Seven Questions with Jess Lee

Jess Lee is a partner and CPO at Sequoia and the former co-founder and CEO of the social commerce website Polyvore. She is also a founding member of All Raise, a nonprofit dedicated to diversity in funders and founders—as well as an avid cosplayer.

What is something you’ve learned that you lean on daily?

A mentor of mine, Cheryl Dalrymple, once told me you can only move three points on a ten-point scale. So it’s better to find the areas where you’re already a seven and work to become a ten, rather than to beat your head against a wall trying to get from a two to a five. Know your strengths and focus your energy there. Know your weaknesses and manage around them by hiring great people to fill those holes.

When I was at Polyvore, I once did a 360 review that revealed that I had very high tolerance for ambiguity—but that was the opposite of what my team wanted at that stage. All the data showed they were hungry for more clarity and more process, and I was probably a four on process. If I’d worked super hard, I might have gotten to a seven. Instead, I hired a COO and PMs who were already tens.

What one piece of advice would you give someone starting a company?

You have to get comfortable being uncomfortable, whether you’re successful or not. Obviously, it’s hard when a company is failing. But it’s still hard when things are going well. The company is growing so fast that it’s changing underneath you, and you’re struggling to keep up. One day you’re the CEO of a 30-person startup and you’ve finally figured out how to do your job, but then you get to 60 people, or 300, or 2,000, and everything that used to work keeps breaking and you have to learn your job over and over again. It’s a rollercoaster.

You need to have grit to push through those tough times, but the other thing that helped me was community. You need a support network, especially other founders who can give you advice or at least commiserate. That’s part of what we do at Sequoia, too, because many of us are former operators who’ve been there before.

What small change has made a big difference in your life?

I stopped thinking in terms of success or failure and started thinking in terms of growth or stasis. That’s something Marissa Mayer told me very early on, when she interviewed me for my first product manager job at Google. I’d just graduated with a CS degree, and I was planning to be an engineer. I’d never even heard of a product manager. But she said, “Optimize for learning. Take the more challenging path.” So I accepted the job and tried something new. Ever since then, I’ve consistently sought out roles where I can constantly learn, rather than taking the safe path and optimizing for guaranteed success.

At Sequoia, that’s extended to exploring sectors that aren’t necessarily in my immediate wheelhouse. I don’t have a background in robotics, for example, but I think autonomous vehicles are going to be a huge consumer trend one day, so I’ve learned as much as I can—ridden in many self-driving cars, met with founders, read up on sensors, gone to Detroit to talk with auto manufacturers. If I thought only in terms of my odds of success, I’d probably stick to the things I already know, like community building, women’s spaces and the future of work. Those are still my primary focus, but I think it’s also important to get out of your comfort zone and push yourself to learn something new.

What don’t you know that you wish you knew?

Before I got into tech, I wanted to be a graphic novelist. There’s still a part of me that would love to do creative work, whether that’s write or draw or make movies. Video in particular is such an incredible form of self-expression, and I wish I knew more about cinematography. I think it would be so cool to be a director—to combine all that technical knowledge and storytelling ability and create something that really moves people or makes them think differently.

What books are on your nightstand right now?

I’m reading One Punch Man, which is a comic book by the manga artist ONE. It’s a guilty pleasure. It’s about this overpowered superhero who can take down villians with a single punch. But he doesn’t look the part—he’s skinny, he’s bald, he doesn’t have a cool outfit—so he never gets credit. Everyone always thinks it was one of the other, cooler, better-looking superheroes. I love a good underdog story.

Whether it’s manga or books or movies or TV, I almost always choose fiction over nonfiction, especially escapist stuff like sci-fi and fantasy. I just like being transported to another reality or realm.

When did you realize you were wrong about something?

My startup journey felt like an endless string of tiny, daily failures. I’ve been wrong about a lot of things, but the most painful ones were people. Hiring is tough, and it’s hard to admit it to yourself when someone isn’t working out. You might know in your gut that it’s not a good fit, but you think, “Well, maybe they just need a little more time. Let’s wait and see how it goes.” You want so badly for it to work that you keep making excuses and wait too long, and that’s always a mistake. That said, when you do act on it, it can’t be a surprise. It’s on you to make expectations clear and make sure people know whether they’re meeting them.

I think it’s also important be transparent with your team whenever something isn’t working out, whether it’s because you made the wrong choice in the first place or because your organization has outgrown what you’d built. Something is always going to be broken. That’s startup life, and that’s okay. It’s inevitable. What’s important is that you recognize the problem, fix it and learn from it.

What unit of time matters the most and why?

Every second matters, because time is our most precious resource. It comes with the highest opportunity cost. So if there’s a better way to use any amount of time, you should find it. That’s not to say you shouldn’t relax or recharge—I think those are actually good uses of time. But each second does matter.

When I’m making a big decision, I often try to ask myself how I’d think about it if I had very little time left. “Will I regret this when I’m 80 or 100 years old?” The decision to join Sequoia was a good example. I wasn’t entirely sure at first that I wanted to be a venture capitalist. But one of the best firms of all time was asking me to join and it felt like a once-in-a-lifetime opportunity. I wasn’t 100 percent sure that it would work out, but I was 100 percent sure that I’d learn a ton, and that if I turned it down I’d look back and think, “What if?” Thankfully, I decided to go for it.