Venture Capital

“We were a horizontal platform, which was great. You know, VCs love it. It's actually a horrible go-to-market problem because you know, where do you start? It's about repeatability, right?”

“Our asset class is five to six trillion dollars of value, and the dynamics around companies staying private longer, They're not going to reverse.”

“The top decile outcomes, I think, used to be ten billion and now they're like forty billion.”

“Like, we've looked at the data of 3000 venture capital firms in the U.S. Only 20 have achieved consistent three X net returns over the last two decades.”

“Venture-like returns are possible in late stage, but your best company should be five, 10% plus of your fund. That way you can actually return the fund on a single company. Fund returning math in late stage didn't exist before. It now does.”

“If you look at Cambridge data, the average venture return over the last 10 years is one to two x net. You will do better in private equity. You'll definitely do better in the public markets. You don't need to lock up your money for 10 years.”

“We will see deal structures that are objectively bad for the company done more and more often to win deals, whatever it takes.”

“From a VC perspective, you're like now combining hardware with biology, With software, like talk about like the double black diamond of a startup, like that's really difficult.”

“Every venture investor has made the mistake of selling to early their winners, every single venture investors, because if you look at the great companies, they've compounded 20 years after the IPO.”

“You got growth investors who usually do CD doing A's and B's. You got A and B investors doing Seeds, you got seeds doing pre-seeds, you got pre-seed investors trying to invest in people before they know they have an idea, right? So it's like this knock-on effe…”

“There's only so many large enough seminal companies in an era that you're either in them or you're not. And if you're in them, then the valuation doesn't matter.”

“We did double track between VC and NP, and P was much more adapted for the next phase of the dummy, doing more and more M&A, consolidation,”

“I've had several venture bets that, you know, we've gone into and they've, you know, they've gone to zero where I've lost, you know, several million dollars. Now one of them was cause the person was a bad person is ultimately in jail.”

“I think the, where you turn small dollars into big dollars, they have to be controversial.”

“Ultimately what matters to you is how much ownership you have and how big the company can get. And that will be true only when that investment crystallizes in almost guarantee that will happen for the biggest outcomes in markets that are more mature as opposed…”

“Having done both, I think I can say it's like much, much, much harder to run a company than being an investor.”

“Sometimes that is actually much worse than the counterfactual. Because if I, let's say I start with an idea I'm not passionate about. And I don't think it's gonna work. But maybe like a big name VC comes and invests in that. Then there are two problems. One, I…”

“I think BCI is a category, kind of like how pharma is a category. I think sometimes you, I'll talk to VCs and like, oh, we have a BCI bet. Like, do you have a drug bet? You made one bet on a drugs? Like, that's that, that's how you think about the category.”

“I think that the future of innovation is going to come from the Less flashy industries than what we've seen historically. I believe it's going to come from the regions and areas that, as I, listen, I born and raised California, love the West Coast. I do believ…”

“A couple of times I've said on the other side, I don't know that it creates such a strategic arm race that everyone just gets picked off instantly. That, that might be a VC partial myth.”

“Something like 56% of all twenty-twenty-five venture capital dollars were raised in the San Francisco Bay Area.”

“If you just go take the first term sheet, Getting around done will actually take longer because there's no alternatives. You don't have alternatives. And then it gets weird. And then the VC will just keep pushing, pushing, pushing, pushing, getting more, more,…”

“The way I think about it is an operator who's running a company is a, if they're good, is a grandmaster of chess. The VC, and by the way, that grandmaster of chess, this operator, entrepreneur, Is playing this chess match somewhere between 60 and 80 hours a we…”

“Like if an antelope limps in the Serengeti, the lion will take it down even if it's not hungry. Can't even fucking help it. It's just what is, what he does. And that's kind of the nature of most VCs. This, the nature of it is they will, if the, if you are on t…”

“10%. And then the one percent is helpful.”

“This is going to move the data center game out of the VCs and into the big leagues.”

“Recently, relatively recently, in the last few years because outcomes have gotten so much bigger and these markets are bigger and everything else, The circle of high cash on cash multiple opportunities is bigger than just early stage. And it's not so, so big t…”

“I turned down a company the other day that went from one and a half, and they were gonna go to five, and then they were gonna go from five to 15, and it's just not enough anymore. It's just not interesting. I'm sorry for venture. We have an opportunity cost of…”

“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…”

“The job is to be in there five years or 10 years ahead, and it's not where the momentum is. It never is.”

“So the returns at the top are going to be Incredible. They have to be now. And I think that that capital is going to spill over into venture and all sorts of investing.”

“The reason this never happens is because big fancy investors, not us lowly seed investors, but big fancy ones, have no interest in the write down, right? It's a massive write down, right, for them. And they'd rather just stick it on their books and pretend lik…”

“And so I do think we're going to see a ongoing rise in valuations most likely over the next year or two, much more than we've seen today. And obviously there'll be some great things in there and there'll be a bunch of stuff that doesn't deserve it, but I actua…”

“I think that we've benefited from the millions of dollars that this competitor is pumped into advertising in the market. And then when they Stumble and fall and aren't as good of a solution, then they go looking for another point of sell system. And so we've b…”

“And at the end of the day, a VC that invests in you and the seed round, all they need to really think about is will there be an investor that leads the A round, right? And the A round for B and the B for C.”

“If you cannot crystallize it for your investors, You won't be able to crystallize it for customers, and VCs are not necessarily forward indicators of the market, but there's some derivative of what your customers are seeing, because if everyone wants to buy yo…”

“Every time I go on a call with the VC, that VC probably wants me to be the best founder that they've ever met. I mean, that's their job. They want to invest.”

“One prediction on way on which I, I'm just, I turned out to be wrong was I would have expected this kind of productivity gains to come all the way on the stack along the stack. Like I would have expected that, for example, the number of let's say good venture …”

“Venture debt is underwritten against your next venture raise. It's not underwritten against anything else.”

“The challenge that I have with that group of investors is that oftentimes the advice that they give to founders, or the guidance that they give to founders while they're on their boards, is often not as informed as it should be, but is given as very definitive…”

“If you look at the data for how much money flows into climate in the US, like, VC is not the dominant.”

“You have to be in the big outliers to drive great returns, and you're better off being in them at a very small percent than owning a large percent of a company that exits for three to 500. Those just aren't going to move the needle.”

“I think one of the worst performing groups in terms of venture in this vintage will actually be the small boutique seed funds, which is what every single LP that you speak to today, Matt, wants. Every LP. This is the funniest thing. Every LP wants San Francisc…”

“We set out to build a balanced portfolio where we wanted to have allocations everywhere from early incubator stage of venture capital straight through to pre-IPO, now IPO-ing companies that have been growing massively.”

“We could not have gotten Jeff's offer, and six months later, some VC would have given us a massive check that sounded super impressive, and it would have destroyed the business, and then we would have sold our independence, and we would have been fucking miser…”

“The VCs you have as a private company, they spend so much more time on your company There's so much more concentrated than the public investors. Like public investors have, they're looking at, you know, 20, 30 different names. They come in and out of these nam…”

“Even if, as the VCs, we have board control, 70% ownership, and a drag along for the founders. Jason knows this. If the founders who are core to the business don't want to sell, it's not going to happen.”

“I think the real pressure is, it means anything below that growth stage, you better be a damn good picker. Because it used to be when Rory and I met, Series B, even into Series A, you actually didn't have to be a good picker. You just had to be good at math an…”

“So it's not a bubble that's going to impact most people in the room, right? Or most people across the U S but it could just destroy a lot of VCs and a lot of funds and a lot of PE, right? Because they're going all in.”

“In reality, it's really a sales job, right? You're selling people to take a meeting with you. You're selling people to take your money”

“The constraint actually is not capital, as I've realized over time, there's a lot of money in this world. The constraint is talent. Right. There's a lot of people who want to start companies. So that's not the constraint. There's very few people that are reall…”

“In our business, I think three things matter in that order. I think number one, it's a parallel business. So you've got to be in the best companies. A few companies end up driving the returns, whether it's for your fund or for the industry, and you've got to b…”

“Historically, 70 cents of every dollar we would give as VCs to founders would go towards hiring engineers, right?”

“In the early stage, when you're on the board, you can't invest in two competitors. In the late stage, structurally, you have to.”

“No one knows the answer and most VCs are betting both ways. They're chucking a bunch of money in at a modest 300 or six hundred billion pre at Antropic. And at the same time, they're doing a whole bunch of investments that only make sense if in fact there is r…”

“Why don't you call their founders and find out and not the ones they tell you to call. Here's the trick I tell my founders. You have a VC like, okay, great. Give me some references. Great. Here you go. Okay. Now give me the list of the founders you funded, or …”

“If you're a scammer bank, your bank's going to be the most beautiful bank in town. And if you're a scammer VC, wow. Are you going to have a nice website?”

“We're paradigm shifting system engineers. We're trying to bridge that gap between basic science and something that's like venture investable, but that's like often a five or six year gap that gets filled very badly.”

“It's very difficult for those companies to get funding because the story is, well, okay, fine. You grew 200% last year, but you know, you're only on an absolute terms. You're only at eight million of revenue and you're seven years in. Whereas I think literally…”

“Like I've been shocked at sort of how hostile Insider bridge rounds really are. I think this is like an under-discussed part of venture. Just they have like, you know, three ex liquidation preferences or warrants or ratchets or other things.”