The Ledger, every show

“I think switching costs is less going to go to essentially zero because over the next one or two years, ability to port data, your data as a business or consumer from any ecosystem to another ecosystem is going to be very easy.”

“You either need to be managing 50 humans, or you need to be an IC. And so they would, there's something called span of control, which means how many people you manage in some ways. And so span of control less than 10 should not be allowed at any company at thi…”

“I think this is 100% overreaction because not all software companies are created equal, and we can talk about what the differences are.”

“And then people are going to be able to replicate almost pixel by pixel. The experience you have with one product in a different products, you'll have clones popping up left, right, and center and data portability is going to be easy in that case.”

“Software earlier was a scale game where because you had produced a lot of software, it was cheaper for you to produce a lot of the guess what? Now everybody can produce software as cheaply as anybody else.”

“And I think that's the way that a net suite or a sales for the system record needs to operate. They have to commoditize a compliment. They can't just wait around for other people to build on top of them.”

“Most bolt on players are not doing it. They're simply using a GPT or anthropic model. And they're basically just adding a thin layer. You have to rebuild the entire experience end to end.”

“Model capabilities are improving every six months because if you have too long a product roadmap, you're going around your program and the model comes and just blows it out of the water. So you've got to really understand what the capabilities are of each new …”

“If you're moving money, you're generally in a good place. So anything touches money, We feel there's a very strong moat there, a much more defensible.”

“Data and workflow moats are the two things you're really hanging your hat on as a software investor, because if you're not doing FinTech and then I think it early stage is too hard to know what a distribution moat is unless they have some hack and these hacks …”

“The first thing that's happening is businesses are outsourcing to third party BPOs, many of them in India, Philippines, et cetera. That spend is the easiest to cut because now you can offer the same service, higher quality, faster, and 20, 30% cheaper. The sec…”

“A bunch of them are going to become zombie companies, And they're going to try to add AI features as a last resort, not succeed and be sold to PE.”

“Now, the big challenge is seed based pricing, which you alluded to, is it breaks when the product's core value is not about access, but it's about something doing the work on your behalf. So at that point, charging per user doesn't make sense because user isn'…”

“I think we saw in the first way of AI, we saw many chat GPT, like there was a company called Jasper, not to pick on them, but they went from one to 40, and then they came back from 40 to 10 or something like, or maybe one to a hundred and a hundred to 40 withi…”

“I think the best venture capital, I, someone asked me what's the best venture capital bets. I talk about a paradoxical one. I think it's Mike Moritz betting on Instacart. Why? Because he lost three hundred and seventy million on web van less than a decade ago.…”

“Even in V work benchmark made money. Genchmark made money at WeWork because they invested early enough.”

“Maybe you can do a couple of deals like that, but I don't think you can build a series A fund doing deals at three or four hundred million. Because it's not going to be enough ownership. These, some of these are going to fail, et cetera. But most deals, I thin…”

“If you're a startup, which is directly in Google's roadmap, like directly, you should not be building it because Google is very good when something is directly in order. They're like a tank. It will just roll over you even slowly, slowly, but it doesn't matter…”

“Not possible. I don't think with our fund it's possible. I think the ownership is just literally the first round for these companies is, like you said, a billion dollars. So I think it's just too high a, the risk reward is just not worth it.”

“They've basically gone and they deploy fifteen million dollar checks almost as an option and a lead lead generation for the next run. And the strategy is obviously to have an index at the A of every single good A company and then double down on the ones that t…”

“We see many examples actually in mega funds of partners leaving the fund and the companies orphaned within the mega fund because their partner has left. And now they don't have a single person to advocate for them in any way, shape or form, and they're adrift.”

“I used to think pure remote would scale for early stage companies if you have the right culture, but I don't think that anymore. I think you've got to be in person at least a few days a week.”

“I would say the best technical CEO, Larry Page, the best growth-centric CEO, Mark Zuckerberg, The best design-centric CEO, Jack Dorsey, and the best physical world operational CEO, the most likely to be Jeff Bezos next, Tony Xu.”

“I've actually invested in more dropouts as an angel now over the last few months than I have invested in in, in, in, by the rest of the last 15 years I've been investing.”

“The number of designers and product managers related to the number of engineers, when I was growing up in product, it used to be, one to three or one to 10. It's going to one to 20 now.”

“Slack has done it most publicly. Slack is owned by Salesforce. They cut off access to Glean, where Glean can no longer access Slack data. And the reason is they don't want Glean to build on top of them. And then slowly suck out the value that Slack has.”

“So the agent companies have no option, but to also start building and offering a system of records. So every company I know is now trying to figure out how do I build the entire platform and not just a system that does some workflows. I think last year, everyo…”

“That's why I think many of them probably need to go private Because they have to make this business model transformation in private. I think it's going to be hard for them to say public.”

“The reality is it runs your whole business, and there is no compelling reason for someone to put their career at stake by ripping out NetSuite. I know there's a lot of, ah, over the last year, there's been a lot of AI-enabled ERP businesses, but there is no co…”

“And I came up with the example of Sierra, which I think unique asset is Brett Taylor. I mean, they have full control of Brett, who's one of the best salespeople, chairman of OpenAI. He can make a call to any company, any country, and they'll take his call. You…”

“Zuck was and is actually, I think, the greatest mind on growing, building, Growth and engagement in building consumer products broadly.”

“So pure self-serve product would never have any reviews of any kind. You're going to be immediately activated Go on, and we'll do checks in real time based on what you're doing versus banning you or stopping you.”

“ChatGPT. Their combination of intent and identity data is unparalleled. I mean, Google had intent data but not identity. Facebook identity but not intent. These things have been brought together.”

“There's going to be almost certainly a cottage industry of companies that are going to come and say, I'm going to help you optimize ads in ChatGPT. There's already companies that help you optimize placement In what is called these answer engines called AEO ins…”

“The good news is the being first doesn't matter. Why? Because you control, especially if you're in category one, which we described, you control your first party inventory. In fact, being second or third, you can learn from the iteration of mistakes as the fir…”

“So I think what the number one skill that is going to be relevant two years from now, probably even one year from now, is to become a functional expert that knows how to build AI agents to do that function and orchestrate an army of AI agents to do that functi…”

“The other thing I always recommend to CEOs is a board role is like a marriage. Once you get into it, it's very hard to get out of. So never, ever, ever invite anyone to join your board before spending at least a year with them.”

“You cannot be a single product company. Critical products, you've got to really own full stack. It's harder otherwise to be a ten-plus-million-dollar company.”

“So I think I ultimately, my core investing thesis is that if there is not remarkable product, all the go-to marketing distribution in the world will not save you.”

“Mark, I think is Mark Zuckerberg is probably the best. I would say distribution genius in the world.”

“You have to have, you cannot be a single product company. You've got to make sure, and most importantly, your product number two needs to emanate very naturally. It can't be like this completely separate product. It has to be very adjacent product number one.”

“Companies need to be very clear which are the profit pool products and which are the retentive products. If you confuse the two, your teams don't know and they're built for the wrong outcomes.”

“Coinbase, when I'm on the board, is a great example. They have MTLs, money transmission licenses, state by state. There is with the Fini, CN, all of those things. It makes it impossible for a company to use anybody else than Coinbase to custody their crypto be…”

“AI can vibe code the ability to access restaurants, but it can't vibe code liquidity, courier density, reputation history, all of those things. So marketplace density is a network effect, which is structural.”

“Any one of these modes is not enough. But what you want to do is you want to take a company and score it across them. Maybe you assign one point to each mode they have. And I think anything four or more, you're pretty damn secure. But if you have a two or thre…”

“Atlassian has, you could argue they have proprietary data. Now they need to use that data to build products. They have unique proprietary data on all the code out there because it's being checked in. There's a lot of stuff they have, which they need to use for…”

“Monday probably has a score of one, I think. They have a workflow mode. I'm not sure if they have the other modes. So you're right. Monday, in theory, has a much weaker score, I guess, than Atlassian on this.”

“I don't think Shopify will build it. Shopify is an investor, and Shopify, I think, has decided, at least in my opinion, that this is, Shopify has these things called missions, and I think they've decided this is not part of their mission to build this product.…”