No Priors Ep. 122 | With Rippling Co-Founder & CEO Parker Conrad

(instrumental music plays) Hi, listeners. Welcome back to No Priors. Today, I'm here with Parker Conrad, co-founder and CEO of Rippling. Parker needs no introduction, as one of the most admired founders in Silicon Valley. We'll talk about his founder redemption arc, why the conventional wisdom is wrong and the biggest companies are actually platform companies, the future of the SaaS industry in the age of AI, leading teams with ownership, how he thinks about going public, and why you should only start a company if you have no other options. Welcome, Parker. Thanks so much for doing this.

Yeah, thanks for having me.

I think there's a very apt phrase that's, "The best revenge is massive success." What do you think you got wrong at Zenefits that you've done differently at Rippling?

You know, in some sense, there, there are kind of some superficial things. Um, but I think, like, mostly, like, Zenefits failed for, like, dumb reasons. And so, I, you know, I don't think there were, like, a, a ton of lessons. Um, you know, there are, obviously, there were sort of some of the specific things that kind of, you know, led it to not work that, you know, you, you wanna make sure not to repeat. I mean, we're, like, ex- we try to be, like, really extremely, extremely careful about compliance at, at Rippling, and regulatory compliance in particular. And then I think at, at, at Zenefits, we, we prob- we leaned way too much on, on ops. And I think, like, Rippling has, as a result of that, you know, maybe just, like, a deep aversion to, to that, and may- maybe actually to our detriment in some cases, um, you know, where we perhaps should be willing to, you know, do things that don't scale, um, a little more. But we tend to go just really deep with, with software at, you know, and, and sort of not take on, um, sort of, like, operational, you know, builds and overhead. Um, so those are, those are probably, like, the biggest differences. I think there are probably some other things that, like, I, I took away from the experience, um, but they're, they're much more general. I mean, like, I think, um, you know, for a long time early on at, at Rippling, like, w- uh, you know, I, I felt like it was just much easier to manage, like, my own sort of psychology on this stuff. I mean, it's, it's just really hard. I always found it personally, maybe I was just sort of not cut out for this-

(laughs)

... but always found it personally, like, very hard to sort of deal with kind of the psychology of running a company, like the big ups and downs. And, um, you know, at Rippling, it was, it was a lot easier, because no matter how bad things got, I, I sort of always had this thing where I'm like, "Oh, man. This, like, just pales in comparison to how bad things were," y- you know, right at the end and just after I left at Zenefits when things got, like, really very dark. And so there's this sort of, like, idea in Silicon Valley that you should learn a lot from failures, and I, I, I'm not sure that I agree a lot with that. I mean, I think that actually people probably learn a lot more from their successes. And, you know, companies fail for, like, many dumb reasons, and, like, it's really hard to sort of take a lot of lessons away from that. Um, and actually, you probably learn a lot more by being at a company that's working and seeing, like, how, how it works.