Ravi Gupta

I didn’t know anything about technology when I graduated from college. I grew up in Chicago. I was an econ major. I was totally an outsider to it. Once we moved to California, though, there was this incredible energy. I wanted to be a part of that. So I pushed hard to find a way to work at Instacart. I’m so glad I did.

Sequoia’s approach reminds me of the way I grew up—my parents did not choose between being demanding or supportive. They were both.

My grandfather came to the U.S. from India in 1957. He left five kids and my grandmother. He was 35 and upended his whole life because he saw the possibility for something better. Three years later, he brought my grandmother and his youngest daughter, and left my dad and his brothers in India. I think about my grandfather as the founder of our extended family. His decision impacted everything in my life, my parents’ lives, and my children’s lives. There is an obligation—you have to honor the fact that someone did that. I think about that a lot.

What am I on the lookout for? One is a founder that captures my imagination. Two is a market that I believe will be much different tomorrow than it is today. Three would be some traction or a unique insight that demonstrates there’s a kernel that’s working. It could be one customer who says, “I couldn’t live without this.” The reason I went to work at Instacart was that when I asked my wife what she thought of it, she said, “If you wanted to move, I wouldn’t go unless Instacart delivered to our new house.” That was crazy—I couldn’t stop thinking about that. Each company I’ve invested in on behalf of Sequoia has something like that that I can’t stop thinking about.

I have been lucky to be involved in companies across industries—consumer and enterprise, fintech and crypto. More than anything, what I look for is someone I want to talk to at 10:30 at night if they have a problem. Instacart gave me empathy for the ups and downs. It is so easy to say what somebody should do—and so hard to do it. Businesses are not numbers on a page. They are a collection of people going after a shared mission.