Grand slam

Executive: Arnie Bellini, chief executive officer of ConnectWise, a 700-employee company providing IT management software. With annual revenues of $109 million, the Tampa-based company provides software to 95,000 users. Over the last three years, the company has grown 76%, landing it a spot on the Inc. 5000 and Software 500. In the last four years, the company has made four acquisitions, with two more planned for the end of the year and an additional three to four expected next year.
 
Diversion: The “grand slam” of long-distance open-water swimming: completing the 20-mile swim across the English Channel; the 21-mile swim from Catalina Island to Los Angeles; the 29-mile Manhattan Island Swim around the island; and the 24-mile swim for the Tampa Bay Marathon. Bellini is the oldest person to complete the grand slam in one year.

BHAGS: Bellini is adamant that a successful businessperson must always have BHAGS, or big hairy audacious goals. It's good to have a crazy goal in business and “one outside the business, just to keep life interesting and to keep a balance,” he says. “Slow pace just doesn't balance me out.”

Bucket list: When Bellini turned 50, a friend asked him what was on his bucket list. Bellini told him that he wanted to do a full Ironman triathlon. His friend pushed back saying, “Take it off your list, you're 50!” “He was roping a dope,” Bellini says, because his friend wanted a training partner. Bellini completed three full Ironmans after that first dare. Bellini realized he enjoyed the planning and preparation that went into the long-distance races. At the same time, his business “was growing like a mushroom. It was growing so fast, I needed to do something crazier,” he says.