After years of long hours building a billion-dollar business, the investor Steve Cucchiaro of Boston sold his company and returned to what makes him happy: sailing. Once a member of the United States Olympic Sailing Team, he now finds a balance between running a new business and sailing.

“I feel like I had the chance to compete against the best in the world and sail at the highest levels during the 1970s,” Cucchiaro, 67 , said. “I stepped away from sailing, but some time would go by and I would start to miss it.” He returned to serious sailing in 2014 and will compete in the Maxi Yacht Rolex Cup on Flow , his Nautor’s Swan 601 . This conversation has been edited and condensed.

When did you first start sailing?

My dad first exposed me to sailing. He was an inner-city kid in Boston, and he was in a program that introduced sailing to kids that otherwise might not get that opportunity. Years later, when I was about 4, my dad was invited to join the local sailing association. He remembered how much he had loved sailing as a kid, so we started racing as a family.

Finally, my dad suggested I take the boat over and start racing with my friends. I did that every Saturday on a 110 — a 24-foot keelboat. We would go out there and usually get last place or next to last, but it was a good learning experience.