The Ledger, every show

“I will also say that any seed investor competing with a multi-stage firm will go very, very out of their way to instill this Wild fear in the founder's mind about like the risk of that.”

“I mean, these companies are compounding it over a hundred percent year over year in the billions of run rate. We have never seen that before, right?”

“And so when you look at investment like open AI at thirty billion or anthropic at sixty billion, you know, I can tell you these are opportunities that I personally believe have the upside to generate multiples versus say IRR.”

“Is these are opportunities where you can invest 500 to a billion dollars in one of these companies, and if your underwriting plays out, potentially turn that into, you know, three, five, 10, maybe even twenty billion dollars if these companies turn out to be m…”

“This can become untenable very quickly for these smaller funds, where, you know, investing at 50, 60, 70 caps is, you know, pretty hard to imagine how you make a lot of money as an, ah, you know, a thirty million dollar fund, for example.”

“We're talking about going from talking about 30 to fifty billion dollar outcomes to multi-trillion dollar outcomes in the form of SpaceX or OpenAI or Anthropic.”

“None of that matters if you don't maintain a lot of dedication to early stage investing. If you're Sam Altman or you're Dario and you're asking yourself, do I want to hitch my wagon to one of these firms by raising billions of dollars from one of them? You kno…”

“OpenAI famously saying, hey, if you're an investor in Glean, you don't get to be an investor in OpenAI, which would foreshadow they plan to play in that space.”

“I'd certainly be a little nervous about how the code gen stuff is going to play out today, because it seems like that is just far and away the killer use case for LLMs and therefore the one that these big model providers are going to lean into next from an app…”

“It doesn't appear as though the supply of capital from platforms like the one that I've just joined or some of the others that we've talked about is going to go up in, in, in size. And so again, you could argue that these five to six firms kind of have this ca…”

“These software companies that are not just augmenting, but in some cases replacing the work that humans do and the budget allocated towards paying them for that work, these companies are going to get bigger, right?”

“Having that extra, you know, two or three years of runway can actually be really, really punitive Given the opportunity cost associated with amazing founders time.”

“If you go and talk to a CIO or a CTO of a large enterprise today, they're furiously seeking out ways to apply AI to their business. And the reason for that is because their CEO and their board told them, you're going to get fired because the entire fate of our…”

“You think it's the domain expertise that matters. It is without a doubt The AI expertise that is more scarce and therefore matters more.”

“And so what I've really come around to is that it's these products that are going to be built on top of these models, even inside of the model labs, not just by third parties that are going to be much, much more compelling businesses long-term than say the mod…”

“It seems very likely to me that in some form or another, Every single one of these frontier model labs will begin building both business and consumer facing products.”

“And so I think as a result, like to me, AGI feels like it's here in a lot of ways, and even if we were to kind of say, hey, the capabilities that we have today are it, and it's not going to get any better, We are so early in bringing these capabilities to bear…”

“I see a world in which both ends of the barbell really, really continue to rise, meaning small dedicated specialist firms on one end and large platforms on the other end. And I think that uncanny valley in between is is, is going to be an increasingly challeng…”

“These companies that could be worth trillions of dollars someday. The SpaceX's, the Anduril's, the OpenAI's, the Anthropics.”

“And I think that to the extent these new products get introduced to the industry, it's gonna be because they see an unfair advantage, ah, in their ability to deliver on that because they have this unique insight into, like, what these companies really need and…”

“None of this matters if you don't have a compelling brand that I believe can only be forged at the earliest stages.”

“Because if you marry wrong, it's tragic, but you can get a divorce, right? You can make a change. Once you pick a general contractor, and I know this from personal experience, having remodeled the house with my wife a couple years ago, you are stuck with that …”

“Don't not take investor meetings because you're not raising. And the reason for that is because you can do it in a contained way that allows you to understand what these people are about and who they are and do you vibe with them or not? And I think the proble…”

“That said it's not clear to me that, that construct needs to exist at seed and pre-seed in a way that necessarily, like, makes the company better off. And so typically what I see is that there are cases where, like, the founder wants to form a board, they want…”

“There are definitely certain funds that come to mind that I won't name who have decided the strategy that they're going to employ is to use valuation as a lever to win.”

“The big mistake that some investors make, especially earlier in their career, because thesis driven work is, is a little bit easier to do than say developing relationships with people, which takes a lot longer. Is they tend to go and find the best company that…”

“The moment I lose the desire to go on Hacker News or go on Reddit or go on X and just figure out what's going on in the world and what people I don't know that I should get to know, that's the moment that I should probably hang up my cleats and move on because…”

“Look, for me, I think ASI is here in narrow pockets, right? Like when I use deep research, like I've seen the future. It's just absolutely incredible.”

“The act of sizing a market is just, at least from my experience, so imprecise that it borders on being a fool's errand.”

“And I think for that reason, it's really clear to me that having the chip stack that these large platforms have is, is really uniquely beneficial at this point in time.”

“We're talking about billions of dollars of run rate growing in excess of a hundred percent year over year. I don't think we've ever seen that before, right? Like you talk about ServiceNow doing, you know, billions of dollars in ARR and growing, you know, 20, 3…”

“And I think what you're seeing with, say, Andreessen Horowitz is they're trying to invest in every one of these companies. And I think it's a rational strategy so long as you have buy-in from the entrepreneurs so as to not ruin that relationship.”

“If we really are talking about companies that are going to get to some level of AGI such that they're going to be, you know, not just multi-trillions, but potentially larger than that. If we're talking about how Starlink and, you know, the kind of assets being…”

“And when I look at like a trend like robotics that is still so, so early, but at least in my mind, I've convinced myself that this time is truly different in terms of the industrial prep in terms of the industrial applicability of these products. It really, to…”

“And so my view is that these spreadsheet investors are just going to keep getting pushed later and later stage.”

“There are so many scenarios in which preserving optionality makes a huge, huge difference, and therefore keeping dollars in and your, you know, the value of your four or nine A or your post money of your last round as low as possible is very, very beneficial.”

“And right now, to your point, the bar is going up for what best idea looks like when it comes to growth rates and momentum. We can talk about the quality of that revenue and how it's very mixed, and this has been discussed many times on this show and outside o…”

“Look, these parlor tricks exist. Every firm engages in them. Depending on founders, like, they either respond positively to it or not. But ultimately what I've found in practice is that none of that stuff really matters. What matters is did you put the work in…”

“Being domain focused really, really helps with that picking aspect of picking who to spend time with, who to position yourself with for when they do decide to raise.”

“Look, so that strategy can definitely work, but I would argue, and this is maybe world's smallest violin, that picking is actually much, much harder. In these larger firms that have notoriety in the market. And the reason for that is because the opportunity se…”

“And so I personally have a view that I think the industry's in a healthy place and it's just hard for me to say there's too much capital chasing too few opportunities.”

“Usually what I find is that it's like, it's just like the quality of the company at that stage and how they've executed against the milestones that they set forth that determines like the series a success rather than say like the whimsical taste of the multi-s…”

“Having to generate revenue and build a business that you can take public someday is, is, is going to come with short term thinking.”

“My sense is, without going overboard on conflicts of interest, being in as many of these companies as possible, given what I know today, is very rational. But I also think it's rational and becoming to say, Hey, we're gonna, we believe in one of them. We're ju…”

“And right now that appears to be very unlikely, at least in the near term, but at some point it could happen. But I also have just learned to never bet against human ingenuity, and given the best and the brightest are now so heavily concentrated concentrated i…”

“I think Mamoon is known as someone who is very metrics driven, and I think that could not be more false. He has this incredible taste in people.”

“I've already told you why I think people are more important than everything for one, and I think that some of the biggest mistakes I've made as an investor is when I've ignored traction because I've had reservations about the market. Traction is so hard to man…”

“I do not think it's a permanent structural challenge because I believe that in the same way that great entrepreneurs flock towards white space, there will be solutions and new products that get devised by investment managers to solve for these liquidity challe…”