The Ledger, every show

“David really sort of He hired a sort of a comms person that he works with a lot, this guy named Lanny Davis, and they just focused on like attacking me, like over and over and over again for like six months, and it became this huge thing. And David, well, he w…”

“I got to this point where I was convinced that you know, David was not really interested in making Zenefits successful. And, you know, almost every decision he made at the company was wrong. You know, he the decisions he made from a product perspective, from a…”

“Companies like Deal and like Remote actually have not built underlying global payroll or payroll really of any kind. And so those companies are sort of secretly running on Other payroll systems country by country.”

“David was not really interested in making Zenefits successful. You know, almost every decision he made at the company was wrong. The decisions he made from a product perspective, from a strategy perspective, the people he. Fired the people he promoted, like al…”

“If I had fought at my last company, being forced out by A-sixteen Z and David Sachs, and had stayed in place, like, if we could replay the videotape, what would the outcome for that company have been? I believe that it would have been very different”

“At my last company, I had board control and everything, but when investors sat me down and said, look, if you don't resign, we're going to sue the company, we're going to go to war with you know, suddenly you're like, crap, how do I survive that?”

“There's this sort of like idea in Silicon Valley that you should learn a lot from failures. And I, I'm not sure that I agree a lot with, I think that actually people probably learn a lot more from their successes and, you know, companies fail for like, Many du…”

“The public markets have kind of become something of like a retirement community for, you know, very slow growth, but very profitable companies.”

“People should not spend any time trying to optimize for like a fundraising outcome. And like, you should just basically wait until You're getting investors that are emailing you term sheets that are signed with like a blank for the valuation. And they say, jus…”

“You know, there's a lot of advice out there to kind of stick with it, Keep going. Don't give up. And I think it's terrible advice. I think if it's not working, like give up immediately.”

“This conventional wisdom is wrong or at least extremely limiting, and there exists a set of companies that could be built that are often not built that break this rule.”

“That's why Slack is owned by Salesforce now, because, like, Teams is free and the Microsoft bundle.”

“Deal was actually, until very recently, a Rippling customer in the United States. They ran, you know, in fact, their global HR on, on Rippling because they didn't have all of these other systems in place.”

“Most you know, most companies there, there's sort of a conventional wisdom around startups that you ought to do like one extremely narrow thing. And that focus is like the way to build companies. And I think that at least for Rippling, we've sort of taken the …”

“I think, I mean, one of the sort of easiest things for usually investors to talk about is how the secret to startup success is focus, focus, focus. I think it's actually wrong. It might have been true at one point in the past. Today, the biggest problems that,…”

“The power that investors have in companies, you can structure things so that you have board control, you can structure things so that you have voting control, none of those things actually really matter. The power that investors have over you is more than anyt…”

“These artisanal software companies really can't afford to invest in a set of underlying capabilities that are ultimately what make these applications powerful for their customers. And that end up being repeated across a lot of these different application areas…”

“I, like, am very skeptical that AI will be employment conserving because I just think that, like, in basically every area, like, we have not seen, and I think most large engineering orgs have not seen, like, a huge number of efficiencies from these sort of, li…”

“At Zenefits, we kind of had this theory that was ultimately, I think part of like the downfall of the company that, you know, we could move through the market more quickly by doing a lot of things manually. And then, you know, we would just replace it with sof…”

“A lot of the sort of deeper problems within organizations can't really be solved by very narrow point solution software products. And that if you can build A whole suite of really seamlessly interoperable applications. You can build much better products for bu…”

“I think it's possible that compound software businesses are the wave of the future. And also like, there will be three of them, you know, and there's not, it is actually an argument for many fewer businesses. But much larger and more successful ones, if that's…”

“What'll happen is it'll just destroy outbound the, as a channel, it will cease to work and cease to function because it'll just get so overwhelmed at that point.”

“AI is going to help companies like 2000 person companies be run more like 200 person companies and 200 person companies be run more like 20 person companies.”

“And so I think that the fact that these systems can read and their context windows are so large is actually Much more powerful for B to B software than the fact that they can write. Like the generative AI is actually really a misnomer. It's actually the, it's …”

“One, I think you need really good executives and you don't want to do the founder mode thing unless something's broken. You know, like you kind of want, cause you can't do it everywhere. Like you need people to help you run the company and like, and so you wan…”

“At this point, Like, ah, you know, 15 years ago, you could start a SaaS company in any vertical, and you'd be the first one, and it would probably be pretty successful. But now, like, every, every space has got two or three things in it. And so the focus, n…”

“What we can do is we can go a hundred times deeper on those capabilities than any of our competitors can afford to go, and so whenever we're going up against a point solution competitor that only builds in one area, we know that we're going to win in those are…”

“The most important thing to start with is like the, that the integration is the product. You want to build in a space where there are problems because of disconnected systems or business process, and that you have these advantages where if you combine everythi…”

“If you have a VP of sales that's got, you know, 25 SKUs that they're selling, they're gonna pick, like, the three or four that are the easiest to sort of help them get to quota, and inevitably you get products that are just not gonna be as material An input to…”

“Generally speaking, you want to build products where those five advantages are maximized. And so, you know, the first one was like integration. So you want to build products where the integration with the other products that you've already built matters. Integ…”

“Our goal is, is to be able to, you know, match or really exceed in a lot of ways, the capability of the current sort of best in class products in the market with like, 20% of the R and D investment.”

“At almost every stage of growth, you know, companies between zero to 25 employees, companies, you know, like between 500 and a thousand employees, they have almost double the number of people in HR, IT, and finance for companies that don't use Rippling than co…”

“Often like early stage companies look like they have very good margins that then get worse as they scale.”

“No, I think, I mean, we have a really robust partner ecosystem, and I think you know, our goal is to have you know, companies that we partner with that, that compete against internal rippling products on even footing. And not just in the sense that, you know, …”

“Wherever you would value like sort of a singular SaaS company a company that produces like a meta company that produces, you know, that produces SaaS businesses, you know, probably should command I think a higher multiple.”

“There are investors that bring this sort of brand imprimatur to a company. That, you know, immediately, you know, this firm invests, and suddenly things get easier. Like people that you email from prospective employees are more likely to respond to outreach ab…”

“But I actually think that, like, almost every business system a company uses is full of information about employees, and that because of that, employee data is the right foundation for sort of a broader business systems management platform.”

“If you look at the really big outcomes, most of them end up being compound companies. You look at Microsoft, Salesforce, those are all companies that succeed because they have this broad product portfolio, and because of the ways that all of these products int…”

“One of the biggest advantages that you have as a compound startup is that you can run circles around competitors from a pricing perspective, because you can maximize the price of your bundle rather than the price of any one SKU. And so that means you can actua…”

“A big part of how I think about Rippling is that this is a way for me to sort of prove, mostly to myself, But also to the extended community, to my friends and family, to the general public, and all that kind of stuff, that this is how things might have turned…”

“I think Rippling is going to be the Salesforce for employee data.”

“In Utah, the insurance commissioner in Utah decided to take action, said that, listen, one of their missions as a DOI was to make sure that there was fair competition between all brokers in the state, and everyone was on a level playing field, and they said th…”

“Some people would argue like, well, AI is sort of like a similar kind of shift from like on-prem to cloud. And I probably don't agree. I think it's actually probably more centralizing as a technology”

“There was a period of time where, you know, yeah, if there was no sort of SaaS application for I don't know, whatever, like, time tracking or expense management or something like that. You could build a standalone thing for that, and it would get, like, very r…”

“People like to come to CEOs with what I call, like, CEO in the box options, where they say, look, you can have A or you can have B. Like, which one is it gonna be? You tell us, like, what the priority is, and it's this sort of illusion of choice where, you kno…”

“If you make it easier to build software, I think the demand for software will actually go way up.”

“And I think what will happen is that like actually as the cost of software building applications comes down, it will let the sort of core companies build a lot of like industry specific, industry, industry specific vertical applications.”

“And ultimately, I think like all of these AI agents are going to need to inherit the permissions of a person.”