AVOID PASSION

“Somebody called me and said, specifically, I'm selling the company, and it was a company that was doing performing quite well. And they told me they were selling for half their valuation. And I was shocked because this is actually one of our best investments that we've made over the past like three or four years. Companies doing well, growing fast... And then I was like, oh, so it sounds like you're giving up, right? Like you would only sell your company for half of the valuation if you were giving up. And the founder said, yeah, I'm going to go start an AI company.”

“There's a great video that that Pink references that we can put in the show notes where Bezos has asked about the decision to leave D. E. Shaw and start Amazon, and he said he used a regret minimization framework. He said, oh, it's only a nerd could do that. But he said, that he imagined himself being 80, and would he care that he left D. E. Shaw maybe for win a bonus? Or would he care more that he didn't take this chance, this kinda instinctive chance that he felt like he had to take? And he immediately, after thinking about it in that way, wanted to go do it.”

“The Invest America accounts, now known as the Trump accounts, right, are more capitalism. They make every child a capitalist from birth. A private owner gives them a thousand bucks in a four zero one k like account that they own and control, their family has on their phone. At the start today, there are 65,000,000 kids in the country qualified for an Invest America account. Every kid under the age of 18, and every kid under the age of two will automatically get a thousand bucks in their account. Remember, the accounts have to be funded and established by our 200 birthday, 07/04/2026.”

“I've basically come to the consensus that investors, and this is probably my maybe most controversial statement, but investors will never approach a founder about paying them more money. In my entire career, I can think of it less than five times that it happened. It is just not top of mind on the investors' tasks to do. And I actually don't think it's like bad intentions or malice. I think it's just not in the regular course of business things that come across investors' desks.”

“The Internet's niches are way bigger than you think they are. So if you think you're writing about a niche topic, the Internet being a global community of four-ish billion people means that any little niche, there might be six people in your geography that care about it in your local town, but there's millions of people online. All outputs can scale completely independently of your inputs.”

“First of all, the best investments I've made at seed, the majority of them have actually ended up being pivots, meaning that the company I invested at the time, if I had hired BCG and done a month of diligence on the company, the results of that research would have been irrelevant because what actually worked out from the company was a completely different business model later. It's not all of them, of course, but it is the majority, which sort of surprised me. And so I think that that just calls into question, like, what is the decision-making process to make a seed investment?”

“Coinbase and Circle have done this deal where Coinbase will allow you to earn 4% on your stablecoin balance, which, you know, to to get that kind of return at another bank, even a neobank, you have to have your direct deposit go there. Here, whether it's $10 or or a million bucks, you know, you put it in stablecoin with Coinbase, and you start earning 4% daily. And on top of that, you can transact immediately out of that account. So you don't have to, like, move it from your savings to your checking to get it to do ACA. But you can send stablecoin immediately in microseconds, and it'll cost you a few pennies.”

“This is Mag five CapEx as a percentage of their operating free cash flow bill. And if you look at it in 2025, so that's this year, they'll spend about 66% of their operating cash flow on CapEx. In 2023, their total CapEx was a 156,000,000,000. And this year, it's 379,000,000,000. Right? So radical step up.”

“It appears to me that OpenAI, through all these partnerships and announcements, is trying to create escape velocity. You know? And that could be against the model providers. It could be against a hosting provider depending on how you think the market plays out. But it'll it it creates an interesting stress test for anyone else in the ecosystem to say, are you gonna lay chase? It just feels like they're they're daring people to to follow them, and and I suspect a bunch don't.”

“Berkshire, we learned so many things from. We got really obsessed with the circle of confidence, that it's okay to have a giant too hard pile. There's a bunch of things that I'm not intelligently saying no to. It's basically admitting that like our opportunity cost is so high, like the things that we say yes to are so awesome, that it's okay to say too hard to just a giant amount of things.”

“One of the more peculiar of all the deals is, and this was disclosed in a core we've filing, was NVIDIA has promised to buy any of CoreWeave's service availability that they can't sell to anyone else. That is very unusual. That's not the same as making an investment. That could easily help CoreWeave with their debtors and and getting more debt financing. But it also means as a investor, we we don't know what's going on with real demand for CoreWeave because we probably won't be told if they start moving into the world where they're offloading to NVIDIA or not.”

“I'm gonna read this out loud. As part of its aggressive economic and political campaign against Brazil is investigating PIX, accusing the payment system of unfairly utter undercutting US financial and technology companies like Visa and Apple. I mean, that's the most absurd thing I've ever heard. Undercutting Visa? Like, do do they realize they have Visa and Mastercard have, like, the top two operating incomes in the history of American business? Like like, there's there's no one that needs less protection than these guys.”

“When I picked the name Pipedream, there were a few people that said, you can't name your name Pipedream because you're saying it's like a fantastical thought, therefore it's impossible for it to come into existence. But the true story is we had a meeting at Chime where we were sharing what we were working on and the CTO of the company basically said, I mean, it sounds interesting, but I think it's a Pipedream. That was kind of his response to our business. I didn't honestly, I don't think I really understood that time by the way that it's actually a drug reference.”

“I generally don't like the advice of follow your passion. I've never really liked that advice because I found that many people I know have amazing passions that are terrible businesses and they're able to apply the exact same like enthusiasm and energy to things that are much better uses of their time. So I feel like maybe, you know, enjoy your passions, but not necessarily follow them professionally.”

“I feel like I have a public service announcement to deliver. And that public service announcement is that Silicon Valley is the center of the tech universe. There was a period of time where people thought that that either was not true or was no longer going to be true. And that is incorrect. Austin is great. Miami is great. They are not even casting a shadow on Silicon Valley in terms of tech innovation and where companies are being started.”

“Founder Control was a huge one. We sought some advice and we went to one of the best investors ever. He sort of sat there and he thought a minute and he said, I have seen so many founders become trapped in prisons of their own making, in their own companies. You guys have avoided that fate, don't go down that road.”

“I'm a little concerned for what I call like the first generation AI companies. And that's basically like companies that were built on top of the models, and they were building feature sets where the models didn't have capabilities. And the argument was, oh, as the model gets better, my product will just get better. And that was the sort of shared thesis of many of these companies. And I actually thought it made a lot of sense... I think what people didn't fully appreciate, and I definitely didn't appreciate, was that the acceleration and the capability of these models would actually start like, if you think of it as concentric circles from the core, they would just start eating these adjacent concentric circles faster and faster.”

“Low skew count drives everything. If you only sell 4,000 things, it doesn't take a lot of volume before, very quickly, you are a meaningful seller to every single one of those products. On average, it takes them 27 days to sell through their entire inventory, which means that's on net 30 terms, three days of grace, where the inventory is actually financed by the vendors and then some. There's no working capital in this business other than building more Costco's.”

“We did this survey and asked people if you could start your career over again, would you do things differently? And in that survey, 70% of people said yes. And we did it again with Wharton just to make sure we had, you know, a a true academic survey going on, and they did a lot more people. And that number was still six and ten. There's a great book called The Power of Regret by Daniel Pink. He said, one of the most robust findings in the academic research and on my own is that over time, we are much more likely to regret the chances we didn't take than the chances we did.”

“Both Nintendo and IPL, they were the first listening experiences for some incredibly influential people who have changed the trajectory of acquired. Specifically listened to by one person on the Meta executive team who found it, thought it was amazing, sent it to the entire Meta executive team. Without the Nintendo episode, Mark Zuckerberg doesn't join us.”

“I think anybody that's been a student of financial history has, you know, studied different types of activities that that historically, let's just say historically, have created red flags. And the reason that, you know, any AI you talk to would know what you mean if you said circular revenues is because someone has used it in the past in a way that that wasn't good. And I just described those things to Chai GBT and ask it for its analysis both as an accountant and as a financial investor. And the AI itself, you know, would would find its way toward company names like Enron and WorldCom and those kind of things merely by describing the type of transaction.”

“Language is a lossy compression of thought. And uncompressing information, it's so funny when you and I are communicating. I had a thought, I compressed it into a very narrow bandwidth thing of speech. I told it to you, you uncompressed it into your brain. It might actually mean a pretty different thing to you than it means to me.”

“The NFL, because the product is scarce, and then they have very smartly cultivated that and engineered it to be more scarce, more of an event-driven sport, that's made all the difference. To me, what we do is insane for the podcasting industry. It's completely insane. We release, for the last three years, we've released 12 episodes. The next year, we're going to do eight episodes for the whole year.”

“I bought these shares in 2008. When I was working on Going Infinite, I was talking to a publicist completely unrelated to Warren Buffett. She said, I also represent Warren. She said, and I told Warren that I had been talking to you. He said, is he the Michael Lewis who bought shares back in the Mitchellites? And he said he bought it like the book value to that thing, that ratio, he bought it as cheap as it's ever been. So can you imagine that Warren Buffett is taking the time to watch who is coming in and out of the A shares and thinking about it?”

“You're not taking risks if it doesn't work sometimes. Right? But it's the difference between, I mean, do you know how your heart sinks when someone gets up at a podium with a script with a speech and they're going to read their speech? The audience is waiting for you to get through this thing because they know nothing is going to happen. If you get up and you just start talking, the audience also knows, oh my God, this could be a disaster. They don't know where it's going.”

“QSBS is basically a tax paradigm in the United States where if you invest in a startup that meets a certain amount of criteria, I believe the criteria used to be 50 million in value. It had to be less than 50 million in value. It has recently changed to less than 75 million in value. And you had to hold that investment for originally five years. And now there's like a proration period during that five years. But if you met that criteria, then you paid no federal taxes at all.”

“The only thing I know for certain is that software companies are completely mispriced. What I don't know is are they completely mispriced and massively overvalued? Or are they completely mispriced and massively undervalued? Because the current value of the software company is basically a probability that in 10 years things go really bad for them. And so if they do go bad, then the companies are overvalued. And if they don't go bad, then the companies are undervalued.”

“We interviewed Doug Leone, who was one of the two stewards of Sequoia. He told us that after the dot-com crash for the Sequoia fund that was the dot-com bubble fund, every other venture firm out there after the bubble popped were taking mulligan funds. And he said, the best line anyone's ever said on Acquired, he said, we looked at each other and you could burn cigarettes on our arms and we wouldn't flinch. And they spent the next like five years, they didn't raise another fund.”

“If we implement 50 different state rules that these companies have to jump through and companies that are that are competitors that are competing in the broader world don't have any of them, there is zero chance that's not gonna create mud and slow down The US players. There's just zero chance. And I'm certain the people that are writing these laws don't understand that there might be some global, you know, consequence of what they're doing.”

“I mean, I think fundamentally seed investing has always had the highest annualized returns of any asset class with Inventure. And so it's where everyone would like to put the majority of their capital if they could. And obviously the reason is because you're investing earliest at the lowest price and you get the largest ownership for the smallest check. And so if you can get in the marquee companies, then it's the single best place to be.”

“I've been using the analogy lately of tech competition feels much more like professional sports now than it ever did. Maybe over the 2010s, it was more like D1 sports, and maybe before that, it was more like high school sports. It is optimized to a degree that it was almost unfathomable a decade ago, and that's at every level. That's at the engineering level, that's at the product level, that's at the company building level, that's at the venture level. There's really no pocket where you can say, wow, this is really amateur hour.”