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Parker Conrad | Jan 14, 2022

Having the Chance to Do It Again

Starting a company can be a terrible and miserable experience and you should definitely not do it twice if you can avoid it. But there were some enormous advantages that I had in doing what was effectively a very similar company, or at least in a similar market or space over again for a second time.

When Parker Conrad was 17, he entered the annual Westinghouse Science Talent Search, the nation’s top contest for aspiring scientists. The object of his scientific investigation? The brain cells of a creature called aplysia, more widely known as the sea snail.

He finished with a third-place prize along with a $20,000 scholarship. It had all the makings of a promising career in the sciences — indeed, Conrad later studied chemistry at Harvard University. But a larger passion would pull him in a very different direction.

Over the next decade, Conrad helped build three startups — the last two being Zenefits and then Rippling.

With Rippling, Parker set out to create the first system of record for employee data — one place for businesses to manage and automate everything that touches their employees; their payroll, benefits, computers, apps, and more. And the idea has resonated powerfully: given the most recent Series C financing round, Rippling is valued at a whopping $6.5 billion.

We spoke with Conrad to learn more about what’s gone into one of the biggest second acts Silicon Valley has witnessed in years.

Q: You were born in New York. Your mom ran a nonprofit and your dad was a law partner at Davis Polk. How did their example impact you?

I love both of my parents tremendously, but we wound up taking different paths. My dad worked his entire career — 35 or 40 years — at Davis Polk. There are some things I find really appealing about that, but it was a very different kind of career path than what I did. I didn’t know exactly what I wanted to do when I graduated college, but the one thing I did know was that I did not want to be a lawyer.

Q: But before you got to college, when you were still in high school, you won a scholarship and were among the top finishers in the Westinghouse Science Talent Search. What was it about the brain cells of sea snails that you found so fascinating?

It was largely by accident. I was interested in neuroscience and neurobiology generally. Reading through one of the scientific journals — I think it was the journal of neurobiology or something like that — I wrote to one of the authors of a paper I read by Sam Schacher. He ran a neuroscience lab at Columbia Presbyterian and was studying a creature that ended up being a model that a lot of people used because of the size of its neurons.

So, you could use these tiny little tools to pull out individual neurons and then culture them in a Petri dish and create miniature circuits, and then do electrophysiology experiments where you put probes into the neuro cells and study reactions that induce in the next cell. The thing that was really exciting was this idea that you could get at the chemical and the electrophysiological underpinnings of learning and memory and consciousness and all that stuff.

Q: Did that trigger your interest in studying chemistry at Harvard?

I knew that when I went to college, I wanted to do something in science. I started out in my freshman year taking organic chemistry, which was a class that I was expecting to really dislike — most people talk about organic chemistry as a pre-med requirement that everyone hates and is really hard. I actually thought it was really easy. It just made sense to me and came very naturally. So, I ended up majoring in chemistry.

Q: Were you a good student?

What happened is that I had such an easy time of it as a freshman that I kind of took everything for granted. I didn’t really go to class that much but still got really good grades. Then I did more advanced levels of organic chemistry in my sophomore year and also almost never went to class — and still did pretty well. But in my junior year, when I started taking graduate-level organic chemistry classes and physical chemistry classes — and didn’t go to class — I failed right out, just bombed. So, I was not what you would call a stellar chemistry major. Some people graduate summa cum laude or magna cum laude; I graduated “thank the laude.” I was all the way down at the bottom. I spent most of my time in college working on the Harvard Crimson, the student-run daily paper.

Q: How did you wind up as the paper’s managing editor?

I really resented the fact there was all this busy work at school. I felt that it didn’t matter, that there was no way the world was being impacted by me having to fill out some paper just to prove that I did some reading for class. That just grinded my gears. At the Crimson, I felt as if I was doing something real, that what we were doing mattered, and that it was impactful. I ended up becoming managing editor of the paper in my junior year and working there for something like 75 hours a week, never going to class. I had a lot of fun with it.

Q: Did you ever give serious consideration to going into journalism or was that just a college thing?

When I took a year off — or got kicked out of Harvard for a year — I had to get a job and actually wound up working for the Arkansas Democrat-Gazette covering cops and crime. I had a great time there and made a lot of friends, but the people I was working with there all wanted to be like Ernest Hemingway. That sort of literary aspiration never appealed to me. What I liked working on at the Crimson was taking on the administration and this feeling that we were like this band of pirates taking on the British Navy. I actually spent a long time trying to again find that feeling. What came closest to that for me was doing a startup.

Q: What about the experience of beating cancer at such an early age? Did it color the way you approached your future?

Not really. I had a very mild form of cancer. It was scary for a moment and then it was gone. I didn’t think about it much after it happened. Once it was clear that it was going to be okay, it was sort of out of sight, dynamite.

Q: After graduation, you spent a few years at Amgen and then you co-founded SigFig, and after that, Zenefits and Rippling. What was it about entrepreneurship that got your juices flowing?

I was doing well at Amgen and lived a couple of blocks from the beach in Santa Monica, California. It was an awesome life. But you could only get promoted every two years. And at every level in the organization, you’d have to spend time both in-house in a marketing role, as well as in the field in a sales role. If you added up the number of years, I realized at one point that, crap, I’ll be dead before I get anywhere. I felt like I was on this train to nowhere and looking for a way to get off. Then my roommate from college wanted to start a company and I was like, “That sounds great.”

Q: Sounds as if the opportunity presented itself at just the right time. But it wasn’t part of a longer-range plan?

One thing I tell people is that every time I’ve started a company, I’ve done it out of necessity. The first time, I didn’t know what the hell I was getting into. And if I understood what I was getting myself into, I definitely would not have done it. The other times, I understood what I was getting myself into and definitely did not want to do it — but felt like it was the least bad option available to me.

Q: How did you get to know Josh Stein at Threshold?

I met Josh in 2007 when I was raising money for my very first company. We got very close with Josh and, luckily for him, he ended up passing on the investment. I think he was intrigued enough with what we were doing and we stayed in touch. We regularly met for breakfast over a number of years, and I was able to get his general advice about Silicon Valley and fundraising. It was extremely helpful to have his perspective. And even in tough times, Josh was extremely supportive of me when being supportive of me was not a very popular thing to do. When I was raising my seed round in Rippling, Threshold was an early phone call.

Q: What did you take from your experience building Zenefits as you started thinking about what to do next?

My point of view was that HR software needed to move beyond HR. At Zenefits, we had been making early tentative forays into things like app provisioning and some of the early kind of IT stuff that we ended up really doubling down on at Rippling. I felt that if I wanted this thing to exist, I needed to build it. There were a lot of very specific things that I wanted to do differently at Rippling.

Q: Having done a startup before, you also knew the enormous amount of work that it would involve. Do you need to be a bit of a glutton for punishment to take on something like that?

Yeah. I think I have this sort of very unusual experience where I started a company in the same area twice. There are not a lot of founders who have done that because most people, if they do it the first time, they get to not have to do it the second time. And I, unfortunately, was the unlucky person who had to do it another time. There are a lot of things that are easier about doing it again in the same general market or vertical. There are a lot of things that you know will work and what’s not going to work. I understood a lot of the market contours and had pretty good instincts for what was going to work. My opinions about the business generally turned out to be right because I had done it a previous time.

Q: Did you need to master any new skills as you grew Rippling out of the early startup stage?

Things evolve and you need to evolve, but it wasn’t a different skill set. It wasn’t as if I had to completely reinvent the wheel because a lot of the techniques and tactics that we had used were now being used by everyone. Starting a company can be a terrible and miserable experience and you should definitely not do it twice, if you can avoid it. But there were some enormous advantages that I had in doing what was effectively a very similar company, or at least in a similar market or space, over again for a second time.

Q: Take me inside your creative process. Do you lock yourself inside of a room and bang your head against the wall until the light bulb goes off? Or do you take your lead from events in the market?

I think it’s actually much simpler than that. Our company is now a thousand people, but I run payroll, I manage insurance and benefits, and I approve every hire and every change in the system — all that kind of stuff. And so, I am doing all of the things for our own company that anyone who is a client of Rippling would be doing. I think that I have a very sensitive perception to repetitive, annoying things that you might have to do to run your company. I view it as my job to just go and stamp them out. I think about it like this: what are the things that I hate doing in my job as the guy running the Rippling software for our company and how do we fix that?

Q: Do you think the social media attention where everyone’s breathing down your neck 24 x 7 makes it more challenging to be a successful entrepreneur than it was a few years ago?

Oh, I don’t pay much attention to that. The Venn diagrams between spending time on social media and building your business do not intersect. If you’re the founder of a company, it’s probably a big waste of your time.

Q: What’s a big difference between being an entrepreneur nowadays and when you started out?

Well, nowadays anyone can raise money for anything. I wish that there was a way to have the fundraising success that I have now with the hiring market that existed 15 years ago. I would have been able to build the biggest and most successful company in the world. Also, there wasn’t the competition that you have today for hiring great talent, which is a direct result of how many people can raise money, obviously.

Q: Can you tell me something about yourself that would really surprise your employees?

I was a child actor. When I was in middle school, I was the understudy for the Colin Craven character in The Secret Garden when it was on Broadway.

Q: Do you have a favorite book?

Not really. I suppose I should have a great book that makes me sound smart, but I’m basically about work and my kids. As far as books go, right now I’m reading Harry Potter with my daughter. We’re on the final book, so that probably counts.

Q: Okay. How about a favorite movie?

Snatch. That was like my go-to date movie in college.

Q: Is there one person who’s had a determinant influence on your career?

The one person would definitely be Paul Graham at Y Combinator.

Q: You live out on the West Coast nowadays. What do you most miss about Manhattan?

Family. My parents live in New York and my sisters both live on the East Coast. Beyond that, I miss the fall, the leaf piles, the smell of fall, apple cider donuts — none of that exists on the West Coast.

Q: And I thought you might have said Zabar’s or Barney Greengrass!

Zabar’s would have been on my list, but I’ve started having bagels shipped from them and it’s not that expensive. They sell three dozen bagels, and the shipping costs are something like 10 bucks to ship in a sealed box where the bagels are frozen. It’s great.