Seven Questions with Kevin Systrom

Kevin Systrom is co-founder of Instagram and served as the company’s CEO until October 2018. In early 2019, he decided his next challenge would be learning to fly; he had his first lesson (in a decades-old “lawnmower with wings”) that afternoon and got his pilot’s license three months later.

What advice should first-time founders heed?

I tell first-time founders to make sure their product solves a core problem in people’s lives. Far too many entrepreneurs build whatever they think is cool and forget to ask whether it will actually be useful to people. The great companies start by defining the problem they’re going to solve, and then everything they do is rooted in that effort.

In general, though, I think entrepreneurs should be careful about taking advice, because it can go stale pretty quickly as things change—and because it’s so often colored by someone’s own experience. One person will tell you the freemium model is best; another will say you should never do it. One person will say you have to have a co-founder; another will tell you co-founders never work out. Your best bet is advice that feels true in almost every situation—that matches patterns over time. But what’s most important is finding an advisor or mentor who can see all sides and has the self-awareness to think through the edge cases and changing circumstances where their advice might not apply.

What question are you asked more than any other?

A lot of new founders ask how to scale their time. As a company grows, more of your time is spent running it, which means less time to think up new products. But as a founder, it’s important to realize you don’t have to come up with all the ideas. You should carve out time for that kind of thinking, but you should also hire smart people who will come up with their own ideas.

That was a leap we had to make at Instagram early on. Many projects failed because we founders didn’t have the expertise, the time or both. Eventually, though, we learned to bet on our people. My job as CEO was to keep them focused on our mission and make sure everything we worked on served that goal—and then to help make their ideas a reality. When we gave them enough room, great things happened.

If you try to be the factory that produces ideas, you’ll always be constrained by your own time, ability, energy level, creativity. Instead, build that factory. It’s just as challenging and interesting as building a product, but the outcomes are so much greater.

What experience shaped who you are?

Becoming a dad. Being directly responsible for another human being makes you ask questions you might not otherwise—including about the products you’re building. We were already thinking a lot about how kids use Instagram. We built machine learning to protect them from bullying and hateful content, and features that allowed you to see, and set, limits on how much time you spend on the platform. But parenthood underscored all of that work. It made me think more about what our goals should be in terms of the utility of the product versus the time you spend on it.

The conversation about technology and kids tends to assume it’s a negative relationship, but that wasn’t the case for me. My first computer opened a lot of doors. I learned to program; I learned to think about the world differently. For kids, and all of us, I think it’s about redefining that relationship. It shouldn’t be about distraction or not being present, but about growth and productivity.

What’s the best interview question in your toolbox?

I like to ask candidates what they’re interested in outside of work, because I’ve found a strong correlation between having broad or unique passions and being able to think creatively. One person I interviewed liked making salumi and told me all about the meats he was drying in his basement. Another person raced cars on the weekends and talked about the importance of suspension. They both ended up being very successful in their jobs. I think there’s really something to the idea of being a renaissance person.

Having interests beyond your work also helps you maintain a beginner’s mindset. Most of us learn a lot until we’re in our early to mid-20s, but then it falls off. You might learn a few things on the job, but you don’t explore entirely new areas—unless you do it on your own. I think it’s important to never let the doing overtake the learning, because learning is where great ideas come from.

What book should every company-builder read?

The Hero with a Thousand Faces, by Joseph Campbell. It outlines his theory of storytelling, where a hero is called to adventure, faces crises, wins and comes back transformed. I think understanding where you are in that journey is really instructive for an entrepreneur or anyone who’s at a big moment of transition in their life.

I read it toward the end of my time at Instagram, so for me, I was thinking a lot about what comes next. We were able to work with wonderful people on wonderful projects and we learned a lot. The company had occupied 99% of my life. All of a sudden, the question was, “What now?” How do you share what you’ve gained, whether that’s through philanthropy or coaching and mentoring? My journey may be different from someone else’s, but I want to offer whatever I can to help them.

What’s a lesson you learned the hard way?

To prioritize the important but not urgent over the urgent but not important. It’s a painful lesson when the urgent is something like the site being down for an hour. But if you don’t make time for long-term, strategic stuff, it will always get crowded out. In the early days of Instagram, we got stuck in a loop where were spent so much time fixing the servers that we didn’t have time to find the people who could help us fix the servers! We didn’t hire nearly quickly enough.

It’s a tough trade-off to make, because you get an instant reward when you focus on the urgent. I catch myself doing it even today. But I try to remind myself to get out of that pattern. When I was working, I would ask myself every week how much time I was spending on things that were important, whether they were urgent or not, and I put time for long-term thinking on my calendar. In the long run, that effort does pay off.

What invention do you hope to see in your lifetime?

I’d love to see artificial intelligence used to replicate specific people so you could have a conversation with some of the world’s leading thinkers. Imagine you could speak with Nikola Tesla or John Adams. When I was at Instagram, there were lots of people I would have loved to talk with, so I could hear about their own experiences with some of the things we went through.

When I started this new chapter, I sat down with a bunch of interesting people who had made similar transitions, and that really helped me understand what the future might look like. Drawing on personal experience is always helpful, and if you talk to enough people, you find their answers have a lot in common.