My Company Failed. So I Drove For Uber. Now I Run A $1B Investment Firm in NYC.

In my interview with Jason Shuman, I asked him, “How did you get into venture?” Here’s his story:

“I launched a company while I was an undergrad. It was a direct-to-consumer footwear company with my best friends and my brother. We hit rocky times after college, and I felt like my whole self-identity was tied up in this startup, but I also felt a lot of responsibility for my friends, my brother, and their future.

I knew that I didn't have it in the tank to keep going, and nor did I want to do it for the next 10 years. So I pushed them to go find jobs, and I was going to wind down the business.

But as I picked my head up to figure out what I wanted to do next, I was looking around and thought, ‘This venture capital thing, it seems super interesting, but how do I get a job in it?’ I didn't go to an Ivy League school, so that's really hard to figure out.

The only way I knew how was to go out and find potential companies to invest in for VC firms [in Boston]. VCs just don’t have the bandwidth to research at the level of depth that I could. I created that bandwidth for them.

But you can't source deals for free, pay the bills, and eat food every day. So, to create enough flexibility, I went out and drove for Uber.

Funny enough, I was in a meeting here at our offices a few years ago, and this guy came in. He's a partner over at a firm called Avenir. I went up to shake his hand and said, ‘It's really nice to meet you.’ 

And he was like, ‘Oh no, we've already met.’

I’m like, ‘What do you mean?’

He said, ‘You were my Uber driver about 10 years ago, and I will never forget it because it made me love Uber because you were an entrepreneur telling me your story.’

Ever since then, I'll never forget that business.”

Listen to Jason Shuman’s full story on Spotify below.

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Have a productive week!

Shamus