The Ledger, every show

“My thoughts is he's still probably vastly underpriced and he should probably 10 X his prices overnight.”

“Yeah, financially speaking, most likely, yes. I think the expected financial outcome for the median one, probably, is probably higher, particularly if you get a job at the FANG with, you know, in Silicon Valley, those kind of U.S. Type salaries.”

“Do I think it's likely to outcompete Twitter? No. I think Elon is more likely to ruin Twitter himself than Threads is to outcompete.”

“I think that much in terms of success for founders, I think a lot more of those successes will come from the companies that are able to steer in a more sustainable path, get to break even at, you know, at best, something like that, maybe with a small bridge ro…”

“If it's an obvious idea and a huge competitive market with large incumbents, you know what? Those guys are going to take that. That's they're going to own that piece. And so like building your startups around that and thinking like, oh, I'm smarter. I'm more n…”

“And so I think the moat that exists from building out and managing and quality assurance on a team of people in the Philippines say, I think that's going to go away.”

“Like the best example of this is all these like copywriting AI companies, you know, basically like you could do whatever it is that they do. Using Open GPT and it'll be much cheaper than their interface. But the fact is their customers don't care that much. Th…”

“I don't think the stock market will be worse off.”

“I think B to B SaaS will be relatively, relatively insulated. And I think, and honestly, I think most of the pain that Payton in that sphere is done.”

“I think Stripe should buy Mercury. That's what I think, and not because I just own the founder. I think that would be a good acquisition.”

“It is a certain level of privilege to be able to bootstrap a lot of the time. It means that you have Either it's a bunch of savings, you made a ton of money doing something else, or a lot of the time your spouse makes enough money so that they can cover the wh…”

“So, if anything, I actually think it's easier to raise money when you have no revenue, if you have a good story.”

“18 months. That's a lifetime. I still think they're around. They raised so much money. I mean, I think they raised, didn't they raise like a hundred million or something insane? So I still think they're, they'll be around. Yeah, I do.”

“I sort of somehow doubt that a Shopify plugin will become, will IPO as a billion dollar business.”

“At least last year or two, it's been the case that like a B to B SaaS business Which usually selling for some sort of an ARR multiple gets discounted if it's a service, it's a business that serves WordPress clients, you know, exclusively.”

“If you're adding features, then just don't add it to these guys' plan, and just be like, eventually, some of those people will be like, hey, I want this feature, in which case you're like, great, now you need to upgrade. Out of your lifetime plan or whatever.”

“I do think there'll be a fundamental shift in sort of the expectation. I think probably mostly from the employee side and it'll probably start with like tech companies and things and then trickle down where it's like, okay, Maybe they'll be there a portion of …”

“I think, in general, commercial real estate is a bit screwed. Particularly in California, if, like, Prop 15 passes with the tax increases and things, I don't know what they're going to do.”

“I think actually there's like a diminishing return as you start doing PhD coming out of, this is a problem actually with some of the people I did, you know, who were in grad school with me and later on. They were like, yeah, like, I can't even get an interview…”

“Give existing customers a significant discount. So there's still customers on the other side. I wouldn't volunteer it. I would probably Yeah, I would be like, you know, if people start canceling, I'd reach out and say, hey, what's going on?”

“I think it'll get even, I think it most likely it'll get to the point where now the Fed's buying equities of companies just to prop things up.”

“From where I'm sitting, it seems to me like, at least in the U S both the fiscal and the stimulus response. So this would be both what the fed has done in terms of unlimited quantitative easing, printing money basically to keep the markets going. And this, the…”

“I feel like certainly in prior recessions, you know, 2008, 2002 1001, I think the companies that did the best are the ones that, you know, did a deep cut early, but then didn't have to do anymore.”

“The incentives are now for companies to not give you access to your, even your own data through API, like because of this, that's the key difference, right? It has to make sure that the data flows in, but doesn't flow out”

“Dealforma is a good one where, like, data goes in and doesn't necessarily just flow out immediately, and even if you took a snapshot, like, what good is that? You know, like, you still need the next, the data next month, or the month after, and then every sing…”

“We had a business that we were selling. A company was called Zyra Talk. It was basically a AI voice agent, like a receptionist for like HVAC and all this stuff. This business had great metrics on every measure, on growth, on retention, integrations, they had e…”

“It is true that like, it's such a weird, opaque market, this Sort of two to twenty million of ARR and like even pretty sophisticated founders who may have even raised, you know, tens of millions of dollars or feel like they understand the space they operate in…”

“Most of the time you're going to need to be at like 10 or maybe even 15 or 20 to be considered a true platform.”

“When are they most likely to buy a token? Well, it's when they've had it for six to 12 months and you know, whatever, not when they've been holding it for five years.”

“The kinds of buyer changes. And so like the kinds of buyers that are looking to buy 10% Or zero percent or 15% ARR businesses are sort of the value buyers end of things. And basically what happens is the bigger growth firms and the folks that are buying tuck i…”

“Between that, sort of, two and twenty million ARR range, it's an extremely opaque market, and so what that translates into is, like, You can very easily end up in a situation where you as a founder get bad advice, so you end up selling your business for like a…”

“A lot of people have a view of, I like to joke, like a private equity is like, you know, like a Bruce Springsteen Movie or a song where it's like, you know, they're always bad and always pay poorly, but that really is a misunderstanding of really the biggest b…”

“My rule of thumb is like around about a million of ARR typically, it starts to become much more common to do stock purchases.”

“All things being the same, you're going to get slightly more money In an asset purchase than you would do in a stock if you're negotiating correctly.”

“Like, it's a new software capability, and so applying that to, like, public soft stock is, like, basically the bet, if you're betting against SaaS, you know, or certainly, like, established public SaaS, if you're betting against that, what you're basically arg…”

“The big unlock for me was, like, Claude code. Like, it was the harnessing around it. The fact that it could go on and, like, understand, like, a whole quote unquote code base. None of the stuff I'm doing is a code base. It was always something else. But that h…”

“I just saw there was a stat out about Carta where it says like, you know, basically on, on, and DPI is the term distributions to paid in. And basically says like, you know, over 12 years in only about half the funds have returned one X DPI.”

“In fact, the actual math is more like two X. I think it's 2.1 six or something. If you as a venture fund in that decade, which was a good decade for venture funds, returned 2.1 X, then you were in the top quartile of funds.”

“There's a good number that, that returned less than one X. It's probably 40% of funds. You don't even get your money back. That's pretty common.”

“What is amazing performance, like world-class looked like, and that's actually in that quartile, it was just over five X. So if you five X, if you were a venture fund at five X, then you were in the top five percent of funds in that timeframe.”

“If you're going to have a better than 50% chance of at least breaking even, you should be making at least, I think it's somewhere like 15 and 20 bets, like investments rather than bets.”

“If you push valuations as high as possible, investors are going to put control provisions in there that sort of says, okay, look, the reason why we're giving you this high valuation is because you're saying you're gunning for this enormous outcome. So we're go…”

“I remember looking, I was like, oh, about 30% of the companies have raised money, and that's what I used to say, like, about a third, and then I was coming around the fundraising again, I was like, okay, let's look at this, and actually, it's like, it's eight …”

“And because of the length of these funds, most of the time, like a successful VC can raise several funds without returning any money at all.”

“Our sort of base case valuation, which is most of the numbers we share out, it's basically some sort of a revenue multiple based on, on growth mostly. And it's somewhere between two X and somewhere between seven X.”

“Like, we're not vastly increasing the size of our fund, which is, you know, quite common. Like, in the VC world, it's very often like, You start with a small fund, then you quadruple it, and then that works out and you quadruple it again. And like, we're not d…”

“Just because you're good at writing 250,000 dollar checks does not mean you're good at writing five million dollar checks into later stage companies. And your competition might be different, and your deal flow might be different, and your pricing power might n…”

“You know, it's not quite apples to apples, but certainly like, you know, CARTA came out with a venture benchmark report here earlier, earlier this year. And like, we're basically in the top five to 15% of most metrics of venture funds.”