What it takes to build an $11B startup: an interview with Parker Conrad, CEO of Rippling

There shouldn’t be a “trade-off between speed and quality,” Parker Conrad, CEO & Co-Founder of Rippling, explains in his October 3, 2022 interview with Harry Stebbings.

He continues, “Yes, it is possible to do things fast and bad. But it’s very rare that you see projects that move slowly and end up nailing it at the finishing line. Usually what happens is they’re slow, and then when they get done, they’re also bad.”

The interview continues with discussions of Rippling’s unique business model (particularly its ability to produce multiple best-in-class solutions simultaneously), Parker’s founder journey, how he brings out the best in his team, and much more.

It’s worth a listen. And for those with intimidatingly large podcast backlogs, we’ve highlighted some memorable moments below.

Listen to the episode >

The highlights

• Why speed vs. quality is a false choice: “I agree with the trade-off between speed and quality. Yes, it's possible to do things fast and bad. It's also possible to do things slow and bad. Speed is often more aligned with quality than the other way around. You rarely see projects that move slowly and end up nailing it at the finish line. […] Having urgency on fixing underlying issues and building a high-quality product is a virtue.” 

• On doing great work: “As a CEO, people often come to me and say, ‘we can do this thing, or we can do that thing, but we can't do both.’ I don't want to have to make that choice. Is the second law of thermodynamics violated if we do A and B? What is the fundamental impossibility of getting both of those things done? [...] At times that means being perceived as an unreasonable CEO, but often I think it forces people to think about and pressure-test their underlying assumptions about what's possible and what would be required. [...] We should refuse to accept the set of implicit assumptions that people come to us with about why certain things are possible, and certain things are not possible.”

• How to make a compound startup work: “Step one is finding someone to be the founder of that product within Rippling—often that person has founded a company before. [So much of what we do] wouldn't be possible if we weren't hiring people that were preternaturally inclined to run something.”

• On raising nearly $700M—and why fundraising isn’t the end goal: “At Zenefits I raised money at a massive valuation...and less than a year later I was out, fired, deeply depressed, and worried about being broke. I probably have a bigger appreciation than most people about what a financing round is and is not: it's money to get where you're going, and that's it. I think people make too much of financing rounds and what people are raising, and what that means. I look at it very practically. [...] I think that the real sign of our success will be [when we’re considered like] Salesforce, but built on a different underlying primitive."

• The power of a “brand name” VC: “There is a magic pixie dust that gets sprinkled on your company when some of these firms with really big brand names invest. It is very real. It's not about this sort of particular behavior or competency of the investor; it's about the brand halo that comes from that.”