The Ledger, every show

“At a very high level, I just don't believe the Fortune 500 will employ fewer people in 30 years than they do today, because the ones that try and cut all the people will no longer be in the Fortune 500.”

“I bet if you went back over the last five years and looked at the top three or four companies in each of those five years that were at that point in time the fastest growing SaaS companies in history, I bet a solid 50% of those companies turned out to be garba…”

“Cursor has taken mediocre engineers and made them good, but it's taking amazing engineers and made them gods.”

“From an IT standpoint, you normally don't allow software to just be used across your organization with access to your organization's data and have no idea what's happening. We're letting that happen in AI all the time.”

“The usage on these tools in the enterprise is less than People would think today”

“The worst way to measure productivity is I'm going to send a survey to my employees and say, do you feel more productive today from using ChatGPT? First of all, there's a definition issue. Second of all, people are going to answer the way you hope they'll answ…”

“Turns out companies don't really like firing people. Companies do fire people if they have to, but I've actually never met a CFO that got excited about firing 30% of the workforce.”

“And one of the things we found is something like 70% of leaders we talked to said, We are sure we are wasting money here.”

“To the extent that AI is going to drive up your margin, that will be all of your competitors opportunity to be less profitable and compete with you.”

“If you're not spending your time with your average customer and figuring out, you know, why is this particular customer nowhere near as big as this other bank I mentioned earlier? It's, on paper, it's the same size. Why isn't that really happening, and what ar…”

“And I really do think we'll see the same thing in AI now.”

“80 something percent of our customers find far more tools being used by their employees than they know about and they've licensed.”

“So I'm not sure I really buy in the next couple of years, you will see people in large companies actually just working half as much”

“There's like, seven hundred billion dollars being spent in enterprise AI. It's growing very, very quickly. It's gonna keep growing quickly.”

“80, 85% of the companies we talked to said they really believe they only have the next 18 months to either become a leader or fall behind.”

“I've yet to find the CEO who wakes up in the morning and wants to run a smaller company. He wants more employees and he wants more profit.”

“If you're not one of the primary sellers for your company's product in the early days, to me you have no business starting and running the company”

“And they'll show me all these cool logos and all these great pilots they have going on. They've given away for free. And I tend to think those don't mean anything.”

“You're much better off Growing a little slower if you're going to actually ensure that you have very high LTV.”

“It's very important to have the relationship with anybody who reports to you that there's no issue with you having one-on-one conversations with folks that work for them on their team. And if you have insecure leaders that are worried about people under them t…”

“I, to me, I feel very strongly that until you've well past raising a Series B, really the only two jobs in the company are selling and coding.”

“Yeah, there, there's a lot of parallels, really, to what happened in the nineties with advertising and the growth of the internet and what we're seeing with AI.”

“If you really want to drive employee usage of tools, you have to make them feel safe so they won't look dumb. And you have to make them understand that they can use this safely without getting fired.”

“And AI is going to break all of that for sure.”

“Today, our customer is the CIO. I think over time, our customer becomes a partnership with the CIO and the CFO.”

“Anytime you see some giant shift in budget, You're going to build a set of very important, but very boring tools.”

“And to me, when you get into your B, it's still important as a CEO to spend half your time with your customers, with your existing customers, with your prospects.”

“And by the way, if you're an enterprise SaaS CEO who doesn't spend part of your day thinking about what new sales came in, and does it, is anybody angry with you that day, you're doing a bad job. That, other than the early building days.”

“At any company under a couple hundred million in ARR, your VP of sales should be someone you're very proud to fly in to meet with the CIO of Nestle to help close the deal. And if they don't want to do that, they're a bad fit.”

“JPMorgan Chase's global IT spends on the order of 18 or nineteen billion dollars, and they spend a couple hundred billion dollars a year on people.”

“Today about 70% of our pipeline Has very little to do from a marketing and messaging standpoint with what we were selling customers the value 18 months ago.”