Skip to main content

Seven Questions with Roelof Botha

Classic advice for founders from the Sequoia community.

Since joining Sequoia in 2003, Roelof Botha has led partnerships with companies including Eventbrite, Evernote, Instagram, Square, Tumblr, YouTube, and Unity. He started his career as CFO of nascent PayPal while finishing his MBA at Stanford—and took the role based on a combination of intuition, interest in the company, and a very real need to pay the rent.

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

“Friends come and go; enemies accumulate.” At Sequoia, we meet with thousands of companies every year, and only partner with 15-20. That’s thousands of interactions where we run the risk of making a negative impression. Regardless of whether we end up partnering with them, we always want founders to know we respect them and their ideas. I’m mindful of how I treat people and I think about the long-term consequences of my interactions. The people we meet with will tell others about their experience, good or bad.

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

You need to address an authentic, personal problem, not just manufacture an idea because you think there’s a market opportunity.

Square is a great example. One of the founders, Jim McKelvey, is an engineer, but he’s also an artist—a glassblower. He once lost a sale at his studio because he couldn’t process the transaction. That was the inspiration for Square.

When you’ve personally faced the problem you’re solving and you understand it on a visceral level, you’re much better prepared to address the specific challenges of building your company.

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

It’s not one small change as much as a system for change. I think it’s critical to confront the danger of habits. It’s not about avoiding them entirely—routine can be very effective. But we can also get stuck in suboptimal grooves.

I frequently reassess my routines and ask myself, “Am I accomplishing what I want to accomplish?” That means taking the time to think about what really makes me happy, and then setting specific goals.

When I was in high school, I wrote my goals on two signs—I put one on the wall above my desk, and one on the inside of my door. When I got tired of studying, I’d look up and see my goals on the wall, put my head down, and keep going. If I got up anyway, I’d see my goals on the door and go back to my desk. It didn’t always work—sometimes you just need a break. But that system helped me remember what I was working toward.

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

Everything! My fantasy is omniscience. I used to watch Groundhog Day and daydream that if I were stuck in a time loop, I’d go back to university and read every book in the library.

It’s not just about knowing things, it’s about deep understanding. To gain true insight, you have to peel back the layers of something and understand it fundamentally, at its core.

What books are on your nightstand right now?

The 2017 edition of The Best American Science and Nature Writing just came out, and I read that every year. I write down my takeaways from each article and store them in Evernote, so I can always refer back to them.

Another one is The Sixth Extinction by Elizabeth Kolbert. She argues that the planet is undergoing a man-made extinction event. With the way our global population is growing, I don’t see how we won’t eventually hit a global temperature humans can’t tolerate. So it’s a sad read, but again, it’s about gaining knowledge and thinking about the long-term consequences of our decisions.

And I’m reading The Best of Roald Dahl, which is a collection of his short stories for adults. They’re twisted and very funny. He has this way of making a protagonist so vile that you want them to fail—but somehow you can’t help but root for them, anyway.

When did you realize you were wrong about something?

I’m wrong all the time; as Yoda says in The Last Jedi—“The greatest teacher, failure is.” When I realize I’m wrong about an investment decision, for example, I try to learn not only from the things I missed at the time, but also from what I didn’t anticipate. What ended up happening that I failed to imagine? Once you’ve made up your mind, it’s difficult to go back and revisit those preconceived ideas. But that’s how you avoid the same traps next time.

What unit of time matters the most and why?

I think it depends on your age. In my 20s, I never really had a five-year plan. I prioritized pursuing new opportunities more than imagining where I’d end up. When you’re younger, I think three years is a good period of time to consider. It’s short enough to feel real, but long enough that you can make meaningful progress and big changes. As you get older, though, five or ten years starts to make more sense.