The Ledger, every show

“Like, risk is just all the investors and, you know, especially when they want to, Extract a bit better terms or, you know, bully you in a down market or whatever, right? They will tell you, like, oh, we would lose you. We'd hate to see you lose everything, rig…”

“I kind of always disliked the whole You should pick us as a VC. We know it's a 40% discount to the other guys, but we are smart. Ah, like the smart VC, like, story, because the reality is, like, if I need to give us 40% discount because the VC is so smart that…”

“And I like what David Heinemann says, like, he banned politics in, in, in in signals and I think that's absolutely right. I think we shouldn't sit around the table discussing all this stuff. We should just build something and make it work, and if we're allowin…”

“We just honestly like vacation a little bit too much. We like coming home at five with the kids. Like we're starting to have other things that are other benefits, right? Because I mean, like, look, the very best people in the world in, in say AI or engineering…”

“Salesforce don't have a human in the center. Salesforce makes you into a robot that has to click buttons in a certain order.”

“Everybody who's pushing for AGI level AI right now, they're going to be sorely disappointed. I think it's an asymptomatic curve, and I think we're going to end up with Waymo-style cars, meaning you almost have a lawyer, but not quite, and the five percent you …”

“I'm so sorry, but Salesforce is just a database. And LLMs are really good at talking with databases and querying data. You don't need 15 layers between you and that database to do it.”

“I think the copyright issues are trending in a direction where I don't think it's going to be a major problem. I mean, fair use, I think, is, is, is, is covering this fairly well”

“One of our competitors, you know, Ariba, they've for a long time gone out to these huge companies and said, hey, we will help you Digitize your supply chain, and you just got to buy our platform, and then they go and they invite all of the suppliers in the sup…”

“The first thing is, for 99% of startups, you know, I mean, No offense, but VCs is gonna own most of your company by the time you have worked for six or seven years, and your salary will probably be less than if you had worked anywhere else combined.”

“In the latest financing round for trade shift, I refused to sign the papers until the employee stock option pool got moved from common to prep two, because I did not want All of our employees to be underwater in any potential transaction in the future.”

“I used to always take out one or two slides of the deck, like I'll make the perfect pitch deck, and then I'll remove the team slide. All VCs will then ask the question, but what about team? And that's the question I want them to ask instead of asking some stup…”

“At one point we fired 50% of the VPs in TradeShift. And there was no drop of productivity.”

“We found out in trade shift very early on that there was an inverse relationship between price and speed of sales cycle. The more we charged, the faster we closed.”

“And I think, by the way, everybody will be making a mix, make a big mistake if they count Apple out of the AI race. They're gonna come With a hundred miles an hour, I mean, they come in, it would be really, really good.”

“Because enterprise is a multi-polar world. It's not winner-takes-all. I mean, Peter Thiel's power laws works really well in consumer, but in enterprise, there's so many modes. I mean, compliance, regulatory, Incompetence.”

“There would be a new generation of user interfaces that haven't fully been invented yet, but we will look at all of the screens of the applications we use every day as dinosaurs in less than three years.”

“I think we're gonna absolutely move to consumption-based pricing. It's the only way. I think it's gonna be very hard to hold the mold mode on, on recurring revenue as it is today. Because customers will want to see more value, and they'll want to see a more so…”

“99% of the money going in is going to be lit on fire, and two, we are underestimating the impact of AI.”

“AI is Essentially as interesting as saying database or, you know, we have an HTML rendering layer or whatever. It's a set of technologies, and I think what is really, really important, and I think most people right now that are rushing into, as you said, AI is…”

“I think actually that one of the biggest impacts of AI and LLM is that most application-based brands are going to be really struggling because the brand is the UX.”

“And to try to build a consumer tech brand and hold on to any population of users is going to be very, very, very hard in a world where innovation is almost free and LLMs can make anything.”

“The biggest differentiator in the world to come is going to be proprietary data.”

“We never, ever lost a customer that got on live.”

“80% of the jobs that disappeared in US manufacturing did not Go to China. They went to technology.”

“I think we're going to absolutely move to consumption based pricing. It's the only way I think it's going to be very hard to hold the moat on, on recurring revenue as it is today, because customers will want to see more value, and they'll want to see a more so…”

“I almost died of anemia, actually, because I just didn't have time to go to the doctor.”

“So yeah, you absolutely sacrifice your health over, over this process.”

“As the leader, like, you're a symbol in a way, right? You can't go in a town hall in the whole company and say, listen, guys, I'm actually getting severely depressed at doing the work, or like, you know, I'm suffering from burnout, and I'm not sure I can go th…”

“If you think about the type of funds and capital managers and people you deal with at a late stage growth startup, I mean, there's probably as much space to have that mental health conversation as there is on Wall Street in general, which is not a lot, right?”

“We used to have a Skype group, and Skype was a thing of a few people in the company that was called, Late night motherfucking XYZ. And that was because at two AM we were all sitting, solving some problem, getting something done, getting somewhere, and we were …”

“What I found is like, even when it goes down a little bit and you feel less of the anger or less of the motivation from that, I didn't lose my drive.”

“VCs will always want to have a question that makes them sound smart.”

“Actually, that's why ChatTBT is kind of screwed, because it just want to give a perfect answer to everything, and it can't say, hey, could you clarify? I don't know, or whatever.”

“One of the things we put into what we're building right now is that That we are a team, not a family.”

“IT corporate budgets, they went from three hundred billion to seven hundred eighty billion dollars in enterprise software over the last 10 years. At the same time, we doubled the amount of people in shared services, eight to sixteen million, and we doubled the…”

“But nine months later, I was running on my laptop a model that was as powerful as ChatGPT three and a half that was released as open source by Facebook.”

“So co-pilots are the last breath from the existing enterprise applications to remain relevant.”

“The better solution is to remove the application that's shit and just talk straight with AI.”

“It doesn't matter if you have 10% different data if you train on one trillion parameters. It doesn't matter because it's such a big data set that that actually is such a small, Rounding error in, in what you get out on the other side.”

“I know, but on, on the investment side, right, I mean, beyond work, we worked with Moonfire, and they're really interesting because they actually tried to build an AI-first venture fund. Yeah. They went out with a real framework, invested heavily in, you know,…”

“Yeah, I mean, I think there will still be a lot of money going into the long tail, but you're right that the concentration will happen in the top, but I think ultimately there will still be more companies getting funded just because some of the smartest people…”

“Look in B to B, capital is everything. You can literally draw a straight line between the best performing B to B public companies today and how much capital they have access to.”

“Every sales SaaS account goes through, like a value, it's almost like the hype cycle. In the beginning, you have the honeymoon, everybody's happy you've done the sale, and the lowest, absolute lowest point in that journey is go live. Because that's where all t…”

“Very soon, that will be completely commoditized. And again, AI will do the same to manufacturing that it's doing to software.”

“The thing you really need to invest in is actually free renewable energy, because if you have free renewable energy, we have less of a social impact as jobs go, because we can actually produce food, we can produce almost anything we want, and it gets a little …”

“If you have universal basic income, the things you tend to strive for tend to be bigger. That's actually a reason that a lot of the startups coming out of the Nordics are aiming big, which is we don't need to aim small.”

“And what you end up with is what I call hostages, not customers, right? You know, if you have a customer, they love your software. They invested in using it.”