YouSaid · the spoken record

Miles Dieffenbach

lines on the record: 112
first: 2025-08-04
most recent: 2025-08-04
sittings or episodes: 1
sources: podcast

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“The bad one, I mean, this one forever stands out was we underwrote a manager in 2023 that was holding OpenSea at $13 billion, which”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Cyanne was like, well, we need to settle this. And I'm like, it's like 9 p.m. like we had just finished dinner. And I'm like, yeah, I mean, I don't know how we do this. She's like, I'll find a ping pong bar. Sighing gets on her phone, finds a ping pong bar. We all go to a ping pong bar at 9.30 p.m. in San Francisco and Lee and I play ping pong for about an hour. One”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Okay, the good long journey ventures, which is an incredible partnership between Lee Jacobs, Cyan Bannister, and 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.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“When I first started 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 what we've talked about. And so 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 speaking to founders, like we don't take a lot of founders time, right? So they have a lot of better things to do than speak to measly LPs like us, but really understanding why did you choose that partner? Why did that partner choose you? What's that relationship been like in understanding that dynamic is critical for us?”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, if it's hairy, you know, that makes the decision a little bit tougher. I'd say in general, we would lean to someone that has been through multiple cycles and has the scar tissue of that. And so I'd say we probably lean to the 55-year-old, but we're open to everything.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“That we've gotten much more sophisticated on our reference work. We build our own attribution tables, right? So like that is another huge red flag and lie that we get from, 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 not the partner on this home run deal. We understand why they do it. Like 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 incredible partners who led these incredible deals are all still here. And so we through reference work and through longevity, we build our own partner attribution.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Key thing we go back to is people really trying to understand who are the people driving the returns at that fund. Do you think you move?”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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've got Kevin Hart's, you know, multiple time founder took in his company's public, been through a lot, seen a lot. You've got Gotham, who was COO, CFO of Uber, you've got Bennett, who did some incredible deals at Kotu. 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 multi-stage fund is going to have 99% of, I think, is pretty rare.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Probably raise a bigger fund, but I'll say, I think Kevin Harts and A stars, I think they've done fabulously well as a partner. What do you think?”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. It's a very important data point for us. 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 one of them is GP commitment. It is an important factor for us.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, that's a great question. I would say, Miles, this is the perfect fund size for us. We want to be a union square. We want to be a benchmark, 300 to 400 million. This is the perfect size. We're never going to raise a bigger fund. I hear that. I kid you not, at least every other, every other intro meeting I take with a firm.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“No, no. You know, they're charging $2.20. I don't think they should charge that. I think a core early stage fund, if they have produced incredible returns over the past 15, 20 years, they deserve $330.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“My background comes from a sports background, right? So I play football growing up in college. And I was used to hard coaching. Hard coaching, you don't love it in the moment. You don't love a coach MFing you and screaming you and telling you you're playing terrible and you need to do this better, 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. Like they don't want you to fail. Like they are incentivized for you to do the best work”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Are advertising driven companies, Google, Meta, Amazon is now a very large income revenue line of advertising and advertising, which is also a cyclical business. And you have a global downturn. Like there is a really plausible scenario that revenue drops 20%. I think that would be conservative, you know, 20 to 30 percent. 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 24 times, which has been a trough multiple for NVIDIA. You just blinked and you just had a 70% drawdown. So like to think that that's like not a possibility in the future, I wouldn't say that. I'm not going to guarantee you that's going to happen in one year, two years, or three years, but I think it's a possibility.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I do not think that it's too highly priced for the business today. One of the benefits of our rules we're generalists, right? So we get to invest across buyout, hedge funds, real estate, public equities. And so we get to witness some of the best investors in the world, across the world. And so, you know, a man from your hometown, Chris Hone, like this guy's one of the most incredible investors of all time. And he thinks a lot about peak earnings and peak multiple, which is a common theme, obviously, 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 20 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 GPs.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 2024 to 2027 estimates, it's a trillion dollars of CapEx they're putting into the ground. And then you add on ventures and industry investing, say the run rate's $100 billion here in the US. And 80% of that's going into AI companies. Now, sure, not all of those are going to be CapEx 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 10 years there will be a lot of pain.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“10 years gets closer to, I thought you were going to maybe say three or five, which I'd say no, right? I think these technological transitions take a pretty long time historically to bleed into GDP creating industries. Opening eyes are obviously incredible company, but they burned up all their GPUs in April because people were making like emojis, right? They were making like cartoon figures on the app, right? Like that's not like a GDP boosting product. Clearly, like they're making inroads, right? But like all these things take time.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“To say, like, slam dunk, these are going to be trillion dollar companies five years from now, like there is a lot that can happen within that five-year period, right? And so we would say there's still a good amount of risk in both of those businesses.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“SpaceX 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% gap 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.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Real and people are going to overinvest. And so I would find it extremely anomalous if there was not a bubble that popped here. And so 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 open AI and your prep stack, what's their pref stack today? 70 or 80 billion, you know, stuff hits the fan and no one's willing to write you a $40 billion equity check anymore because the capital markets have completely gotten smoked. Like what happens?”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 12 months? Not because they want interest income from the cash on the balance sheet. It's because they're burning five to $10 billion a year, right? In my opinion, the music will stop eventually, right? Like 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. Inherently for the long term, it's a good thing, right? Like it shows that this AI thing is.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“If Wiz gets approved, every other large MAC 7 company is going to 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 billion 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 big worry that I think those companies see today from our purview is that the AI landscape is changing so rapidly that the 12-month time period, it could take to go through a review to get that acquisition done, that company could be obsolete in 12 months.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, we've got incredible partners there that we've had 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 frankly, a lot of the best Chinese founders have chosen to raise elsewhere, whether in the US or Singapore or London. It's a tough place.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It's a very high bar for us today in a very hard place to invest. I mean, there's a couple really big headwinds. One is the U.S. executive order mandating U.S. 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 these R&B funds are from local governments and municipalities. And most of the time for the past 15 years since the China venture industry has been around, those funds were paraphrased. 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 think the last data checked 70% of these deals in the US are AI companies. I mean, it's everything. And so that's a big alignment issue, right?”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“We are agnostic. We do not have a mandate or a rule saying we're only going to do thematic funds or we're only going to 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.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, it's been such a dearth of liquidity over the past three years that like one year is not going to solve the industry's problem, right? So we're going to need like multiple years of really good liquidity to get back to a normal state. So like there's still a lot of wood to chop here, but it'll help, right? Undoubtedly, absolutely.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, exactly. 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. 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. We understand why they don't want to go public. But the public markets are now pricing risk very differently than they have over the last three years. You look at circle, you look at Nebius, you look at Corweave, you look at Palantir, you look at Cloudflare, like these are all businesses trading at extremely healthy multiple. So my message here to all venture capitalists now is the time. Please take your companies public.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“So that's a positive. But on the flip side, there's still a lot of liquidity that sure, it's been announced, but the whiz deal, right? That's going to be a Q1 2026 event, right? That's got to go through FTC approval. Figma hasn't gone public yet, you know, Dream Games set in the article. They've got to get European approval for that.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“We are thankful to say that we're now self funding in our venture book this year, which has give us a round of applause. I mean, it's the first time since 2021.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm not sure certain ones with real liquidity needs. I think they'll have to, right? And so that'll be a forcing function. But still, I mean, there's not a ton of secondary capital out there that's going to be able to swallow all of that nav, right? So if every billion dollar endowment 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.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“That's a great deal. That's what I meant. Yeah, sorry. Fantastic deal. Not knowing the underlying GPs in that fund and not knowing the mix between buyouts, real estate, or venture, I would have guessed, Yale's got incredible management 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 have put on the board.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm sure Yale would do well. That's a fantastic team with a great portfolio, but it just goes to show the risk of these fat tail outcomes in these funds.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Of selling secondaries as a long-term venture investor is that you're going to have these crazy right tail outcomes in the fund that could come to fruition at years 8, 9, 10, 11, 12, 13 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 Clecle was going to trade it 100 times EPIDA in the public markets and that stable coins in a year and a half? We're going to be like the hottest sector in crypto. You could not have predicted that. So I'd imagine Yale probably did the same. They probably underwrote that and they're like, there's probably not a Jew.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I was reading that's one. My son woke me up one morning and I was up early. And so I'm reading the S1 kind of as just, you know, for fun and I'm looking through the cap table and 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 billion, you know, three and a half billion-ish valuation. And you look at Circle and it's a $50 billion company today. This is the 13 year fund that is essentially going to do an extra three turns on the fund in its 13th year. Unbelievable. And so the article with Yale and Calpers was Calper's bought a very large piece of their portfolio of which part of it was general catalyst and circle was the largest position in that fund and essentially in a two months time frame I think it said in the article they bought 500 million you had a hundred million dollar write up from circle alone that's the risk”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think there's a lot of factors that go into it, one being the headwinds we talked about to the endowment model. But you look at Harvard selling $1 billion. It's a $50 billion endowment. I mean, like, so $1 billion, it's not like some monumental thing for them. That's probably just a refresher the portfolio. But like, I think there's real lessons learned. I mean, there was an article out today about Yale and Cowpers. Cowper's was the buyer, you know, a piece of Yale's portfolio. And I was on the phone with our CIO this morning, you know, just take a step back. We had a venture capital to fund that we committed to in 2012. This fund was in its tail life 13 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 companies 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 bucks.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“There's always going to be an extreme distribution right tail income in these funds that is going to be impossible for us to underwrite, right? And that's the beauty of venture capital. So we acknowledge that. We're not going to, you know, our valuation of the company, we know it's probably going to look quite different three, five years down the road, but we just want to know, are these good fundamental businesses that are growing in value and that give us conviction and that these are going to be real durable businesses one day?”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“They're in the peak. Growth has slowed down. There's not much of a market for a hundred million dollar ARR SaaS company growing 15% with break-even free cash flow when you can buy Microsoft growing top line at 14%, growing earnings at 17% with real GAP profits buying back 1% of the company every year with the strongest competitive moat in the world. People get frustrated when it's like, oh, no one's going to 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?”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Lot of different reasons. I think 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 the dot-com bubble, it took you 13 years from the peak of the dot-com bubble to get back to par on your public equity position in the queues or the Nasdaq. Like that was a real downturn. It makes obviously 2021 look like pennies. And you had more IPOs raised than 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 a price.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes. You look at the data both at European venture fundraising and U.S. fundraising, we'll see what Q3 and Q4 will look like. But in the US, this is going to be the lowest year since 17 in Europe. Same. It goes back a bit further maybe to 2016, but it all goes back to liquidity.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think certain folks would have in it today bear hugged their GPs for not playing the game on the field in 2021. You know, we're not investors, but Mark Suster, 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 bear hugging him for that brutal market.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It's very important. It all stems from what did that GP tell you they were going to do? If they told us that, hey, this is a two-year fundraise cycle. We're investing it in two years and they come back to us 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 going to take three to four years and you come back in two years, then we'll have some questions for you and we'll want to work with you to understand why. What's the reason? Because time diversification is extremely important.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I'll never blame you for doing that. And I'll never blame a GP for GP saying, oh, how dare you? Right? It's the market. And you've obviously done.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Think certain LPs choose to just not even think about it, frankly. And so certain LPs, you know, such as ourselves, I will never blame you, Harriet, for raising $10 million. Like I will give you a”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“We have an investment committee that we go to for approval. That's our governance committee, and we write a detailed memo for any reup or any new name in the portfolio. And we got to present our merits and concerns. But we've educated our governance, which is such an important part of any LP that's wanting to get into dementia, having the proper governance set up to allow you to take these very long-term bets. We educate them on the math and the risk adjusted return of the funds and the fee structures. And so their very understanding of our strategy and how we think about the world.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Get why. I think it goes back to an incentive problem in the LP industry. For me personally, I could be your janitor here at 20BC offices and I'm going to be the best janitor you've ever had. These are going to be the cleanest floors you've ever had. This is going to be the cleanest table you ever had. If my name's going to be on it and I'm going to be a part of it, I am going to put my 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 from buying IBM, right? That's the classic quote. That's a problem. And frankly, there are”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Depends. It depends on how different that fund is and how different the strategy is, right? And it very much is dependent on the situation.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“If you're raising that early stage fund, the core $500 million series A fund, charge us two and a half and $20. And if you're good enough, two and a half and 30, we're okay with that, right? But 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 zero in 10 or budget-based, right? Based on the team. But 10% care. I mean, that's the number for a passive, long-only investor.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Increase 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 05 to 07 then at 2010 to 2013.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“This is the one 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 manages 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 pay them whatever they wanted to be in that fund. And so what's hard for us to understand today is I shared the performance data with you. The performance is you don't look at that data on a $7 billion fund and think God, like we will pay whatever we need to get into those funds. And so what our hope is, 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 2 and 20. Performance was incredible for a very long period of time. All the funds.”
2025-08-04 · The Twenty Minute VC · 20VC: 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 · IDENTIFIED FROM THE TRANSCRIPT · source