Why I Love Getting Rejected by VCs (And You Should, Too!)

I’ll never forget my first phone call with a venture capitalist. I was in my early-20s and a few months into working on a new startup.

The VC was a prominent, seed-stage investor out of the Bay Area. We spoke for 30 minutes, I shared my venture, he asked some thoughtful questions, and the call ended on what seemed like a clear highnote: “You’re doing some really interesting work,” he said, “I’d love to hear more. Let’s keep in touch.”

I was ecstatic. Immediately after, my co-founder and I began plotting how we’d spend our first million dollars.

Every month for the next three years, we sent that investor a personalized update email. And every month for three years, the response we got was: “Looks great! Keep it up!”

Fast forward 15 years and you’ll be not-at-all-shocked to learn that I raised exactly zero dollars from that particular venture capitalist.

As luck would have it, I caught up with the same VC a few months ago because we were both invited to speak on the same panel. He didn’t seem to recognize my name when we were introduced, so I didn’t mention that we’d spoken in the past. Instead, after the panel concluded and we were saying goodbye, I asked: “Do you remember that we’ve spoken before? I pitched you my first company.”