In 2003, founder Bob Diener sold his portion of the business to what was then InterActiveCorp (and the parent company of Expedia) in a deal that valued the company at over $5.5 billion. As part of the deal, he agreed to a five-year non-compete contract.

“I advised the company for a while after we sold, but eventually I was done with It was very difficult to let go. I started that company from scratch. It felt like I was sitting idle as I watched someone else raise my kid.

I was used to such intensity in my daily work routine, and not going into the office and interacting with my employees—that was a rough period for me. It was difficult to overcome. I was constantly going at 100 miles an hour. I had dreamed of having free time, but when I finally got it…I guess the grass is always greener, as they say.

The day after my last day of work I went to kite-surf camp in Costa Rica. It was something I always wanted to do. It was a great diversion, being in another country, in a remote part of the world. It was a great way to get my mind off of letting go of the business. I also built a house, learned to snowboard, got involved in charities.

I still felt a big void. I felt like I wasn’t being productive enough. I’ve just been that way my whole life. Very intense, very focused, very goal-oriented and driven. Having that sense of accomplishment—that’s what drove me to start a business again. We had no plans to go back into the hotel business. But right at the five-year mark, we went into a deep recession, the hotels needed help, and consumers were looking for new ways to book hotel rooms. We saw great opportunity, so we launched in July 2009.

During my non-compete, people would ask my kids, “what does your dad do?” They didn’t really have a good answer. Part of the reason I started is because I wanted them to have a good answer. Now they all proudly talk about the business, which they’re very involved in. They walk around wearing shirts with our business logo. It’s been a really special thing for me to show them what it’s like to grow a business, to start it from scratch—what it’s like to be an entrepreneur."