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Seven Questions with Ravi Gupta

Classic advice for founders from the Sequoia community.

Ravi Gupta joined Sequoia as a partner in November 2019 and previously served as both COO and CFO of Instacart. He likes finding opportunities to simplify big, complex problems—in part by asking himself a clarifying question he learned from his manager in his very first job: “What’s the ‘so what’?”

What advice should first-time founders heed?

Make sure you have people around you to be vulnerable with. The life of a founder can be lonely, and it’s tremendously valuable to have someone to talk to during the difficult moments—because those difficult moments will come. It might be a fellow founder or a member of your team. If it’s someone on your board, that’s fantastic, because you need board members who will really get in the boat with you. When I was at Instacart, Michael Moritz was one of those mentors for me. We had a standing phone call—every week at first and eventually every three weeks—where we talked about everything that was going on, and it was so helpful to me.

There are some basics for who to choose as a mentor. They should have experience that’s applicable to your situation, for example. But as far as whether you can be vulnerable with them, I firmly believe the old adage that the best way to figure out if you can trust someone is to trust them. You just have to take the leap and see if they earn the trust you have placed in them.

What question are you asked more than any other?

I get a lot of questions about how to measure a business—which numbers to look at and which to ignore. The actual metrics you track will vary, but I do think the best companies are able to identify the one or two things that are most important at any given moment, and then focus on improving the leading indicators of performance for those areas.

It’s also important to understand how those metrics tie into the larger story of your company. Early on, when you don’t have many numbers, it’s all about that story—your idea or vision. But later on, once you have financial metrics, they should still be supporting that same story. “Our mission is X, we’re going to achieve it through Y, and we’ll measure that through Z.”

We took this approach at Instacart. We were clear on what mattered most. But our role as leaders was just to set direction, ask the right questions, and define the metrics that we would track. It’s the rest of the company that came up with the right answers and accomplished things we would never have thought possible.

What experience shaped who you are?

Being a parent. We have three kids, and it’s been awe-inspiring to suddenly be responsible for something beyond ourselves. It’s also clarified a lot of decision-making, including around work. Every day in a startup, something happens that could be a reason to stay late. But when that means missing time with your kids, you’re forced to have more perspective about how big of a deal it actually is. You ask yourself, “How important will this be in a year or two?” instead of “How important will this be tomorrow?” It teaches you to delineate between the standard ups and downs and the true crucible moments.

That’s important as a dad, but I think it’s also made me a better leader, because part of the job is to be the “cooler head.” When people trust that you have a high bar for what’s important and that you won’t manufacture crises, they’re that much more likely to follow your lead when something really is a big deal.

What’s the best interview question in your toolbox?

There’s actually no one question I always ask. My goal is to figure out whether I’d want to work with this person on something that’s really challenging, and the way to do that will be different with different people. So I try to really invest some time and get to know more than one aspect of their personality. We might meet in the office and then switch to another setting, like going for a long walk or having a meal.

One question I do ask frequently is, “What’s the hardest thing you’ve ever had to do?” That gets at how open someone’s willing to be with me, but the actual content of the answer is interesting, too. It tells me about the values they rely on when they’re doing something challenging. It also tells me what’s important to them—but without asking that directly, which can lead to more formulaic answers. Anything that’s been truly hard for you is probably something you care about deeply.

What book should every company-builder read?

One of my favorites is How Will You Measure Your Life?, by Clayton M. Christensen. It’s a seemingly simple question, but one that too many of us don’t ask. What will success look like for you? What are the decisions you’ll feel good about when you look back on them? I think it relates well to building a company because it reminds you to keep your purpose in mind when you are going through the day-to-day.

Another favorite is Shoe Dog, by Phil Knight, the founder of Nike. It’s beautifully written—he really brings you all the way into what it was like to build that company, from the crazy amount of time they spent developing the sole of the shoe to the absolute adoration and respect they have for athletes. It wasn’t just about business for him, it was about making people’s lives healthier and better, helping them live more fully. I think it really helped me understand the founders I know and have been inspired by.

What’s a lesson you learned the hard way?

When I worked at KKR, I worked with portfolio companies on the operations side before I became an investor. And for a while after I switched roles, I tried to rely on the skills I’d built up in that first job rather than actually learning the new one. I wanted people to think I already knew what I was doing and was too embarrassed to ask questions about the things I didn’t understand. But eventually, I realized I was robbing myself of the foundation I needed to do the job well.

So I stopped trying to play it cool and started doing my homework. And when I came across a problem I didn’t know how to solve, I asked someone to explain it to me. I realized the answers I needed existed in the people around me, if I would just quiet down enough to hear them. I love the expression, “There is a reason you have two ears and one mouth.” We are supposed to listen more than we talk.

What invention do you hope to see in your lifetime?

There’s so much more I want to read and learn than I’ll ever have the capacity for. I wish there was some way for me to download it all, Matrix-style, and still have time for family and friends and work and everything else that’s important to me. I’d love to study more math and world history. I’d also download every single thing David Foster Wallace ever wrote. But I think the first thing I’d do is dig way deeper into philosophy. I have my own thoughts on why people are the way we are and make the decisions we make, but they really are strong opinions, weakly held. I’d love to open myself up to the full breadth of perspectives.