The Ledger, every show

“I think you look at like Databricks versus Snowflake and it seems like Databricks has had some advantages by not being public you know, in, in that fight.”

“I think a lot of consumer businesses end up being kind of random that, you know, whether things sort of work or not feels like very much outside the control of the company. It's one of the reasons I, Hate consumer businesses, and I think a lot of entrepreneurs…”

“Investors sort of shift their view of what's gonna work every six to nine months. And I was like, geez, it takes It takes years to build a company in these spaces. And so there's no way, you know, the attention span that investors have on this stuff is always …”

“Getting that pace and urgency, you know, just making it a part of the fabric of the company really early on is like a really hard thing to do when you're starting a company, because it feels a lot like being unemployed. Like you kind of start out and you're ki…”

“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 didn't just want all in one, they wanted the allest and onest. And that was the way to win.”

“The answer is like, I'm not sure that you really can. I think you kind of have to Almost like a refound the company or, you know, sort of like rewind and reverse and start over and go in this different direction.”

“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,”

“I think what happens is the companies that start with one thing with like this plan. Yeah, yeah, but someday we're going to build like the next thing. They very rarely get to the next thing. Like the first thing just sucks up more and more time and energy and …”

“The market that people call identity right now is actually fundamentally about employee data as well. It's just employee data in the IT department instead of the HR department, and so that's why we sort of built that as well because we thought, look, you shoul…”

“People come, come to you and they wanna do what I call like the CEO in a box where they sort of say, look, we can do A or B. Like, would you, do you want us to do A or do you want us to do B? We can do it quickly or we can do it high quality. We can do this th…”

“I mean, we have sort of millions of dollars in net new ARR every month from cross sell, which is selling, You know, existing customers on new SKUs within Rippling.”

“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%.”

“I sold some stock, not, not in our most recent round. So I didn't sell anything in the most recent round. But I sold some stock earlier on before that, before the most recent round. And when I've done so, it's always been whenever I've sold stock as a founder,…”

“Often like the best candidates are not ones that that you find through exec recruiters. They come in, you know, through personal networks or through through sort of like, you know, GPs and investors and things like that.”

“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've had some big ups and downs, obviously, in my career, and I think there's a platitude in Silicon Valley that you learn a lot from failures, and the only thing I've ever really learned from failure is how much it sucks and how much you don't want it to happ…”

“And so if you want to do sort of a really narrow point solution SaaS company, the odds are that someone's already done that.”

“The marriage thing is weird. Like, I mean, I think about the relationship that I have with my wife, and it's very different from the relationship that I have with my investors.”

“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.”

“They're just these natural constituencies for consumer technology companies, because there are so many consumers that are using their service. But for like a B to B SaaS company like us, where we're selling to businesses, they're just, Fewer constituents that …”

“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…”

“What I think is going to be very durable with AI is, like, everything that I've seen is, like, building the applications is, like I mean, I don't want to say it's, like, trivial, obviously everything's hard, but what's much harder than building AI applications…”

“We came up with a bunch of ideas that sounded like good ideas, but were actually Terrible ideas, which is usually what happens when you decide to start a company and then try and figure out what you're going to do.”

“The challenge of a compound startup is that you need to be good at parallel execution across all of these different products, because you're never, you're only as strong as your weakest link. and so if you have one crappy product, and a customer is buying se…”

“And then there are a lot of organizational challenges where you've got to often organize the company into business units with sort of strong entrepreneurial leads that can run individual products relatively independently to sort of paralyze execution.”

“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 have an internal, effectively like an in-house system that is effectively like an ad system that we use internally that, that basically individual product teams can, Place, like, ads and promotions inside of our product, and we have a lot of, I hate myself …”

“I think what happens is, like, your company will probably go back and forth, you know, every five to seven years or so between these two extremes of one sales team versus You know, individual sales orgs per product based on, like, what you're bad at as a compa…”

“I think it's probably the thing that we have found to be the most challenging about our business is like, The sort of brand question of like, what is rippling and how do we describe it? because there isn't something, there isn't another analogous thing like t…”

“The thesis of the company is that actually employee data matters in a lot of other areas outside of HR. Like one of those examples being things like finance products, like, you know, expense management, bill pay, corporate cards, where actually An understandin…”

“We actually started very purposefully at Rip Lane with three things. So on day one we had like, literally, like, two or three people working on payroll, building payroll and HRIS, two or three people working on device management, so, like, mobile device manage…”

“Usually we love hiring former founders to run specific product lines and build them and really run them as general managers. We've been, you know, really successful at recruiting. I think we have now probably around 50 former founders that work at Rip Lane.”

“And the idea was that employee data, because it's a lot more distributed, we think, than just the HR department and HR business systems you know, companies need a system that manages employee information. In a way that's not merely just about HR that sort of a…”

“A lot of times I think people think that, you know, the difference between, you know, like, you know, the same set of people or the same organization, maybe it's like, if you work really hard and you sort of burn the midnight oil, maybe you get sort of, you kn…”

“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.”

“That one ad unit, You know, adds, you know, 300 K a month in net new ARR for that SKU every single month, like clockwork.”

“We, I mean, so most, we really target you know, we try and maintain sort of 70 to 80% software margins for all of our products. I think the biggest exception to that for us is actually payroll where you know, payroll is much lower margin for us”

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

“The sort of media view of like founders it, it's sort of like, You're either a superhero or a supervillain, and there's only room for those two. It's like you're, you know, and there's such a like, You're either, it's either like saint or super villain and the…”

“So I think Rippling has one secret underlying insight, which is that employee data is a lot more distributed across a company than most people realize.”

“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.”