Rippling

“When rippling is hoovered up 30, and owners hoovered up 20, and Revolut's hoovered up 10, you just, that strategy worked three years ago. Like, it's too late. Like, everyone is just sitting there hitting refresh, hoping these smart YC companies fail so they ca…”

“Xenefits was worth about five and a half billion at peak when he got fired. And his next company, Rippling, which I invested in, is currently worth 17.8 billion dollars.”

“I was the first investor in Rippling. Put a big check into that. Did really well.”

“Good SaaS companies that aren't AI first are going to trade at fair value, which means if you've created value, you'll get value. And I think Canva and Rippling have both created enormous value. So they'll get value, but what they won't get is that stupid, 30 …”

“So if they were at less than 511 months ago, which I do know. Right. And they're at a billion growing 70 something percent. Do the math with me, Rory. They're accelerating. It's not just 70, which is enough. They're accelerating.”

“It's better than Figma by the numbers, right? It's better than Figma by the numbers by far. By far.”

“At many companies, which there are clients of ours, like Scale AI, Rippling, Glean, and many others, as you scale up, The problem is exponentially.”

“And I think nobody in the world does that better than Parker Conrad.”

“And I think like, I don't regret not breaking the rules in general, but you know, this would have been a time when it could have been worthwhile.”

“And I think like this concept of Always, always pushing or squeezing the last bit out of a product, a technology, an opportunity, or a team is a hallmark of the highest performing teams and companies.”

“When I joined Rippling, we were at something like four and a half million bucks in revenue, which by itself is a very exciting number, I think, going from zero to something. But in hindsight, obviously, it was very, very early in the company's business, in the…”

“The idea is like, hey, go read the support tickets, go look at the source code, go attend the customer, you know, meeting and go sit next to them and look at what they do in the product, whatever it is, the, you know, doing that 100% of the time is going to gi…”

“The trick is to do the minimum amount of process you can get away with which is almost always more than zero, but almost always less than a whole lot. And you know, I think of processes as really important ingredients to reducing the volatility of your company…”

“Every time you find yourself doing meta work, you should have a micro panic attack because you are burning precious time on something that yields no benefit to your business. It's a necessary evil, but it should be minimized. And so you asked about like, you k…”

“And I think in the next five years, a lot of the value of AI is going to be most apparent and captured by the businesses that have the underlying data and tooling to do quote unquote deterministic things or perform tasks in the software world”

“I am skeptical as to the survivor, the survival rate of many of the AI companies that I see starting today because they're going to perpetually drink their data through a straw from other systems. And those other systems are never, ever, ever going to let othe…”

“Toast. No chance. Because it doesn't have e-money licenses in the UK. Because it doesn't have PEO licensure in, you know, the 18 states in the US or whatever the number is that require it. Because it doesn't have the regulatory arbitrage that we have, because …”

“Parker runs payroll for the, for all 5005 people don't even believe us on this. They're like, there's no way that Parker personally runs payroll for 5500 people. The answer is you're wrong. He really does.”

“The Justice Department opened a criminal investigation. Grand jury subpoenas were sent out in recent weeks.”

“And so that's the way we work at Rippling. Everyone is constantly asking for more resources. And of course, where we can afford to and where it's appropriate, new resources arrive. But it is really important to me that we feel that we've deliberately understaf…”

“There's more to glean from seeing how it's done right than there is to glean from I'm seeing how it's done wrong.”

“We had a hiring mistake in engineering leadership where the product leader at the time had to sort of run engineering. We subsequently had a mistake in in product hiring. And a lot of us had to sort of pitch in and Parker and I sort of stared at each other thr…”

“When I jumped in, I was like, man, you know, we need to establish some basic standards for test coverage. We need to establish some basic standards For how we do what I call a factory inspection on a product once it's ready to roll off the assembly line. Do we…”

“Processes in a business exist for the sole purpose of lowering beta. Processes are for decreasing volatility in the output of the system. The downside of a process is that it suppresses alpha.”

“Parker is the sole payroll administrator for Rippling for all 5200 employees. He personally runs payroll always. There is no exception for all 5200 people.”

“And so I added a line to the fucking pickle that said you are allowed to have one feature flag that governs your entire product at ship.”

“Every product person at every seniority level is given the same case study.”

“Rippling had it been started in 2014 would not be what it is today. I think rippling had it been started today would not be what it is five years from now today.”

“The takeaway lesson is that every company succeeds on the foundations of the idiosyncrasies of the founder. The idiosyncrasies of the founder. Rippling succeeds for almost the polar opposite reasons that notion succeeds. But in both cases, the companies succee…”

“I was one of the first investors in Deal, if you've heard of them. I, you know, I was able to exit, I was able to exit that position, and then, you know, hopefully that company's going to zero with their criminal behavior, but whatever.”

“Don't work for a chill boss. Don't be a chill boss. It's the most pejorative label I could give you. Chill boss or chill PM. Don't be chill. Chill doesn't accomplish shit. Be intense, be good, be respectful, be intense. Don't be chill.”

“We have an escalations team at Rippling, which sounds weird, but it's people who are just particularly skilled at pistol whipping other people in the company to get to real root causes, not like throw away the word root cause.”

“What I can say there are tens of thousands of companies that now run on Rippling. We're less than one percent of the market.”

“And like the market cap at sixteen billion, I think now under values where we are from a revenue perspective by a long shot.”

“Inside the KP portfolio, ok, are top eight companies. Let's take five exec roles across the top eight companies. Companies like Rippling and Glean, ok. 38 out of 40 of those roles, ok, those executives report to the CEO for the first time in their career.”

“It was give money to the best people. You know, we did Reddit at a higher valuation. We did rippling at 25.”

“Rippling and Reddit. We sold a little bit of rippling on the way up, just because, like, our LPs wanted money and, you know.”

“If you think about his huge, huge winners, whether it's Figma, Glean, Rippling, they all have like a common through line of the, you know, it's B to B software, but it's almost like consumer like software that, that demands really high user love and engagement…”

“Counter examples to that, of course, you know, Rippling would be one great counter example to that as this, you know, this compound product that's shipping, you know, lots and lots of features over, over a long period of time.”

“At the margin, I'm, of those two choices, I would bet at the margin, despite a little distaste for what went on in terms of the de-espionage thing, I would say, maybe I want to say is the TAM and the, Competitive matrix is more attractive for deal.”

“The demo can be kind of broken up into everything that comes before showing the workflow builder and then everything that comes after, because before you show the workflow builder, people are bored and everything you show them, they think they've seen before. …”

“I think it's unfortunate that the way they're trying to compete is through media and through headlines and things like that.”

“Rippling have the Silicon Valley Illuminati around them, and in the same way for me, like, there are some media companies, which I'm not going to name because they'll hate me for it, but, like, they just have the Silicon Valley, the Collison's, and the YC's ar…”

“Well, I think you should read our lawsuit in Delaware. You know, three years of poor way of competing in the market.”

“Palmer Luckey is another one where I backed Andrew in the very first round, and he was controversial given what happened at Meta early on with him. I think in both cases, they basically got thrown under the bus in one form or another.”

“The only other company I'm aware of that, that had a similar strategy is rippling. They call it compound software. But it's the same approach and it just enables significantly greater flexibility and use cases and also velocity and shipping product.”

“A lot of CIOs would, You know, you love to go, okay, yeah, I've vibe code workday and I just saved my company all this money or whatever, but okay, you actually peek into the hood of a workday or a rippling. These are very complex pieces of software that have …”

“In the Bay Area, it lagged for a long time. For a while, including, I'd say, almost until 18 months ago, The only scaled modern company that I think was in office basically all the time was Rippling.”

“Like in the tech world, we're seeing a very interesting story play out between Rippling and Deal, which are these two payroll processors, and Deal planting a spy, and the spy, like, running into the bathroom, and then trying to flush a phone.”

“We're already seeing this consolidation in e-commerce if we want to chat about where they're becoming one tool already. I think it's a real risk for all these cool ones. Like we just don't need five of them going to Rory's point. We may, Rippling's a good exam…”

“Rippling needs another two years is my guess in the oven to get to that.”

“I think there's like two types of startups. There's innovation startups and execution startups. So an execution startup is like a rippling or a MongoDB, where it's just like, if you build a better database or a better HRIS system, you have line of sight to bil…”

“I got an angel check into Rippling. I got a first dollar check into Solana, four cents a token. I got a seed check into Clay. I got a seed check into Cherry, a seed check into Newfront, a bunch of crypto companies. I got into the management company round of a …”

“Within the first 47 companies that I'd funded two of them, you know, Ripple and Solana, have coin market caps of north of a hundred billion dollars today. Rippling is, is approaching a twenty billion dollar market cap, and everything else I mentioned is, you k…”

“At one point Lightspeed invited me to be a scout for them, and, you know, I put half my scout fund into the seed round at Rippling, so that worked out well.”

“Their fund two is going to be a 10 X fund, I think with flock safety rippling and others.”

“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…”

“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…”

“We're building a variable compensation product right now.”