For me, AOL was a 20-year journey. It was really two chapters: The first 10 years was really more of the pioneering, figuring-out phase; the second 10 years was more the commercialization, scaling phase. While the fame and the fortune came in the second part, I really preferred the first part. I was better at it. I didn’t foresee AOL becoming as dominant as it did. Fifty percent of all Internet traffic went through AOL at one point. It was the first Internet company to go public, in 1992. We had a market cap of $70 million. Eight years later, we had a market cap of $150 billion when we decided to merge with Time Warner. One of the personal lessons for me with Time Warner was that it’s important to have authority and responsibility aligned. It’s not a good situation if you’re unable to influence the outcome but you’re held responsible.
When I stepped down in 2003, I considered other options: more philanthropy, politics, retirement. I’m interested in policy, but I tell my friends that I don’t have the charisma to get elected or the patience to govern. I pretty quickly decided I wanted to roll up my sleeves and go back to the garage. A lot of people warned against going back into the entrepreneurial space. They said, “You’ll never be able to top this first act. Just do something different.” But I didn’t want to. I wanted to help build new businesses with other investors. There were concerns: Was I serious about this? The transition from entrepreneur to investor/mentor doesn’t always work. I had to build a track record before launching a venture fund, which we did last year.
What I’m looking for are disruptive businesses with the potential to change the world. The growth of a sharing economy led us to companies like Zipcar. I think other regions around the nation are where the next generation of companies will be created. LivingSocial is in Washington, D.C. Zipcar is in Cambridge, Mass. Most of the capital and talent is focused on Silicon Valley. That’s an investment opportunity, to fish where others aren’t. Americans talk about other countries copying our secret sauce. It’s true, but others are still envious of what we have in terms of talent, culture, and resources. I want to prove you can build a model around entrepreneurship. I love disproving skeptics. — As told to Diane Brady