E361: Why Venture Capital is Not an Asset Class

What if venture capital isn’t really an asset class—but a game where only a handful of managers actually matter? In this episode, I sit down with Ian Sigalow, Co-Founder and Managing Partner of Greycroft, to discuss why venture returns are driven by a small group of firms with consistent access to the best companies. Ian explains why diversification often hurts venture outcomes, how the industry splits between “access” and “craft” investing, and why conviction, not consensus, drives results. We also explore what defines great founders in the AI era, how venture firms build brand and culture over decades, and why the intersection of multiple skill sets is becoming the foundation for generational companies.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Weisburd?

  Graycroft today is $4.6 billion. You're both managing partner, but you also founded the firm. And last time you told me something interesting. Venture capital is not an asset class.

• 0:09Speaker 01

  That's right.

• 0:10David Weisburd?

  What do you mean by that?

• 0:11Speaker 01

  So I think it's manager selection masquerading as an asset class. So let's say you do what everybody tells you to do. You go out, you're an LP. You go out, you evaluate the universe of managers out there. You say, hey, I've got my emerging managers to my experienced platform managers. I've got my specialists to my generalists. I go pick firms across those buckets. You are almost certain to underperform. Because the asset class itself has a mean and median return that not only underperform the NASDAQ, but they're negative in most vintages. So diversification makes your returns worse. And that's just a statistic of the asset class. In general, you have to pick not only top quartile managers,

• 0:52Speaker 01

  but really top decile managers in every vintage in order to outperform.

• 0:57David Weisburd?

  Just to push back on that, the median for venture is horrendous. It's like 6% to 8%. It'd be the worst asset class in the world. So if you picked the average, the median fund. But the mean is actually quite good. It's in the high teens. It's a difficulty because it's so fat-tailed. It is very difficult to get the mean.

• 1:13Speaker 01

  Let's look at statistics for a minute. So we all know that this is a power law industry where there's a few companies that drive the vast majority of the entire industry's returns. I think about that as roughly 20 companies a year that really matter. And there's a few firms that have access to those 20 companies in a meaningful way. So those firms themselves drive the vast majority of the entire industry's returns year after year. There's quite a lot of persistence in that group of firms. So it's a universe of thousands and thousands of managers. But when you distill it down, there's only a couple of people on the margin who are really generating outperformance. And I think about outperformance a little bit differently. Like 5%, 6%, 7%, that's not interesting to me.

• 1:55Speaker 01

  Nor should it be interesting to any LP that's listening to this podcast. They're thinking about, I have to sell the S and P 500 every single time I make a venture investment. Right? The S and P 500 today, like the 500 best companies ever built. These companies have experienced management. They're all audited, they're profitable, they're growing. They have huge moats. I've got to sell that group and invest in a manager that is going to build a portfolio of 10 or 20 startup companies. Like, how hard is that to do? Well, only a few people can do it, every single vintage. And that's why this industry is so skewed.

• 2:29David Weisburd?

  So what does an LP do in that case?

• 2:31Speaker 01

  Well, they have to evaluate managers based upon criteria and they have to bet with conviction. The same thing that venture managers do. You know, I think there are, there are really two businesses inside of, inside of venture today. And, and ventures changed a lot over the past 25 years since I started in the business, but today there's two. I'll call one business, the access business, which is basically taking the Russell 2000 and converting that into the private market. Okay. And these are companies that are 1, 2, 3 billion dollar and up valuation businesses. They're really hard to get access to those companies, particularly the best ones that are growing at 100% a year. Because they're going to end up in the S and P 500 someday. That's one business. It is scalable. It's super interesting. It's relatively new.

• 3:14Speaker 01

  And then there's the craft business of venture, which is the QSBS seed business. It is unsexy. It is very hard. And it's actually what I want to talk to you about today because I think it's the most interesting part of the entire venture business.

• 3:28David Weisburd?

  So let's talk about that. So the seed business, what you call the craft business, although some people now have half a billion, billion dollar seed funds. But regardless, talk to me about the art of seed investing and presumably that's also not an asset class.

• 3:41Speaker 01

  It's not because it's not scalable. Right? So I think to be an asset class, you have to be able to deploy billions of dollars a year against something. And that business is just, I mean, tens of billions a year, hundreds of billions a year. It just doesn't absorb that much capital. What's interesting about the, the seed business, and I'll, I'll think about seed as kind of within the confines of QSBS, which for your audience, you know, companies with $75 million or less of assets post-investment. Right? First off, you've got structural alpha in that business. It's triple tax-free, no state, no Fed, no local, except for California, which has its own special.

• 4:18David Weisburd?

  And New York is trying to.

• 4:20Speaker 01

  Trying, but it got thrown out thankfully. So you already start with this massive tax advantage. Second, if you can pick well and you can provide value to those founders, you can make money on these investments. But it's really hard to do and you gotta, I've been doing it for 25 years. I didn't even know if I was good at it for at least a decade. Because you have to have so many shots on goal. You've got to live with these founders. You've got to go through cycles. You're investing in companies today that you won't exit like until 2036. And how much the world's going to change in the next two years? Think about how much it's going to change in the next 10 years. So when you make these bets, you've got to kind of figure out where the market's going to be, what your freedom to operate is. It's just a very tricky and challenging and I think really interesting place to play.

• 5:00David Weisburd?

  I want to go back to 25 years ago when you first started Greycroft in 2001. First of all, talk about timing. But what was venture like back in the 2000s?

• 5:10Speaker 01

  So I started Greycroft in '06. In '01, I had graduated from MIT and I got my first venture job at a firm called Boston Millenium Partners up in Boston through on-campus recruiting. In 2001, the party was over, but people didn't know it yet. So I recall the winter of '01 up in Boston. We went to this huge holiday party. I'm trying to remember what the venue was, but it reminded me in hindsight of like the scene out of Hogwarts where they all descend upon the Great Hall and have dinner. And there were banners and venture firms were flying their flag and you had all-you-can-eat sushi. And that was like the last of the great holiday parties in Boston because the market, of course, tanked.

• 5:51David Weisburd?

  That was the first thing that went away.

• 5:53Speaker 01

  Yeah, the first thing that goes away is the multimillion-dollar holiday party. So what happened in '01? Couple of things. The venture world thrives on large companies buying software from small companies, right? It's an ecosystem. If you can't get your first 10 customers, you can't get your next 10 customers. And you never get fired for buying IBM, back then at least. And so what happened where the big companies stopped buying from small companies because they were worried that the small companies were going to go out of business. And then that just accelerated the rate at which the small companies went.

• 6:24David Weisburd?

  It became self-fulfilling.

• 6:25Speaker 01

  It did. And two, all of the public companies of that era, they all traded way down. So all of these firms that had unrealized gains and weren't able to sell yet in the public market, their fund performance went way down. Most people allocated way too fast. And as a result, fundraising dried up. Firms persisted on for some time. Most were not able to raise a follow-on fund. I went to business school. That's the short story there. But after 36 months, it was brutal. I mean, we would take all of these meetings with founders and like most of these companies just couldn't raise capital.

• 7:01David Weisburd?

  And you came back from business school and you decided to double down?

• 7:04Speaker 01

  Go back to venture again.

• 7:06David Weisburd?

  Why?

• 7:08Speaker 01

  I went to business school to start a company. And Columbia had this thing called the Lang Fund, which was attached to a greenhouse program. And I started this business, Strong Data, which was an encryption business. And I came out of school fundraising for that business. I said, I'm not going to go work somewhere. I want to be a founder. And when I was out fundraising, I met a venture capitalist named Alan Patricoff. And Alan is unbelievable. He was unbelievable then. He's unbelievable today. But he was, I think, 72 when I met him. He had built a firm called APAX, A-P-A-X, which stands for Alan Patricoff Associates Cross Border. And he retired. And then he decided to get back into venture again.

• 7:53Speaker 01

  And I had an opportunity to learn from Alan. I said, well, this is like a once in a lifetime thing. Alan's contemporaries are the founders of Sequoia, the founders of Greylock, the founders of Kleiner Perkins, the legendary venture firms. And he grew up with these people. He was on the board of Apple. He was on the board of AOL. So on my second day of work, he called Steve Jobs because his iPod wasn't working. He was like an unbelievable person to learn from.

• 8:28David Weisburd?

  Do you think the skill set of venture capital, is it a skill set? Or is it something like a founder that gets reinvented every five to 10 years?

• 8:38Speaker 01

  So I think all VCs live in a paradigm where there's a builder persona and an investor persona. And if we were more builder, we would be running a startup company. And if we were more investor, we would be running a hedge fund. But we're all somewhere in between. And where you sit in that paradigm ultimately determines what stage of investing you will gravitate towards. So if you want to do late-stage, pre-IPO investing, you are far more of an investor persona. If you want to do pre-seed and seed, you're far more of a builder persona. And I think if you're in that builder Persona, you do have to reinvent yourself every three to five years.

• 9:21Speaker 01

  Because the stuff that you're interested in and focused on today is not going to be investable 36 months from now. It's going to be too old. The qualities that make somebody a good, let's say you're 80% builder, 20% investor, for the sake of argument, to be in that kind of, you know, very early-stage bucket. I think you just have to be motivated because you're naturally curious about the way the world works. And I think that characteristic shines in the best people who are very early-stage investors.

• 9:48David Weisburd?

  And today you have AI-native founders. Everybody's waiting for this one-person unicorn. There's been reportedly several companies that accomplish that. Are founders looking for something fundamentally different today than they were even two years ago? Or is it still the same mentor and partner that has capital?

• 10:06Speaker 01

  Founders are becoming far more educated about what they get. And I think that's a good thing. One of my friends runs a big brand consultancy and she said to me, "Look, Ian, if you think of the world as a two-by-two matrix, everything that's known and unknown, good and bad. The internet's so good at picking the bad, unknown, and making it known. And so if you're a founder today and you want to learn a lot about Ian Siglo, you can go learn a lot about Ian Siglo. Like, you can listen to this podcast, but you can go out and research me." That was not available to people 10 years ago.

• 10:41David Weisburd?

  It was information asymmetry.

• 10:42Speaker 01

  Yeah. And I actually encourage everybody I work with, that you should reference me. Because this is a harder relationship to get out of than a marriage. Once you pick me and I pick you and we decide to work together. So I think that information asymmetry is significantly narrowing and may even advantage the founders today versus the VCs. And I think that's a good thing. And I think the best founders really do their homework.

• 11:10David Weisburd?

  You operate in a market, you don't operate in a vacuum. You're competing against some of the top firms in the world, the Sequoias, Andreessen's, the benchmarks. How do you compete with them, given that sometimes you're writing $10 million checks?

• 11:21Speaker 01

  At the end of the day, when founders make a decision to work with a firm, they are making a decision to work with first a partner and then a firm. The way we compete is we go head to head with those firms on a partner by partner basis. You want to work with me, you want to work with my partner Dana, you want to work with my partner Marcy, Dylan, Pete, Mark. Sometimes you want to work with a principal because they've figured out a way to create a great bond with that CEO. Then the firm comes behind and you leverage the teamwork and the culture and the resources of the firm, but it is really a personal bond between the lead investor on one side and the founder on the other. We're in a talent business.

• 12:04Speaker 01

  The startups we invest in are in a talent business and those founders have to have that sort of relationship with their lead investor. It is particularly important the earlier you go. So if you start at seed, they really look at you like this person is going to be my partner for the next 10 years, almost like a co-founder. If it's pre-IPO, they're probably thinking more about credentialing, maybe some additional resources you can bring to bear on, helping them draft the S1. But that doesn't get you pricing power at the pre-IPO round. At the seed round, you can get certain pricing power.

• 12:42David Weisburd?

  That may be the case with the founder. They want the best thought partner, but they also have to think about how do you recruit? How do you get the early customers? We talked about the first 10 customers.

• 12:51David Weisburd?

  And how do you compete against a Sequoia where every engineer in the world wants to work for a Sequoia-backed company?

• 12:58Speaker 01

  Our approach to this is highly customized for every company. There are three things that all companies need help with. One is recruiting. I generally don't recruit rank and file staff engineers. That's not where I spend my time. But if you're building kind of your first 10-person team or 20-person team, You should be able to count on your venture partner to help you recruit the VP and C-level executives that are going to help you build that business. And the best VCs are expert at this.

• 13:27David Weisburd?

  That's the highest leverage.

• 13:29Speaker 01

  Very high leverage, because those people recruit your staff engineers, to the extent you even need them in the age of AI anyway, which is a second question. The second is you need design partners, proof of concept partners. We help you do that. So we will walk you into the C-suite at Fortune 500 companies all the time. And that enables you to close those pilot deals and it gets you your first customers, which of course gets you your first couple of million of revenue, which gets you your next financing. And then the third thing, and the third thing is a little bit flexible, but we help you think about strategy. Like, how do you position the company? What's coming around the corner? How do you price this?

• 14:08Speaker 01

  What should be in the product? And that is the creative part. And I think the best early-stage investors are expert at that.

• 14:16David Weisburd?

  And tell me about your latest fund and what is your strategy?

• 14:20Speaker 01

  So the last funds we closed were Partners 4 and Greycroft 7, an early-stage fund and a growth fund. We raised $1 billion, final close in 2023.

• 14:32Speaker 01

  That strategy spans the very first check, the couple-million-dollar pre-seed, all the way up to the pre-IPO strategy.

• 14:41Speaker 01

  As I mentioned in the beginning, I think venture is this craft business and this access business. And I think that in order to compete in 2026 as well as 2023, you need to do both of those things really well. Because the access business credentials the firm, and the craft business, we credential the startup. And there's a flywheel that exists around those two things.

• 15:04David Weisburd?

  It's kind of like an arbitrage.

• 15:06Speaker 01

  Kind of like an arbitrage, but you want to have a well-branded firm. And a well-branded firm helps you get access to great companies. And it helps great companies, I guess it makes it such that great companies want to approach you for their funding. To your point, you mentioned Sequoia unprompted. They're a well-branded firm. They've been around for decades. We started the firm 20 years ago. And to get from far-left field into the infield was a real exercise in how to build a great venture brand. And venture brands, no matter what I say, a venture brand is created by what other people say about you. So you've got to go out.

• 15:40David Weisburd?

  That's what people say behind your back.

• 15:41Speaker 01

  Exactly, when you're not in the room. So that you only get through repetition and through a lot of, a lot of cultural work.

• 15:48David Weisburd?

  Expert calls have always been one of the most powerful ways to build conviction. But today, investors are asked to cover more companies, move faster, and do it with leaner teams. With AlphaSense AI-led expert calls, their TGS call service team sources experts based on your research criteria and lets the AI interviewer get to work. The magic is in the AI interviewer, purpose-built and knowledgeable-based information to conduct high-quality, context-rich conversations on your behalf, acting as a trusted extension of your team. Then they take it one step further. Your call transcripts flow natively into your AlphaSense experience and become queryable, searchable, and comparable, so your primary insights plug directly into earnings prep, digital work streams, and pitch books with zero tool switching.

• 16:32David Weisburd?

  And with AlphaSense expert call services, the AI-led expert calls are just one option because we know the importance of a hybrid expert research approach. AI for coverage and efficiency, humans for complexity and conviction. It's the institutional edge that scales research without scaling headcount. For hedge funds, that means validating thesis assumptions across dozens of experts before earnings instead of a handful. For private equity, it means faster pre-IOI scans and deeper commercial diligence. For investment banks and asset managers, it means pulling real operator perspectives straight into models and sector positioning without disconnected tools or manual handoffs. All of it lives inside the AlphaSense platform, trusted by 75% of the world's top hedge funds

• 17:15David Weisburd?

  alongside filings, broker research, news, and more than 240,000 expert call transcripts, turning raw conversations into comparable, auditable insight. Take advantage of AlphaSense AI-led expert calls now. The first to see wins, the rest follow. Learn more at alpha-sense.com/howainvest.

• 17:36David Weisburd?

  You've obviously evolved over 20 years. What's the process for evolving your firm, evolving your brand? And how do you make sure that you know exactly what people are saying behind your back?

• 17:45Speaker 01

  I don't think anybody knows exactly what people are saying behind their back.

• 17:50Speaker 01

  We go out every day and we do our very best and we hire people with a specific ethos. And that's where you start when you build a company. Because you think about every employee as doing their day job, but also being a brand manager for the firm. This is something I learned over decades, but you have to be actively building the culture of your company. It's not something that just happens in a vacuum, right? So if people aren't a good cultural fit, we have to fire those people. We have to find new people and you have to move quickly on those things.

• 18:21David Weisburd?

  Perhaps a dumb question, but how do you build your culture?

• 18:24Speaker 01

  First off, every company should have a set of values and-

• 18:28David Weisburd?

  And these have to have inherent trade-offs.

• 18:30Speaker 01

  Of course.

• 18:32Speaker 01

  I'll give you one example-

• 18:33David Weisburd?

  One of those values isn't make the best investments. That sounds good, but it's not the act-

• 18:37Speaker 01

  That's an outcome.

• 18:39David Weisburd?

  Yeah.

• 18:40Speaker 01

  That's an outcome. Raise the most money, make the best investment. Like, these are outcomes.

• 18:44David Weisburd?

  Find power loss.

• 18:44Speaker 01

  Exactly. Compound a little every single day and get incrementally better times a thousand, you know, like that sort of thing. But I'll give you an example. One of our values is teamwork, okay? And you can go very fast alone, but you can go very far together. And they say also if you have children, you go neither fast nor far, but that's a side note. But, you know, as you think about going far together, there are definite trade-offs. Because some people want to operate as like a solo GP, right? So they wouldn't be a good fit for our culture. Because our culture, we have to share, you know, everything you're working on, what you're thinking about. Because we believe that the collective kind of hive mind of Greycroft leads to better decision-making

• 19:29Speaker 01

  and a whole bunch of other good things.

• 19:30David Weisburd?

  What's your philosophy around making decisions by consensus versus individual?

• 19:37Speaker 01

  I think conviction trumps consensus.

• 19:40David Weisburd?

  So if one person is really keen on making investment, the governance allows for that?

• 19:46Speaker 01

  Absolutely. If that person is a partner.

• 19:49David Weisburd?

  You're known for incubating companies. How does that work within the structure of a large fund? And what have you learned from this process?

• 19:58Speaker 01

  We really started this activity maybe 15 years ago. And incubated is a strong word. They didn't work in my office. So it was like, we were the first capital. Sometimes we brought the team together. Sometimes it's our idea, sometimes it's somebody else's idea. Often, we are the only money.

• 20:15Speaker 01

  And that was the case for a company like Hidden Road, also the case for public.com. It was the case for branch insurance, handful of other businesses. Some worked, some didn't work. The way we approach this, first off, is you have to structure these like a normal seed round. So we don't look to get super economics. I want the things that were germinating at Greycroft to be and look like independent startup companies in the future. Other people have to come into those companies later and provide follow on capital. Second is you need real founder CEOs. So not people that we go hire to do that job. These are people who you would feel fortunate to work for.

• 21:00Speaker 01

  And when you find those people, you're really betting on them to breathe life into this idea. So, because ideas at the end of the day are free and cheap. It's the execution of that idea that really creates the value.

• 21:13David Weisburd?

  When does it go from just a good idea to something that has tangible value?

• 21:17Speaker 01

  There's a moment where things start working in a company. And it's kind of like a magical moment. It can take a long time, it can take a short time. But we'll have a really good board meeting. And the CEO will be bouncing. One of my CEOs called me. She was like over the moon excited about three things that happened in short succession. And you get this feeling like this is now an independent business. They don't need my help anymore. They'll get it, but they don't need my help because the flywheel is turning. Like they figured out how to package and sell a product to a company that's going to pay them a whole lot of money. And if they continue to execute, they will build a winner take all business in a category.

• 22:03Speaker 01

  And you can see kind of like the dominoes start moving. And it's fun to watch because there's like a point where you know a secret that no one else in the whole world knows except for the CEO of this company. Because we figured something out.

• 22:16David Weisburd?

  And how long does it take before the market realizes that's good? What's that gap?

• 22:24Speaker 01

  It can be as short as a couple of weeks. And it can be as long as like six to 12 months.

• 22:31Speaker 01

  My very favorite, so Mike Lazaro, CEO of Buddy Media, his business started working in 09. And he canceled, I think he canceled two consecutive board meetings. He just said, guys, I'm sorry, but I need to be selling.

• 22:51Speaker 01

  And the numbers were stacking up. And like, he was closing a million a month and two million a month and three million. Like, these are like ACVs booked per month. And, you know, when the market-

• 23:01David Weisburd?

  AI numbers, pre-AI?

• 23:03Speaker 01

  It was, yes, yes. And, you know, when the fish are jumping in the boat, you know, you've got something.

• 23:08David Weisburd?

  What changes in the AI era in terms of founders? What exactly are you looking for?

• 23:14Speaker 01

  At the seed stage, three things. First, I call it the master of two domains. This is my new thesis, by the way, for seed investing. Master of two domains for me is product slash engineering excellence. You know how to build software at the frontier.

• 23:33Speaker 01

  Combined with the second domain, which is you can sell me stuff.

• 23:37David Weisburd?

  Same person.

• 23:37Speaker 01

  Same person. That's a really, really rare profile. I find a lot of people who can sell me stuff and I find a lot of people who can build software, but I don't find a ton of people who can do both.

• 23:48David Weisburd?

  Why do you need it to be one person?

• 23:50Speaker 01

  Because the biggest companies are built by one person that can do both. Mark Zuckerberg, Elon Musk, Larry and Sergey both, Jeff Bezos, like really big generational founders, Steve Jobs. They could do both.

• 24:04David Weisburd?

  It kind of wraps up to what we were talking before. It may not be the median company, but when you're looking for that power law, that exceptional company that is one person.

• 24:11Speaker 01

  Yeah, one person. So that's number one. And I work with a lot of first time founders. So I will take some risk on those two things. I generally don't take a lot of risk today on the technical slash product expertise. I will take some risk on the sales expertise because I feel like I can teach people that. So anyway, that's one of the three things. The second thing I look for, something I call an earned secret. And an earned secret means that if you figure something out about a market or a product, that if you execute really well, it's going to turn into a winner take all business. Okay. And these are really scarce, too. And when you hear them and when a founder articulates their earned secret, for me at least, it's like, oh, my God, that's an unbelievable

• 24:56Speaker 01

  observation about the way the world works. The third thing I look for is if you're successful, you can get this thing to a billion in revenue within 10 years. It's also really hard to do, but I think like a billion in 10 years, I raise a 10 year fund, it's got a couple one year extensions attached to it. That gives you a shot at being a public company. Those are the three things I look for.

• 25:18David Weisburd?

  So you have this focus on the solo founder. Is this just a founder that has both attributes? Or are you really focused on solo entrepreneurs?

• 25:27Speaker 01

  I almost never fund one person companies. I need to, part of being this master of two domains person is that you are already recruiting people because they want to follow you wherever you go, right? So I will go and meet with the small number of people that constitute that early stage team.

• 25:48Speaker 01

  And eight people generally recruit other eight people. When I find those people, I'm always impressed at the quality of the people they're able to get to come work for them, usually for free.

• 25:57David Weisburd?

  Is the recruiting game fundamentally different now? Post AI and post these kind of crazy evaluations?

• 26:03Speaker 01

  The executives who are in really high demand. So the N of one engineer, product person, they are getting professional athlete compensation.

• 26:14David Weisburd?

  Even in startups?

• 26:15Speaker 01

  No, they are getting professional athlete compensation at OpenAI, at Microsoft and Amazon and wherever else. And they are making a determination of leaving that job to go work at a startup.

• 26:28David Weisburd?

  And what's the most compelling pitch to get somebody earning tens of millions of dollars to leave their position?

• 26:36Speaker 01

  Everybody is motivated by different things. So let's take somebody who's made 50 million bucks at Microsoft or Google, wherever, over the course of the last 10 to 20 years. They are already really post-economic. Like, they never really have to work again. They probably have anxiety about that, but they never really have to work again. The right profile of person who wants to leave that job at Google and take that startup job, they're very interested in learning at the frontier. They're very interested about the quality of the people they'll get to work with. They're very interested in moonshots, right? Like, if this works, what can it become? Can I be employee 10 at the next Google? They start to think about their legacy at some point.

• 27:21Speaker 01

  Like, what have I built? What's my name on? When I'm having those conversations with people, that's how I know that we've got them at least interested. And then they have to pick that company to work with. You know, and the founder, this is why having a founder who can sell is so important. Because the founder is the person that ultimately convinces that person to leave and take a very large cash pay cut in exchange for what could be life-changing amount of equity, but you have to really build a big company for that math to pay out.

• 27:48David Weisburd?

  The founder's sales skill. Is it about truly believing in your product? Or is it about almost this pathological ability to sell?

• 27:57Speaker 01

  I think authenticity is really required to be a good salesperson. So if you don't believe in what you're selling, you're not going to fool people.

• 28:09David Weisburd?

  Do you find that the ability to sell is really, is it just a confidence thing? In that if you can get somebody to really believe they're going to be a good salesperson? Or is there's actually a skill there that goes beyond just having a lot of confidence?

• 28:26Speaker 01

  I think part of this is learning how to listen. The best sellers I know ask a lot of questions. Like, because-

• 28:33David Weisburd?

  Paradoxically.

• 28:34Speaker 01

  Paradoxically, yeah. It's like, well-

• 28:38Speaker 01

  Before I tell you anything about what I'm doing, I want to know everything about you. Everything that I can't figure out in advance of that call. I want to know what you're looking for. I want to know how decisions are made. I want to know what your biggest pain points are. I want to know everything you will tell me. And then when it comes time for me to sell, I'm just connecting dots. And teaching people how to do that, if you're really smart, I'm pretty sure I can teach anybody who's really smart how to do that. It doesn't come naturally to people. Like, I grew up in a house. My dad was a trial lawyer. My mom was a child psychologist. I feel like I got it from both sides, you know, at the kitchen, dining room table. But, you know, you do learn how to listen. Different forms of listening,

• 29:23Speaker 01

  if you're a trial lawyer versus you're a psychologist, but you learn how to listen. And I think that's just such an important skill set, both for founders and for investors.

• 29:32David Weisburd?

  What's something that you've changed your mind on the last 12 to 24 months that dramatically changes how you go about being a VC?

• 29:40Speaker 01

  A founder said to me about, this was four weeks ago, at a dinner. He said, Ian, and this was a totally new way of thinking about AI. Everybody says that if my engineers become 5X or 10X more productive, I'll need fewer. He's like, I want to hire a lot more. And I said, oh, tell me more. And he said, look, the thing that keeps my business from growing, if you think about my ideas as an iceberg, I have all of these underwater ideas. And I bring them to my team. And I'm always hearing back, we don't have time.

• 30:24Speaker 01

  We don't have capacity. It's too risky. And I think about this from the perspective of my business as a VC. I talk to my partners. We don't have time. It's too risky.

• 30:37David Weisburd?

  All the focus.

• 30:38Speaker 01

  Need to focus. And if we are entering a paradigm where all humans are going to be 10 times more productive.

• 30:50Speaker 01

  I think I may hire more people. Because I think like the number of ideas that I have on a weekly basis, like unlimited. So many cool things we can try to do. And the ROI in hiring those incremental people is going to be so much higher because they can do so much more work.

• 31:09David Weisburd?

  Implicit in this idea of cost cutting and lowering engineer count is that you're maximizing on reducing costs instead of maximizing on profit, which is what's in business.

• 31:22Speaker 01

  Growth, right? I think people exist in a mindset that's way too constrained.

• 31:27David Weisburd?

  What do you mean by that?

• 31:30Speaker 01

  I mean that like, I can only grow this fast. I have to deal with... The reality of my situation is whatever I make the reality of my situation to be.

• 31:38David Weisburd?

  Is arbitrary speed bumps.

• 31:40Speaker 01

  Yes, arbitrary speed bumps. And I'll give you another example. I am asked all the time. I'm a dad, other dads ask, which I recommend my kids study. Okay? It is the hardest question. It's the hardest question because depending on how old your kid is, their career path may be jobs that just don't exist today. In fact, highly likely to be jobs that don't exist today. And how do you prepare people for an economy of the future that's going to look so different? And, I mean, how long will it be before we have some sort of a space colony or asteroid mining or all of our data centers are in outer space, like whatever it is?

• 32:21Speaker 01

  And you need to understand all sorts of physics and math and biology that we haven't really thought about as a species in our history. I don't know what to tell people to study. You know, like you've got to study something that, for a job that doesn't exist right now, but it will exist 10 years from now or 20 years from now. And the rate of change is increasing so fast on a day-to-day basis, it's just very hard to grapple with this.

• 32:45David Weisburd?

  So what's the answer to that question?

• 32:47Speaker 01

  What I always default to is like, what are your kids good at? And what do they really like to do? And push them to do things that they're really good at because mastery of stuff is always valuable.

• 32:59David Weisburd?

  And it goes back to your framework, which is you want to be good at multiple domains.

• 33:03Speaker 01

  That's right.

• 33:03David Weisburd?

  If you could learn two different skills, paradoxically, the more different they are from each other, the more valuable they are.

• 33:08Speaker 01

  That's right. And I think at the intersection of two domains is where all the great idea babies are formed. So the, and the more variant those two things are, oftentimes, the better and bigger the idea is.

• 33:19David Weisburd?

  You need to learn grit, perseverance.

• 33:21Speaker 01

  That, too.

• 33:21David Weisburd?

  How do you learn that as a kid?

• 33:23Speaker 01

  Be born in Ohio. I was born in Akron. You know, the Wright Brothers autobiography starts with some great quote around like, if I had a wish for any young man today, be two loving parents and the great fortune to be born in the state of Ohio. And I was born outside of Akron, raised outside of Akron, went to public school, same kids, K through 12. And it was an unbelievable experience. What you learn growing up in Ohio, one is, Ohio is, it's like a great, you have this great sense of like, what's going to work in America? Because if it works in Ohio, it kind of works everywhere. And it's true

• 34:06Speaker 01

  for commercials. Like my mall, growing up, used to pull us in and pay us 20 bucks, which was a lot of money in the 90s, to go watch commercials and rate them. And they knew if like, if it passed the Ohio test, it would work in America. Also, why politics are kind of important in Ohio, too.

• 34:26David Weisburd?

  Purple state.

• 34:27Speaker 01

  It's a purple state. Depending upon what your ambition is and what you're trying to achieve, coming from an environment where you see kind of America, and you understand where you stand, and you understand what you have to accomplish to get to where you want to go, I found that to be really empowering. Growing up there prepared me so well for what came afterwards. I had, I had the very best chemistry teacher in high school. My public high school chemistry is unbelievable. And he, he wrote me this great letter of recommendation. I ended up getting into MIT in large part because of his recommendation. And, you know, it was a great setup. I think there were like four kids from Ohio who went to MIT that year.

• 35:14David Weisburd?

  You mentioned at Greycroft, you have so many ideas, you're starting to implement them. What are you most excited about as a firm?

• 35:21Speaker 01

  I think venture is both an art and a science. And I like, I like how AI is enabling us to implement the science part at accelerated speed and scale.

• 35:37Speaker 01

  So I'll give you a couple of examples. There is a, there's a website called Archive, A R X I V.

• 35:47Speaker 01

  I'm the first person to talk about Archive on this podcast, but it's owned by Cornell University. It's like the Wikipedia of computer science. And Archive gets, on a weekly basis, thousands of research papers from all over the world. And these are like 50, 100-page academic papers about transformer models and model distillation and the LoRa adapter and all sorts of bits. A human cannot read Archive. Like, you can read pages of it, but you can't read the whole thing. A machine can read the whole thing. So we partnered with Cornell a year and a half ago, and we started machine reading the entire corpus of Archive, including all of the new papers that come out every single week. And we built this research atlas. Today, if we wanted to have, I had to prepare for it.

• 36:32Speaker 01

  I didn't prepare for like an attention mechanism conversation or a harness conversation about what's going to happen with Claude code now that the code base is out. But if I want to be prepared for that, I can literally sit down and in like five hours, I can read virtually everything there is to be known about, you know, all of this, gradient-free recursion, whatever it is. And then I could sit down with the founder and it's like, I've read all of your research.

• 37:00Speaker 01

  And I've got five questions. And like, oh my God, how did you read all of my research? Well, we just did.

• 37:08Speaker 01

  Anyway, I think that's super interesting because as you know, like I'm constantly looking for kind of these frontier ideas. Second is you can start to track people who've been attributed and cited on these various papers. And those people like Noam, who was one of the inventors of the transformer, they end up building really big, important businesses like Character AI. And then Google buys them and then Noam ends up coming back to run the Gemini team. So you can see those people emerge in the academic literature, oftentimes years before they're leaving to start a company. And it's a great basis to start our hunt for kind of the next great founder.

• 37:46David Weisburd?

  Oftentimes, these academics need the most help to

• 37:48Speaker 01

  They do.

• 37:49David Weisburd?

  building a business.

• 37:49Speaker 01

  They do.

• 37:50David Weisburd?

  Learning the sales skills, those things that we discussed.

• 37:52Speaker 01

  Yep.

• 37:54David Weisburd?

  Do you think AI is going to replace VCs?

• 37:58Speaker 01

  Well, if they get to AGI, which I think is a moving target and unlikely in the near term and probably unlikely in my career. If they get to AGI, then yes, because AGI technically should be able to do my job.

• 38:13Speaker 01

  Without AGI, I think there will still be room for specialists like us.

• 38:21David Weisburd?

  I know you've listened to a lot of the podcasts. First of all, thank you. I've only asked this one other guest ever, Alex Hermosy. What questions do you have for me?

• 38:29Speaker 01

  Let's say you put yourself in the seat of a CIO today of a modest sized endowment, you know, 3 billion, 5 billion, whatever. And they said-

• 38:38David Weisburd?

  Perfect size.

• 38:39Speaker 01

  Perfect size. And your board says to you,

• 38:45Speaker 01

  "Look, we have an alt target of 30% and we want it in a third of in venture. So you get to allocate a couple hundred million bucks to venture." What would you do?

• 38:55David Weisburd?

  I think about this a lot, as you can imagine.

• 38:59David Weisburd?

  Venture is difficult and also the CIO's job is difficult. And there's two different difficult areas. One is if you ask 50 top CIOs of endowments, probably 90% of them would want more access to quote unquote, "top quartile venture." Why? You alluded to it earlier. There's persistence. University of Chicago, Professor Steve Kaplan previously discussed- Absolutely, yeah. 52% of top quartile funds stay top quartile. It's more persistent than any other asset class, any other large asset class. So one is you want to access top quartile, but it's difficult, if not impossible, if you're not already in top quartile. So then the intuition for a lot of them is, well, what do I do?

• 39:44David Weisburd?

  Do I do second quartile? Which some of them implicitly or explicitly make a decision to go into second quartile. The problem, I think, with second quartile venture is the returns are very similar to what you would get in lower middle market, but without the volatility. Yeah, it's a bad sharp. It's a bad sharp ratio. And then you could go the emerging manager route, which is the third intuition. And the issue with emerging managers is several fold. One is it's difficult to build a business where investing in emerging managers, there's literally thousands of them. So it takes a large team and every LP that I've ever met. So one consistency is everybody is understaffed.

• 40:25David Weisburd?

  Two is, and perhaps this is one of the dirty secrets in venture capital, there's no data set that I'm aware of that shows that, on average, emerging managers outperform. No, they underperform. They underperform. So then you have this whole issue of, if I don't know who the very top emerging managers are, AKA if I don't build out an entire team to manage them, how do I access them? Of course, you could use a fund of fund, but that comes with its own issues. So more questions than answers. But that's how the CIOs look at it. On top of that, there's principal agent issues, specifically in venture, or more pronounced in venture than any other asset class. Why is that? Because of what we talked about in the beginning. If the VC doesn't know until year 10 whether he or she is good,

• 41:10David Weisburd?

  the LP doesn't know until year 10, probably longer. There's probably some lag between when the VC realizes, "Holy crap, I got into the wrong career." Yeah. So there's this whole issue of by the time that the CIO- Is credited with the decision, he or she is most likely in another seat. The average CIO tenure in pension funds is six years. I think the fool's errand is trying to wait in line to the access constraint managers. I think that's very time consuming and extremely difficult unless you're maybe a Yale or Harvard or that type of elite.

• 41:41Speaker 01

  Aren't you already in those managers if you're a Yale and Harvard anyway?

• 41:45David Weisburd?

  There are some top LPs that for whatever reason have not built out their venture books. There's not that many, but there are. And they're just top, top LPs. But to your point, most of the reasons why they became elites, CIOs and elite LPs is because they were in venture, because they did the Swenson model.

• 42:00Speaker 01

  So what do you do?

• 42:03David Weisburd?

  There's a question of what do you do and what is done?

• 42:05Speaker 01

  I want to know what you would do.

• 42:07David Weisburd?

  What, what I would do is I would try to find alpha in emerging managers, in some emerging managers, and then I would also try to find access to co-invest alongside the top deals as well. Thank you, Ian, for jumping on and, and sharing your wisdom and looking forward to doing this again soon.

• 42:27Speaker 01

  Thank you very much.