Why Platforms Win and Point Solutions Fail with Rippling CEO Parker Conrad

**Sarah Guo** (0:05)
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.

**Parker Conrad** (0:32)
Yeah, thanks for having me.

**Sarah Guo** (0:33)
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?

**Parker Conrad** (0:42)
In some sense, there are some superficial things. But I think mostly Zenefits failed for dumb reasons. I don't think there were a ton of lessons. Obviously, there were some of the specific things that let it to not work, that you want to make sure not to repeat.
We try to be really extremely, extremely careful about compliance at Rippling and regulatory compliance in particular. Then I think at Zenefits, we leaned way too much on ops. I think Rippling has, as a result of that, maybe just a deep aversion to that, and maybe actually to our detriment in some cases, where we perhaps should be willing to do things that don't scale a little more, but we tend to go just really deep with software and not take on operational builds and overhead. Those are probably the biggest differences. I think there are probably some other things that I took away from the experience, but they're much more general. I think for a long time early on at Rippling, I felt like it was just much easier to manage my own psychology on this stuff. It's just really hard. I always found it personally, maybe I was just not cut out for this, but always found it personally very hard to deal with the psychology of running a company, like the big ups and downs. At Rippling, it was a lot easier because no matter how bad things got, I always had this thing where I'm like, oh man, this just pales in comparison to how bad things were. Right at the end and just after I left at Zenefits, when things got really very dark. And so there's this idea in Silicon Valley that you should learn a lot from failures. And I'm not sure that I agree a lot with, I think that actually people probably learn a lot more from their successes. And companies fail for many dumb reasons, and it's really hard to take a lot of lessons away from that. And actually, you probably learn a lot more by being at a company that's working and seeing how it works.

**Sarah Guo** (3:01)
I remember talking to you during that period, and when you were just starting the company. And I think you said something to me like, starting a company sucks, especially when you were not in Silicon Valley and the social sphere is good graces at the time. You were sort of fighting a big reputational battle. You described it as like, well, you're just like sitting in your parents' basement again, and nobody believes in what you're doing. That sucks.
What made you do it anyway and start over?

**Parker Conrad** (3:27)
I felt like I didn't have a lot of choices, to be honest.

**Sarah Guo** (3:31)
You weren't going to work at Google?

**Parker Conrad** (3:32)
I mean, I didn't have an offer. You know, like I think I was personally like probably pretty radioactive. And I think it would have been hard for me to get a job. I've started three companies, and I think the first company I started because I was naive and didn't know what I was getting into. And the second company I started because I sort of looked around and I'd been at the first company for like seven or eight years. And kind of it was sort of worthless from a resume perspective and was sort of like totally unqualified for, you know, any job that wasn't sort of like entry level, other than like maybe starting another company. And so I felt like crap, like this is I guess I'm doing this again. And then the third time around, it really felt like, you know, this was kind of there weren't really a lot of other options. And also this was kind of like the one path that I sort of saw that maybe there was this sort of narrow ray of light when sort of it felt like I was being buried reputationally. That like, okay, if I could like build this specific company and make it really successful, you know, maybe there was some future world where, you know, there would be like a different story or a different narrative or, you know, a chance to kind of like, you know, sort of tell my side of the story on it.