The Ledger, every show

“In the past, I'd never seen anybody pitch, like, a core part of their pitch as being, I'm close to administration. I've heard so many pitches about that now, which is kind of sad, honestly, but it is what it is.”

“So anyway, I think it can be used and can be super useful, but because of those regulatory bound like guidelines, I'm not sure it's going to like be a step change in underwriting.”

“But I think if you look at, if you did an index of companies where founders took You know, a lot more than that, what I described, like, one X ARR off the table. You have a very negative returning fund.”

“I think there's this overhang of valuations and we haven't yet seen the drop that is going to come and it's going to be so severe.”

“And I think, so I think they're doing a really good job now, and I think I think it's gonna be a much smaller fund, and like you said, it's gonna be a ton of their own GP money, but I'm excited about them. I think they're good actors.”

“So I think it's happening and that never used to happen. You wouldn't have like a tier one fund taking Eight percent ownership in a Series A. But that's happening.”

“You think about those vintage years from a fund perspective, that's 2010, 11, 12. Those are the best years of venture and it'll be tough to replicate going forward.”

“So like the Jones Act basically says that if you, if you're shipping goods between two U.S. Ports, you need to use a U.S. Built ship crewed by U.S. Citizens and owned by U.S. Citizens. So like it's super protectionist to the U.S. Shipbuilding industry and U.S.…”

“Seed valuations have actually increased from that time, and it's basically kind of been like a straight line upwards, and what he's talking about actually started happening in twenty-twenty-two”

“I'm skeptical that this is gonna happen again. Or that it's gonna re-accelerate and prices are gonna go up. I don't know. We'll see. Well, we should make a bet and have Peter Walker from Carta give us the data in a year.”

“And the problems are, one, they're wasting a ton of food. Like you cannot predict how much food you need on any given day. And they were like, yeah, we have this AI model, like we're going to Predict if there's a Giants game, it's this, if this, it's actually …”

“I never found any evidence of that actually happening, though. Like, people have been, like, Provide me evidence, and I don't think there's actual evidence of that happening. There is with the Better Business Bureau, by the way, but not with Yelp, from what I …”

“So, okay, on that company, I met a guy who invested in that company early, or relatively early, and it was a data-driven VC. And I was like, what data do you have for this company? And he was like, we have all this data on, like, number of shares on Facebook o…”

“I don't think so. I know that that's happened in the past. I don't just, I just don't see it happening this cycle. And probably if it were to happen, it would have already happened.”

“People started paying, like, seed rounds at twenty million dollar valuations, and in, in a market that's gonna be a really tough path to get to a billion dollar plus exit.”

“And this close that we were supposed to do in March, everyone who had already committed, including people who had signed, backed out.”

“My fund zero was fifteen million, then we went to 75, and now we're two 25 total. But we don't want to grow from here.”

“I don't think many of these folks are going to continue on. Like their fund two, fund threes are going to be really tough.”

“Is a lot of, let's say a lot of the like multi-stage funds, typically historically leading series A's, they used to have an ownership threshold of. 20% minimum. And now they have a lower ownership threshold, 15.”

“I haven't read a book in a dozen years, and I've found that, like, I know authors, I find that, like, books are too long and full of fluff, I get a lot more out of reading articles, long form articles or listening to podcasts.”

“What we mean is many companies in the future will be FinTech companies and specifically, especially companies that are marketplaces or vertical SaaS businesses. If you have distribution and you have a data advantage, you can layer in other stuff like lending, …”

“I'm in a bunch of like these longevity groups in San Francisco and WhatsApp and people are, People were, like, trying to buy the company.”

“Stripe had built RAM. Stripe had a corporate card. And it didn't work. Like, they ended up investing in RAM and deprecating that card.”

“She built this to a million dollars in revenue all on her own, and you're like, oh, I need to see more proof?”

“She built this to a million dollars in revenue all on her own, and you're like, oh, I need to see more proof?”

“I think we'll see more. I think we have to.”

“Even though I invested in 70 plus companies, there's only a handful of them that really matter, and the one The one biggest one represents a five X on the fund.”

“Seed valuations in fintech, for some reason, haven't really fallen much. And so our 20, 22 numbers are actually higher. We're investing at a higher valuation than we were then.”

“Particularly second half of last year, all of the series A's in our portfolio, like we were doing them at the price that, you know, we invest that, and then they were getting done at the hundred to 125 range.”

“And you've seen it with the likes of Uber, you know, today, a fifty billion dollar enterprise value. There's twenty-five billion dollars of venture capital money that went into that company.”

“We averaged 10%, and in this fund, we're hoping to average closer to 15.”

“What they depict is not the reality of venture capital. And the majority of the companies that get funded on the show don't actually get funded, all sorts of issues.”

“So even today for when people retire, the median American, when they retire, Almost 80% of their net worth is the equity in their home.”

“A buddy of mine who has a company called Deep Lawn. All they do is they help lawn companies quote. And so the lawn company you put in the address, it looks at satellite imagery. Using some AI to determine how much grass you have, comes up with a square footage…”

“Yeah, so it costs roughly, 150 to 200,000 dollars.”

“Where like load factors were, I think like in the mid sixties, 20 years ago, now they're upwards of 80%.”

“I know that, like, United, for example, is locked into a shitty contract with DirecTV on a bunch of their planes.”

“And at this time, Facebook was limited to college campuses. And the way that they monetize Facebook at that time was you could set up a flyer. So like I went to Carnegie Mellon, I could pay 10 dollars a day to have the sidebar at Carnegie Mellon. And it was ba…”

“So ours is, we'll probably have about 10 companies in this We're thinking six to 10, and we're investing a half million in every company.”

“And, you know, through that, through the course of Kiva, we've done several billion dollars of loans, all at zero percent interest.”