The Ledger, every show

“They're too big to bail. So it's not too big to fail. They're too big to bail. They're so big. They're bigger, the Swiss government does not have the underwriting power to underwrite it, and I could see them failing and bringing down Switzerland with them, and…”

“Last year, as I was thinking through what are safe havens for cash, I was thinking of putting a lot of my cash in Swiss francs in Switzerland. And I did an analysis, and I realized, and I actually came to the conclusion that it's the opposite. I think Switzerl…”

“They're too big to bail. So it's not too big to fail. They're too big to bail. They're so big, the Swiss government does not have the underwriting power to underwrite it. And I could see them failing and bringing down Switzerland with them.”

“Endural, and look, I'm an investor in Endural. The problem is their cost is extraordinarily high, and so the way you measure this is cost per kill, and they're not battle-tested.”

“We're still in the middle of an AI bubble. If you look at like the amount of money that's going into AI versus every other category in terms of valuations raised, the amount, the number of companies getting funded.”

“I want to say the cheat code I use for IR, why I still can get 30% IR today, is the virtue of being diversified means I own two, one to three percent of any of the companies, and so what I've been doing is getting secondaries on the way up. So, I've been doing…”

“Right now, we don't have the manufacturing capacity. We would lose a war with China right now.”

“For 15, actually, probably for 15 years, every document that was ever sent to me, legal document that was sent to me, SPA, Anything like companies selling, et cetera. I auto signed, or my, actually, my virtual assistant in the Philippines, who had my signature…”

“The degrowth movement is bullshit, like no one wants to go back to being a farmer and having a life expectancy of 29, starving multiple times a year, so the only way we solve the problem is actually through technology-led productivity growth and deflation”

“Every document that was ever sent to me, legal document that was sent to me, SPA, anything like company selling, et cetera, I auto-signed, or actually my virtual assistant in the Philippines who had my signature would auto-sign for me all the docs that I never…”

“Crypto is not An inflation hedge , it's still a risk asset”

“The degrowth movement is bullshit. Like, no one wants to go back to being a farmer and having a life expectancy of 29, starving multiple times a year. The only way we solve the problem is actually through technology-led productivity growth and deflation, and t…”

“We tried doing reference checks on founders and realized that they were a negative signal. Some of the very best founders were horrible employees. They would talk back to their bosses. They would work on their startup at their job. They had the worst reference…”

“I think it's the best time to invest, but the, in a way, investing in venture right now is contrarian, and I think you should be investing in funds That are not going after the lovingy, you know, AI, all AI, all the time category.”

“I feel people are underestimating the risk of zeros, even though something can go from zero to a hundred million AR very quickly, and usually they're priced accordingly. And I, you know, I care about, like, what am I, what returns, what do you need to underwri…”

“The AI disruption is actually benefiting startup incumbents, because they have the data modes, and so it doesn't benefit eBay, you know, because they're slow and big, but it benefits, you know, an incumbent startup that has already liquidity, that is the most …”

“At the fundamental LLM level, I think the horizontal, you know, GPT may just win most categories. The same way that Google won search reasonably read large, except maybe kayak for travel. I suspect, I think OpenAI and JGPD win most of the LLM type categories”

“While I do think eventually a winner to emerge and they'll have the proper pricing power, and I do think in the long run you're able to extract value when you create value, there may be a lot of investor value destruction on the way up because people are compe…”

“I'm investing a lot actually in Ukrainian defense startups, because I think my vision is that Ukraine could become the manufacturing hub for defense.”

“And so I created a setup for a process for deciding in a one hour meeting if I would invest or not in a startup. And that's essentially one that we still use to this day, you know, with refinement over time.”

“History trumps macro, right? Like, the last 200 years of I've been a history of technological progress that has led and innovation that has led improvements in the human condition. And over the last 200 years, despite world wars, the great depression... If you…”

“If you're deploying twenty billion, You really don't get out of bed and write a ten million dollar a check very often because it just doesn't move the needle. Like there's no, you're not deploying enough capital. It's like a return of capital that you can make…”

“When you start the statement with, this is a foundational generational company, and the founder is extraordinary, and I'm going to regret this decision the rest of your life. You are. Do not, if you write that, make the investment.”

“In the last 24 years, and I've realized I are 45% a year. And then in the unrealized, we have like 650 companies or so, it's like also 45% implied IRR.”

“Today, in my probabilistic terms, I'd say there's a 20% scenario that we probability that we end up with a optimistic outcome from where we are, and I can explain why. Maybe a 60% scenario of what I call the Great stagnation, and another 20% scenario of, like,…”

“As an early stage investor, like pre-C, seed, and A, it doesn't really impact me too much because the macro I care about is the macro is seven, 10 years in the future.”

“Where I'm most excited about opportunities to deploy a lot of capital at good prices in the coming 12 months, yes, it is the B and beyond, or C and beyond, because I think we're going to see major repricing.”

“And in fact, I wouldn't even read any of the legal docs they ever sent me. I auto signed or docu signed every single doc they sent me from the investment docs all the way to the exit without even reading them.”

“AngelList did a study of all of their different mini funds on AngelList to see which ones were the most successful. And their ultimate conclusion was The more qualified deals, and of course we need to define what qualified means, you invest in, the higher your…”

“We will never be a 10 X fund just because we're too diversified for that. Any one fund will never be top to sell.”

“And number three, founders we backed in the past that have done well for us, we will back them blindly in whatever they do next.”

“If you find Uber or Airbnb early, if that's all you do for the vast decade, you're probably going to do better than with my approach.”

“Now, we don't do that for all of them. We do it typically for the fifth to 35th percentile companies in the portfolio. The top five percent usually don't need us, and the bottom 50th percentile will tell them where they send, will tell them what we think they …”

“We went from something that was criminalized to then being medicalized, to then decriminalized, to then legalized, and that led to the creation of countless of companies in the category. I think the same thing is going to happen with psilocybin, with ketamine,…”

“So we're seeing an entire reinvention of finance, and frankly, of the web, in a decentralized way. And that's going to go from fringe to mainstream, despite the fact that there are bubbles in that market right now. The bubble will burst, but the same thing tha…”

“And so the barrier to entry, in fact, if we look at how we select companies to invest in, and there's a bunch of criteria barriers to entry is not one of them because the barriers to entry or something you build, By virtue of executing, you build a brand, you …”

“Over the years, I've invested, as I said, around the 210 startups. We've actually made money in over 50% of the exits. On average today, we've done about seven acts and over 70 or 80% of IRR.”

“I'm coming in at Four pre at pre-seed, at 10 pre at seed, and at 20 pre at A's, and I feel very comfortable that in 10 years, these will be much, much larger with valid business models, and we less risk of disruption.”

“If you're at a hundred million revenues, it's easier to go from a hundred to 200 in the US than zero to a hundred anywhere else, and that's true at a billion.”

“My personal net worth is still 60%, basically early stage startups, because they can grow very dramatically.”

“This goes to show that crypto is not an inflation hedge. It's still a risk asset have been marked down dramatically.”

“There used to be 5000 seed funded startups per year in the U.S. That would raise 500 K or more. And last two years, it was almost 20,000. So we tripled, we more than tripled, I mean, it was over 15,000. It was between 15 and 20,000. So we tripled or quadrupled…”

“My asset allocation, my personal net worth is still 60% basically early stage startups”

“It means we have fewer exits in the next few years. It means the valuations at which these exits happen are lower which means that the IR we get are lower”

“I mean, last year we didn't do a single deal C and beyond, just because prices are too high.”

“Where I'm most excited about opportunities to deploy a lot of capital at good prices in the coming 12 months. Yes, it is the B and beyond or C and beyond, because I think we're going to see major repricing”

“There used to be 5000 seed-funded startups per year in the U.S. That would raise 500 K or more, and last two years, it was over 15,000. It was between 15 and 20,000.”

“I don't think they're going to screw up the A and B market and asset class because they're going to play. It's not going to be the bread and butter.”