The Ledger, every show

“So I think Microsoft have done a crappy job of AI generally.”

“I look in the rear view mirror and I go, everything I've sold pretty much has been a mistake. So I'm a contrarian.”

“I think that DPI could be dead.”

“Those guys were just like a casino. One call to John at Tiger. Like, 20 on 80, no problem.”

“I would say generally founders who've had enormous, enormous success and exits come to the next opportunity with some degree of hubris. I speak about this personally. I sold my first business And I thought I could conquer anything. And they look at any vertica…”

“So Live Nation Ticketmaster, that merger should never have been allowed. But once it's allowed, we will occupy, monopolize that position all day long.”

“I think it's insanity. I just think it's insanity. Like, I think when, I think you market those winners, and again, it's great PR fodder, it's great to, like, attract the investors in the next fund, but I think it's insanity to go, it's like that huge, you kno…”

“Sequoia will, it doesn't matter, by the way, I don't want to single out Sequoia here, but it doesn't matter if you take your check from Andreessen, Sequoia, Axel, you name them, right? They will never, they have no incentive to matchmake. They have no incentiv…”

“There's very little evidence yet that These hot, hot AI companies that are raising huge amounts of money are capital efficient, right? They're anything but capital efficient. There's, like, the jury's out on whether that's going to work still.”

“I mean, the scale of how much you have to win, right, is different based on your price. It's pure math. So, uncapped notes suck at the seed stage.”

“You know, these ten-year funds are taking 18 years.”

“And I think in, you know, OpenAI and Anthropic and SpaceX, we're seeing that already. Like these are the Metas and the Googles of our era, highly likely.”

“Like, 95% are not going to be there.”

“A little less since twenty-twenty. Like, if you look at the DPI analysis, like, the jury's out from twenty-twenty onwards.”

“I think that that's the momentum business, and I think knowing how and when to get out quickly with some of those really, really matters, and that's not really my business. So my business is value, is getting involved early, and trying to find value opportunit…”

“Sovereign wealth funds and public investment corporations are looking for IRR. They're not measuring this in how many times do you X the fund.”

“Subsequent to twenty-twenty, like the TVPI is there, and some, in some cases, they're on steroids. The DPI is less there, if you look at the actual stats.”

“The more embedded you are, like the more difficult you are to dispense because real time, Thousands, billions of orders are being run in your system, or like mission critical biotech research is being run in your system. The more embedded you are, I think the …”

“Even in your top names, sometimes taking 20% off the table, if you can return 25% of the fund, particularly if it's a newish fund, so if it's a, you know, if it's a twenty-twenty-four fund and you can give back 25%, like, why wouldn't you do that? And you're s…”

“By the way, we've seen fund of funds do secondaries of their entire fund, So we go, oh my god, you're in fund two, or you're in fund four, like, you should never sell, right? Like, this is what's, and it's like, it's not about you, right? Like, you're a roundi…”

“And I think overall we've done a little better on second time founders who didn't do that great up front. They didn't, they did okay, right? It's life changing. Like the first million dollars is so life changing. But they're really hungry. They've learned some…”

“Are we headed for another dot com crash? Definitely. If, like, Is not a question. When? Nobody knows, right?”

“It may just be in, like, angels putting money all over the place, and some of those angels are going to know people that worked with them or for them, and they're going to, you know, I think you can bypass traditional venture to a great extent, and that's the …”

“Do I think that we're going to have mass unemployment because of AI? And you're seeing a lot of leadership now agree with the viewers. No, I think we're going to see tremendous productivity gains.”

“That anthropic and open AI are going to be disrupted. It's like unequivocal. Like our whole careers are about disruption. Those platforms never, ever stay forever. Where is it going to come from? Excellent chance it comes from China. It's coming.”

“In my view, if you say in 10 years time, and I am not a thematic investor, but I am such a deep believer in The status quo being changed always, and not, and like nothing stays the same. I think photonic computing is coming down the line, and I think that's go…”

“Anyone in my seat who says, I knew, is just full of shit.”

“Often there is an investor on the cap table that's been there for a long time, and their model, it's like the tail wagging the dog here, their model is they need to see some liquidity for the next fund, so they're often very problematic reasons.”

“Sometimes like the mistake we make is we take pressure out of the system by giving the founders some kind of liquidity. But we don't think enough about the rest of the team. And then the team's playing on the founders.”

“I still think of, like, pro rot as, like, the original sin against entrepreneurs.”

“In that situation, I broke every rule under the sun, and we put in a hundred K check, right? I broke my rules. But we don't do that.”

“You know, you're in a world of hurt because someone that the world thought was, like, very, very serious and very smart about you just said no to you. Go try sell against that. I think it's very, very difficult.”

“They didn't do, but I was, they don't understand that 90% don't get follow on funding.”

“And the PREF stack, like peri-passu, feels like something of the past. There's a real PREF stack coming.”

“Fund, our Fund Three is a 20 18 vintage. No DPI yet.”

“I think pre-election in the US, IPOs are pretty much closed for now. I think post-election, one or two or three great IPOs, every single, you're going to have like this swarm of JP Morgan and Goldman Sachs bankers coming to tell you, like, it is open.”

“Fund returners, you need four or five good fund, good companies. If we sell four companies at two hundred fifty million dollars each, right, we can return a fund. If we sell 10 companies at a hundred million each, like, nobody cares about that, we can return a…”

“And if entrepreneurs get a ten million dollar, you know, check from XYZ, you know, large scale fund, And a partner doesn't join the board. That is not a good signal.”

“I think for entrepreneurs and for LPs, right, size of fund, check in company versus size of fund tells you everything. Everything.”

“I do. I do. You know, I think it's for the entrepreneur, It's like, there comes a point where it's like, you can have, it goes back to your earlier question, you can have words, you can have as many discussions. If the business is just not working out, like, d…”

“If I look back, I go, like, never sell a single thing. If you could, and, you know, people have to live and People have various desires, but if you could, never sell a share. And I know we've gone through the up and the down cycle, but great companies, compani…”

“And these are these legacy companies, a great example of them is the PBMs, the Pharmacy Benefit Managers. Companies that were very innovative 40 years ago, So a PBM connects the pharmacy to the insurer. You know, 40 years ago or 30 years ago, they were great c…”

“I actually gave I gave testimony to a panel of lawyers for the Department of Justice.”

“Is Josh in the winner there going to make two X, and maybe much more than that, but bet against the two X? I wouldn't bet against the two X. I think his LPs will make two X on that.”

“When I see those rounds at like 25 on a hundred, pretty much we're out. We're pretty much out. Again, team versus theme. So, you know, there are rare instances where we see someone who's just like, you cannot ignore, you wake up in the morning, you go, oh my g…”

“Rearview mirror on this, you can't build a fund on this. Rearview mirror, you can think about that one that you missed, and they're one or two in a generation. There are these generational companies, or maybe there is one a year, and if you're in that company,…”

“So I think in short term, we're going to be, you know, underwhelmed right now. I think if you look at like the amount of capex that's being spent, and you look at the actual earnings that will be generated in the short term, there's just no way it makes sense.”

“We look at a company and go, can we 10 X that? Can we 10 X? And if we can't, then we shouldn't invest.”