The Ledger, every show

“Like, there's this canonical question, I think, in our industry. Is it the market or is it the team, right? And I think many great firms would argue that it's market. In my view, it's very clearly the team.”

“There's so much long tail risk in a company that I feel like the exercise around pattern recognition benchmarking as just like two examples, risk mitigation as a third are exercises in psychological safety.”

“TAM is a trap. Like, go back and look at the S-ones of some of the biggest public companies today. Their market caps are bigger than what they thought the TAM would be.”

“But when I think about conviction in people at the earliest stages I think you can be really elastic on price. At late stage, if you have conviction, price is just a representation of like future expected, expected free cashflow, right? So you're probably not …”

“So I'm not thinking about averaging down my cost basis. I'm not thinking about incrementally increasing my ownership. I'm building a net new investment case on, can I create, you know, a fund returner? And with that, like I do all the work again. So if I think…”

“It's super dangerous. I think to say there's a safe two X, there's no such thing. And you alluded to this with the memory of all of the activity from 2021. There's no such thing as a safe two X. And so what we're looking for is definitely five X plus upside, e…”

“Bottoms up, the, you know, the business in, in, in four years, the company has grown faster than any company of all time with unbelievable productivity in different segments, in different geographies.”

“It's especially hard in a venture firm in light of the power law, right? Again, very few companies are going to Create returns, which means there's likely to be concentration among different investors. Which suggests that you can have a skew of ego or insecuri…”

“For founders, like the best founders probably didn't grow aggressively enough. For investors, investors probably didn't maximize liquidity opportunities.”

“If your goal is to be the best version of yourself and your firm's goal is to be the best firm on the planet, there's no room for assimilation and confirmation, right? Conforming to other norms. So I think it's absolutely wrong. I think if you try to assimilat…”

“The game on the field, if you're a venture investor, is to invest in a fund returner. If you return the fund, don't worry about it.”

“When it comes to patterns of selection and patterns within people, The only pattern is there is no pattern.”

“The sins of omission for us distilled into three lessons. One don't be cute on price. Two don't overthink it. Three don't pass on generational founders.”

“Every investment in Datadog I was at a high price every, it's not an outcome yet, of course, but every investment in Wiz has been at a very high price. I feel great about each of those decisions.”

“When we invested in Olivier and Alexi Series A at Datadog, so he was not a great fundraiser.”

“I really think that the sins of omission Are much more significant than the sins of commission.”

“In the seed market most seed investors are using signaling as part of an objection to work with a multi-stage fund.”

“Like I definitely don't encourage founders to have like a party round. It ends up being, An exercise of herding cats.”

“Don't take money from customers, right? It's fraught with a conflict of interest.”

“If you come across an entrepreneur who you believe is on the spectrum of unethical to incompetent, you should sell immediately.”

“It really irritates me when I hear, ah, investors say it's an exceptional founder, ah, an A-plus founder, without any, like, specificity or substantiation.”

“Not firing fast enough.”

“Every meeting ideally would have two people in it. So that's a super high bar for taking Any meeting, like I'm asking to prioritize someone else's time in addition to mine, which means the threshold for a meeting is super high.”

“When we started our first growth fund our hypothesis was probably three to five X over three to five years, right? I'd just come out of a private equity firm as had some of my colleagues. And so we had like a, we had that mentality. And when we looked at the p…”

“If we're making a series B investment, it's by exception, like elastic. Series B investment. Terrific return. Confluent. Series B investment. Terrific return.”

“If you think about most software, like functional software areas, the market leader commands north of 20%, 25% market share.”

“When you have a disagreement or challenging conversation, walking like movement plus heading heading in the same direction can actually be really stimulating. So it's actually a really good tool.”

“Generally when I meet a founder at a seed stage, I'll tell him or her, I'll underwrite the entire round. So there's no financing risk, but We should split it into three sleeves. One sleeve is for index, one sleeve is for a seed fund, and the third sleeve is fo…”

“Doug Leone. Great board member in a very, very different way. ... Doug is incredibly intuitive. He can inspire confidence in, in a decision which is really, really different.”

“The goal is to buy and hold and let other people help inform like when to sell. So, and that's true for kind of the winners that make up the power law contributors, which is the business that we're in to find fund returners for like.”

“Given it's such a, and the industry is so driven by the power law, like, I think people can withstand cycles longer than we probably give them credit for.”

“And so I overestimated like uncapped market upside, underestimated the capital intensity of a company. Voted in favor with high conviction on the investment, and yeah, I think one of my partners is doing a great job of finding a path to, you know, returning ca…”

“We're a large investor in a company. We invested early stage company got acquired for about a billion dollars by a public company. And within a week of receiving our proceeds I asked our team to distribute the whole position.”

“25% of series A's in New York are related to healthcare. That's a really different mix than San Francisco.”

“When I started my career every meeting default was an hour. Danny reminded me that I probably know the answer in 15 minutes, and so now the default first meeting I have is 30 minutes.”