecting society.
David
So you see from one side, VCs buying secondary to add to their positions. You see some VCs selling in order to generate DPI, what other types of investors, whether institutional or non institutional investors do you see regularly in the secondary market?
Andrew
Family offices have been an interesting one. I think family offices are a little bit less self guided than a VC fund or a hedge fund would or an institution because a lot of times they don't have access to the level of diligence that some of these institutions do. So they tend to follow a lot of their managers into opportunities. So what we see sometimes is, hey, we own this company through a fund that, you know, one of the large VC owns. But if you offer it to us, we would size up and buy more. You know, we would go into an SPV that has that name because we're really bullish on it and it'll add to our position, which is somewhat diluted across this fund. So we see that. And then obviously, and this is where markets get very frothy is retail, right? And so the high net worth investor is being pitched a lot of these deals through the typical Morgan Stanley, Goldman Sachs platforms, Merrill lynch. And they're saying, look, buy SpaceX, right? Everyone wants to say at the cocktail party that they own SpaceX. It's a terrific name to own. Obviously they're doing very, very well. But it shows you that the retail market is focused on several names. And if that name becomes available across one of these bag platforms, they're literally devouring.
David
Interesting. SpaceX used to be strictly a family office trade, almost like a cocktail trade. And then it went to an institutional trade. Maybe again, it'll be so expensive via family office trade.
Andrew
Again, yeah, yeah, look, institutions are looking at it. Obviously SpaceX, the business model is an interesting one. About 65% of the projected revenue is in communications. And the satellite business, which is a $99 a month product, which is focused on the maritime industry, emerging markets, frontier markets, which to be honest, many of them can't afford a $99 subscription. So Elon has really built a great business with the military payload business and obviously Starship, which is the best business of SpaceX because it's really long term government contracts. And that's what everybody wants to see is long term revenue visibility. And so that's what investors are really focused on. But the communications business, although it will grow very fast, things tend to trade in an AT and T Verizon multiple. So it'll be interesting to see when the, when these companies hit or SpaceX hits the public market, what is the public market going to value? The communications business, what it's going to value. The starship and Pay launch business.
David
SpaceX really is, and we're shareholders is many different companies in one. Like you said, high revenue, low multiple, some low revenue, high multiple. Never thought about it that way. Previously you were the president at a $5 billion hedge fund. Tell me about that experience.
Andrew
It was great. I mean we were, you know, this was during a period that the multi manager business was really taking off and this is when really Citadel, Millennium and others were really raising a lot of capital and really starting to take off. And we were trying to do the same. It's a very capital intensive business. It's a very leverage intensive business. And finding the right portfolio managers is a very challenging thing to do. They expect, you know, large upfront payouts before they've even generated $1. And so, you know, for me it was more of a personal decision that I thought the private markets were going to generate a lot more alpha in the future and was a good time for me to segue into private markets.
David
Explain to me as a third grader why it makes sense to have multiple strategies at a single hedge fund. Thank you for listening. To join our community and to make sure you do not miss any future episodes, please click the follow button above to subscribe.
Andrew
It's, it's, you know, these strategies all trade with different risk characteristics, right? And you know what we call in the hedge fund world factors, right? And they're all driven by different factors. Some people factor, some strategies are growth factors, some strategies are em factor, some factors are currency related and some factors are just unmeasurable. And so you always have to have a variety of factors in your portfolio that you can recognize and hedge. And that's why you want a strategy where you have multiple factors going on to deliver a smooth return profile on the strategy. A lot of times portfolio managers get very, very stuck in their own strategy. Managers so focused on generating returns from that one segment of the market, which may be out of favor. And so that's why a lot of money has been raised to these multi manager strategies. It's just been able to smooth out the volatility, smooth out the returns and smooth out the risks. Now that being said, they're telling portfolio managers, please join Citadel or any other multi manager fund, here's $2 billion and make 3% and we're going to lever it, you know, 15 to 1. And that's how these firms generate a lot of returns. So it's not without risk. Everyone looks at the Millennium fact sheet, you know, punching out a nice 12% annual return. But if you look at the overall leverage that Millennium is Managing it's massive. I mean it's billions of dollars when stated AUM is $60 billion. And so it's a very interesting strategy and I think investors have become very enamored with it.
David
Is that leverage somehow isolated or can one strategy blow up the entire fund?
Andrew
Look, it'll go unnamed, but there was one fund that they generated 60% of their return in 2023 from European natural Gas. Had that trade gone wrong, you could have seen a major firm go under. When we look at some of these funds, it taking on a lot of risk to generate small measure of return that then the firm can control at the top level and manage the risk and manage the leverage. And so far they've done a great job. But you know, who knows what's going to happen, you know, if all the factors unwind and everything basically melts down at the same time. It'll be interesting to watch.
David
While you were at the hedge fund, you were recruiting portfolio managers. You were essentially scout for talent. What did you look for in portfolio managers?
Andrew
A lot of it was, you know, a specific skill in a specific market. When you're building a platform like that, you really need to focus on guys that understand a market very very well. And not only is they understand to 20 names extremely well, they understand the industry very very well. It was very hard to find a portfolio manager that was good across all industries geography.
David
You're looking for the best individual player at that position.
Andrew
Really we're looking for that best individual player that necessarily wasn't the best. He had to be a great stock picker, but he had to really understand and be able to do great research. One of the guys that we interviewed, I remember during the the bird flu days, he was literally flying to farms and the egg farms to understand how many queen chickens were being affected by the avian bird flu. You know, it was that type of research just getting such great primary data and investing in things that they had only the most granular data. And that to me is a great portfolio manager. A great portfolio manager these days, you know, cannot sit behind a Bloomberg and understand what his portfolio is doing. You really had to get in there. Had another portfolio manager, he was an expert in the battery space. He would go to China and translating headset while BYD was presenting because his, his company in the US it was a battery company, was literally about to announce earnings the following week. So he wanted to understand in Chinese but literally in person and go meet management and sit there with a headset and understand what the dynamics were in China. So before it hit the US market for earnings, he would know how to hedge it and what to do. And those were the kind of guys you were looking for. This is like above and way and beyond what any other.
David
It's, it's analogous to the high frequency traders that shut up SOPs across from the exchange trying to get that data point one second. But this one was doing it through a translator.
Andrew
And at the end of the day, it all came down to fundamental research. And a lot of these guys were really, you know, some of them were just way above the crowd in terms of understanding their companies.
David
What were some mistakes that you made around portfolio managers that looked like they could be really good and ended up being poor choices?
Andrew
We had one guy that was doing commodities and he was rolling contracts and commodities and it was kind of a based on buying contracts on, on oil. And he ended up just losing so much premium rolling these contracts that his strategy went from being able to deliver, call it 10 to 12% annually pretty consistently to really only delivering 1 to 2% because he was losing so much in the role of the yield in oil contracts. And so his numbers looked great. But when the market changed and volatility got a lot more expensive, the premium he was paying was prohibitive and he was just not able to make money. So when market factors change, a lot of you have to really look, well, how do you actually make money? And what market factor is really driving your returns? Right. And for him, it was a premium of volatility. And when you're selling volatility or buying volatility, the cost of volatility is going to affect your returns significantly. And so that's one thing that he thought he was going to be. He said, look, it's not a problem. I know how to adjust to this. But he was never able to adjust to it. So he didn't lose money, but he didn't make any money either.
David
What do you find in terms of clear thinking and the ability to sell a simple story? Is that positively correlated to returns or does that mean that somebody's on a strategy that that's pretty commoditized?
Andrew
If you look at the top guys, Right. It's very rare that you find one guy that's doing one thing very well without a great team behind them? Right. Most of these guys have also, Ken.
David
Griffin will say, he'll say Citadel, his number one skill is actually recruiting.
Andrew
Absolutely. Because the guy that's really good at industrials, Right. Or really good at, you know, some subset of industrials has really generally Two to three great analysts with him. He's got two research guys, he's got a data scientist. It's very difficult to be good without a team around you. And that's why it's become so hard to launch these individual hedge funds, right? Because they require so much data, so much risk, so much technology, so much talent to really do it properly that you as one person, it's impossible. Right. And so these guys really have to develop a real infrastructure around them to deliver market beating returns. And it really comes down to that, and that's why a lot of these guys end up at major pods, is because they'd rather have the capital, the infrastructure and the team at these pods rather than go out and try to build it on their own and have to raise the money and deal with LPs and, and all the rest of the headache.
David
Given the current regulatory climate and hedge funds getting more and more complicated from a compliance standpoint, what is the true minimum viable size for a hedge fund today?
Andrew
I mean I've seen hedge funds launch it, you know, 100, 200, then it was 500, I really think it's a billion now. Problem is, is that you're trying to attract people from other funds and generally when you're attracting people from other funds and you're trying to attract senior investors, the issue is, is there's got to be enough carry to go around. So if the main PM is getting call it 40% right, of $300 million and the fund is flattish and there's only management fees to feed the team, you really don't have a lot to work with. Yes, because they know they're not going to make any money. Right. So they basically aren't leaving anything on the table. Right. I saw a really surprising move the other day where I saw a pretty senior hedge fund PM go to a large secondaries fund right in the private markets. He was a technology investor at a multibillion dollar fund. And I think these guys are realizing, look, it's difficult right now when, when indexes are ripping, when technology in the Nasdaq is up 25, 30% and you're going to your investors and saying hey guys, we have this short book, we're 25% hedged and a lot of it's index hedges and a lot of it's just not attributable to real shorts because there just isn't a lot of good shorts out there. Investors start questioning what am I paying you for? I'm paying you 2 and 20, plus expenses, plus pass through plus all this and you're, you know, giving me returns that are 60 below the NASDAQ. What is this all about? So that's why a lot of investors have gone passive into ETFs and are just saying look, hedge funds just aren't worth it. The alpha is just not there like it used to be. There used to be a lot of seams and there was a lot more accounting fraud. There was these big WorldCom, there was Tyco, there was, you know, every year there was like these big blow ups, right? And hedge funds would just clean up on these things. Regular regulation has gotten more stricter and obviously and much more. And compliance has been so much more of an issue in terms of audits and all of this. You're just seeing less of that, right? And you're just seeing that shorts are just much harder to find on an individual basis. And so for a regular true hedge fund, where's the short alpha? It's hard for them to prove where it is because it's just non existent.
David
When you're pulling these, you know, genius level quants. And portfolio managers, how much of the time are they leaving for primarily economic reasons versus cultural reasons, they hate their boss or other less rational reasons?
Andrew
You know what, we see a lot of different things. I would say one of them is at some of these firms it's very, very difficult to work there, right? Because single move you make, is that a feature or a. I think it's a feature. And I think, you know, it's funny because I talk to a lot of LPs as well and they're like that's great. I love that they get rid of guys really quickly. You know, this guy, you know, he's, he's not performing so he's out.
David
I think turnover rate across the board is the most silly metric for successful startup. I think a successful startup should have somewhere should not have, you know, 100% retention rate. I think that's a, that, that's a sign that it's too there.
Andrew
Yeah, that's right, that's right. And I think a lot, you know, investors are saying be strict, you know, pull the trigger when you see that something's not working now, you know, but when you're the portfolio manager, right, And I know an example, a friend of mine was at one of the multi manager firms and he says if I, and he was billion dollar industrials portfolio says if I went to the bathroom and they saw one thing in my portfolio, it was already hedged and they would close me out. Of, you know, 60, 70% of my positions. Right. So that's how tightly this is being controlled. Right. And if you got one thing wrong, you know, that developed your returns from being 3% down to, you know, 2.7, you know, that's, that's a factor to get fired. And so it's a, it's a really cutthroat world. So a lot of guys are saying, look, from a lifestyle perspective, this is a lot of pressure, this is a tough way to live. And so they, they decide to want to go out.
David
And I think people will, will live in that tough way while they're near there. And the moment the money goes away, they're like, why am I doing?
Andrew
But you are seeing a lot of spin outs now, you know, because once they build that reputation, the track record and the, you know, the, the celebrity around what, there's a lot easier to go out and raise. Not 1 billion, but, you know, 5 billion.
David
I have a big thesis on spin outs and I think spin outs will continuously produce a lot of really interesting opportunities. And a lot of people say, well, what about consolidation and when will spin out stop, stop being a thing? And most people don't realize spin outs are an arbitrage between talent and economics. So you might be at firm, the top talent, the top two PMs might have 90%. Maybe they founded the firm. In some cases they're providing 90% of the value or 90% of the alpha. In most cases they are not. So the question is how uneconomic could it be before the top talent decides to move out? Or how much money do they need for cushion in order to, to have the comfort to spin out?
Andrew
It is the age old question. And I think, you know, you're dealing with some massive egos. I just had a firm the other day. It's a $3 billion technology hedge fund on the West Coast. And one of their main producers, since they launched in 2018, was let go. He was a significant partner in the firm. The main partner let him go. He had, you know, gotten a couple of ideas wrong. He always wanted to get paid pretty much the same as the founder, and they pushed him out, kind of that cutthroat. Now he obviously made a lot of money during the last five years, but, you know, this was an example where, you know, they were up 50% in 2020. The Nasdaq was up 50%. They all took home several hundred million dollars and investors were like, well, gee, that's great, but I didn't even beat the nasdaq. Yeah, that's what investors are, you know, kind of pushing.
David
Hey, look, you had to diligence. A lot of portfolio managers that may have had egomaniacs at the firm. How did, how did you go about referencing? Do you all, did you ever give them both benefit of the doubt or did we say, you know, if the previous firm didn't like the manager, there's probably something wrong with them?
Andrew
You know, it's pretty interesting. We would back channel a lot and I think back channel is always the best. The references they give are not the ones that you want to speak. Yeah, it's the off list, right? It's LinkedIn. It's asking people at the firm. One guy, he was ultra successful, was running $3 billion at one of the big multi manager firms. I mean, the guy was a rock star. And he just said, every single person we spoke to, he is the biggest jerk in the world to work for. And if he comes to your firm, he's going to ruin your culture and you know, so you can have everything look perfect on paper. He even interviewed well and he was very charming in the interview. But then when people are like, literally there was a rumor that he like tried to stick a pencil through one guy's hand because he was so upset that he got wrong. And so, you know, you have these stories and you're like, oh my God, you never know that if you just called standard references.
David
Thank God for references. So tell me about Next Round Capital. What do you guys currently do and what's the future for Next round?
Andrew
Yeah, so we're really, you know, we're very, very busy right now. I would say 50% of what we do is on the secondary side. The other, you know, call it 40% is on CO investments and then 10% is, is really kind of very niche, sometimes even credit oriented or ideas that we get that we work on and that we'll invest in ourselves. So, you know, on the co invest side, a lot of it's technology, a lot of it's AI. We're working on a data center deal that we're launching in a few weeks.
David
And here you're like following Andreessen's doing the round, you're co investing alongside.
Andrew
Yeah, I mean, either, you know, Andreessen's doing the round or somebody that we've been been introduced to. Again, there's a lot of connectivity between, you know, you know, the, the network that we built in Silicon Valley and some of the rounds that we, that we participated in. One example is Grizzly, which got, they had you know, a group of executives just. And you know, the guys that built the whole logistics network around that just left and started a new startup. And I was extremely interested in what they're doing. And so we're going to invest in that. And so, you know, we get these ideas and some of them are great. Some of them are, hey, this guy's got this great new AI idea and he's using very differentiated sources. And ask him, well, what's that source? He says, well, Wikipedia. And I said, well, Wikipedia is really a source for XAI and OpenAI and Anthropic. So why is it unique? Well, we can scrape it a lot more efficiently than they do. And so you have to start to wonder what's really the edge here, right? Because everybody right now is really. We're in the days right now of the Netscape browser, the AOL Lycos, when everybody sort of was trying to build the technology and these companies and everyone was just pouring money into each technology. If you think about it, that's where AI is right now. It's really a money loser. And the technology is just being built to make it the most efficient. The next wave of this is going to be the monetization. How do you make money from it? Right? And it really wasn't until Google figured out how to make money from search, the search really took off. And that's really when the Internet and E commerce took off is really. Because you were able to search and you would see ads and they were able to make money from search. And so that's where we are today. Because the only way you make money right now is OpenAI is saying, hey, pay 2199 for OpenAI Plus. Great. That's not going to create a massive business, right, While you're still losing $8 billion. So until the enterprise side is figured out, how you can charge companies a lot of money to, to use your service, that's when AI will become really, really valuable. Today it's valuable because we've discovered the technology, but there's going to be so much more money lost and VC money burned during this period while everybody figures out, okay, so what's the business model? Right? How does this actually generate a lot of revenue and how do you actually get profit margins out of it? Right? I made a comparison yesterday. Tesla versus Ford. You know, Tesla in 2010 was worth, you know, $1 billion. Ford was worth $44 billion. Today, Tesla is worth a trillion. Ford is worth 56 billion. Right? Why? But Tesla's not the only one. E.V. e.V. Maker out there. There's Lucid, there's Rivian. Well, Tesla figured out a way to make each car profitable. So Tesla makes $9,000 per vehicle. 9,200. So it's profitable unit economics. Rivian loses $37 per vehicle, and Lucid loses $137,000 per vehicle. So it can be a great idea, but it's the business model because Elon integrated production. He integrated acquisition and streamlined the manufacturing process. He created gigafactories. He did things that he knew would. Would create a business and that he could make money from it. Right? So futures just went bankrupt because it's all a great idea. And that's where we are today in AI. It's a great idea. It's going to revolutionize everything. But the problem is, is people have to figure out the business model first so it survives. At the end of the day, investors are one day wake up and say, I'm no longer going to fund these losses. And that's where the rubber is going to meet the road.
David
What would you like our listeners to know about you, about Next Round capital or anything else you'd like to shine a light on?
Andrew
You know, just have a lot of fun, what we're doing. We're always, you know, looking to see what's next, obviously, in the name, and we're really excited about what's coming in the future. I got to tell you, when I started the business in 2020, just a few months before I launched, my brother had been diagnosed with pancreatic cancer. And so for me, it was always a goal to have my own firm nameplate on the door. We brought him to treatments around the world, trying to really see what we could do for him. And unfortunately, he passed away in 2020. And that's where I really felt like life is. You know, you got to take the opportunities that you see now because it can all end in a flash. And that really taught me that life is very fragile. And, you know, thank every day that we're here and, you know, enjoying what we do.
David
Absolutely. Well, we've known each other since 2016. We partnered together on DraftKings, and it's been great to partner together and look forward to continuing a conversation.
Andrew
Great. Thanks for having me, David.
David
Thanks, Ken.
Andrew
Take care.
Podcast Summary: How I Invest with David Weisburd
Episode E129: The Number #1 Predictor of Startup Success w/Ken Smythe
Release Date: January 14, 2025
In Episode E129 of "How I Invest with David Weisburd," host David Weisburd engages in a comprehensive discussion with Ken Smythe, alongside Andrew, delving into the critical predictors of startup success, investment strategies, and the evolving landscape of venture capital. This detailed summary captures the essence of their conversation, highlighting key insights, notable quotes, and the nuanced perspectives shared throughout the episode.
Ken Smythe opens the conversation by identifying the most potent predictor for new company success. He emphasizes the significance of key executives transitioning from large, established private companies to early-stage startups.
Ken (00:07): "The signal for us has especially in recent times, been key executives that leave large private companies to join early stage startups."
He illustrates this with the example of an executive moving from Apple to a startup, highlighting how such moves often precede substantial growth, as these executives bring invaluable experience and relationships.
Ken contrasts the impact of executive movements with traditional venture capital (VC) signals. He argues that large VC firms managing billions may not provide as strong a signal compared to the significant career risks undertaken by key executives leaving established firms.
Ken (01:45): "The large VC funds are managing 10, 20, $30 billion. So to say that you're leading around with say a $5 million check... isn't a strong signal because the VC firms themselves are so over capitalized."
This viewpoint underscores the importance of individual leadership and the depth of commitment required when a top executive chooses to join a startup.
Further exploring the theme of risk, Ken explains how executives leaving stable positions to join Series A startups represent genuine calculated risks, potentially indicating that these startups have a higher upside than their established counterparts.
Ken (02:20): "The risk that a VC is taking by leading a $5 million Series A is much, much less than a key executive who owns 100 million of equity in a very established firm to go to a Series A."
This perspective highlights the deeper level of confidence and potential foresight executives possess when making such transitions.
When discussing investment themes for the year, Ken expresses enthusiasm for advancements in AI chatbot agents and defense technology. He anticipates significant growth in these areas, driven by innovations and strategic executive movements.
Ken (04:41): "We think AI chatbot agents are going to be a huge business... defense tech... is just going from a true transformation."
He draws parallels to the early days of AI, emphasizing the importance of foundational technology development and the subsequent monetization strategies that will drive future profitability.
The conversation shifts to the current state of venture capital, where Ken notes an abundance of capital chasing a limited number of high-quality deals. This scarcity breeds a competitive secondary market, with various institutional investors seeking liquidity and opportunities to expand their positions in promising startups.
Ken (06:50): "It's a wide mix, but I would say it's obviously the large institutional investors... are getting."
Ken elaborates on how secondary transactions are influenced by the need for DPI (Distributions to Paid-In capital), with VCs seeking to free up capital from legacy investments to reinvest in new, high-potential ventures.
Andrew adds to the discussion by highlighting the growing involvement of family offices and retail investors in the secondary market. He explains how family offices often follow the leads of VCs, investing in companies they are bullish about, while retail investors are increasingly attracted to high-profile names like SpaceX.
Andrew (09:20): "Family offices have been an interesting one... the retail market is focused on several names."
This diversification signifies a broader acceptance and interest in venture investments beyond traditional institutional players.
The dialogue delves into SpaceX's multifaceted business model, which combines high-revenue, low-multiple segments like communications with high-potential, high-multiple ventures such as Starship and government contracts.
Andrew (10:36): "SpaceX really is, and we're shareholders is many different companies in one... high revenue, low multiple, some low revenue, high multiple."
This analysis underscores the complexity and strategic diversification that make SpaceX a compelling investment, balancing stable income streams with innovative projects poised for exponential growth.
Transitioning to Andrew's experience as a former hedge fund president, the conversation explores the intricacies of managing multi-strategy hedge funds. He discusses the challenges of portfolio diversification, the necessity of leveraging different market factors, and the high-stakes nature of risk management within large hedge funds.
Andrew (11:45): "It's a very capital intensive business... finding the right portfolio managers is a very challenging thing to do."
Andrew shares valuable lessons on recruiting portfolio managers, emphasizing the need for specialized market knowledge and relentless fundamental research. He recounts instances where seemingly promising managers failed due to an inability to adapt to changing market conditions or maintain disciplined risk management.
Andrew (16:40): "It all came down to fundamental research... understanding their companies better than any other."
These anecdotes highlight the critical importance of due diligence and adaptability in portfolio management.
Addressing the trend of spin-outs in the hedge fund industry, Andrew explains that spin-outs are driven by the interplay between top talent seeking autonomy and the economic incentives necessary to support independent operations. He notes that as long as top-performing managers can secure sufficient capital, spin-outs will remain a vibrant aspect of the investment landscape.
Andrew (23:22): "Spin outs are an arbitrage between talent and economics... how much money do they need for cushion in order to have the comfort to spin out?"
Discussing Next Round Capital, Andrew outlines the firm's current focus areas, which include secondary investments, co-investments, and niche opportunities. He emphasizes the firm's connectivity within Silicon Valley and its proactive approach to identifying and investing in promising startups led by experienced executives.
Andrew (26:01): "We're really very busy right now... a lot of it is technology, a lot of it's AI."
He underscores the importance of distinguishing competitive edges in emerging technologies, drawing parallels to the early internet era where business models evolved alongside technological advancements.
Concluding the episode, Andrew shares a personal story about founding Next Round Capital amidst personal tragedy, highlighting his commitment to seizing opportunities and valuing life's fragility.
Andrew (29:56): "I got to tell you, when I started the business in 2020... that life is very fragile."
This heartfelt reflection adds a personal dimension to the discussion, emphasizing resilience and purpose in the investment journey.
Key Takeaways:
Executive Movements as Investment Signals: The transition of key executives from established firms to startups serves as a strong indicator of a startup's potential success.
Risk Profiles Differ between VCs and Executives: Executives taking significant career risks by joining startups provide deeper confidence signals compared to large VCs making relatively smaller investments.
Thematic Investment Focus: AI chatbot agents and defense technology are poised for substantial growth, driven by technological advancements and strategic executive leadership.
Venture Capital Landscape: An abundance of capital with limited high-quality deals has intensified competition in the secondary market, involving a diverse range of institutional and retail investors.
Diversified Business Models: Companies like SpaceX exemplify the benefits of diversified revenue streams, balancing stable segments with high-growth initiatives.
Hedge Fund Insights: Effective portfolio management requires specialized knowledge, fundamental research, and adaptability to maintain performance amidst changing market conditions.
Spin-Outs and Talent Dynamics: Spin-outs remain a dynamic aspect of the investment industry, driven by top talent seeking independence and the necessary economic support to sustain their ventures.
Personal Resilience and Purpose: Personal experiences and motivations play a crucial role in shaping investment strategies and the pursuit of success in the financial sector.
This episode provides a rich exploration of the factors influencing startup success, the strategic decisions within venture capital and hedge funds, and the personal narratives that drive investment professionals. Listeners gain deep insights into the nuanced interplay between leadership, risk, and market dynamics that shape the future of innovation and investment.