The Ledger, every show

“I turned down a company the other day, Because they were going from, like, one and a half to five to 15, and there's an opportunity cost of capital to say that's very real, and the growth expectations are just very different. In other words, triple, triple, do…”

“Pretty much only hire immigrants. British people don't work very hard.”

“I think it's Clubhouse of our era. And so they have brilliant channel market fit, which is they crush it on Twitter for very specific clips. When you look at any of their view rates, very little. When you look at their retention on engagement rates, fuck all.”

“If I could do anything without fear of retribution from my LPs, I'd put my four hundred million fund into OpenAI.”

“I think the quality of European founders is much worse than the US”

“I think this generation is fucking lazy. They do not work, sorry, I'm on a rant now. They do not want to work hard, they do not want to come into the office, they get paid top dollar, and actually, they want great package, they want all of this, and they don't…”

“I don't buy remote by the way. I think remote is one of the most poisonous things.”

“You know, it is, but I'm seeing now I've seen four this month where the series B's are saying, Hey, preemptively we fucked up, but give us our cash back and we'll give you a million each.”

“I think most of the people who invest in there are incompetent and shouldn't be given dollars. This will definitely be taken out, no doubt. I think this is like, you know, you're empowering people who should not be investing. They do not understand public mark…”

“I don't think we fundamentally live in a democracy anymore, because I know I don't, and I know that pretty much everyone around me is too afraid to say how they truly feel.”

“Well, I think with all candor, that's because of incredibly poor management. And hiring, and that was theirs to take, and they fumbled the bag across every spectrum.”

“If Zuck expired, Meta's stock price would increase.”

“Cognition raising round at forty six billion dollars reportedly. They will end the year at 1.6 billion in ARR. Currently doing 800 to 900.”

“I'm an investor in McCaw. I never thought this would be as big as it has got as quickly as hit, as it has done. It's crossing out two, two and a half billion ARR. They're doing a new round led by General Catalyst at twenty billion.”

“Surge are doing three, three and a half. McCaw are doing two and a half. Handshaker doing one. Micro One are doing half.”

“I think the comparative landscapes they sit in mean that the Chinese open source providers are just inherently advantaged, sadly.”

“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 a billion dollar valuation is the new series, eh? And you're like, whoa, Harry, whoa, whoa, kiddo, calm down, listen to the facts. We used to do a fifty million post and hope it would become a 1,000,000,020 x, without dilution, blunt. Now, you enter at…”

“I just think Sam Altman is someone who I would never, ever bet against, and I think he's the best politician in the world, and I think when he says something, he says it with intent, and when he says we should give five percent away to the administration, he's…”

“I think Series A is the worst place to be today, and my partners always hate me for this, because all Series A founders are like, great, we won't go and see them but it's the worst place to be. You have, like, one to three million in revenue, and you're at 200…”

“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…”

“I think better, I think founders are better and investors are better when they are already rich. If I'm being blunt, I think you make more rational, sound decisions that are not made with economic impatience.”

“The worst place to be is a 50 to a hundred million dollar seed fund. You will get crushed by the large funds who are able to write large checks and lead rounds, but you're also not small enough to be collaborative. Very difficult middle ground to be in.”

“You can't do Series A unless you have a four hundred million dollar fund today. Absolutely no chance.”

“They were finishing the year at one and a half million ARR, finishing next year at five million ARR. Today, brutal as it is, this isn't good enough to raise a good Series A.”

“Menlo will make ten billion dollars in carry Spot will too, plus Founders Fund will make more than that from SpaceX.”

“Sam Altman just offered two million dollars In open AI tokens to every YC startup in the current batch in exchange for equity.”

“San Francisco is the worst place to start a company today because it is so expensive and difficult to acquire talent.”

“Struggles in parental relationships often signify very successful founders, sadly.”

“If I'd invest in every founder that I'd met, every founder that I've met, I'd be 17 X more successful. One seven X more successful. I would have had two and a half percent of deal. I would have had two percent of 11 Labs. I'd have a seed check in Flettersport,…”

“If you've been at Salesforce for 12, 1314 years, I automatically think you're not great. I'm like, you got stuck in your ways. You've been there for way too long. Seriously, you were happy just in this kind of melee of Mediocrity for 1213, 14 years.”

“Every dollar wants its home in Anthropic right now, and it's caused secondary market prices to surge to a trillion dollars for Anthropic.”

“I think customer support is uninvestable today, and I get so much shit on Twitter for this, because everyone shits on them, but I'm like, Sierra and Dakagon, obviously two market leaders in terms of brand, and how much money they've raised, and you've got 16 p…”

“When you take institutional money, it's a great responsibility taking on someone else's money, and you have already made a promise to your employer that you will devote your best efforts and all of your energy to making them successful and the company successf…”

“It's the best thing for OpenAI not to buy Sierra, incorporate that as a customer support product, and have Brett Taylor come in as the day-to-day CEO, and Sam can be fundraiser, Sam can be master of...”

“The amount of Sequoia rounds where it's like, oh, you know, X raises money from square five billion. Trust me, Sequoia got in at one, but they just club it together and then announced the sum and then the latest valuation. And it's just very misleading.”

“My takeaway is, honestly, you can't do early, and you're going to kill me, Rory, with less than a billion if you're going to compete to lead A's.”

“Cursor announces their movement from a billion to two billion in revenue in, in three months. Rumors of secondary round being done at fifty billion.”

“If we want to add in Waymo and what it'll do for self-driving within a four year period, Gosh, I think you could see 30 to forty million people.”

“If they sell per seat, we're not doing it. We need to replace jobs. Like labor displacement is what we're investing into. And that's the only way that we can actually return the amount of money that we need to now to make funds worth it.”

“And the single most common feature is a broken relationship with their father.”

“I think there's a chance that Cursor loses half of their revenue this year with the cannibalization of them by claw code.”

“Claude Code, Has cannibalized a lot of Cursor's business overnight and everyone's canceling Cursor.”

“I think another prediction of mine for 2026 is I think we're going to see like the demonization of tech and tech leaders like never before, as you see the first real instantiation of job losses and job displacement in, in large parts of the economy, like in lo…”

“The worst place to be investing is Series A. You either need to be pre-seed or pre-IPO today. To make money.”

“Series A is the worst place to be investing. Company progression is minimal. Price is four to five X, the seed price. And we're paying a 150 to 200 X ARR with little signs of product market fit.”

“So I hire, bluntly, Asians or Eastern Europeans, and very young, sub-twenty-three, 24. That is a sweet spot for us.”

“I think seed in SF is for suckers.”