The Ledger, every show

“So when I think about reserves, I would say over-reserving is the bigger mistake than under-reserving.”

“Our job is to say yes, not to say no. And our job is to communicate that decision to a founder in a transparent and quick way. And our job isn't to waste people's time and our job isn't to mislead people. And I think as I've looked at this business for years, …”

“I think there's a power law dynamic in venture that is very hard to break. And I think the best firms will continue to be the best firms until they are suddenly not, mostly on internal errors and unforced errors.”

“If you have a multi-stage firm on your cap table that can lead your next round, and a new multi-stage firm shows up to explore your next round, very rarely are they like, will you get the answer from the other firm?”

“The success of a company is dependent upon employees one through 10, 10 through a hundred, and the founders. Like, that is what will make or break a company. The investors, the outsiders, the advisors, the mentors, the coaches, that part of a company building …”

“We will do an uncap safe. We will catalyze an uncap safe.”

“We truly hold to the idea that we want to invest in companies we're excited about, and if what we're able to invest is not in perfect alignment with the math, we're willing and able to make exceptions.”

“So I don't obsess over the ownership and the portfolio construction in a way that I think it matters on a deal by deal basis. I think it matters on a portfolio basis.”

“The macro change in the environment impacts our prior investments much more so than our future investments.”

“And that's the, like, venture gets viewed as an asset class, and it's not. These are all very small businesses with independent investment styles and independent investment beliefs.”

“The trend to me that's most interesting is that people are bored with today's consumer products. None of them are fun.”

“I don't think geography matters for startups. And I think you know, we're based in New York because we live here and we want to live here. And just cause we're based in New York doesn't mean that we invest only in New York and Greg, our partner lives in San Fr…”

“It is important to be price aware on a portfolio basis, and I don't think on a deal-by-deal basis, price is a determinant of making a decision. Pretty simple. If you love a company, and you want to invest, and the deal is what the deal is, you make a decision …”

“Do I think the only way to buy up in a company is to start by investing in the company? Yes. And the only way to buy up in a company is if you are worthwhile of the founder prioritizing you going forward.”

“So if I'm getting as much money as I want at a price that I want from a person that I want, it's a no brainer. You take the money.”

“We don't want to lead seed rounds. We don't want to lead series A rounds. We want to be sort of second or third biggest check on a cap table.”

“We don't sit on boards.”

“Our view is that seed should be a collaborative experience for both The founders and the investors in the sense of a founder wants to surround themselves with a group of people that can ideally create the right infrastructure for them to lean on as they go abo…”

“I generally think that, and your podcast is probably helping this in many ways, in a good and bad way, there's too much focus on the venture capitalists. There's too much focus on the investors. At the end of the day, why companies are successful is because a …”

“So I think you see great firms with amazing returns just stay incredibly disciplined. Whether that's Harrison Metal or an IA Ventures, it feels like they don't change their playbook. And then there's other firms that are totally adaptive to a market condition …”

“And I think we've gotten to the point where the romanticism of startups is gone.”

“So as the sort of word unicorn got spread, what to me has happened is we've seen the development of the unicorn hunter. And so as somebody gets deemed a unicorn, out come the claws and the people trying to kill that unicorn.”

“When you see Instagram and Snapchat open up their advertising products, they're basically mature on day one.”

“If you had asked every single venture capitalist at the If dating was an interesting space, nobody would have raised their hand.”

“The youngest demographic that is active on technology, so call it the, like, 18 to 25 year old demo, is not using a product that's built by somebody of their generation.”

“I think very few founders want the radical transparency of why somebody passed, and at the end of the day, a lot of the early passes are around teams.”

“I think that the big companies get punished and shit on by our industry just to sort of feel good. There are total negatives that The big companies are contributing to, but in reality, if you ask a normal consumer, do they love Amazon? Amazon will bring them w…”

“The negative of what's happened here in the past seven years is you haven't seen the true emergence of a destination company, right? We have incredible companies that are building incredible foundations here. Some have went, went public already. Some will go p…”

“Trying to sort of assume you have it and have figured it out this soon I think is, is probably a mistake.”

“The 20th employee at a company is exponentially more valuable than you know, a seed stage investor when a company's taking off.”

“I don't believe the phone is your remote control. I think there's other input methods that are going to allow you to interact with technology.”

“I think two years ago we were saying like, 30 to 40% of the companies we see talk about AI or are oriented around AI. Last year was like 90, and this year it's a 170%. You don't meet non AI companies right now.”

“So if you think about new entrances as funds into the early stage market, most of the ambition is to become a bigger fund, and in doing so, you Become later by nature of scaling your business.”

“What has been amazing to me about YC is they've just continued to compound quality of the satisfaction to their customer. They are not free, right? You're giving YC equity. And yet if you look at like the happiness factor, the MPS or whatever cheesy acronym yo…”

“Whatever you do in New York, it's like an incredibly harsh environment. And in order to stand out and win in New York, you have to fight friction. No one cares. And that's, what's actually fascinating to me about tech in New York is like, if you went on a subw…”

“We are a, as of recently we just closed our sixth fund, so it's a two hundred and twelve million dollar early stage fund.”

“No, I, we don't try to compete. I think if we tried to compete, we would lose our ability to work well with others. And I don't think our value proposition is to say, pick us instead of somebody.”

“And if you as the human investor Aren't aligned with that journey on the down and on the other side, aligned with the journey on the up as a human. I don't think you're going to be in this business for very long.”

“Seed has shifted, the word seed has shifted from a million to three million dollar round to a five to eight million dollar round.”

“Tech shifted from a vertical to a horizontal. So the places, the types of businesses that venture and early stage tech venture capitalists were funding fundamentally expanded at a huge level too.”

“If we, instead, every fund cycle changed our strategy, changed how we operate, where we invest, like the style of investing, you have no ability to actually get better and to try to find that zone of clarity To make investments.”

“If I looked back at the quality deals that showed up in our inbox that we missed in that, like, and sometimes we see it a year later and it comes through a warm source and we're like, oh my God, it was sitting there. Like, this is an interesting deal. Or like,…”

“I think 10 years from now, the bigger firms are bigger. There are In, in many ways, less big firms.”

“I just don't believe in evaluating venture, especially seed venture on a minute to minute, year to year basis. It is an incorrect use of energy and mind.”

“If your series A lead is not doing their pro rata in your B, that is a material data point.”

“I think if you didn't have the turn of the market in 22, you were going to see enormous amounts of capital pointed at seed.”

“We are we are going to run whether you like it or not, the same model for a long time. And I think what that does is it aligns us with founders who are also going to build their business for a long time. We are consistent. We're not going to suddenly be a Seri…”

“I think the Collison brothers have, you know, built a investment portfolio that's probably quite unique and doesn't get sort of discussed as much as some of the louder operator angels out there.”