What If the Whale Wins?

Damon Darlin, the long-time technology editor of The New York Times, is taking a new role at the paper as international business editor. We met six years ago in 2006, when Redfin was just launching its service. The story of our meeting conveys some of the madness of a start-up's early days, and what I learned from Damon about how to deal with it.

My flight to meet Damon for the first time was at 6 a.m. out of Seattle. As I drove away from the house, I realized all at once that I was late, and then, a heartbeat later, that I was really late.

I merged onto 99 doing 60, skidding into the next lane. A van plowed into my Civic, pushing the trunk to within a foot of my ear. The van pulled over, and so I did too.

I got out of the car waving ten $20 bills at the driver. He was lavishly stoned. Behind him were a half-dozen used bicycles. We instantly agreed not to call the police. I roared off.

When I got to the airport, I remembered that my license was in my laptop bag, which was in my mangled trunk. I borrowed a crowbar from a cab-driver to retrieve the license. While a group of the driver's friends slowly gathered to sip coffee and watch, I began beating my car senseless. The trunk wouldn't open, and my journey had ended.

On the way home, I noticed others gaping at my car; I heard the sound of the road all around me. I came upstairs, laid down next to my wife, and said, “It’s over. I blew it.” I was a new CEO, the company was just launching, and no one but Damon was interested in us. It was the most complete failure I could imagine.

Sylvia told me to call Damon and tell him the whole story. “He won’t believe it,” I said.

“Tell him about the crowbar,” she said, “and he will.” I explained to Damon the delay caused by the car accident, then the additional delay caused by lying face down in a bed for two hours. I left out the crowbar to avoid scaring him. Damon chuckled. I remember thinking, “What a strange, jolly man.” He asked if I still wanted to fly down.

You expect many things from a journalist: curiosity, crankiness, fairness, wariness. But if you belong to that great unwashed class of start-ups with no revenue, three months of cash, and a product no one uses, the last thing you expect is a full hearing.

But that’s what Damon gave us. He wrote a small story that happily concluded Redfin might be like the first penguin to jump from the ice to the ocean, first to eat or first to be eaten by a whale.

I thought about this often. For years afterwards, it seemed like the whale would win, but Damon gave me a way to think about it that didn't seem so bad.

(Photo credit: Randy Stewart)