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.”

He had a confused look on his face. Clearly he didn’t remember our conversation or my emails. “That’s OK,” I said. “You have no reason to remember me. I would have been shocked if you did. But I remember you because you were the first VC I ever pitched.”

“Yeah?” he said, with a grin, “How’d that work out?”

“You told me you really liked what were doing and asked me to keep in touch. So I sent you monthly update emails for three years.”

“Oh yeah?” he said. “Sounds about right. Sorry about that. It’s just kind of how things work. We tell all the entrepreneurs we meet with to ‘keep in touch’ because it’s better for us than saying ‘No’.”

A decade ago, if I’d heard him reveal that he tells every entrepreneur to “keep in touch,” I’d probably have been pissed. These days, however, I’ve got enough perspective to understand why VCs often end their meetings with entrepreneurs by…