Written By: Bruce A. Percelay | Photography By: Kit Noble

From AOL to the NBA, the remarkable life of Ted Leonsis.

There is an unmistakable air of serenity about Ted Leonsis that belies his type-A résumé. As the former president of AOL, the owner of the Washington Capitals, Washington Wizards, Washington Mystics and the DC Verizon Center, the former co-CEO of Groupon, a successful movie producer and author, and the recipient of various man-of-the-year awards, Ted Leonsis’s wide range of accomplishments seems almost improbable.

Screen Shot 2015-06-28 at 5.47.16 PMBorn in Brooklyn, New York and raised in the working class suburbs of Lowell, Massachusetts, Leonsis had every opportunity to become average. When his high school guidance counselor evaluated his skillsets the counselor concluded that young Ted was destined to work in a grocery store. “I didn’t have much money growing up, so I always had these little jobs,” Leonsis remembers today from his summer home on Nantucket. “I started this little lawn mowing business, and I mowed the lawn of a man named Jim Shannon.” Unlike most teenagers given the pedestrian job of cutting grass, Leonsis went to the library and studied how best to mow Shannon’s lawn. His performance so impressed Shannon that he helped Leonsis get into his alma mater, Georgetown University. “That changed my life,” he says. “My horizons were expanded.”

The man who expanded Leonsis’s horizons at Georgetown was an old Jesuit priest named Joseph Durkin, who was assigned as his mentor during his junior year. “I remembered being really disappointed. What would I have in common with this seventy-five-year-old priest?” Leonsis says.

Father Durkin kept pushing Leonsis to get started on his senior thesis. Looking for an easy way out, the undergrad went to the library and checked out the shortest book he could find, Hemingway’s The Old Man and the Sea, and told Father Durkin he was going to write his senior thesis on this classic piece of literature.

Screen Shot 2015-06-28 at 5.48.50 PMAs he delved deeper into Hemingway’s writings, Leonsis began to theorize that parts of The Old Man and the Sea were in fact written years earlier than its copyright claimed. Father Durkin suggested that Leonsis use this theory as his senior thesis, and more notably, he suggested that he use a computer to prove it. With Father Durkin’s help, Leonsis developed an algorithm on Georgetown’s only computer that proved his theory. The thesis earned the undergrad some renown around the Georgetown campus and in literary circles, but more importantly, it taught him the power of computers, a lesson Leonsis would run with in the years to come.

After returning to his hometown of Lowell where he got a job at Wang Laboratories, Leonsis started a publishing company and then a media company, which he later sold to America Online. The acquisition resulted in Leonsis becoming president of AOL, where, over the next fourteen years, he helped co-founder, CEO and chairman Steve Case grow AOL’s membership from 800,000 to eight million. Revenue also soared from $100 million to $1.5 billion. “There was a decade when we were the number one performing stock on Wall Street,” he says. “We literally got America online.” Leonsis had come a long way from mowing lawns in Lowell, but his most valuable accomplishment was yet to come.

Screen Shot 2015-06-28 at 5.43.39 PMWhile aboard a flight on Eastern Airlines, Leonsis experienced what he describes as “a reckoning” when his plane suffered a mechanical failure and the landing gear wouldn’t lower. “As this plane was going down, I started to pray,” Leonsis remembers. “People were crying on the plane and my prayers felt a little bit inauthentic.” So instead of praying, Leonsis made a pitch: If he made it through the flight, he would devote his life to giving back more than he took away. When his plane miraculously touched down safely, Leonsis set out to make good on his pitch.

“I’ll play offense with the rest of my life,” he vowed. “I won’t be a whiner. I’ll be prone to action…and do well by doing good.” From that day forward, his focus took on a new dimension. He wrote a list of 101 things he wanted to accomplish before he died, and got busy ticking them off. “The list really highlighted the lack of tools available to somebody on how to craft a full life,“ Leonsis explains. “I made the list because I was unfulfilled.”

One of the major objectives on the list was to own a sports team. He got that chance one day when he was approached to buy the Washington Capitals hockey team, but declined. That night he told his wife about the opportunity. “What if you get ninety-nine of the 101 things crossed off and you never get to buy a team or win a championship?” he remembers his wife saying to him. Before he fell asleep, Leonis decided to buy the team.

Screen Shot 2015-06-28 at 5.43.52 PM“The list became important, but it drove me to become a student of happiness,” Leonsis explains. “So for the last fifteen years of my life, all of my investments, all the businesses I get involved with, are outgrowths of the research I did, the best practices on what makes for happy people.” His theories eventually became the inspiration for a book entitled, The Business of Happiness, which has become his life’s operating manual and the source of inspiration for legions of readers. “If you’re happy, you can be successful,” Leonsis explains, but “if you’re successful, it doesn’t mean that you’ll be happy. ”

Leonsis is a living example of the American dream, but he feels this concept is flawed. The simple notion that hard work will yield a better education, which will yield a better job and thus more money, falls short on the idea of creating true happiness, which is life’s ultimate reward. “Success doesn’t yield happiness, but happiness can yield great success,” he says. Fulfilling the pitch he made on that plane all those years ago, Leonsis is succeeding in showing many others the ways to finding true happiness.

From mowing lawns to attending Georgetown to growing AOL, Leonsis sees his life as serendipitous. But for people who are governed by good intentions, blessed with innate intelligence, and a willingness to work hard, serendipity tends to find them. Ted Leonsis has made his own serendipity and found happiness in the process.

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