Pod Insights How I Invest with David Weisburd E369: Midas List VC: Why Smart VCs Are Buying Secondaries About this episode What if the best opportunities in venture today aren’t in new deals—but in existing companies right before an inflection point?
In this episode, I sit down with Ryan Moore, Founder of Revenant VC and longtime venture investor, to discuss why he made the shift from primary venture investing to secondaries after more than two decades in the industry. Ryan explains how longer liquidity timelines are reshaping venture capital, why secondary investing is less about discounts and more about information asymmetry, and how founder relationships and insider alignment create the best opportunities. We also explore organizational metabolism, LP evolution, and why small, focused funds may outperform in a world dominated by mega-platforms.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 David Weisburd? Brian, you've been a VC for over 25 years. Prolific career, including being on the Midas list, the list of the top 100 VCs. Couple of years ago, you made a structural pivot to go from primary investing to secondary investing. Why did you do that?
0:14 Speaker 01 I mean, as I got older, I started to recognize more and more the time to liquidity for seed investing was just stretched to 15, in some cases even 20 years. And I felt it was a much more interesting place to play and a much more rapid payback. And I was starting to see some of the LPs start to question the asset class in the payback period. And I felt secondary was a more interesting way to tighten that loop.
0:37 David Weisburd? And a secondary asset class, is it a way to access opportunities?
0:41 Speaker 01 I felt the secondary market was ripe, and I felt there was an opportunity to frankly, create a new aspirational brand because there's some good secondary, pure secondary firms out there. But I felt I could bring a venture capital kind of mentality, service level approach to entrepreneurs and cap tables, and access really good assets via the secondary market and to create frankly, a new brand in the asset class.
1:03 David Weisburd? Give me a sense of what stage you're investing in when it comes to secondaries.
1:07 Speaker 01 What I try to do is quote unquote inflection point invest in advance of a P and L inflection point, a value inflection point, where I'm trying to buy shares a couple of months, a couple of quarters before that inflection point. So the key for me is not just access, but real detailed information and frankly, leverage relationships so I can get that access and that information.
1:28 David Weisburd? I've had this thesis, and maybe it's more of a thought experiment, that some of the best opportunities via secondary is not buying some asset for 30, 40%, it's really actually buying quote unquote at par for an asset that's grown two, three times in value since the last round.
1:42 Speaker 01 Hundred percent. Yeah. Why I wanted to get into the secondary market, I thought with the VC, I wasn't super focused on like pencil pushing and FMV and discounts, so to speak. I'm just trying to access some of the best businesses that I know that are maybe misunderstood and frankly, less followed. And that's where you can frankly, find the value, if you will.
1:59 David Weisburd? And it's interesting because you're competing against other secondary investors, not primary investors. So they don't have the same skillset or track record of fundamentally underwriting a business. That's why they have to go for these large discounts.
2:11 Speaker 01 You got it. So. When I think about like my competition, of course I run into secondary, pure secondary buyers. Like that's, that's the business we're both in. But I view the real competitor as the incumbent cap table member. Like I think that's
2:24 David Weisburd? Insiders.
2:24 Speaker 01 Insiders. Insiders is the real competition that, you know, when I talk to my LPs about who do I run into? And who, who do I fear the most? It's the insiders for they've got governance, knowledge, relationship, all of the things that I kind of employed at Accomplice when I was buying secondaries. I'm not saying like the other secondary groups aren't good. It's just I can differentiate from them for given my background, but insiders are a much more a real competitor, if you will.
2:48 David Weisburd? And the flip side of that is insiders are not buying. That's also itself a signal.
2:52 Speaker 01 What I have found is you can play a role and co-invest alongside the insider because hygiene. An insider leading a secondary round on its own deal, it doesn't necessarily pass the mustard. So I've, I've looked at a couple of transactions where I've played the role of pricer. And that just clears hygiene. And to your point, I love to see an insider doubling down. There's no better signal. And, and I've, I've kind of used that signal as actually a filter for diligence.
3:16 David Weisburd? There used to be these firms that would come in and price rounds for the Sequoias, for the Greylocks. And then give most of the round back to those firms, but they needed that, that third party underwriting. This is kind of a secondary version of that.
3:26 Speaker 01 We'll add my fifth deal to coming up here in a couple of weeks here, and it's exactly like that. Introduced by the insider, splitting the insider, cutting the insider in. And then I had to, you know, negotiate for my, my slice. And I paid a service of pricing it and doing all the work and they're coming in and doubling down, actually even in an SPV out of the fund and, and within their LPs. And that's the best signal you can get.
3:46 David Weisburd? In that case, you're solving the problem, not just for the seller, but also for the buyer.
3:49 Speaker 01 And the entrepreneur, continuity of the cap table. Don't underestimate like the continuity of the cap table when you're a founder. You just want to know the people you're dealing with and you want to, you know, you want your, the people who've been with you for the last decade, staying with you and concentrating more capital in your business.
4:02 David Weisburd? Such as less problems, less headaches.
4:04 Speaker 01 What I learned in, in venture for two decades is like it's, it takes 20 years and there's a lot of things and along comes a secondary buyer. You don't really know them at all. So in a perfect world, you would rather have your insiders concentrate more equity. Because it, it solves it, you know, entrepreneurs understand they need, they need liquidity or their seed investor needs liquidity. But they don't necessarily want to entertain a new relationship.
4:27 David Weisburd? They want to be building their business, not building their cap table.
4:29 Speaker 01 Focus. Credit is not their problem.
4:31 David Weisburd? One of the novel things that you did, I've heard a lot of GPs talk about this, but you actually execute on this is you had 30 GPs invest into your fund. Tell me about that strategy and how's that played out?
4:42 Speaker 01 Revenant was created off of a practice that I was running at Accomplice. Over the last 10 years, I did 35 secondaries, all within the Accomplice portfolio. So I kind of knew the model, but as, as the GP and the person co-running the fund, I had all the relationships, all the information, and I understood where to create alpha. So when I left and wanted to create my new fund, I wanted to do it on quote, quote, someone else's book. So I went out to 30 friends in the business, people I've either co-invested with, worked with, had done deals with. And one, I wanted them to endorse me in a certain way. And then two, I wanted deal flow. I wanted their, I wanted access to their portfolios. The thing that I can see here now, like what, eight months since I closed those 30 GPs, those LPs is I've got both of those things for sure.
5:26 Speaker 01 But the other thing which I didn't appreciate was how much information flow you get from having 30 GPs. And not only about their portfolio, but everyone has an opinion on another deal. So the information flow has been probably the thing that I most valued, but I didn't appreciate when I created it.
5:40 David Weisburd? Similarly to making a small investment in a startup, a lot of people
5:45 David Weisburd? don't realize the downstream consequences of investing in a fund and how tied in you get. Very different, by the way, than having an equity stake or advisory stake, but having that skin in the game, even if it's a small check. This is why I don't write small checks into funds or things that I don't want to be really active in. It, it becomes very problematic from, from that perspective. So building the strategic LP base around GPs is a very high leverage way for you to run businesses.
6:12 Speaker 01 I live in a world where I think founder-led businesses are worth more. That's been proven in the last 15 years. And a lot of the GPs that are my LPs are seed funds because their relationship they have with the founder is on. Once you put somebody in business, they look at you different. I don't care if you own 0.1% or 5% of the business, but if you're a first check kind of investor, the entrepreneur will always, always um, hold you in a certain high regard. And I've learned of Essentially, when competing with quote unquote incumbent insiders, I'm going to have to go to the founder and ask for a favor. And there's no better currency I can find than a first investor. So I have used that in the past where I've gone to, you know, one of the GPs is an LP in my fund. And I'll say, hey, can you get so and so to help me waive the like waive some sort of governance? And in my world, for the most part, you would agree,
6:57 Speaker 01 founders usually carry a certain amount of cachet and and they can steer governance your way. And that's another like tactical reason I brought that group in.
7:06 David Weisburd? At the end of the day, it doesn't necessarily matter why seed investors have this way or first investors have this way around a founder. But how would you explain it if you had to?
7:15 Speaker 01 I would say um, for every founder, you have you're obsessed with something. And that first person, whether it's a customer or an investor that says, yes, I believe in you. I believe in your vision. And I don't only I'm not only agreeing with you, I'm putting my skin in the game. I'm investing behind you and I want you to be successful in this mission. 20 years of seed investing, those are those relationships that get forged in the earliest stages of a business are the strongest. And they can go the other way when they get when they go negative. But I have found that first investor relationship is very unique because they believed in you when no one else did. And I've I've used that as a calling card and drawn on that relationship with my with my LPs.
7:58 David Weisburd? What's the half life on that?
8:00 Speaker 01 That's a great question. I would say it's 30 years because I used to think about what's the half life of an entrepreneur relationship? Let's think about it. You probably get one, two, three deals out of the person. They probably introduce you to your best deals. Because when I think back about everything that we did really well at accomplice, every great deal came from another entrepreneur. And so what's so like the value of?
8:22 David Weisburd? Why do you think that is?
8:24 Speaker 01 I think talent recognizes talent at its core level. Relationships are very, very valuable. If I'm going to step out and put my neck out there and say and endorse you to one of my investors or one of my friends, I'm I don't do it a lot. And I'm really, really, and I think the the bar is very high for that.
8:40 David Weisburd? VCs are obviously very smart. Oftentimes Ivy League, double, double degrees, all this. But do you think there's something to be said that founders are more at least first principled or more in touch with cutting edge technologies versus the venture community?
8:53 Speaker 01 100%. I mean, I actually think.
8:57 Speaker 01 I haven't been for another podcast, another time, like I'm kind of a sell on the whole education and the brand around it. I actually think, you know, I've lived a world where 99% of the value creation is the execution, never the idea. And I've found the most interesting entrepreneurs have in their life been trained in resilience. And whether they went to school or not, it actually doesn't even matter. It's they have lived, they're obviously smart, they're obviously passionate. And I think more and more like the third party like validation of what intelligence is, is going out the window. That's like, pretty exciting. That's one of the exciting byproducts of AI. But I come back to like, what have you done in your life that required survival? Because that's what it is. And that's like, that's that I'm drawn to that.
9:39 David Weisburd? I completely agree. As a double Ivy, I agree. I know you went to Ivy League as well. So it's we're trashing our own, our own pedigrees. But I think it's necessary, but not sufficient. I'm not up to date on generation alpha and generation Z as I probably should be. But there still seems to be this from the door, this opportunity that comes to those that have the Ivy League degrees, even if you, I would argue, you don't learn that much, or you don't learn something that you couldn't learn online, let's just say, or through AI today. But it still seems to be very important. And I have such a hard thing to AB test. Obviously, this is why Peter Thiel created the Thiel Fellowship. We backed a fund based on Thiel Fellowship called
10:21 David Weisburd? Valerian for this very reason. I'm a huge believer in that. But even that's credentializing. So if you're not part of the Thiel Fellowship, which I think many people will take over a Harvard, Princeton, Dartmouth, etc. You still need that stamp, don't you?
10:35 Speaker 01 I think the brand of education still exists in the world. But I think back in my own experience, because I was a middle class kid up in Philadelphia, went to school at Princeton. And I think back, what did it do for me? It probably gave me validation, whether I deserved it or not, I don't know. Did I learn anything? No. But what it really triggered in me was ambition. Because the one thing you can say about the Ivy League, there's a lot of people there who have who have come from a fair bit of wealth and affluency and it triggered ambition. And then I'm a competitive person by nature. So ambition and competitive, I wanted to win. And and and one of the ways you win is being successful against your peers. And that's the thing I look back on with 30 years of hindsight. At the time, I had no idea.
11:18 Speaker 01 But I look back, I'm like, man, I was really, it ignited an ambition that I probably didn't appreciate.
11:23 David Weisburd? You also saw what great looks like. That doesn't mean everybody at Princeton was smart. But the top 10% of Princeton are shaping society and doing all these things. You got to see what what does it mean to be extremely smart? The average person, if I think correctly, does not necessarily know the difference between a very smart person and extremely smart person. They just don't have that context. Going to Ivies, you're able to see, you're able to also see your gap. When you meet somebody just exceptional, you're like, holy crap, there's like levels to this.
11:48 Speaker 01 I 100% agree. And I think even the Stanfords and like, like the other schools, like, you want to be impactful. You like, I think every entrepreneur by their nature, they want to change the world and create something, but they're also competitive as hell. And they want to be the best in their class, whatever that means. And I think you have to harness that and believe in it. And that's why I think these founders, they're so valuable to frankly, society.
12:12 David Weisburd? You've seen venture across multiple decades. As I mentioned, you were on the Midas list. You went out and raised $100 million for Revenant's Fund One. What did you learn from that process?
12:22 Speaker 01 I learned in the the whole idea around a small fund was to get in business. And then also, one of the interesting things about Revenant is we have a co-invest program. So every deal we do, we try to offer co-invest to our limited partners. And as a student of venture capital, and really in the last 10 years, I started to see a lot of these smarter family offices want direct access. They love their blind pools, but they love their direct access. So Revenant was purpose built to be small. So I need co-invest partners, people who can actually do it and write a check alongside me into a cap table. So it was literally, that was part of the mousetrap. The foundation was the GPE LP, and then I went after all family offices. That actually could do co-invest.
13:06 Speaker 01 So it allows me to flex up and be a little bigger than 100. But also, I think you can create meaningful multiples of capital with a $100 million fund.
13:13 David Weisburd? Yeah, your fund size is your strategy.
13:14 Speaker 01 Yes.
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15:11 David Weisburd? As I've interviewed hundreds of LPs and GPs across the years, I realized one extremely obvious point in retrospect, which is everything is upstream of your first close. If it's very difficult to do $150 million first close today and do a $300 million fund, do the second best thing, which is do a $50 million first close, do a $100 million fund. And by the time you would have gone to that $300 million, which I would argue would be highly unlikely. I'm not even saying it would take two years. I think more likely than not would not have happened. You're going to be on your second fund, which at that point you could do 200, 250. And people are just, I think they're set egotistically on a number or they're just anchored on a number. Or again, it goes back to this memetic copying. Their friend from Princeton raised a $200 million fund.
15:56 David Weisburd? They're like, that guy's an idiot. I should be able to do a $300 million fund, not understanding all the context. Maybe they raised two years ago. Maybe they had an anchor investor that came in early. Getting into business is just so underrated in every aspect, but certainly when it comes to fundraising, which is more binary than people realize. People think it's like a typical sales process, like a SaaS company. You go talk to 100 investors, somewhat of them convert, and then you have this magical kind of pool of capital. It's not like that. It's a momentum game and it's entirely contingent on that first close.
16:22 Speaker 01 A couple of things to unpack here. One of the ironies of asset management is you can run a strategy with a smaller fund, be very successful. Then you raise too much money. You can't run the same strategy. You have this brand, people back this brand. And I was a big believer in like, you want to run the strategy you want to run to keep the fund size at the right level. You can create ancillary products and ancillary things to take on more capital, but do it in a more intelligent way that works for the LP and works for you. But keep the integrity of your fund size the same. Where you're going was like, one, the GPs gave me deal flow and validation. Then I got some pretty well-known family offices. And then you're downhill and you play the scarcity game. And there's no better way to fundraise than scarcity. And the way you do that is you keep the fund size tight.
16:58 David Weisburd? How do you communicate scarcity, have a scarce product?
17:00 Speaker 01 Yes, well, so, I mean.
17:04 Speaker 01 You do a lot of marketing, you get yourself to a certain level, and then when you launch, you're scarce.
17:09 David Weisburd? Last time we chatted, you said something that shocked me, especially given that you've been in the industry for several decades. You said you're not looking for power loss.
17:16 Speaker 01 My career has been made on underwriting really good people and underwriting some semblance of information. My experience in the quote unquote power law game is I have an hour, maybe 12 hours, maybe a day to make a decision, and I have very stifled access. And it feels like I'm playing a momentum game. And it's very successful that those are comfortable, that those can do that. I live in a world where I want to sit across or at least have a Zoom with somebody I'm backing, and I want some semblance of information to underwrite. And the power law, there's been such a frenzy and there's so much competition around it that my process doesn't necessarily work in that world. I still believe in it. I don't think about what I don't do. What I do do is I underwrite great teams in really interesting markets and I come in as a secondary buyer, oftentimes solving a problem.
18:00 David Weisburd? Just to play devil's advocate, doesn't that break the venture model? Don't you need that power law outcome to drive the entire portfolio to three, four, or five X?
18:08 Speaker 01 Secondary buyers look at their loss ratio. Venture people don't. You know, well, my loss ratio should be close to zero, right? As a secondary buyer, because I'm coming in and underwriting in a meaningful moment when it's a more mature business.
18:19 David Weisburd? Second stage, are you going into?
18:21 Speaker 01 Like I said, I mean, as early as I've gone is 25 million revenue and a big as 900 million. So it's a very wide swath. I'm really trying to pinpoint an inflection about to happen to the business. And that's how I've been, that's how I've kind of been underwriting.
18:37 David Weisburd? Is there no opportunity to buy secondary in a fast-growing AI company that has an incredible cap table and has some implied expected value and potentially a very high expected value?
18:50 Speaker 01 We look at these deals when we can. Our challenge has been, or at least my challenge has been, really trying to get access, the right amount of access, which I committed to my LPs. In terms of access to a team, a little bit, access to some semblance of financials and what's happening in the business. I kind of hold myself to that standard, a higher underwriting standard. And it doesn't add to the deal. Like, I would love to do a late-stage AI deal. If I got to meet the founder and I do, you said earlier, maybe I pay 10%.
19:15 David Weisburd? There's a trade-off.
19:16 Speaker 01 Yeah, maybe I save 10% above par. Like, probably, I'm not looking to discount. If I want to be in a business, I'll pay the price I need to if I've underwrote it appropriately.
19:24 David Weisburd? Mark Andreessen recently said, there are no diamonds in the rough, only diamonds. Do you agree or disagree?
19:29 Speaker 01 Well, first of all, it's a little self-serving. If I ran a $15 billion platform, I would probably say something like that to some degree. I guess he's right, but I don't view the company as the diamond. I view the founding team, I view the founders as diamonds.
19:39 David Weisburd? So tell me about your portfolio construction.
19:42 Speaker 01 Yeah, so my portfolio construction, like I said, it's a wide swath, industry agnostic, not focused on themes here or there. What I'm really focused on is this inflection point. Am I buying into a business right before it triples? Am I buying into a business right before the valuation doubles? And so I traffic and I need to be introduced at the right time in that moment by usually one of my GPLPs and then I access some shares and then enjoy hopefully the performance that happens afterward.
20:10 David Weisburd? Last time I took a deep dive into the secondary market, I saw this natural gravity to push prices close to the 490 or to the last round. Is this something that you're benefiting from this natural, I guess, discount in secondaries that could take on?
20:24 Speaker 01 A lot of times I am very efficient, because I was a VC myself, around can I make five times my money? So I really price things off of what I believe the potential will be versus a discount. That's why in some examples, we have bid par or even north of par, because you see the inflection point happening, or you have really good inside knowledge from maybe an insider that X, Y, and Z is about to happen. And that gets you comfortable that you can pay a price, but I'm really trying to underwrite to three to five X quickly. And that's how I think about pricing, less than a discount.
21:00 David Weisburd? You have several pet peeves about the venture industry. What's your number one pet peeve?
21:04 Speaker 01 Man, there are a lot of pet peeves. I probably would say group think.
21:11 Speaker 01 I would say I think the industry from LPs down tend to talk each other into the same kind of deal. And I'm a big believer in you got to go where people aren't. And the group think mentality is probably the thing I dislike the most. Close second is.
21:32 Speaker 01 It's all around, it's really the founder. VCs like they sometimes get a little bit caught up in the investment they did when they really, they just found a really good team and they executed and they overly attribute their role in the success.
21:44 David Weisburd? I invested in seed round, I took the company from seed to a hundred billion dollar company.
21:49 Speaker 01 That might be my greatest pet peeve, that they don't appreciate, it's really all about the founder. And you were fortunate to witness greatness. And I'm sure you made an introduction here too, but you witnessed greatness and you took a risk. You should be applauded for that, but let's just, let's be really clear on what you actually did in building this business.
22:03 David Weisburd? Just to play devil's advocate, they're not VCs that come in and completely change the trajectory of a company.
22:08 Speaker 01 VCs, it's an, it's an asset class that lives with brands. And I think there is something to be said about if a branded VC comes into your cap table, it facilitates talent aggregation. That's really it. And I'm sure there's some introductions here and there, but to me, when I'm a big believer and it's all around the execution and, and hiring great people, I do think VCs can definitely influence that.
22:29 David Weisburd? And that's particularly at the early stage.
22:30 Speaker 01 Correct.
22:32 David Weisburd? Because great talent is more effective at amalgamating great talent than the next VC.
22:37 Speaker 01 Ninjas want to work with ninjas. When I was a seed investor, I was like, your first three hires have to be absolute ninjas. Because if I'm coming to join a company, how good are the other people? It's the first thing I think of when I leave. So you really have to hold that bar really high.
22:48 David Weisburd? How scarce is great talent? Is this something that's pretty scarce? Is it just extremely rare?
22:54 Speaker 01 I actually think it is probably the rarest thing. And I think that's what zero interest rate environment mediocre people got funded. And that's really hurt the asset class.
23:03 David Weisburd? Obviously, there's the SpaceXs, the Andorls of the world. But across the board, is it very common to see these clusters of talent at companies? Is that more the rule than the exception?
23:13 Speaker 01 Is the rule. Cause I really think, like I said, talent aggregates more talent. I think talent compounds maybe more than anything. And then before you know it, you've just got an awesome team. And then they're going to born out the next set of companies. Obviously, the PayPal mafia being like probably the most, the poster child for it.
23:28 David Weisburd? And the opposite is also true where you have no talent, somebody extremely talented comes in, then they friction off in six months.
23:34 Speaker 01 If there's a really average person at the company, you're looking around like, why is he, why here, she's still here? And then you start to question the leadership. Like, why, why are they suffering, why are they, why are they allowing mediocrity in our company? Because it's kind of the lowest common denominator. Mediocre people hire worse people than themselves. And then before you know it, you've got a really average team.
23:53 David Weisburd? Yeah, it's a Steve Jobs saying A's hires A's, B's hires C's.
23:56 Speaker 01 Yeah, you got it.
24:01 David Weisburd? As I've gotten to know you, you're, I won't use the word contrarian, but you're a great first principles thinker. How do you invest your money outside of Revenant, your own money?
24:10 Speaker 01 I'm such a sucker for innovation and you know, you'd think I would be a little more diversified in my own like personal finance. Yes, I have some real estate here and there and some safe stuff, but I'm still a very active angel investor. Because I still want to be, you know, and actually one of the deals they quote unquote sourced from Revenant, I was the GP as an angel investor. I'm a secondary buyer buying into later stage businesses today, but in my person, my PA, I would much rather give an entrepreneur a $50,000 check than put money in an ETF.
24:41 David Weisburd? I have some good news for you. So I sat down for what I didn't realize would be a therapy session with the CIO of Mark Andreessen Ben Horowitz's family office, A60Z Perennial, Michelle Del Funa. And I let him know my portfolio construction, which was over 90% startups now across so many different verticals, hundreds of positions. And he said something that was very surprising to me, especially somebody in asset management, is that it's not necessarily a bad portfolio. It's a very illiquid portfolio, but it is not fundamentally flawed and even more so, it's not fundamentally not diversified. There's this dogma in asset management, they have private credit, private equity, bonds, stocks.
25:22 David Weisburd? The opposite is true, by the way, as well. In 2022, investors woke up and realized their stocks and their bonds were correlated. They thought they were diversified and their models said they were diversified. Obviously, the models were based on previous correlation, but they weren't diversified. So I've evolved my thinking, this was just a couple of weeks ago, in that sure, liquidity is very important. And sure, you want to have some diversification.
25:48 David Weisburd? And sure, you should never put your eggs in one basket, but if you have a sizable enough diversification, being overweight to where you have alpha, where you have access, all those things is not the craziest thing.
26:00 Speaker 01 And also so many of these asset classes that I'm not involved in is there's often a middle level management. One of the things I love about startups is I'm looking across from the person I'm actually writing a check to or sending a wire to. And there is something tangible, feasible about that. And that's what, you know, if you're going to invest, I'd rather like know who's going to be managing my money, this founder. And I love the creation of that. And I love just being involved in that hectic stage of startup.
26:25 David Weisburd? I love that the founder is your wealth manager.
26:28 Speaker 01 Pretty much.
26:29 David Weisburd? He just has a very small stake.
26:31 Speaker 01 Exactly.
26:32 David Weisburd? You played football at Princeton, you were a linebacker. You went into venture capital, started this firm called Accomplice, you were the first investor and angelist. You had the story career, as I mentioned. If you could go back and give yourself one piece of advice when you had just graduated Princeton, one timeless piece of advice, that would have either accelerated your career or helped you avoid cost of mistakes, what would that be?
26:54 Speaker 01 Trust your instinct. When you're young, you're taught, you don't know anything, you're inexperienced, especially in the 90s when I was kind of growing, growing up in my, in my, in my investment career. And I look back and your instincts are often right. And you got to trust them, even though, even if you're not experienced. So I look at my investment career, and when I trust my instincts, they're far greater than my experience. So if I was 22 or 23, I would have trusted my instincts earlier.
27:20 David Weisburd? Is this around founders?
27:22 Speaker 01 It's around everything, frankly, like what do I want to do with my career? Do I want to go work at a bulge bracket? Do I want to go do something more startup oriented? Trust your instinct. And, you know, like I learned really early, I'm a much better, like throw me in the deep end. I learn a lot by doing. I wasn't a great student per se, but I'm a great worker because I've got a quick mind, it can iterate quickly. And then what I've learned is I should have trusted my instinct the whole time, but I was kind of taught you're inexperienced, maybe your instincts wrong. And in hindsight.
27:57 David Weisburd? There's this, there's this Gary V meme, which is one hour of, of doing equals 100 hours of thinking.
28:03 Speaker 01 Gary Vee's got a lot of great ones. That's a great one.
28:05 David Weisburd? And it's a, it's a trap. And the higher IQ people, your classmates at Princeton, mine at Dartmouth and Harvard, that is a very common trap, the over thinker. And the more IQ you have, the more ego you get, and the less you want to look stupid. We talk, my business partner Curtis about this all the time. The first 150 episodes or so, we didn't have a lot of listeners and it's brutal for the ego. And now you have an identity around this. Now I have an identity around doing something that a lot of people don't listen to. And it's a brutal thing and having the ego strength to do that is a significant competitive advantage. And it's one that I don't believe is priced into the market.
28:41 Speaker 01 One of the things that I learned as a seed investor in the last 20 years was people were like, how did you know what to double down on? Was it P and L? No, P and L can be a lagging indicator. It was organizational metabolism. The teams that move super fast are the teams you want to be in business with. The teams that are breaking glass, making a mistake so quick and iterating before you even knew it was a mistake. That's where we made all our money. P and L had nothing to do with it. It was like organizational metabolism and speed and instinct. And that's kind of where I would, that's why I want to get access to the teams I'm backing. Cause it's really hard to do at scale.
29:15 David Weisburd? Perhaps a dumb question, but how are you able to tell the organizational metabolism of a team?
29:20 Speaker 01 It's part instinct. It's part like conversations with people on the board or investors. And you know, that's kind of like really why I try to hone in on, I'm still trying to back teams. And in this, just as a secondary buyer.
29:36 David Weisburd? Ben, in hundreds of investments, you've seen thousands of deals. What have you changed your mind on the last couple of years?
29:44 Speaker 01 That's a great question. You know what's probably changed my mind on? I used to be team, team, team, team, team. But I recognize really in the last few years is I don't care how great the jockey is. You have to be in a good market. Market tailwinds will drive success as much as any great team. And sometimes I've backed some great teams in mediocre markets and they're actually so innovative. They're shrinking the TAM they're in. And I've recognized more and more, you gotta have the combination. That's the one plus one is five. Great team.
30:13 David Weisburd? Where is the revenue going to be in five to 10 years?
30:15 Speaker 01 It's a great question. Hopefully on our fourth fund with a great cabinet of LPs that love the co-invest partnership that we've created. Small funds, maybe different kind of products, but I think we'll always keep the integrity of the fund small if. And it's one of the brands, an aspirational brand in the secondary market. We want to be sought out by our GPs and our founders to solve liquidity in the view of a secondary. And that, that would be a win.
30:46 David Weisburd? We have this unique vantage point here on the podcast and I have a pre-interview and interview and now roughly 360 episodes. And one of the things I think GPs are not aware of is this pullback. We started the conversation talking about this, but this pullback from the dedicated blind pool funds and how little appetite there is for LPs to back new brands. Some people see this as fatalistic. They decide not to be a VC, they go out to do something else. And other people are leading with their co-invest, are leading with their innovative structures to give the customer, AKA the LPs, exactly what they need. And those are the funds that are going to succeed. If you think about this extinction level event that's happening in the merging manager
31:27 David Weisburd? market, somewhere between 2,500 to 3,000 merging managers a couple of years ago, some accounts, some people think 50% of them will be gone, some of them 75% will be gone, meaning they won't raise another fund. On the opposite side of that, there's a lot of opportunities. And the question becomes, how do you get over that hump? How do you pass that chasm between default dead and default alive when it comes to emerging managers? And the answer is give your customers what they want. I've had Ivy endowments that are telling me, all things being equal, they want to deploy into pools of co-invests or other pools of capital where A, they know the assets they're getting and B, they don't have to wait through these kind of 14 years. So I think you're on the right track in terms of product innovation, how you're building your firm.
32:09 Speaker 01 I probably did 35 secondaries when I was at Accomplice and a lot of the dollars I raised for these deals, because we didn't have a dedicated secondary fund, I did it via the three level, but a word SPVs before it was a thing. And I did it with family offices and I recognized firsthand, those that if you give them the right amount of information, let them underwrite it, it's a great product. So when I sought this, when I started this fund, I targeted family offices that had that muscle, because I think it's really important and I think it's where the industry's going. It's great to hear the institutional LPs you talk with and traffic with that frankly, I don't allow.
32:44 David Weisburd? I was surprised by it to me.
32:45 Speaker 01 Yeah. An endowment going direct. I know for years in the buyout land, there were these co-invest vehicles, but I think more and more across every asset class, it's a very interesting product that makes a ton of sense and frankly is healthy for everyone, because you don't wait for the waterfall, the fund to pay out. You can, you can win, when a company goes public, it's a win for you and then you can reinvest a proportion of that into the next thing. And I think for too long, people have been scared of that.
33:10 David Weisburd? Just double click on what you said. You said that you looked after. Family offices that had a predisposition to do co-invest. I've never met a family office that didn't say they want to do co-invest. How did, how were you able to?
33:22 Speaker 01 They have a track record of doing it. Everyone talks about it, but then you know, you know, the game. Can you really pull the trigger in 60 days? That's a little fast.
33:29 David Weisburd? And you asked the LPs before they?
33:31 Speaker 01 For sure. For sure. Cause I say to them like, listen, I'm offering co-invest. Know what this means in practice? It means when I bring you a deal and you want an allocation for it, you need to close it within 40 days, sometimes sooner. Do you have the muscle memory and the ability and frankly, the staff and the risk appetite to do that? And very often not, not yet. But we want to, can you show us?
33:53 David Weisburd? It's a great framing. Well, Ryan, you're an absolute legend. It's a pleasure to have you on the podcast. Looking forward to doing this again soon.
33:59 Speaker 01 Thanks. Thanks for having me.
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