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20VCAug 4, 2025

Inside Carnegie Mellon's $4BN Endowment

Why 90% of LPs Shouldn't Invest in VC · The $140BN Problem with Multi-Stage Funds · The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

With Miles Dieffenbach · Harry Stebbings

Full transcript · 87 min · 17,547 words · 2 speakers

Cold open

So my message here to all venture capitalists, now is the time. Please take your companies public. I breathe investing. These business models these GPs are creating are some of the best high margin businesses ever created. My question to any new allocator or an investor is do you think you’re going to have access to top decile managers? Because at that point, top decile, you are achieving returns above the PME consistently. But below that, even top quartile, you’re not.

Miles Dieffenbach0:00

This is 20 VC

Harry Stebbings0:28

Intro

Harry Stebbings

with me, Harry Stebbings. Now the best podcast is shows where you’ve never heard the guest on any other show and you hear truly unique stories. Well, today, we dive inside the $4,000,000,000 Carnegie Mellon endowment fund with a first time interview with this guest. When we uncover what they look for in managers, red flags, how they view venture today in their portfolio, the rise of multi stage funds, what specific funds they love and what they don’t. And joining us in the hot seat, Carnegie Mellon’s managing director of investments, Dieffenbach.

Now this is a newfound friend for me, and this is one of the joys of doing the show, making incredible relationships with awesome people. A very special conversation today. But before we dive into the show today,

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Harry Stebbings1:11

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Conversation

Harry Stebbings4:38

Miles, dude, I’m so excited for this. Listen, we’ve been friends for a while. I’m so excited that we could also make it happen in person. What no one knows is I dragged you around London for a walk last night and it poured with rain. You were so patient and great, but thank you for joining me, man.

Miles Dieffenbach

Thank you for having me. It’s a pleasure to be here. You’ve had some incredible guests on the podcast and I’m honored to be one of them.

Harry Stebbings5:00

It’s amazing given the fact that I’ve known you for a while and then also, like, in the research for this, learning more and more about you because I didn’t actually realize this. But at 26, you went through a cancer experience and, you know, you’re a cancer survivor now. Pretty unbearable to think about given the fact that I’m 29. That’s just the most incredible strength. How did having cancer and facing your own mortality change your mindset? And I’ve never asked that question to start a show before.

Miles Dieffenbach

Well, let’s dive into it. We’ll dive into the into the heavy and hot. It’s a surreal moment when that happens. You know, I think everyone at that age thinks you’re invincible. I did. And you get that news, and you’re in a bit of shock. Right? And it was so abnormal to me when they told me I had lymphoma. I said, Oh, great. What’s lymphoma? I thought it was like a cold. I didn’t even know what it was. And they said it’s it’s it’s cancer and it’s progressed, you know, quite substantially and and we need to, you know, start a chemo process here within the week.

And so, like, I’d say most all people, I I sulked for about twelve hours, went home, was mad at the world, didn’t wanna speak to anybody. Why me? And and I woke up that next morning. And one of my college football coaches had a had a great quote that that really stuck with me, which was, you know, success in life is 10% what happens to you and 90% how you react when happens to you. And so I took that running that next day. I said, I’m gonna attack this.

I can’t change the situation I’m in, but I can change how I react to it moving forward. And so I basically said, you know, cancer can’t kill me if I don’t stop moving. So I basically started, you know, a pretty insane regimen of of workouts. And when I would go in and get my chemo, that was like my R and R. That was my recovery period. I’d get out. I’d I’d I’d start that again. And flash forward four months, I was cancer free, and I have been so ever since.

Harry Stebbings6:48

Do you remember the moment you were told you were cancer free?

Miles Dieffenbach

Yeah. It was crazy because I I I got in there. You get a scan right before, and then you go into the office. And I waited two hours in the office post scan. Usually, it’s, thirty minutes. And I’m sitting there, like I I might be, like, biased towards negativity. I’m like, it’s it’s gotta be bad news if he’s waiting two hours. And he came in. He had his arms wide open. He gave me a big hug. It was a it was pretty incredible.

Harry Stebbings7:14

Wow. That must be the most special moment.

Miles Dieffenbach

Yeah. It’s special. And, you know, looking back on it, you everyone’s know, had adversity. You know? You’ve had adversity in your life. You know, a lot of people do. Everyone does. No. Life is is perfect. But there’s there’s beauty in the struggle. Right? Like, that makes you who you are as a person. Right? And and it builds you into a stronger person. And so the trials of life are many, and and, you know, I wouldn’t change anything. Did it set a benchmark of shit that now everything else seems kind of okay?

Oh, I mean, the the perspective you have, you know, moving forward after that is one of the great blessings of that. Right? Life is an incredible joy and a blessing. Right? And so there’s there’s not many things that can that can take me down, you know, mentally at this point.

Harry Stebbings

How on earth does one go from, like, surviving cancer, beating the odds, amazing, to the endowment model. There we go. I mean, it’s a pretty smooth transition for me. Give me credit. I do wanna start with just laying the kind of landscape framework for how CMU operates, is structured today. If you think about, like, a construction that’s easy for everyone to understand, how does that portfolio construction look like for CMU today from a top down?

Miles Dieffenbach8:21

From a top down perspective, we manage 4,000,000,000 on behalf of the university. And so starting at the highest level, we think of equity and fixed income as as kind of the two parts of the endowment. 85% of the endowment is equity, 15% is fixed income. That is our allocation. And and we manage to that on a on a quarterly basis. One step below that then is the sub asset classes within that. And so our target is 50% of the portfolio is in privates. That’s a mixture of venture capital, private equity, real estate, natural resources, private credit.

The other 50% is hedge funds and liquids, which the liquids are public equities and fixed income. And so that is the the top down management of the portfolio within that private bucket. We have free rein into the underlying allocations within that. So we call it a best athlete portfolio. So how do we find the best risk adjusted returns globally across all of those different private asset classes so we can have the best risk adjusted return for the portfolio?

Harry Stebbings9:18

When you look at it today, how has that makeup changed over time in terms of where the private commitments lie?

Miles Dieffenbach

Yeah. So we, you know, from a liquidity perspective, we’ve been fortunate compared to most endowments where that private equity book has been self funding the past three years. So our distributions have paid for our capital calls over the past three years. Now, the sub asset classes within that have had much different performance. So our buyout portfolio, our private equity portfolio has contributed the most to those distributions. Venture has been the largest detractor of those, but it’s been self funding. Right? So our private equity book at at kind of that 50% number has stayed relatively consistent for the past six or seven years.

Venture, as the distributions had slowed down over the past three years dramatically, has risen as an average, but there’ve been markdowns over the way as well.

Harry Stebbings10:05

So when you think about, like, commitment to venture as a whole, what is the percentage commitment to venture as a whole of the endowment?

Miles Dieffenbach

So for us, venture globally is a little less than 25, the total endowment. So almost half of that private equity book. How does that compare to others like you? I’d say we’re overweight venture by call it anywhere from five to 10 points versus most other endowments of our size. We’re underweight hedge funds and real assets, which would be real estate and natural resources. On privates as a whole, we’re right on par with with most endowments, plus or minus five points.

Harry Stebbings

When you think about all of those different asset classes that you can allocate to, how do you think about opportunity cost? And I think you said it before, which is unit of return per unit of risk.

Miles Dieffenbach

We take everything from a lens of risk first starting off. So when you think about the different, you know, private asset classes there, you’ve got real estate, natural resources, private equity, venture capital, which is a mixture of growth and and and early stage. Know, take real estate for example. You know, you could have a, you know, industrial building that does triple net lease rents being leased to Amazon. Those rents increase 3% a year. It’s a very stable asset. There’s a replacement cost to that to that asset.

Not nearly as risky, and so the returns will compensate for that. It is not as risky of an asset. Right? Venture, picture early stage venture. You know, it’s a $100,000,000 fund investing into two or three people in an idea. Could be a completely new idea. It could be an idea going against big incumbents. The company’s not gonna be profitable when they start out. Probably the riskiest asset class you could have. So you want to get compensated. You need to get compensated for that risk you’re taking within that within that asset class.

Do

Harry Stebbings11:41

you think LPs are getting paid for the risk that they are taking in Vastien Venture?

Miles Dieffenbach

Absolutely not. Why not? I mean, we take a very hard look at the data that comes out of the asset class from there’s really good data from, call it, ’98 to today. You look at the, you know, the the the median IRR for the asset class over that time period for mature funds. Right? So so we’ll look at the the ten and fifteen year returns for every one of those vintages kinda stopping at 2016 as that’s gonna be the closest to a mature vintage you’re gonna get.

The median IRR is about 8% net for that asset class, and and and the top quartile, is a bit higher, 15%, but the MOIC is about two and a half x. Right? And the big, you know, the the difference is when you look at that, those performance numbers, then on a DPI number, we’ll stretch that from 10 to 15 year. Top quartile DPI from 1998, fifteen year vintage funds per vintage year up until 2015 is 1.8 x top quartile. And so, you know, when we think about those underlying asset classes and our public equity portfolio, we have a public market equivalent for every private asset class we invest in.

Right? For real estate, it could be VNQ, which is Vanguard’s, you know, REIT index. For our buyout portfolio portfolio, it could be a smaller mid cap value index. And for venture, it’s the QQQs, the Nasdaq 100. And that’s been the best performing PME globally over the past twenty five years.

Harry Stebbings13:09

When we think about, though, like, not, you’re not getting paid for the risk that you’re taking. And then the statement that you said to me before, is 90% of LPs shouldn’t be investing in venture. Who should and who shouldn’t then?

Miles Dieffenbach

That’s the million dollar question. I think you need to have a frank conversation with say say you’re a you’re a new endowment or a new family office, and and you say, we want technology exposure. You’ve got two options. You could do that through the public markets. You could do that through the private markets. My question to any new allocator or an investor is do you think you’re going to have access to top decile managers? At that point, top decile, you are achieving returns above the PME consistently.

But below that, even top quartile, you’re not. That is the question. And I think most people clearly by the data, especially as a new entrant to a major asset class, are not going to have top decile access.

Harry Stebbings

That instantly suggests, though, that you’re working on historical lagging data, which is obviously their prior returns, not a first time fund or smaller micro funds who are in their first vintages. And that is where we see a lot of family offices and even smaller endowment funds playing today. How do you think about that?

Miles Dieffenbach14:15

A strategy that a lot of people are taking, you know, first time funds and and smaller funds as as the incredible performance of the now multistage venture firms have have they’ve scaled as that performance has allowed them to. We spend time in that space as well, but it is a time, a place that is quite risky. New funds, small funds, and it’s a hypercompetitive part of the market. There’s thousands and thousands of managers, you know, specific seed funds, angel funds, operators.

Harry Stebbings

You know what I find funny? Sorry. I want this also to be an an open and free discussion, but I find it really funny how all LPs love 50 to $100,000,000 seed funds. And when you actually run the maths now on average seed fund, seed round sizes, that’s the worst place to be. The average seed round is 4 to $5,000,000. To write a check with ownership, you need three, three and a half. If you want enough diversification, you need 30. And so you need $33,000,000 checks.

Well, that’s 90. Well, you’re not gonna have that with a 50 to $100,000,000 fund. It’s impossible. So then you either have subscale ownership or subscale diversification, or you do what everyone does, which is like they end up writing tweener checks, like $1,500,000 checks. It is fucking hard to get a $1,500,000 check-in a 3 to $4,000,000 seed round when the best in the world want it. Put a 50 k in, but 1.5?

Miles Dieffenbach15:28

Mhmm. My my response to that would be consensus seed deals, either consensus founder or consensus idea, extremely hard to plan because the multi stage firms have have all planted a a flag at seed and have essentially said, we’re gonna all these seed funds are our shrapnel. We’re gonna blow this your model up. A much cheaper cost of capital than you, and we can deploy $510,000,000 checks at seed when when the model traditionally was two to three. But if you’re doing nonconsensus founders, nonconsensus ideas, know, those rounds are usually noncompetitive, and and that shows up in price and ownership.

And so I I’d say that’s the question I’d possibly ask.

Harry Stebbings16:03

That in your portfolios? Because I I didn’t actually know what is nonconsensus anymore. Like, the rounds that were in the old days, they’re kind of not now. I find non AI deals, but non AI deals are still priced incredibly rich. Actually, when you push now, it’s such a mature asset class. I don’t think you have that luxury on price.

Miles Dieffenbach

The true moat of early stage venture capital, the picking skill. And you look at some of the the most incredible companies that have ever come out of the venture asset class. Airbnb, Uber, SpaceX, Amazon, struggled mightily to raise their seed round. So to your question, is there so much capital available at seed today that that’s never gonna be the case moving forward? I hope and pray not as an allocator to the space, and so I still believe there is a a moat around picking, but we’ll see.

Harry Stebbings

So unfair of me. Do you think Venture’s an access game or a picking game? You’re in some of the best brand names. Is it access or is it picking?

Miles Dieffenbach

I think it’s both.

Harry Stebbings17:00

You have to weigh it out of a 100.

Miles Dieffenbach

Oh, weigh it out of a 100. I would say if you are a multistage firm that is, you know, deploying large checks at scale, 70% access, 30% picking. If you are a small and nimble early stage fund that is trying to break into the mold, I’m gonna say it’s, you know, 80%, 70% picking. I’ll flip it. Yeah. 30% access.

Harry Stebbings

So we mentioned that multistage funds go into seed, we mentioned the seed funds, 50 to a 100, well, I don’t like them. What do you like? When you see a fund come through the door, where are you like, that’s straight down the fairway for me, size wise, geo wise, hit me.

Miles Dieffenbach

I think for us, the sweet spot is dependent, one, the GP skill set and what they’ve done prior, but for us and our commitment size, which at the low end, call it $10,000,000, Anything from at the low end, we’ll do an $80,000,000 fund. At the high end, you know, anywhere from 400 to 1,000,000,000. Right? In that range, dependent on the skill set and the track record of the team. But it’s very much dependent on the people, what they’ve done, what they’ve proven, what they want to do with this fund, and the pattern matching and diligence we can do against that.

Harry Stebbings18:10

We said about access and picking. We spoke before this about the pillars of venture. I’d love it if you could just unpack the pillars of venture and how you think about them and where you place more and less emphasis.

Miles Dieffenbach

Yeah. So the five would be sourcing, picking, winning, helping, and selling. Selling is gonna be the most the new of those five, I think, for the asset class as a muscle as a whole. Do you

Harry Stebbings

think your managers have been good at selling over the past decade?

Miles Dieffenbach

Some yes. Some no. You know, Union Square broadly. And we’re not an investor there. We wish we were, but I think they’ve apparently been the best at selling, and they’ve got a very strict protocol that they run through, you know, from years eight to twelve on those funds and with those founders to let them know that they are going to be active sellers. Do you think managers should

Harry Stebbings

distribute shares, stock? Do you think Sequoia are right that the evergreen fund structure, they are best placed, they have asymmetric information? How do you think about that?

Miles Dieffenbach19:02

We like them distribute cash versus stock. Reason being, if they distribute stock to us, there is sometimes a time lag between when we sell that and when others sell that, and so there could be a one to 2% pricing discrepancy on that versus them distributing cash day one is quite easy. They sell that entire book immediately, and they distribute that to all their LPs equally.

Harry Stebbings

Do you think the last generation did a good enough job selling in the 2122 vintage?

Miles Dieffenbach

Clearly not. I I mean, I think that’s a pretty easy one. The one thing I’ll say, the reason it got so crazy was the public markets were were pricing growth assets for an eighteen month period at, you know, the median ARR multiple for a software company was 20 times. And if you were a top quartile grower, it was 40 times. Right? And so everyone looked at their models and thought their company was gonna be worth two, three x what it was in in three years. You had public market comps to support your reasoning of holding stock, but that all changed very quickly.

Do

Harry Stebbings

you believe managers’ books? You know, we all come back with these prices in terms of the marks on our books, which is where we mark our portfolios, latest valuations, so that. Do you think managers are accurate enough in how they price their books? Certain ones, yes.

Miles Dieffenbach20:10

Certain ones, no. We we Who’s the best? Usually, the the the multistage firms think you’re perennial like Excels or Sequoia. They’re they’re they’re taking very aggressive discounts on basically all of their securities, Even if it’s a great company that is maybe achieving even a higher price on the secondary market, they’re still gonna hold that at a at a 20 to 30% discount. Right? But 2021 caused us to create new muscles in regards to underwriting as a group as well. And so for any re up or any new manager we diligence, we’ll look at the top 10 company NAVs within that general partnership.

We’ll underwrite those companies ourselves. And and we will, know, on a rough approximation, determine are these assets extremely overvalued? Are they undervalued? Are they fairly fairly valued?

Harry Stebbings

I think my biggest worry is actually we’ve got a generation of, like, marked books where they’re like, oh, it may not be the five x fund. It might be the two and a half x fund. I’m worried that it’s not even gonna be that. Do you think there’s a realization amongst LPs of of bluntly the dire nature of some of the books?

Miles Dieffenbach21:06

Look at the data. A top quartile TVPI is is 2.5 x. Top quartile DPI is, you know, 1.8 x.

Harry Stebbings

One thing that really pisses me off, because I do do some LP checks when I meet managers, is like, listen. I don’t know if we’re gonna do like a an eight x, but we’ll definitely do a six x. And I’m like, do you know how hard it is to do that? Brutal. Any things that managers say in the early meetings with you where you’re like, oh, no. Just don’t say that.

Miles Dieffenbach

When I I’ve had a few manager meetings where folks come right out and proactively say how easy what they’re doing is and how great much great access they have in in the great performance that they will have. And that with the market they play is just it’s it’s just like shooting fish in a barrel. And that is always to me, like, we’re gonna we’re gonna stop this call early. Just the the kind of hubris I mean, this is the one of the most competitive asset classes in the world, and and we look at returns of everybody.

Right? So we we see how hard it is, like you said, to achieve, you know, a six x net fund. So that’s that’s definitely a big one.

Harry Stebbings22:07

Starting at the start of the I’m jumping around so much, but I love this. Fuck it. We said about the five pillars. Starting at the start of that process, we’ve got the access element or the sourcing element. How many managers do you actually think have, like, proprietary sourcing where you’re actually like, oh, I see. They see shit that no one else does.

Miles Dieffenbach

The premier funds on Sand Hill Road and in in London, such as yourself. Well played. Thank you. You’re welcome.

Unknown

I

Miles Dieffenbach

I think there is no systematic sourcing strategy. It’s the partners and the brands are so strong, and they’re they’re so networked in the s tier founder community. There’s gonna be a first call for a lot of these firms. I think if you are doing a more esoteric strategy such as bootstrapped companies in, you know, in Australia or or some of these tertiary in Pittsburgh. Right? I think you can build, like, automated CRMs to maybe track some of those companies that are gonna be off the radar of your traditional Silicon Valley firm.

But I think those more traditional firms, the brand and and strength of the partners, I don’t think there’s much systematic sourcing strategy there.

Harry Stebbings23:09

The thing I think when you are such a tiered brand name is you just become a de facto meeting in the fundraise process. Whereas like, before I sign the term sheet, I’m gonna go to Index, Excel, Sequoia, you name your firm, but you just wanna be one of the flag posts. I’ll always remember Pat Grady saying to me a brilliant thing, which is he’s like, people think that, you know, we’re so successful, and he’s so humble, which is why I love him so much. He’s like, people think we’re so successful.

Harry, pretty much every software company that goes public, we’ve missed that we’re not in because we do see a lot. That’s on us. And I thought that was, a, incredibly humble, but, b, the flagship, they see everything at some point in the journey. 100%. Yeah. I mean, those partnerships have have stood the test of time, clearly. When you think about, like, proprietary access where you actually buy it, who stands out most to you? On the sourcing side? Yeah. Well, I mean, like, you know So I’d say, like, the Potovies.

Ali Potovy. The dude is in, Yeah. His that fund is incredible. What the Cursor. What the know, few others. Yeah. Amazing, Tim. I’m so pleased for him, but, like, that stands out to me. Any for you? It’s

Miles Dieffenbach24:19

it’s become such a crowded market. There’s so many alternatives. You’ve got South Park Commons. You’ve got Ali Partovi in in their network. You’ve got YC. You’ve got Techstars. You’ve got a thousand seed funds. Outside of maybe a few like Ali, I think sourcing broadly, and I’m willing to to be wrong here, but I think there’s a lot of luck in sourcing. You’re just hustling. You’re going out. You’re getting emails from friends. You’re getting emails from partners. You’re taking as many meetings as you can. You’re on a call with a Harry, and he’s like, wow, Harry is fucking unbelievable.

I’m gonna I’m gonna dive into this. You know, it’s it’s the magic of venture. Right? That’s how I think I see most of it.

Harry Stebbings

I agree with you, which is why in some respects I do think it is a young person’s game. Because it’s about pounding the pavements, being there, showing up at 7AM. That takes youth in a lot of ways. Picking is the next element, difficult to unpack in a lot of ways. Who do you think is the best picker that you know?

Miles Dieffenbach25:14

I love the way Mike Maples discusses picking in his the way he thinks about these companies that are, you know, going against the grain of the universe and are inherently, you know, not gonna be super attractive or super hot because it is against the grain and it is, you know, dysfunctional against the way that, you know, our human minds work today. I’ll never forget. I mean, when I first heard of Uber, thought it was the stupidest idea I’ve ever heard. I mean, that’s how you know I’d a bad venture capitalist.

I mean, I I was in, you know, late in college. I’m I’m gonna get in some random person’s car, and they’re gonna drive me some same with Airbnb. I’m gonna go to some random person’s house. I’m just gonna sleep in their bedroom. I mean, this is the craziest idea ever. Right? Those are the people and investors, you know, sign Bannister, another one, like, who who in a lot of those companies, Uber, right, that we mentioned, like, their ability to see into the future is something that not a lot of people can do, and it’s it’s a superpower.

Harry Stebbings26:06

How

Miles Dieffenbach

do you unpack whether someone’s a good picker? Is it just looking at track? I think it’s looking at track, understanding the true thought behind what what were they thinking when they made that investment and when they met that founder. And then, you know, we speak to founders. And so we wanna hear from from their side of the story as well. What was that pitch like with the broader community? They’ll usually tell you, you know, no one would even pick up the phone for us. Right? No one would respond to our emails.

And, you know, Cyan or Harry, you know, sat down and they had a a blink in their eye and and they saw the idea. They believed in us before everyone else did. We really wanna understand the the depth and and granularity of those stories.

Harry Stebbings

Do you

Miles Dieffenbach

often get bad references? Yes. Do you? Yes. Wow. The way we think about referencing, you know, when we do a new fund, we’re looking for at least 20 references calls, right? 20 reference calls. And we’ll take five from the GP, which those are the worst references we’ll get. Right? Yeah. Miles was great. Miles was great. Yeah. Yeah. And by worst, I mean, they’re gonna be patting Harry on the back. Right? He’s also the godfather of my children. He’s my best friend from school. So, you know, those ones we don’t spend too much time on.

The golden references are are the offshoot references. And thankfully, venture is such a networked community that you spend enough time in the asset class, you’re able to to build those networks pretty quickly. And and so we’re we are proactively trying to shoot

Harry Stebbings27:28

other people’s perspectives on other GPs? Like venture to venture? Does that name one?

Miles Dieffenbach

Perspective on strategy, not so much. We are very much trying to find interpersonal risk and partnership risk. Those are two things that we are really digging. We wanna know, are they a good person? You know, have they created a bad persona amongst other people? Have they wronged others in a in a pretty malicious way? And and then understanding the partnership dynamic, things that they will never tell us on a phone call. We could ask them blunt to their face. Is there any risk in the partnership?

Do you you know, does Harry like Sally? Does you know, how is the mesh? Oh, that’s incredible. This is the the best partnership ever. We love each other. We sit down every day. We we’ve never disagreed on a deal. We spend a lot of time trying to understand that partnership risk.

Harry Stebbings28:14

What is the number one reason you think partnerships break down?

Miles Dieffenbach

Incentives.

Harry Stebbings

Incentives and who’s working the hardest, those are those are gonna be the two every time. Do you think we have a generation of venture firms where the partnerships are staying together for the kids?

Miles Dieffenbach

I I mean, I I personally think you’ve seen partnerships what’s the word I’m looking for? Mean Blowed? The amount of change you’ve seen at partnerships over the past two years is the most I’ve seen combined in my eight year history as an LP. How do you justify that? How do you reason that? I think there’s a lot of reasons. I think I think one, folks who had made a lot of money didn’t wanna deal with the crap that you’re dealing with today. Right? These, you know, three years of of no liquidity, you know, dealing with broken cap tables, dealing with founder transitions.

Like, it’s just a lot of hard work, gritty work that if you made a lot of money, why do it? I think two, if you were a newer GP, you know, you were promised a certain amount of compensation for your role, and part of that was variable carried interest. That carry has evaporated, right, as performance has come down. And, you know, now you’re you’re getting paid 70% less than than what you thought you were. And so why not start fresh? Why not start with a new book, or why not start my own firm?

Harry Stebbings29:24

Why not start your own firm? We’re seeing a lot of spinouts too. Do you love spinouts? I think they’re drastically overrated.

Miles Dieffenbach

Yeah. We historically have not done many, if any, spinouts. Call it from, yeah, you know, your your tier one, maybe clean spinouts. Right? I think we’re less. Think Probably we’re less. Yeah.

Harry Stebbings30:49

It’s the one thing we’re more proactive as Americans than Yeah.

Miles Dieffenbach

So like we really need to be

Harry Stebbings

sure who we’re partnering with. You know what’s fascinating about that, given the duration you mentioned there, is also LP churn. LP churn is freaking real right now. Yeah. Oh my god. How should GPs think about LP churn?

Miles Dieffenbach31:09

One, it’s good to have a relatively diversified LP base, which protects you from that. Right? So a mixture and not everyone can choose their LP base. Right? Sometimes it’s it’s, you know, take yeah. Whatever Take money’s green. Right? But, like, in a in a best case scenario, you’ve got a mix of endowments, foundations, family offices, founders, maybe a couple GP checks in there from from some venture funds. A mixture of folks who are aligned to your long term vision. And and inherently, stuff’s gonna happen. Right?

Like, you know, folks are gonna have a liquidity crunch, a family office, the the family’s gonna say, you know, fuck venture. We don’t wanna we don’t wanna play in this asset class anymore. Like, you’re gonna have some things come up Being open open to that and trying to still be as good of a partner as you can is pretty important.

Harry Stebbings

How much is the right amount in terms of concentration from your biggest investor? Anything more than 3030%? Mhmm. Wow. Yeah. I’ll never forget Mickey Malker, I think it was telling me 10%.

Miles Dieffenbach32:07

Yeah. I mean, case scenario, you don’t have anyone more than 10%. But if you’re raising a $50,000,000 fund or a $100,000,000 fund and you can, you know, secure a $10.20, $30,000,000 check-in their long term line, that still makes sense, but best case scenario, yeah.

Harry Stebbings

Yeah, was lucky we did 10% on the back of Mickey. Yeah. Fantastic advisor. Okay, so totally get that. And so we have the 10% there. In terms of stability, I was always taught that endowment funds are the blue chip for stability. Is there a rubric? How do you think about advising managers on stability amongst different asset class of LPs?

Miles Dieffenbach

Yeah. I mean, I think you’re right historically, endowments being quite long term oriented. The endowment model in The US today has headwinds, in particular certain endowments where they’re gonna start getting taxed at, call it, the 8% range. That’s five endowments. That’s a headwind to their model, to a sense. It’s not as bad as the 20% that it was gonna look like a month ago. Would you expect them to cut positions, downsize? It’s all gonna depend what they do with their draw. Right? So What does that mean?

So an endowment is mandated every year. 5% of the endowment goes to campus to support scholarships, professors’ salaries, buildings. And that can range anywhere from, call it, 4% to 6%. But most endowments have stayed right at that 5% number forever. But if it turns out we’re gonna start getting taxed 8%, you know, we could lever our drawdown, you know, to four and a half percent versus 5%. Because the real risk you run this endowment is eating into the purchasing power in the endowment. Right? The the way an endowment works, you got a 5% draw every year.

And then inflation, let’s call it 3% for higher education here in The US. So just to maintain the corpus, the purchasing power of that endowment, you need the eight percent return. Most, you know, endowments are targeting eight eight to 10% return over the long term, ten or fifteen years. And so when you start getting closer to that number, you run into some real risks. And so it’ll depend on what they do with their draw. You know, if they don’t, reduce the draw, I think venture broadly will be okay.

It’ll still be the idiosyncratic headwinds of there’s just no capital coming back from venture. That’s the headwind to the asset class for LPs re upping today.

Harry Stebbings34:14

What do you advise managers in terms of closes? First closes, many closes, one close?

Miles Dieffenbach

I mean, I think GP should be spending the least amount of time fundraising as possible. It’s not your job, and you make your money investing. But some people are not as fortunate to just do the one and done closes. Right? And so I think it’s very much dependent on your situation. Best case scenario, you have a very timeline. You know, we’re gonna do our first close here. You know, lining up your LPs and and being sure they’re committed to that process and and doing work on the sub docs and the legal work prior to that, really important, and just setting clear timelines.

Do you mind if a manager’s ever sold part of the management company? Yes. Absolutely. Massive red flag

Harry Stebbings

for us, and I would say most institutional LPs. I’m not gonna speak for everybody, but No, it is. But it’s just one of those ones where I see so many first time GPs bullied into it by one large investor, often a family office, and then really regretted over time. It’s the one thing where I’m like, no, no, no, never.

Miles Dieffenbach35:09

The magic of a partnership is the care and interest. And you are now giving that care and interest away to a silent partner who is not going to be, like we said, grinding and, you know, taking a 100 calls a week and and working 996 like you. Yeah. Baby. And so how do you feel when you deliver incredible returns when a silent partner is getting, you know, a decent chunk of that care and interest? It’s the problem.

Harry Stebbings

How do you think about the rise of multi surge platforms, dude? You mentioned there the eight to 10 that these kind of endowment funds in the endowment model kind of relies on to keep that kind of corpus the same. Everyone says, oh, well, it’s gonna be fine because, basically, yes, they will have worse returns being multistage funds, eight to 12% say, but the LPs they have are different now, and that’s good enough for them. How do you think about that?

Miles Dieffenbach

It worries us. The funds are extremely large today, and I think it’s hard to assume the same returns you had from 2010 to, call it, 2017. I think, you know, Masa and SoftBank, I would I would put as the the the flag in the ground Vision Fund one when when all the other venture firms saw that as the opportunity to just absolutely scale their capital base. It’s wrong to assume the returns you had from from those years where most all venture funds were basically raising a $400,000,000 years a fund, all the premier funds.

And maybe they had a maybe they had a 400,000,000 growth fund attached to it. But the fund size has stayed basically the same for a decade. And so it it worries us tremendously. Do you think they will post as good returns then? No. No. I’ll walk you through a very simple math that other LPs can can put in their back pocket. But for for how we underwrite, you know, these big funds now today, simple math, but but I’ll walk you through it. So, and this is a live manager.

I won’t share their name, but this is a, you know, a manager we underwrote a year ago. So we’ll look at their fundraise. So this manager was was targeting a $7,000,000,000 fundraise. And so what we do is we do a dollar weighted entry ownership across their different funds. So this had a billion dollar early stage fund, a 2 to $3,000,000,000 growth fund, and the rest was an opportunity fund. And as an LP, most LPs have to invest para pursue across those funds. So, like, equally as a percent of the fund across those funds.

And so inherently, your your smallest check is gonna be to that early stage fund. Your largest checks are gonna be to the growth and opportunity funds. And so what we do is we look at the early stage fund. So this fund, call it, had 15% entry ownership for that fund. The growth fund had about six to 7%, and the opportunity fund had about two and a half, 3% ownership. And so we we dollar weight that on the funds, and then we look at our check. What is the average entry ownership our check is getting within those funds?

And so this fund was about 5% across those vehicles dollar weighted. And so the very simple math there is 7,000,000,000, you know, divided by 5%, which is a 140,000,000,000. Right? So that’s the enterprise value. That is the market cap of companies that the size of those companies they are just deploying that fund into, a $100,140,000,000,000. And so for us, when we do a venture fund, our target is a four x net. That’s our goal. And so if we want a four x net, these funds, you know, the early stage funds charge two and a half and 30.

Growth funds charge two and twenty. So you’re gonna need a six x gross at least to get a four x net on that fund. You know, 140,000,000,000, you know, times six. You know, you’re close to, you know, 800,000,000,000 of market cap needed to return a four x net for those multi stage funds. Now for reference, 2021, the best exit year of all time, there was 850,000,000,000 ish of market cap exit value from that year. Okay. You need an entire year of IPOs in M and A just for this, you know, one manager.

Clearly, it’s gonna be broken off off of numerous years, but it’s a that’s a staggering number.

Harry Stebbings38:44

My counter to you there would be you’re assessing performance today on the current outcome size, not projecting forward to what it could be in ten years’ time. In other words, now we have $9.10, $1,000,000,000,000 companies. We didn’t have any ten years ago. The outcome sizes are so much bigger than they’ve ever been. If we project forward a decade, there’s a very real chance that Microsoft is worth 10,000,000,000,000. And actually, we have $50,000,000,000,000 companies. If that’s the case, we could see that play out.

Miles Dieffenbach39:13

It could. I we we we acknowledge that we could be wrong, and SpaceX and OpenAI and Anthropic go public at at trillion dollar nations. What we look at and like I said, this is is backwards looking data, but we’ll give you a few data points. There’s been $1,150,000,000,000 dollar IPOs venture backed. 11. The two largest venture backed IPOs ever were Facebook in 2012 and Alibaba in 2014. So we’ve got a decade, one of the greatest venture bubbles of all time, 2021, and we still haven’t had a bigger exit than we were getting in 2012 and 2014.

So so my guess is that a $100,000,000,000 IPO over the next ten years is still going to be a generational outcome. And so the question I throw back is, you know, do you think there’s gonna be ten, twenty, $100,000,000,000 plus IPOs? I do not think so. You You you look at the trillion

Harry Stebbings40:04

I think there’ll be ten, twenty, way more actually, $100,000,000,000 plus outcomes. Because I think what what I’m finding so worrying right now is, bluntly, there are so many exciting companies that I would love to be a part of, whether it’s your Anthropics, whether it’s your OpenAI’s, whether it’s your SpaceXs, can’t get access to them given the extension of private markets. These are all companies that would be in the $100,000,000,000 IPO price range.

Miles Dieffenbach

Oh, Stripe, SpaceX For sure.

Harry Stebbings

OpenAI. Those are all $100,000,000,000 companies today, for sure. But where does the rubber meet the road there? Some at some point, the liquidity can has to be passed to someone who goes, fuck it. I need it.

Miles Dieffenbach

Yeah. And and even still, 2021 is a is a good learning opportunity. Most, if not all, call it except maybe Palantir and a few others, these very large 2021 IPOs are down significantly still today from that price. These were the greatest venture assets of that vintage. And so to say that it’s a guarantee that, you know, OpenAI is gonna be worth, you know, 1,000,000,000,000 in in five years, There is a lot of risk involved in that. And so what we posit back to our team is, you know, what is the margin of safety that, you know, great investors, Warren Buffett and Benjamin Graham kinda coined in these terms?

What’s the margin of safety we want investing in a fund for what we have to believe in to achieve our desired return? I would rather not have to believe in 800,000,000,000 of market cap IPOs and M and A transactions to get a forex net versus other funds where maybe we have to believe in maybe it’s a billion dollar fund, but kind of the entry ownership is 10%, and and we have to believe in, you know, ten, twenty, thirty billion. Right? And and anything above that is where you get the real alpha.

And and so it’s it’s hard for us to imagine on on these very large multi stage funds having that kind of alpha.

Harry Stebbings41:41

Who is the single best performer

Miles Dieffenbach

to you at scale? Index. I think they have to be. I mean, the performance they’ve put up in the last twelve months is I’ve in a in a market that is as bad as you hear in the news and from all the folks on the podcast, the performance that they’ve delivered and are are delivering here in the future is unbelievable. I mean, largest shareholder in in Figma, largest shareholder in Dream Games, largest shareholder in Wiz, second largest shareholder in Scale AI, Revolut. It’s unbelievable. And and I give Index all the credit in the world for not scaling.

They even reduced their latest fund size. They reduced it after the 2021 era. The credit I give them for not ag they could raise as much capital as they want to, and they don’t. They they are the most performant driven culture that we see. And so I give them a ton of respect for that.

Harry Stebbings42:32

Danny has been unbelievably good to me since I was very, very young, 18, 19 years old, which I think is testament to him helping the next generation amazingly. My question to you on the back of that is do you think they’re in for a hard time and not singling them out? But the funds that are in that billion to 2,000,000,000 range, where they’re sizable, but they’re not that sizable. When you’re GC, light speed, soft bank, your cost of capital is just like to throw out a 10,000,000 check.

It’s like, thanks for the coffee. When you’re in the index range, you’re not one or the other. You’re in the middle ground. How do you assess and think about that?

Miles Dieffenbach43:08

I absolutely think they will continue to survive and thrive at that range. I think you have enough capital to write big checks. Right? So you can participate in the abnormally large seed series a, series b’s, and you have enough and so excuse me. It’s a limited amount where you can still drive extreme parallel outcomes within the fund. And I think performance driven culture and and what that brand stands for being, you know, the backer of some of the most generational companies of all time. You had you had Vlad on the show recently.

Should I ask him why did he go back to Index for his new, his new math company? Right? He could have gone to probably a cheaper source of capital. The guy Nikki told him to fuck off.

Unknown

He

Miles Dieffenbach

probably could have gone to a cheaper source of capital and raised from Masa at SoftBank or general analyst or or you name it. Right? But

Harry Stebbings

just to be clear, you don’t actually inherently believe in that fund size range. You actually just think index is so good. And and what do you mean? You don’t love the 1 to $2,000,000,000 fund sizes. You just think the index are so good that they’d make anything work.

Miles Dieffenbach44:10

Well, I mean, most people, right, most funds can’t raise 1 or 2,000,000,000. Right? So so most are inherently gonna be in the lower end. And then the ones that can, they’ve had good enough performance. Most of them scale. They? Most of the big funds have not got great performance. I think so. I I we’ve looked at all of their returns. But, I mean, these these people deserve to raise larger funds. Right? I mean, they’ve they’ve produced really strong performance.

Harry Stebbings

So when do you say enough’s enough. I’m out. It’s too big. It’s not my game.

Miles Dieffenbach

One, we lean on the math where even if you do own 10% of a generational $20,000,000,000 outcome, which is still gonna be generate know, Figma, generational company. It’s probably gonna we’ll see where it prices. Call it 20 to 25,000,000,000. You know, if you’re a GC, their last fundraiser is 7,000,000,000. Say you own 10% of a Figma, which is a generational company, 2,000,000,000, you know, they’re gonna take 20% of that. I mean, you’ve returned what? Point 0.2 x? You need you need you need 15 Figmas. It’s my it’s mind boggling to me.

Harry Stebbings45:08

I mean, my favorite also was Wizz, which was obviously a $3,031,000,000,000 dollar outcome, you know, the GDP of the country. Yeah. And it returned a third of Insight’s fund. Yeah. And you’re like, oh, I’d be really pissed if I was the guy that led Wizz, and I’m like, oh, thanks for the fact. Sure he’s I’m sure he’s happy enough that he still did it. I listen. I’m sure he is, but I’m just like, oh. Yeah. So you go back to core math. We go up we

Miles Dieffenbach

go up to core math and really what we try to understand this is more qualitative, but at some point, the alignment breaks, in our opinion, between the GP and the LP. And when you think about let me let me put this clearly. I I don’t ever blame a GP for raising bigger funds. I I am a I love incredible business models. I study. I live. I eat. I breathe investing. These business models these GPs are creating are some of the best high margin businesses ever created, and they’re stacking funds.

So you think of a firm that has raised, you know, 7,000,000,000 this fund. They raised 5,000,000,000 in their prior fund. They raised 3,000,000,000 before that. 15,000,000,000 of capital. They’re charging full fees on all of that. Right? So they’re making, call it, 300,000,000 a year a year in fees. For often, like, five or six partners Yeah. Where 80% of the fee stream goes. Yeah. We really try to understand has the magic bond been broken between GPs and LPs, which, you know, leads us to, you know like, we think the fee structures need to change to accommodate for that.

Why do you think the fee structures need to change? Because when you’re investing at that size and scale so when you’re when you’re a fund that big, you are inherently setting up for 100,000,000 checks into very well established, well run, well oiled companies. You are essentially acting as a long only public equity investor. Right? You’re not actively, you know, managing the company. They’ve they’ve got their own, HR team. They’re doing all their own hiring. You know, they’ve got a a 20 person product team. They’ve got a 10 person BD team.

Like, this is a well oiled machine. These are what public companies would have been ten years ago. And so you’re charging two and twenty on basically passive investing. Right? You’re not you’re not actively managing most of those positions for the most of the time.

Harry Stebbings47:11

I don’t think the early stage managers are actively managing, and I don’t think they should be. I work with many, and when they actively manage, they do not get the right decisions. They push managers to do things they shouldn’t do. They push them to go enterprise before they should, push them to do more products, push them to scale faster, take more cash on because they want markups. I think you want passive.

Miles Dieffenbach

Yeah. But you you still need the fees for that, you know, in a in a $400,000,000 fund. Right? You need a team to go out and meet all of these people. You need an office to bring these people in. So, like, with a $400,000,000 fund, Harry, like, you’re not gonna become a billionaire off of that. Right? Sadly. Sadly. Yeah. If you had 15,000,000,000 in AUM, which, you know, God bless, I hope you do someday, you’re gonna become a billionaire off that off those funds. Right? And that’s the difference, right, is is you need that capital as a true early stage venture capital firm.

They’re utilizing it.

Harry Stebbings48:01

But so I get you totally, but fundamentally leverage is everything. And these firms can raise the money Yes. Without changing the fees. So they not just go, dude, thanks for the advice. Fuck you. Yes. Yes. Absolutely. So we’re never gonna get this fee structure change. I I I you know, the the performance Like, do you puke when you see three and thirty? Yes. Yeah.

Miles Dieffenbach

Yes.

Harry Stebbings

And that’s

Miles Dieffenbach

nuts. Yeah. It’s remarkable. Right? But you But you suck it up and peg it. This is this is this is the one I the Renaissance tech. Right? You know, the best hedge fund of all time. They were so good that at one point, I think they were charging, like, 60 or 70% carry and, like, 20% management fees. And they kept increasing it. They kept increasing carry and increasing managers to incentivize their LPs to get out of the fund because they wanted all the capital for themselves.

Like, the performance is so good that folks would would pay them whatever they wanted to be in that fund. And so what I what’s hard for us to understand today is, like, I do I share the performance data with you. The performance is you don’t look at that data on a $7,000,000,000 fund and think, god. Like, we will pay whatever we need to get into those funds. And so what our hope is and and the hedge fund industry went through this cycle after the global financial crisis where there were thousands upon thousands of hedge funds.

They were all charging two and twenty. Performance was incredible for a very long period of time. All the funds increased competition. Returns came down. The global financial crisis happened, and you had a complete bottoming out of the hedge fund industry, which obviously rose to these incredible multi strat hedge funds. But fee structures changed dramatically from o five to o seven then at 2010 to 2013. What will fee structures be in venture in ten years’ time? If you’re raising, you know, that early stage fund, the core $500,000,000 series a fund, Charge us two and a half and and 20, and if you’re good enough, two and a half and 30, we’re okay with that.

Right? But those those growth funds that are really for scaled businesses that are mature assets, like, you should be charging long only public equity fees, which are one in 10. And if you really love your LPs, it’d be it’d be it’d be zero in 10, but or budget based, right, based on based on the team. But 10% carry. I mean, that’s that’s the number for a a passive long only investor. Going back

Harry Stebbings50:09

to the size and we scale out of you, so to speak, when you’re too large, Is there ever a case for LPs where it’s like, you know, you’ve made us so much money before, even though we may not believe, like, we’re in for loyalty.

Miles Dieffenbach

You know, think certain LPs, yes. Us, no. I mean, we are in an extreme performance driven culture. But if

Harry Stebbings

a fund does you a six or a seven x net, which is amazing, and then they raise a big ass fund, which most would do post that great number, do you ever like, we’ve gotta come back and you should have a six, seven x net for us?

Miles Dieffenbach

It depends. It depends on it depends on how different that fund is and how different the strategy is. Right? And it very much is dependent on the on the situation.

Harry Stebbings

How do you think about I have a lot of LPs where they’re like, I want to be an x brand name, and I’m like, that’s not the best risk adjusted return as an opportunity cost to your cash. I think you should be in one of these three names. And they go, no. No. You don’t get it. I don’t care about the performance. I just wanna be in Andreessen, in Sequoia, in Index. How do you respond to the brand driven nature of LP allocations?

Miles Dieffenbach51:10

I get why. I think it goes back to a, you know, an incentive problem in the LP industry. For me, personally, I could be your janitor here at 20 BC offices, and I’m gonna be the best janitor you’ve ever had. These are gonna be the cleanest floors you’ve ever had. This is gonna be the cleanest table you’ve ever had. If my name’s gonna be on it and I’m gonna be part of it, I am gonna put my a 150%. But maybe there are certain people that are incentivized to park capital in brand names that won’t get them fired.

Right? No one gets fired buying IBM. Right? That’s the classic quote. That’s a problem. And and frankly, are For you, is

Harry Stebbings

it easier for you at CMU to get a check done into x brand name versus saying, hey. I love Cyan. I’m gonna go out on a limb and get long journey in?

Miles Dieffenbach

You know, we have an investment committee that we go to for approval. That’s our governance committee. And we write a detailed memo for any re up or any new name in the portfolio, and we gotta present our merits and concerns. But we’ve educated our governance, which is such an important part of of any LP that’s wanting to get into venture, having the proper governance set up to allow you to take these very long term bets. We we educate them on the math and the risk adjusted return of the funds and the fee structures.

And so, you know, they’re very understanding of of our strategy and and how we think about the world. Do LPs

Harry Stebbings52:25

not realize that some managers are doing thirty, forty, fifty million a year in fees in terms of, like, back to them at the large multi stage? And do LPs hate it?

Miles Dieffenbach

I think certain LPs choose to just not even think about it, frankly. And and so certain LPs, you know, such as ourselves, I will never blame you, Harry, for raising $10,000,000,000. Like, I will give you a But you’re not gonna write me 1,000,000,000? No. Dude, come on. No. Come on. No. I thought we had such a good one. I’ll never I’ll never blame you for doing that, and I’ll never blame a GP for that. I’ll never bash a GP saying, oh, how dare you? Right? It’s the market.

Like, and you’re you’ve obviously done something well enough that’s allowing you to to raise that capital. It’s it’s our choice to determine is is that the right place risk adjusted for our capital?

Harry Stebbings53:07

I think not enough people see this as a game of levers. And what I mean by a game of levers is, like, you can have a a smaller fund, but deploy it more quickly and actually kind of play that lever game to actually just amass the fee game and the AUM game. How do you think about temporal diversification? We saw a real shift from three year deployment to two year deployment.

Miles Dieffenbach

How do you think about that? I think it’s very important. It all stems from what did that GP tell you they were going to do? If they told us that this, hey, this is a two year fundraise cycle. We’re investing it in two years, and they come back to us two years two years later, we’re okay with that. We underwrote that. Right? But if this is a three to four year investment period, and you told us it was gonna take three to four years, and you come back in two years, then we’ll have some some questions for you, and and we’ll want to work with you to understand why.

Know, what’s what’s the reason? Because time diversification is extremely important. What happens if they’re slower? Is that bad? No. I don’t think so. Because a lot of people say, oh, play the game on the field. Play the game on the field. Right. I think certain folks would have in it today bear hugged their GPs for not playing the game on the field in in 2021. You know, we’re not investors, but Marc Sutskever, I give him all the credit in the world. He’s been in the game for a long time.

He saw 2021 as an insane period, and he strip sailed, like, majority of his portfolios and his funds for a very good price. DPI in the pocket. Like, all of his LPs are are are bear hugging him for that. Brutal market. Tough market.

Harry Stebbings54:30

Brutal market?

Miles Dieffenbach

Yes. Look at you look at the data both at European venture fundraising and US fundraising, we’ll see what q three and q four will look like. But in The US, this is gonna be the lowest year since ’17. In Europe, same. So it goes back a bit further maybe to 2016, but it all goes back to liquidity.

Harry Stebbings

What is the takeaway to that? Is that the lack of liquidity? Is that the concentration of capital to a few number of names you’ve scaled and just eaten up more of that dollar allocations? What is the kind of conclusion from that?

Miles Dieffenbach55:00

A lot of different reasons. I think the the main reason is liquidity. 2002 to 2004, you had more dollars raised in the public markets from IPOs than you did from 2022 to 2024 and with an asset class 10 times the size. And just for reference, like, .com bubble, it took you thirteen years from the peak of the .com bubble to get back to par on your public equity position in the queues or or the Nasdaq. Like, that was a real downturn. It it makes, you know, obviously, 2021 look like pennies.

And you had more IPOs raised the three years following that. And so something clearly is broken in the industry given how bad the liquidity was over the past three years. And I think what really frustrated LPs is you watch the public markets continue, especially the factor exposure of technology, has done tremendously. And I am not a believer ever that the IPO markets are closed. It’s purely a function of price. Right? That is the problem. Folks paid significantly too high prices during the peak. Growth has slowed down.

You know, there’s not much of a market for a 100,000,000 ARR SaaS company growing 15% with breakeven free cash flow when you can buy Microsoft growing top line at 14%, growing earnings at 17% with real GAAP profits buying back 1% of the company every year with strongest competitive moat in the world. People get frustrated when it’s like, oh, no one’s gonna give me eight times ARR, 10 times ARR for this business. Well, like, look at the alternatives. What investors could invest in of a similar factor to your company?

Harry Stebbings56:28

I think PE is not coming to save us like everyone thinks it will. I think people always also have lower expectations of what it takes to buy good companies. Like you said there, you need to be 20% grower and profitable. And there are so many companies where they’re bluntly at 10 and not profitable. That’s a tough spot to be in.

Miles Dieffenbach

Yeah. I mean, we we look at the data. Historically How close do you get to the underlying portfolio companies? Very close. We ask for trending revenue, trending gross profit, and trending free cash flow for the top 10 NAVs, every fund of we underwrite. Does every LP do that?

Harry Stebbings57:01

No. No. Definitely not. So when you look at that, do you think you are able to predictably tell good managers in real time? Yes. Because they’ve got great assets. Even though you have the ones like Circle, say, where for years it’s like, maybe, like, okay.

Miles Dieffenbach

Yeah. And then it turns into an absolute freaking monster. There’s there’s always going to be an extreme distribution retail outcome in these funds that is gonna be impossible for us to underwrite. Right? And that’s the beauty of of venture capital. So we we acknowledge that. We’re not gonna you know, our valuation of the company, we know it’s it’s probably gonna look quite different three, five years down the road, but we just wanna know, are these good fundamental businesses that are growing in value and that give us conviction in that these are gonna be real durable businesses one day?

Harry Stebbings

How did you analyze the Yales and the Harvard’s doing sales without venture portfolios?

Miles Dieffenbach

I think there’s a lot of factors that go into it. One being the headwinds we talked about to the endowment model. But, know, you look at Harvard selling 1,000,000,000. It’s a $50,000,000,000 endowment. I mean, like so so 1,000,000,000, it’s not, like, some monumental thing for them. That’s probably just a refresh of the portfolio. But, like, think I there’s real lessons learned. Mean, there was an article out today about Yale and and Calpers. Calpers was the buyer, you know, a piece of Yale’s portfolio. And and, you know, I was on the phone with our CIO this morning.

You know, just take a step back. We had a venture capital fund that we committed to in 2012. This fund was in its tail life, thirteen years old. We hadn’t looked at this fund in three or four years. There was one asset left in the fund. It was basically fully realized. We have a great analytics team and our analytics system that tracks our underlying portfolio companies, but the company have to be over a million bucks in NAV to us for us to be it in our system.

And so this company wasn’t even showing up Circle, the company, we’re talking about in our system because it was below a million Flash forward, you know, they were holding it, the manager, at a at a 30% discount. Like I said You saw it on TV. No? Well, you said I was reading the s one. Yeah. My my son woke me up one morning, and I was up early. And so I’m reading the s one kind of as just, you know, for fun, I’m looking through the cap table, and I I see our GP on there.

And I’m thinking, oh my gosh. And so I go and start looking through the quarterly reports. And so they were holding at a 30% discount plus or minus to the last round valuation, which was I think their last price round was around 5,000,000,000, you know, three and a half valuation. And, you know, you look at at Circle, and it’s a $50,000,000,000 company today. This is a thirteen year fund that is essentially gonna do an extra three turns on the fund in its thirteenth year. Unbelievable. So the article with Yale and and Calpers was Calpers bought a very large piece of their portfolio of which part of it was general catalyst, and Circle was the the largest position in that fund.

And essentially in, you know, a two months time frame, I I think it said in the article they bought 500,000,000, you had a $100,000,000 write up from Circle alone. That’s the risk of selling secondaries as a long term venture investor is that you’re gonna have these crazy right tail outcomes in the fund that could come to fruition at years eight, nine, ten, eleven, twelve, thirteen that you’re traditionally even if I said to Chuck, I mean, like, I’m not that smart. Right? And but, like, we would under we would have underwrote Circle if we were looking to sell that fund a year and a half ago, And we probably would have sold.

Like, who would have guessed that Circle was gonna trade at a 100 times EBITDA in the in the public markets and that stablecoins in a year and a half were gonna be, like, the hottest sector in crypto? You could not have predicted that. I’d imagine Yale probably did the same. They probably underwrote that, and they’re like, there’s probably not a juice not a lot of juice left to squeeze here.

Harry Stebbings60:32

I have friends at Yale who I’m crying for, and I have friends at Calpers who I’m crying for with happiness. Well, I’m sure I’m sure, you know,

Miles Dieffenbach

I’m sure Yale would do well. That’s a fantastic team with a great portfolio, but it just goes to show that the risk of these these fat tail outcomes in these funds. Dude,

Harry Stebbings

10% discount, I think, was the reported number. How did you analyze that? Higher than you thought? Lower than you thought? Much higher than I thought. You thought it was higher? You thought wow. No. Sorry. Much wait. I I think it’s a good deal for a great deal. That’s what I meant. Yeah. Sorry. Yeah. It’s low. Yeah.

Miles Dieffenbach61:03

Fantastic deal. I I you know, not knowing the underlying GPs in that fund and not knowing the mix between, you know, buyouts, real estate, or or venture, you know, I would have guessed. You know, Yale’s got incredible managers in their portfolio. Right? So they’ll have some pricing power. I would have guessed 20%. You know, that would have been probably the number that I would I would have put on the board. Do you think we will see many more of these large institutions doing strip sales of their venture portfolios?

I’m not sure. Certain ones with with real liquidity needs, I think they’ll have to. Right? And so that’ll be a forcing function. But still, I mean, there there there’s not a ton of secondary capital out there that’s gonna be able to swallow all of that NAV. Right? So if every if every, you know, billion dollar down comes out and says we’re selling 10% of our venture book, I mean, the pricing there, it’s a supply demand market. Right? There’s only so many buyers.

Harry Stebbings

You said about kind of the liquidity problem and that kind of being a driver in terms of the brutality of the fundraising market. Scale, Dream Games, Figma, Revolut, Secondaries, Circle, Coreweave, Hinge Health, which IPO’d, Chime. Are you just drowning in distributions now?

Miles Dieffenbach62:08

We are thankful to say that we’re now self funding in our venture book this year, which is which is give us a round of applause. I mean, it’s the first time since 2021. I think that’s So that’s a positive. But on the flip side, there’s still a lot of, liquidity that, sure. It’s been announced, but, you know, the whiz deal, right, that’s gonna be a a q one twenty twenty six event. Right? That’s gotta go through FTC approval. Figma hasn’t gone public yet. You know, Dream Games said in the article they’ve they’ve they’ve gotta get European approval for Do you think 2026 will be a year where that liquidity really hits?

Yes. And and what’s exciting me is and this is a crazy statement. Right? So it’s not that I agree with the statement, but No. It’s just me and you. Yeah. Exactly. For for the longest period of time, private market capital was cheaper than public market capital, which is the most mind boggling statement as, like, a fundamental investor ever. Like, it’s hard to fathom that. Right? But that was the case. That is why the best companies in the world didn’t go public because you could get a cheaper cost of capital.

You didn’t have to do quarterly earnings calls. You didn’t have to go through all the hoops to go public. Why would you go public? We speak to founders. Like, we understand why they why they don’t wanna go public. But the public markets are now pricing risk very differently than they have over the three year the last three years. You look at Circle. You look at, you know, Nebius. You look at CoreWeave. You look at Palantir. You look at Cloudflare. Like, these are all businesses trading at extremely healthy multiple multiples.

So my message here to all venture capitalists, now is the time. Please take your companies public.

Harry Stebbings63:32

My question to you on the back of that is, Rory O’Driscoll from Scale always laughs at me. He says, my favorite thing about Harry, he goes, yes. So what about me? And I specialize in that. So what about me? If we have this liquidity dropping in ’26 the year, does that mean ’27 you’ll have a load of LPs flush with cash coming back to the venture asset class going, let’s fund some more funds? I mean, inherently, it will help clearly.

Miles Dieffenbach

And particularly, as as maybe folks take that But it’s needle moving on that already. I mean, it’s been such a dearth of liquidity over the past three years that, like, one year is not gonna solve the industry’s problem. Right? So we’re gonna need, like, multiple years of really good liquidity to get back to a a normal state. So, like, there’s still a lot of wood to chop here, but it’ll help. Right? Undoubtedly. Absolutely. Do you love thematic funds like every other LP does? We are agnostic.

We do not have a mandate or a rule saying, you know, we’re only gonna do thematic funds or we’re only gonna do generalist funds. We’re a best athlete. So when we find really great partners aligned with us for the long term who we think have an incredible skill set that aligns with what they’re trying to do in the fund, whether that’s a generalist fund, whether that’s a sector focused fund, we’ll do it. And so, I mean, inherently, you know, we’ve done one new sector focused fund over the past three and a half years.

And so it hasn’t been a huge part of our portfolio, but we are absolutely open to it. What was the best ever performing fund you’ve been a part of? We had a a a fund out of out of China that produced over a 20 x net return to to LPs.

Unknown65:08

Wow.

Miles Dieffenbach

I

Harry Stebbings

hope you sent them a Christmas card. We did. Yeah.

Miles Dieffenbach

How do you think about China? It’s a very high bar for us today and a very hard place to invest. I mean, there there’s a couple, you know, really big headwinds. One is The US executive order, you know, mandating US dollars can’t go into artificial intelligence or semiconductor related companies or defense companies there, which we completely understand and align with. But the big problem what’s so unique about the China venture capital market that maybe a lot of founders or maybe LPs who haven’t spent time there don’t know is that in China, these GPs raise USD and RMB funds alongside each other.

And and these RMB funds are from local governments and municipalities. And most of the time for the past fifteen years since the China venture industry has been around, those funds were parapasu. They they mostly invested in the same securities. That isn’t the case today, especially now that US dollars cannot go into these AI companies, which I at the last time I checked, 70% of these deals in The US are AI companies. Like, mean, it’s everything. And so that’s a big alignment issue. Right? What are we getting exposure to in that fund?

That’s a big worry. Totally

Harry Stebbings66:13

agree and share that. Super interesting. I’m actually more bullish on China than most people give credit for.

Miles Dieffenbach

Yeah. I mean, we’ve got we we have incredible partners there that we’ve had, you know, for a long period of time that are extremely hardworking, extremely smart, and have been great partners to us. It’s a hard market today. And and frankly, you know, a lot of the best, you know, Chinese founders have have chosen to raise elsewhere, whether in The US or Singapore or London. It’s a tough place. We mentioned

Harry Stebbings

the liquidity. The thing that’s also kind of weird and paradoxical to think through is you mentioned the public markets players just having absolutely ripped. You see Meta throwing out 14,900,000,000 for scale. It’s like forty five to fifty days of free cash flow. It’s really not very much for them. You know, Google’s buying windsurf. We all it’s like a coffee. They put $3,500,000,000 into Ray Ban at the same time when no one paid any attention. My point being, we have these kind of opposing worlds of liquidity, starvation, or drought, and then the glut of these public markets players who just are playing with market caps that are 2,000,000,000,000.

How do you think about that?

Miles Dieffenbach67:13

If Wizz gets approved, every other large max seven company is gonna see a green light in regards to making big splashy acquisitions again, which is a good thing. You look at Google, Microsoft, Amazon, and Meta combined. I mean, they’re doing 600,000,000,000 of operating cash flow, just cash coming off the company every single year. And I think they would much rather make very strategic acquisitions than buy back 50 basis points of the company. Right? The the big worry that I think those companies see today from our purview is that the AI landscape is changing so rapidly that the the twelve month time period it could take to go through a review to get that acquisition done, that company could be obsolete in twelve months.

Dude, you saw this with Windsurf. It changed a lot in a couple of months. Lots of of of great hot AI companies have have been very hot and then not hot. You know, Stability AI. You know, lots of companies have gone through these waves, and there will be many more. You know, that chance and you look at the whiz deal, there’s a 10% breakup fee there. Largest breakup fee ever for an M and A transaction. So, you know, say that someone else wants to do a $30,000,000,000 acquisition Perplexity, and Perplexity says, oh, we have to wait twelve months.

Our board’s gonna recommend a 15% breakup fee. Now will those big fund you know, will those big companies risk a $45,000,000,000 breakup fee in twelve months where this company might not be what it was twelve months ago. I think that’s what is is the reason these folks are acting in such a fast way in regards to take the top talent, license the IP, license the tech, get these people building within our company now, day one.

Harry Stebbings68:49

I think it’s the most smart maneuver around it, but it only works when the people and the tech are the assets and not the revenue and the customers. In the whizzes case, the revenue and the customers are the asset. Don’t get me wrong, the team and technology is too. But it also helps us on an AI company. Sure. But, like, without the revenue and customers Yeah. It’s not worth $31,000,000,000. I do wanna ask, you said to me before OpenAI could still be a zero. When you think about that, what did you mean by that?

Miles Dieffenbach69:16

You know, the way we think about it is we very much spend time on unit economics. And from what we see with OpenAI, unit economics are improving rapidly, which is great to see. But still, when you take into account CapEx, you know, why has OpenAI raised two of the largest venture capital rounds ever in a span of twelve months? Not because they want interest income from the cash on the balance sheet. It’s because they’re burning 5 to $10,000,000,000 a year. Right? In my opinion, the music will stop eventually.

Right? Like, I I this would be the ultimate anomaly if a bubble did not pop in AI. Right? You look at past historic incredible technological moments. Right? You think of the railroad. You think of cars. You think of electricity. You think of steamboats. You think of the Internet. Every single one of those, there was a bubble that popped. Every single one that impacted the equity markets at that time. You know, inherently for the long term, it’s a good thing. Right? Like, it shows that this AI thing is real and people are going to overinvest.

And so I I I would find it extremely anomalous if if there was not a bubble that popped here. And so if if folks align with a bubble will pop eventually. If you do not have control of your own destiny and if you’re sitting like OpenAI and your pref stack, what’s their pref stack today? 70 or 80,000,000,000? You know, stuff hits the fan, and no one’s willing to write you a $40,000,000,000 equity check anymore because the capital markets have completely gotten smoked. Like, what happens?

Harry Stebbings70:39

Do you think there is a chance that happens, honestly? Like, when you look at, like, SpaceX, I have so many

Miles Dieffenbach

SpaceX is SpaceX is is is self funding. They don’t need cash. That’s what I mean. So and you look at Google and Meta. Right? When they went public, Google and Meta had, like, 30 to 40% GAAP operating margins. Those were, like, these were the most profitable companies ever. They had complete control of their own destiny. Right? So capital markets, whatever happened, it didn’t matter. They could not be killed. SpaceX cannot be killed. You know, Starlink has reached escape velocity. That’s a very high margin product. They do not need cash.

They’re doing secondary tender offers. OpenAI needs cash. Will OpenAI and Anthropic be independent companies in five years’ time? To say, like, slam dunk, these are gonna be trillion dollar companies five years from now, like, there is a lot that can happen within that, you know, five year period. Right? And so we would say there’s still a a good amount of risk in in both of those businesses.

Harry Stebbings71:32

If AI can Mass has kind of talked about this before about kind of AI’s impact on global GDP. And if it hits 10% GDP productivity growth, then it’s about 10,700,000,000,000 of a $107,000,000,000,000 labor kind of segment. Do you think AI will have that global impact on GDP within the next ten years at that scale?

Miles Dieffenbach

Ten years gets closer to I thought you were gonna maybe say three or five, which I’d say no. Right? I I think these technological transitions take a pretty long time historically to to bleed into GDP creating industries. And OpenAI is obviously an incredible company, but, like, they burned up all their GPUs in April because people were making, like, emojis. Right? They were making, like, cartoon figures on on the app. Right? Like, I that’s not like a GDP boosting product. And, you know, clearly, like, they’re making inroads.

Right? But, like, it all these things take time. But I think the problem is time is not your friend. When you look at the hyperscalers, just take them, for example. You look at, you know, 2024 to 2027 estimates, it’s a trillion dollars of CapEx they’re putting into the ground. And then you add on venture as an industry, you know, investing, you know, say the run rate’s a $100,000,000,000 here in The US, and 80% of that’s going into AI companies. Now, sure, not all of those are gonna be CapEx intent intensive.

Maybe some of those will be application companies, but that’s a lot of money to invest that sum. If this does not come true for ten years, there will be a lot of pain.

Harry Stebbings72:57

We spoke about NVIDIA. This is why we pushed back on your thoughts on NVIDIA, which you said that that’s too highly priced. If you believe AI, you buy NVIDIA.

Miles Dieffenbach73:05

I I I do not think that it’s too highly priced for the business today. One of the benefits of of our roles, we’re generalists. Right? So we get to invest across, you know, buyout, hedge funds, real estate, public equities. And so, like, we get to witness some of the best investors in the world, across the world. And so, you know, a man from from your hometown, Chris Hone, like, this guy’s one of the the the most incredible investors, of all time. And he thinks a lot about, you know, peak earnings and peak multiple, which is which is a common theme, obviously, in in the public equity industry.

But NVIDIA is a cyclical business at the end of the day. You look at their historical financials over the past twenty years. Essentially, like, every three years, they’ve had extreme negative year over year revenue growth. Now it rebounds. Right? But this is a hardware inventory cyclical business. And so back to my question, if folks agree that an AI bubble will pop at some point and the largest buyers of these GPUs are advertising driven companies, Google, Meta, Amazon is now a very large income, revenue line of of advertising.

And advertising, which is also a cyclical business, and you have a global downturn, like, there is a really plausible scenario that, you know, revenue drops 20%. You know, I think that would be conservative, you know, 20 to 30%. And so then earnings, right, if they don’t react on their OpEx quick enough, maybe earnings drop 40%. I looked this morning. They’re trading at, like, 38 times earnings forward. Maybe it drops to a trough multiple of, you know, 24 times, which has been a trough multiple for for NVIDIA.

You just blinked and you just had a 70% drawdown. Right? So, like, to think that that’s, like, not a possibility in the future, I wouldn’t say that. I’m not gonna guarantee you that’s gonna happen in in one year, two years, or three years, but I think it’s a it’s a possibility.

Harry Stebbings74:46

One final thing I wanna touch on before we do a quick fight is founder friendly. Everyone loves to say how founder friendly they are, how founder friendly their GPs are. How do you think about the founder friendly tagging that’s in venture today?

Miles Dieffenbach

My background comes from a sports background. Right? So I played football, you know, growing up and in and in college, and, you know, I was used to hard coaching. Right? Hard coaching, you don’t love it in the moment. You don’t love a coach MF ing you and, screaming you and telling you you’re playing terrible and you need to do this better or you need to do that better. But it’s better for you. Right? And you know it’s coming from that coach wants the best for you.

They don’t want you to fail. They are incentivized for you to do the best work possible. And so, like, I love getting coached hard. I told our CEO, Chuck Kennedy, when I first joined, like, he he shouldn’t have hired me to begin with. And so I told him when I joined, like, in my mind, I I I had a pretty good thought in my mind. Like, there’s a probably a good chance I don’t make it, like, six months. Like, but I’m gonna try my best. And so I told Chuck, was like, Chuck, I need you to criticize me.

Like, I need you to coach me hard. And he looked at me with, like, crazy eyes. Like, I’ve never heard anyone say this to me in my life. But, like, I love hard coaching. No founder is gonna be perfect. Right? Founders are gonna have weak spots. And if you can have, you know, people that are, from a loving perspective, close to the business and can supplement certain weak spots and can bend the trajectory on a company even a bit, why wouldn’t you why wouldn’t you push for that?

Those are gonna be tough conversations. Right? But tough conversations aren’t bad things. Right? When we’re sourcing and we’re doing reference work, that is not something we we we try to dig out. Like, we want we want the most founder friendly GPs. That’s not something we we source for. I’m so

Harry Stebbings76:24

glad. Thank god. I’m sure mine would not say I’m the most founder friendly. Harry says 996. I’m so glad. So glad. Dude, I wanna do a quick fire with you. So I say a short statement, you give me your immediate thoughts. Which venture firm charges 3 and 30 and shouldn’t? Any fund that raises

Miles Dieffenbach

over 4,000,000,000. I think that’s a pretty easy answer. There’s firms that do over 4,000,000,000 No. No. No. Excuse me. On their growth funds. Right? So the early stage funds But they do three and thirty on growth funds? No. They’re charging 2 and 20. I don’t think they should charge that. I I think a core early stage fund, if if they have produced incredible returns over the past fifteen, twenty years, they deserve three and thirty. What’s the biggest lie GPs tell LPs during fundraising? Oh, that’s a great question.

I would say, Miles, this is the perfect fund size for us. We wanna be a union square. We wanna be a benchmark. 300 to 400,000,000, this is the perfect sign. We’re never gonna raise a bigger fund. I hear that. I kid you not. At least every other every other intro meeting I take with a firm. And it’s 99% bullshit? 99.9% bullshit. Yeah. What’s one red flag in a GP that others keep ignoring? I would go back to alignment. I think, you know, we talked about kinda, oh, he’s looking the other way, but alignment is GP commit is one form of alignment.

It’s supposed to interrupt you. Yeah. How do you guys feel about that? It’s a it’s a very important data point for us. The the nominal number is not important for us as what does that number mean to that person? Very important to us. Right? Frankly, like, we have two quantitative data points outside of fund size and past returns that are the best forward looking indicator for future returns of our funds, and and one of them is GP commitment. Yeah. It is an important factor for us.

Who is the most underrated emerging manager today? He’ll probably raise a bigger fund, but I’ll say I I think Kevin Hart’s and A Stars, I think they’ve done fabulously well as a partner. What do you think makes him so good? Kevin, please, if you’re listening to this, do not use this to raise a billion dollar fund. What I think what’s interesting about that team, you know, you’ve got Kevin Hart’s, you know, multiple time founder, took in his companies public, been through a lot, seen a lot.

You’ve got Gotham who was, you know, COO, CFO of Uber. You’ve got Bennett who who did some incredible deals at co two. And I think it’s a very heavy team, a very powerful team for a right sized fund. I don’t think there’s many of those funds around, frankly. And so I think their ability to have really premier access that traditionally a multistage fund is is gonna have 99% of, I think, is is pretty rare.

Harry Stebbings79:02

When you think about a fund investment decision that was a mistake, what did you not see that you wish you’d seen? Key thing

Miles Dieffenbach

we go back to is people, really trying to understand who are the people driving the returns at that fund. Do you think you’re moving attribution. That we’ve gotten much more sophisticated on our reference work. We build our own attribution tables. Right? So, like, that is another, like, a huge red flag and lie that, like, we get from it’s not it’s not an outright lie. Right? But, like, they will give us attribution, and you have one partner leave who retires or goes to another firm. And, like, you’re getting this attribution from this new person who clearly we know was was not the partner on this home run deal.

We understand why they do it. Like, they they have to assign somebody to it, but it could be very misleading to a new LP coming into that fund and saying, oh, these these incredible partners who led these incredible deals are all still here. And so we, through reference work and through, you know, longevity, we build our own partner attribution.

Harry Stebbings

Would you rather back a twenty five year old first time manager or a 55 year old unicorn founder?

Miles Dieffenbach80:04

Well, if it’s Harry, you know, that makes the decision a little bit tougher. I I I’d say in general, we would lean to someone that has has been through multiple cycles and has the the scar tissue of that. And so I’d say we’d probably lean to the 55 year old, but we’re open to everything.

Harry Stebbings

What did you believe about fund investing that you’ve changed your mind on? So, like, for me in investing, was like there’s people, there’s market, and there’s product, say. And I used to kind of weigh them equally, and I’ve completely changed my mind around that. Markets change, products change, and this is for seed. I just massively over index on people, really.

Miles Dieffenbach

You know, when I first started, you know, from a first principles perspective, I was drawn to the data, which we laid out here in the beginning. And you can’t over index that data too hard similar to, you know, what we’ve talked about. And so I I would go back to, at the end of the day, this is a people driven business. You can do all the data work you want, which is important, clearly, as we’ve stated. Really leaning on the qualitative reference and people work to really and and speaking to founders.

Like, we we don’t take a lot of founders’ time. Right? So they have a lot of better things to do than speak to, you know, measly LPs like us. But really understanding, like, why did you choose that partner? Why did that partner choose you? What’s that relationship been like? And and understanding that dynamic is is critical for

Harry Stebbings81:26

us. What fund are you not in that you wish you were in? Union Square. Easy one. Yeah. Yeah. What’s the wildest GP behavior you’ve seen in the fundraising process? Oh, I’ve got one good

Miles Dieffenbach

and and one bad. Oh, go on. Okay. What do you want first? Start with the good. Okay. The good, you know, Long Journey Ventures, which, an incredible partnership, between Lee Jacobs, Cyan Bannister, Ariel Zuckerberg. We had a celebratory dinner out in San Francisco. And we get towards the end of the dinner, and somehow we got started talking about ping pong. I’m a pretty good ping pong player. And I brought up that when I was in college, I won the Pennsylvania State Ping Pong Championship, which is true.

I did. Lee Told Lisa. Lee Lee immediately was like, there’s no way you’re a better ping pong player than me. I am a really good ping pong player. So Cyan was like, well, we need to settle this. And I’m like, it’s like 9PM. Like, we had just finished dinner. And I’m like, yeah. I mean, I I don’t know how we do this. She’s like, I’ll find a ping pong bar. Cyan gets on her phone, finds a ping pong bar. We all go to a ping pong bar at 09:30PM in San Francisco, and Lee and I play ping pong for about an hour.

Who won? I won.

Harry Stebbings82:35

Yeah. And then you wrote the check. Yeah. Exactly. If he beat you, management fees. Yeah. If he beat you, check, check. Cancel. Yeah. That is unbelievable. I love I also love the Americans that you’re like, 09:00, dinner was finished. Yeah. So in Europe, it’s like Just start. That’s when you start drinks. Yeah. That’s so funny. Yeah.

Miles Dieffenbach

The bad one, I mean, this one forever stands out, was we underwrote a manager in 2023 that was holding OpenAI at 13,000,000,000, which, like, that one was like- And you questioned them on it? Yeah, obviously. And they came back? They said, We’re gonna revise our valuation policy and we’re gonna revise that mark. That was a crazy one, yeah.

Harry Stebbings83:12

Dude, that is absolutely wild. Listen, I so appreciate having you in the studio. I so appreciate the friendship. This has been so much fun to do. So thank you so much for joining me, man. Thanks for having me. This has been a blast. We could talk about it all day. The best podcasts are when you hear from people who never go on podcasts and you hear something truly unique inside Carnegie Mellon’s incredible endowment deployment there. So appreciate you listening. You can check out the episode on YouTube by searching for 20 VC.

That’s two zero VC. But before we leave you today,

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Harry Stebbings

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