“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.”
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More from Matt McGinnis
Opinion
MacInnis: Hopes competitor Deel goes to zero due to its 'criminal behavior'
“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.”
Matt McGinnisDec 28, 2025▶ 58:35“I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey
Insight
MacInnis: Silicon Valley's 'never quit' ethos is bullshit designed to serve VCs
“We talk in Silicon Valley about never quit, but that is complete absolute venture capital bullshit. The incentive of venture capitalist is to put money into your company and milk you dry. They never get their money back. There is no way for them to take that i…”
Matt McGinnisDec 28, 2025▶ 44:29“I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey
Insight
MacInnis: Executives must publicly call out every single product bug to managers
“Every time you see a bug, every time you see a bug, not most of the time, every time you go and you drop it at the feet of the product manager or the engineering manager, every time. In public, preferably.”
Matt McGinnisDec 28, 2025▶ 1:04:38“I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey
Insight
MacInnis: Managers must preserve CEO operational intensity rather than buffering their teams
“Your job is not to be one of those buffers. Your job is to preserve that intensity at its highest possible level and let the buffering happen somewhere else.”
Matt McGinnisDec 28, 2025▶ 1:06:33“I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey
Insight
MacInnis: 'Chill' is the most pejorative label for a product manager
“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.”
Matt McGinnisDec 28, 2025▶ 1:09:51“I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey
Disclosure
MacInnis: Rippling deliberately understaffs every project to avoid politics and waste
“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…”
Matt McGinnisDec 28, 2025▶ 12:23“I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey
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