Fighting My Own Ambition

A blown-up business deal made me confront the mysterious forces behind what I thought I wanted

In the summer of 2008, I experienced the moment many startup founders live for: I learned that I would be able to cash out on my company’s success. After an intense period of courtship spanning several months, I was on my way to have celebratory drinks with the CEO of Zappos, Tony Hsieh. Zappos was going to acquire my e-commerce company for wellness products, FitFuel.com.

About an hour earlier, Tony had sent me a direct message on Twitter (his preferred form of communication at the time) asking me to meet him at the Foundation Room, a bar on the 63rd floor of the Mandalay Bay hotel in Las Vegas. I knew that he had attended a board meeting earlier that day and that one of the agenda items was the acquisition. He wouldn’t be inviting me to the Strip if the news was not good.

I’d been pacing around my house all day. I needed the deal to go through. Fit Fuel was burning through cash. Despite our rapid growth over the past two years, the coming months looked ominous. The Federal Reserve had gone into bailout mode and held an emergency meeting to keep the giant investment bank Bear Stearns from going under. The housing market was crashing. I needed to raise a round of investment, but investors were…