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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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“Yeah, but you still need the fees for that in a $400 million 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 million fund, Harry, like you're not become a billionaire off of that, right? Sadly, yeah. If you had $15 billion in AUM, which God bless, I hope you do someday, you're going to become a billionaire off that fund, off those funds, right? And that's the difference, right? Is you need that capital as a true early state venture capital firm. They're utilizing 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
“Because when you're investing at that size and scale, so when you're a fund that big, you are inherently setting up for $100 million 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 managing the company. They've got their own HR team. They're doing all their own hiring. They've got a 20-person product team. They've got a 10-person BD team. This is a well-oiled machine. These are what public companies would have been 10 years ago. And so you're charging two and twenty on basically passive investing, right? You're not actively managing most of those positions for the most of the 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
“We really try to understand has the magic bond been broken between GPs and LPs, which leads us to like we think the fee structures need to change to accommodate 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 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 put this clearly. I don't ever blame a GP for raising bigger funds. 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 billion this fund. They raised $5 billion in their prior fund. They raised $3 billion before that. $15 billion of capital. They're charging full fees on all of that, right? So they're making, call it $300 million a year a year in fees.”
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
“One, we lean on the math where even if you do own 10% of a generational $20 billion outcome, which is still going to be generated, you know, Figma, generational company. It's probably going to, we'll see where it prices, call it $20 to $25 billion. You know, if you're a GC, their last fundraiser was $7 billion, say you own 10% of a Figma, which is a generational company, $2 billion, you know, they're going to take 20% of that. I mean, you've returned, what, 0.0.2x? You need 15 figmas. It's mind-boggling to me.”
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 so. We've looked at all their returns. I mean, these people deserve to raise larger funds, right? I mean, they've produced really strong performance”
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, I mean, most people, right? Most funds can't raise one or two billion, right? So most are inherently going to be in the lower end. And then the ones that can, they've had good enough performance. Most of them scale”
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
“He probably could have gone to a cheaper source of capital and raised from Masa at Softbank or general catalyst or you name it, 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
“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, excuse me, it's a limited amount where you can still drive extreme power outcomes within the fund. And I think the performance-driven culture and what that brand stands for being, you know, the backer of some of the most generational companies of all time. You had Vlad on the show recently. Should I ask him, why did he go back to index for his new math company, right? He could have gone to probably a cheaper source of capital and gotten Mickey.”
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
“Index. I think they have to be. I mean, the performance they've put up in the last 12 months is I've 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 delivering here in the future is unbelievable. I mean, largest shareholder in Figma, largest shareholder in Dream Games, largest shareholder in Wiz, second largest shareholder in Scale AI, Revolute. It's unbelievable. 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, they could raise as much capital as they want to. And they don't. They are the most performant driven culture that we see. And so I give them a ton of respect 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
“20 30 billion, right? And anything above that is where you get the real alpha. And so it's hard for us to imagine on these very large multistage funds having that kind of alpha.”
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, and even still, 2021 is a good learning opportunity. Most, if not all, call it except maybe Palantir and a few others, of 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 OpenAI is going to be worth a trillion 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 great investors, Warren Buffett and Benjamin Graham kind of 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 billion of market cap IPOs and M&A transactions to get a 4X 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 we have to believe in 10%.”
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 could. We acknowledge that we could be wrong. And SpaceX and OpenAI and Anthropic go public at trillion dollar basins. What we look at, and like I said, this is backwards looking data, but we'll give you a few data points. There's been 1150 billion dollar IPOs, venture-backed. 11. The two largest venture-backed IPOs ever were Facebook in 2012 and Alibaba in 2014. So we've gone 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 my guess is that a hundred billion dollar IPO over the next 10 years is still going to be a generational outcome. And so the question I throw back is, you know, do you think there's going to be 10, 20, 100 billion dollar plus IPOs? I do not think so. You know, you look at the trillion.”
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
“And so 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 billion divided by 5%, which is 140 billion, 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. $140 billion. And so for us, when we do”
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, I'll walk you through a very simple math that other LPs can put in their back pocket. But for how we underwrite these big funds now today, it's simple math, but I'll walk you through it. And this is a live manager. I won't share their name, but a manager we underwrote a year ago. So we'll look at their fundrais. So this manager was targeting a $7 billion 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 two to three billion dollar growth fund and the rest was an opportunity fund. And as an LP, most LPs have to invest parapasou across this fund. So like equally as a percent of the fund across those funds. And so inherently your smallest check is going to be to that early stage fund. Your largest checks are going to 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 6% to 7%. And the opportunity fund had about 2.5%, 3% ownership.”
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
“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 MASA and SoftBank I would put as the flag in the ground Vision Fund 1, 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 those years where most all venture funds were basically raising a $400 million series A fund, all the premier funds. And maybe they had a $400 million growth fund attached to it. But the fund sizes stayed basically the same for a decade. And so it worries us tremendously”
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 magic of a partnership is the caring interest. And you are now giving that care and interest away to a silent partner who is not going to be, like we say, grinding and taking 100 calls a week and working 996 like you. So, how do you feel when you deliver incredible returns and asylum partner is getting a decent chunk of that care interest? It's the problem.”
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, absolutely. Massive red flag for us. And I would say most institutional LPs. I'm not going to speak for everybody, but.”
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, I think GPU should be spending the least amount of time fundraising as possible. That'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 crisp timeline. You know, we're going to do our first close here, you know, lining up URLs and being sure they're committed to that process and doing work on the sub docs and the legal work prior to that. Really important and just setting clear timelines.”
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 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 reupping today.”
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, 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 going to start getting taxed 8%. We could lever our drawdown to 4.5% versus 5% because the real risk you run to sit down is eating into the purchasing power in the endowment, right? The way an endowment works, you got a 5% draw every year. And then inflation is called 3% for higher education here in the US. So just to maintain the corpus, the purchasing power of that endowment, you need 8% return. Endowments are targeting an 8 to 10% return over the long term, 10 or 15 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,”
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, 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 going to start getting taxed. They 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 going to look like a month ago.”
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, I mean, best case scenario, or you don't have anyone more than 10%. But if you're raising a $50 million fund or a $100 million fund and you can secure a 10, 20, $30 million check in their long-term aligned line, that still makes sense, but best case scenario, yeah.”
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
“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, you know, take whatever. Yeah, take money's green, right? But in a best case scenario, you've got a mix of endowments, foundations, family offices, founders, maybe a couple GP checks in there from some venture funds, a mixture of folks who are aligned to your long-term vision. And inherently, stuff's going to happen, right? Like, you know, folks are going to have a liquidity crunch, a family office. The family's going to say, you know, fuck Venture, we don't want to play in this asset class anymore. Like, you're going to 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.”
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
“Risk we take openly. I'd say half of our new funds that we commit to, we will not invest right when we meet them over a six to year period and invest in their fund that year. And the other half will take either one fund or two funds into the future, so three to six years will build that relationship over time. And so, you know, the way we think about it is if you're in an early stage venture fund, it's going to take at least 15 years. And when we back a new manager, we want to back them for at least three funds, so call it 25 years of an e-liquid relationship. It's longer, like twice the length of like an average marriage in the U.S. I don't know what marriages are like here in Europe, but”
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 both love Kevin. He was always the founder. Yeah, exactly. And so, yeah, I mean, we traditionally have not done many spinouts.”
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 historically have not done many, if any, spinouts. Call it from your tier one, maybe clean spinouts, right? Kevin Hartz at ASARS is a new partner of ours. He was at Founders Funds for a few years. He wasn't there that long. He was still. And he was kind of too.”
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 reasons. I think one folks who had made a lot of money didn't want to deal with the crap that you're dealing with today, right? These three years 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 and why do it? I think too, if you're 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 getting paid 70% less 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?”
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, I personally think you've seen partnerships, what's the word I'm looking for? I 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 histories in LP.”
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
“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 want to know, are they a good person? Have they created a bad persona amongst other people? Have they wronged others in a pretty malicious way? 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? Does Harry like Sally does, you know, how is the mesh? Oh, that's incredible. This is the best partnership ever. We love each other. We sit down every day. We've never disagreed on a deal. We spent a lot of time trying to understand that partnership 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
“He's my best friend from school. So those ones we don't spend too much time on the golden references or the off-sheet references. And thankfully, Venture is such a networked community that you spend enough time in the asset class. You're able to build those networks pretty quickly. And so we are proactively trying to shoot deals.”
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
“Miles was great. Miles was great. And by worst, I mean, they're going to be patting Harry on the back, right? He's also the best.”
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. The way we think about referencing, you know, when we do a new fund, we're looking for at least 20 references calls, 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
“I think it's looking at track, understanding the true thought behind 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 want to hear from their side of the story as well. What was that pitch like with the broader community? They'll usually tell you, no one would even pick up the phone for us, right? No one would respond to our emails and cyan or hairy, you know, sat down and they had a blink in their eye and they saw the idea. They believed in us before everyone else did. We really want to understand the depth and granularity of those stories.”
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 love the way Mike Maples discusses picking and his, the way he thinks about these companies that are going against the grain of the universe and are inherently not going to be super attractive or super hot because it is against the grain and it is dysfunctional against the way our human minds work today. I'll never forget. I mean, when I first heard of Uber, I thought it was the stupidest idea I've ever heard. I mean, that's how you know I'd be a bad venture capitalist. I mean, I was in late in college. I'm going to get in some random person's car and they're going to drive me something with Airbnb. I'm going to go to some random person's house. I'm just going to 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 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 a superpower.”
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 become such a crowded market. There's so many alternatives. You've got South Park Commons, you've got Ali Partovi and 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 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 going to dive into this. You know, it's the magic adventure, right? That's how I think I see most of 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 think there is no systematic sourcing strategy. It's the partners and the brands are so strong They're so networked in the S tier founder community, they're just going to 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 Australia or some of these tertiary in Pittsburgh, I think you can build automated CRMs to maybe track some of those companies that 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
“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 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 stop this call early just the the kind of hubris i mean this is 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 6x net fund so that's that's definitely a big 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
“Usually the multi-stage firms think you're perennial like Excels or Sequoia, 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 going to hold that at a 20 to 30 percent discount, right? But 2021 caused us to create new muscles in regards to underwriting as a group as well. And so for any reup or any new manager whe diligence, we'll look at the top 10 company navs within that general partnership. We'll underwrite those companies ourselves. And we will, you know, on a rough approximation determine, are these assets extremely overvalued? Are they undervalued? Are they fairly valued?”
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
“Clearly not. 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 pricing growth assets for an eighteen month period at the median air or multiple for a software company was 20 times. And if you were a top quartile grower, it was forty times, right? And so everyone looked at their models and thought their company was going to be worth two, three X what it was in three years. You had public market comps to support your reasoning of holding stock, but that all changed very quickly.”
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 like them to 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 two percent 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.”
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
“Some yes, some no. Union Square broadly, and we're not an investor there. We wish we were, but I think they've parentally been the best at selling and they've got a very strict protocol that they run through from years eight to 12 when those funds and with those founders to let them know that they are going to be active sellers.”
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 the five would be sourcing, picking, winning, helping, and selling. Selling is going to be the most the new of those five, I think, for the asset class as a muscle as a whole”
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 for us, the sweet spot is dependent one on 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 million bucks, anything from at the low end will do an 80 million dollar fund at the high end anywhere from 400 to a billion, right? And 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.”
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
“Way out of 100, I would say if you are a multi-stage firm that is 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 going to say it's 80%, 70% picking. I'll flip it, yeah, 30% access.”
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
“True mode of early stage venture capital, the picking skill. And you look at some of the most incredible companies that have ever come out of the venture asset class, Airbnb, Uber, SpaceX, Amazon, all struggled mightily to raise their seed round. So to your question, is there so much capital available at seed today that that's never going to be the case moving forward? I hope and pray not as an allocator to the space. And so I still believe there is a moat around picking, but we'll see.”
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 response to that would be consensus seed deals, either a consensus founder or consensus idea, extremely hard to plan because the multistage firms have all planned a flag at Sedon have essentially said we're going to, all these seed funds are our shrapnel. We're going to blow this your model up a much cheaper cost of capital than you and we can deploy five, ten million dollar checks at seed when the model traditionally was two to three. But if you're doing non-consensus founders, non-consensus ideas, those rounds are usually non-competitive and that shows up in price and ownership. And so I'd say that's the question I'm possibly asked.”
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
“Strategy that a lot of people are taking, you know, first time funds and smaller funds as the incredible performance of the now multi-stage venture firms have 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 hyper competitive part of the market. There's thousands and thousands of managers, specific seed funds, angel funds, operators.”
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 the million dollar question. I think you need to have a frank conversation with yourself. Say you're a new endowment or a new family office 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 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 maturassic class, are not going to have Tom Dessile access.”
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 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 read index for our 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 25 years.”
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