Venture Capitalist

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

“Every time we would go out to fundraise, even though our numbers were great and we had great revenue, you know, VCs and investors would always be very skeptical. They'd be like, Oh, I don't know if this is a good business. Does it have longevity? Is this durab…”

“And where there's innovation, you can find early teams that are doing science experiments before anyone else is thinking about them. ... I think those are the best places to bet as a venture capitalist, because in the earliest days, they're actually not that c…”

“What our style tended to be was we thought of venture capitalists primarily as, you know, sources of money and, you know, mostly sort of, we wanted when we needed money, we wanted to be able to access capital, no thought leadership, but we, yeah, we really jus…”

“The thing, the key, key thing to understand here is that founders are sometimes a little frustrated with private equity because they think of them more like venture capitalists, and like venture capitalists typically will take, very gung-ho, will take extremel…”

“I've always thought of Wall Street as the buyer of the product that venture capitalists create because of the eventual liquidity is either an M&A or an IPO. And now the price is being set by that group and that institution. So if I know what they value, even i…”

“Venture capitalists don't think about the sell part. They think about the buy part.”

“A lot of these investors are salaried investors. They got no skin in the game, and they've never actually run anything.”

“99% of them are not. They're, I mean. Because they've never been operators. So like, they're just regurgitating, you know, something they heard in another board meeting that they think might be.”

“So if you have a board, like classic Silicon Valley board would be two VCs, two founders, and an independent. That's supposed to be fair because it's two and two balance. That is basically just investors control your company.”

“So I think this raising the next fund nonsense really does impact decision making and actually directly hurts founders with some of these things.”

“Well, the VCs always win. If they do a price round, some of them are sharks. They say we want a 15% option pool at the seed.”

“So what I've learned to do, which is really hard, is literally listen to the idealism Don't say, do I agree or not? Say to myself, will it motivate people enough to do something where there is economic advantage to be obtained?”

“Context feedback loops where you are, you have unique and differentiated access is where progress will be most legible to you. And if there are other teams who don't have access to that context, it'll also be where you have a superior business model.”

“Venture capitalists are terrified to invest money in anything other than these frontier models and things like SpaceX or military modernization.”

“I just see too many VCs running a pre AI enabler playbook. Where, where, where when folks do fall behind a tick or two, the, you see kumbaya activity instead of code red activity.”

“The only kind of M&A that I am interested in as an adventure capitalist is if a strategic comes to you and begs to buy it and is gaga for it and will pay a crazy price. That is the only kind of M&A venture capitalist will care about”

“And I think that's right because realistically, in the journey of what's going on, the only significant things we've done, I've said this before in the podcast, we put in the money and we put in more money when they need it. We decide to hire or not hire and f…”

“Well, I think they're trying to, in many ways, show their for one, show their LPs that they're being selective. And secondly, I mean, it's also true. I know as an investor, I get loads of inbound and we get so many decks from linked over LinkedIn, over email. …”

“That's going to be the deciding factor for venture capitalists. And startups. We're going to be on the same level playing field. How well do we use autonomous agents in our job?”

“Here's what I think. I think we tend to consistently underestimate how big the markets are and consistently overestimate how easy it is to go from zero to one, right?”

“When there are situations of chaos and folks don't know what's going on, the safest thing is to go look at other social signals to make decisions instead of using your own gut. And so I think that that's happening a lot in AI, and hopefully, you know, as the m…”

“You can't leave a founder in a deal Where he didn't want to sell, where he wanted to sell, and you stuck him in the deal, and now he's bitter. And if the thing goes wrong, you have no idea how toxic that will be.”

“We talk in Silicon Valley about never quit, but that is complete absolute venture capital bullshit. The incentive of venture capitalist is to put money into your company and milk you dry. They never get their money back. There is no way for them to take that i…”

“Most VCs don't actually want to do risky things. They want everything de-risked. And then they just wanted to invest on the upside.”

“I went to various venture capitalists, the sort of people who ought to lend to startups, and the kind of response I got was well, you know, it's not a very interesting area. We're investing in restaurants, fast food restaurants at the moment, or we're not lend…”

“I frankly invest off people, not off all these insane rules that a lot of my friends that are venture capitalists put up, these kind of guardrails that they won't go outside of. I've never seen a guardrail I don't try to jump. And I think that's the worst thi…”

“And like the irony is a sort of venture capitalists generally not manage anyone. So they're terrible at management. Like venture capitalists are awful managers, but in general, unless like They were twenty-year operators and they kind of like opted out of it a…”

“The longer it takes you to earn them a return, the lower their rate of return is. And that's what they're driven by. And so the venture capitalists instilled this idea of you have to work all the time because it's good for them because it increases their rate …”

“We were professional venture capitalists in various flavors for eight years after starting the podcast, and never once were tempted by, should Acquired be the XYZ Firm podcast. Sure, sure. Like, that'll kill the whole thing.”

“The right strategy is just be really smart and interesting and just go do a bunch of Free organic media on other podcasts.”

“These little snippets of advice that VCs give, because they watch some fucking podcast, are all fucking stupid, like it's just, there's a lot of depth to these things. You have to know the answer to the next question, and the next question”

“If you have a message they wanna get out, they kind of have to go direct because I mean, if it's your own platform, it doesn't hate you.”

“As I used to say in venture, a great venture capitalist position themselves to get lucky. You know, they hang around in the right places, and they talk to the right people, and they know enough relationships, and they have the capital, but most of the time the…”

“Also, you know, I think we have a, there is a tendency where the, sometimes, you talk about, you know, asymmetry of information, but it goes both ways, where sometimes you're so close to a business, you really see how the sausage gets made, and you can end up …”

“I'll bet you nickels to dollars that doesn't happen because founders are just signing up. I don't know what Brian you see at Sequoia, but founders are signing up for crazy stuff these days. They're signing up for massive stuff. And I don't think a lot of grouc…”

“The public markets are now pricing risk very differently than they have over the three, the last three years. You look at circle, you look at, you know, Nebius, you look at core weave, you look at Palantir, you look at cloud flare. Like these are all businesse…”

“I actually think that venture capitalists are probably the least sophisticated financiers, like on the planet. They just have hope, right? Like it's the only hopeful version of finance, right? Because it is like, you know, you're basically investing in people …”

“40 cents of every dollar venture capitalists give to startups goes to distribution.”

“I had someone tell me, a source tell me, that there are, it's very rare that venture capitalists see the books, the actual accounts, and they almost never see the code base.”

“The biggest problem is they're not really in the hands of the venture capitalists. They're in the hands of the entrepreneurs. If you're an entrepreneur who doesn't want to bother being a public company, they're real questions for institutions about how do they…”

“Venture capitalists who have, like, too many Twitter followers can't really use Twitter. Right. Like you need like the right scale Twitter following of like intense loyalty and people who like are into what you're doing. If you get too broad, it just kind of s…”

“I think that is a crucial part of how everybody should think about acquisitions, which is the buyer should accelerate the target company. It's almost like a venture capitalist investing into a startup, right? You invest money to accelerate the company you're i…”

“It's actually true of every venture capitalist in the world because you got a 50 50 shot when you change the CEO. And why would you put that risk on on your portfolio?”

“A venture capitalist from one of the top, let's, let me put it this way, top three venture firms in the world said that they were using it to mock all negotiations that they do. So they were taking, you know, describing the negotiation then, and then asking it…”

“The true missionaries will take less money from a less famous venture capitalist than the big money from the big venture capital so they can tell their friends, look who I got, you know Or find alternative ways, bootstrapping bank loans, credit card debt, you …”

“Venture guys make really good thematic bets about the next 10 years and are pretty horrible at assessing how the market's going to react to the next quarter's data. Hedge fund guys are the exact opposite.”

“This is going to be the biggest of all of them is the biggest opportunity ever. Right? So everybody agrees on that, but there's complete fog of war because like you're saying, Even the apps that are working get disrupted. There's like so much creative destruct…”

“Bing is actually great. You know, Bing is, is, is a rare type of investor because he is very product minded. You know, he uses the product and he gives us a lot of feedback on the product. He's obsessed with product. Most investors are more, you know, they're …”

“The male and the female entrepreneurs responded to a long set of questions, almost identically. But when you ask the VCs, the question is a male or a female, what are the most important attributes first stack rank them? And then is a male or a female more like…”

“I don't think LLMs will disappear. I think they're useful, but this, yeah, the valuations don't make sense. I mean, I don't see open AI being worth three hundred billion dollars. And you have to remember that venture capitalists have to like 10 X to be happy o…”

“Everybody's got to have a big foundation model AI thing in their portfolio, and they have to be able to show they're also on the board for, you know, status and LP relations. And so that's actually what's driving this.”

“They told themselves other things like we're very humble, so we don't market in this kind of nonsense which is always a rationalization for laziness.”

“I mean, to be honest, looking back it was the only way that we'd be able to raise money.”

“And that then started the ride of really building something that Did not have product market fit, but it had product market fit with our venture capitalists.”

“There are a few great lies of entrepreneurship, and one of them is that you can't grow a big company without raising a bunch of money. And it's perpetuated by an industry that, like, you know, venture capitalists make money when they give you money.”

“You have three things you can optimize for when you're raising money. You can optimize for the people you're working with, like the venture capitalists, You can optimize for the terms, you can optimize for the valuation, but pick two.”

“VCs have been chasing the ghost of Mint for 20 years.”

“I don't see venture debt a whole lot on the VC side because the venture capitalists don't like venture debt. They like to, you know, have their positions, you know, without any issues there.”

“I mean, venture capitalists, they're brilliant and they've seen so many things, but trusting ourselves in terms of like taking that information in, but not treating it as gospel is a very important skill for moving forward in the direction you intend to.”