The Ledger, every show

“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.”

“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.”

“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…”

“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.”

“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…”

“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, …”

“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…”

“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…”

“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.”

“And then the next year, our plan was to go from 20 to a hundred. And we ended up going from 20 to 65, and I got fired, ah, basically within a week of the end of the fiscal year.”

“In the public markets, you know, over the last five years, public companies are spending 50% more on, on sales and marketing but they're adding 10% less in new ARR, like with that increase in spend.”

“Rippling's a 2000 person company. I am the only admin for our system in Rippling. So I personally run payroll for our 2000 person company across about a dozen different countries around the world, ah, natively in Rip Lane. And, ah, I do that, you know, as a pa…”

“Customers very, like, almost, people almost never buy just one rippling product, and they almost never buy all of them up front, and so usually customers are buying, like, call it seven SKUs,”

“The average B to B software company between sort of a hundred to two hundred million in ARR spends about 20% Of their revenue on R and D. We spend now, I think north of 60, 60%.”

“Five years from now? I would I would hope so. I don't, you know, and to like, just to be clear for you know, there's like no plans on any, you know, people are going to be like suddenly like timing our IPO and that's not there. It's not something that we spent…”

“I'm on a very weird and opposite end of the spectrum. Which is that I think that the fact that we lock human beings in cages for these extended periods of time is such an awful thing that we're going to look back on a 102 hundred years from now with just absol…”

“Because in our system, people believe, they believe falsely, that it is juries and judges that decide these sentences, and that's not true. It's prosecutors. Prosecutors decide the whole thing, because 98% of these cases don't go to trial. They plead out.”

“Technically what the bill did is I think it actually didn't change the law. What it did is it clarified that the existing Utah law never made benefits illegal in the first place. So it was a clarification rather than a change to the law”

“If you look at the headcount of the org, like over 80% of the engineering headcount is really focused on the existing stuff. Very little headcount is focused on building the new things. Like most of it is just in continuing to develop and sort of extend all of…”

“We always kind of have like, you know, four or five like new things in the works. But collectively, the teams that are building those are, it's not that large. It's, you know, it might be, you know, five to seven engineers on each one, you know, out of an engi…”

“We went from our customers hiring tons of people and getting tons of free seats because they just are constantly adding new employees in the system. To a 10% drop in our, you know, annual NDR cohorts from a seat basis. But our NDR stayed at like a 130%.”

“The cross-sell business at Rippling is, you know, now over five million dollars in net new a month.”

“We're very close to launching. And I think by the time this comes out, we'll already have launched our spend management what we call our finance cloud vertical, which is corporate cards, expense reimbursements, bill pay.”

“Starting a company is it's a real grind for a long time. Like I desperately want to never do it again.”

“And at the time, there was a question, well, how many of these companies can be billion dollar companies. The answer was like pretty much all of them as it turns out.”

“This was at a stage of the company where we had revenues and cost, but, like, in terms of, like, nailing it down, like, we did not have an accounting function, we did not have anything.”

“For us to start a new product, you know, step one is like finding someone to like be the founder of that product within Rippling. And often that person has founded a company before, but not always.”

“I remember like Ron Conway in particular, who's often, you know, someone that, you know, people talk about as sort of just like a really genuinely decent person in, in the ecosystem, reached out repeatedly and kept wanting to check in.”

“So when I was in college, I started working on the newspaper there and got just, like, really into it and spent all my time at the newspaper, didn't go to class, and they didn't like that very much so I ended up getting kicked out and then came back and gradua…”