Sam Yagan started his first company, SparkNotes, as a Harvard senior in 1999 and sold it the next year for $30 million. In January, he sold his third company, dating website OkCupid, to IAC for $50 million.

We got our first serious offer in September 2010. I never asked for it. Someone said, "Are you interested in selling?" I said, "We're not for sale, but I'd take a look." It was in the ballpark, so I called three other potential bidders. Four months later, we agreed to sell to [a subsidiary of IAC] for $50 million in cash. We felt like it was a chance to give our investors, our employees, and us a great return, and do right by our customers, since Match agreed not to change anything.

For the other 17 people here at OkCupid, nothing has changed. That's part of my job. I have a lot more meetings. I go to Dallas [where Match is based] once a month for two days. I also get to take things off my plate, like finance, HR, and legal, that were less interesting to me. I like being part of a big company's executive team. It's fun to stretch other parts of my brain, considering questions like, How should we think of acquisitions? I get to be privy to things that would never come up at a small company.

Plus, I think this year, my wife and I will actually get to go on vacation.

But on the other hand—all I know how to do is start companies. What do I say when people ask me what I do? "I work for a big company"? I mean, a lot of people do. It's great. But it's almost like having a sex-change operation. Part of me is like, What's my identity, if it's not the company I'm building?

There is a soul search that is happening parallel to my day-to-day life.

My OkCupid co-founders are my best friends. We were in each other's weddings. The other night, we went out to dinner. We spent half our time bullshitting around, and then we started discussing our future. Whether it's now or in a year or five years, do we want to start another company together? What are people's goals in life? I can imagine a life where a big paycheck and the cool perks and being part of the executive team of a big company would be great. I'd love to summer in the Hamptons. But I'm still in a building phase. I'm 34 years old. In most jobs, your early 30s to early 40s are your power years. So if this is my power decade, should I be saying, This is the time for my big entrepreneurial move? Should I try to build a billion-dollar company? Should we put all our money together and say, What is the next LinkedIn or Groupon or Facebook?

If I start again, I can now fundraise better, but I still start at Square One. It's still going to be four guys in a small office with Ikea desks. Part of me is like, Is that still appealing? And it is.

Life is just a set of experiences. As long as there are new experiences for me in a corporate job, I don't think I have to be an entrepreneur. The cool thing about being an entrepreneur is I can guarantee to myself that it's going to be new, because I'm going to make it so.