Chapter 1Fired at the Rest Stop

The Power of Failure

“I'm about to get fired again.”

I was on the New Jersey Turnpike, a long industrial stretch of road connecting cloverleaves in Delaware to my home in New York City. Along the way are rest stops named after people you've sort of heard of. Clara Barton. Vince Lombardi. Richard Fenwick.

My wife, my dog, and I pulled over at the Richard Fenwick Rest Area. I'd just received one of those emails that puts a pit in your stomach. My wife Camille watched me scroll through the email in dead silence. After an eternal minute I glanced up with a deadened look in my eyes. She waited patiently, but quizzically.

It was Friday the 13th, October 2017.

My track record as a startup executive was discouraging. I'd now worked at four companies over the past 14 years and this would be the third time I was fired. My self‐esteem plummeted as I read the message. How fitting to be at a rest stop when my career was in the toilet. Again.

“I'm about to get fired again.”

I thought back on the 18 years since I graduated from the University of Virginia—failure seemed to be a constant theme.

I'd started a record label, moved to a farm in rural Virginia, and tried to become some kind of hipster media mogul. That didn't work.

I'd followed a girl back to New York. We got married. Then the marriage fell apart.

I somehow found myself in the world of high‐tech venture capital–backed startups. I'd thought getting into the C‐suite and working hand‐in‐hand with the ...

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