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.

Swimming: Bellini's mom signed him up for swimming when he was 9 years old, but he wasn't overly interested until she gave him an article about the first woman to swim the English Channel. “It captured my imagination,” he says, “and anything that captures my imagination, I have to do it if it won't kill me.” So in 2010, his goal became to cross the channel. He spent two years training in cold water, swimming in Tampa Bay when the water dropped into the 60s so he would survive the 62-degree water in the English Channel. In the winter, people on Tampa's Riverwalk would see Bellini getting into the Hillsborough River in a speedo.

Training trance: Bellini, 56, trained with coach Bart Cobb, swimming around Harbour Island and Davis Island, building from a 5-mile swim to a 16-mile swim. Every weekend he'd do one long swim, and every other day, he'd swim a mile in the lake he lived on in North Tampa.

Challenging waters: “I trained to the point that I knew I would make it. It never dawned on me that I wouldn't,” Bellini says. But four miles from the finish at the coast of France, Bellini was forced to quit because he was going into hypothermia. Heartbroken, Bellini didn't let the first try defeat his goal. He came up with 20 things he could have done better, and focused on those 20. He rebuilt his stroke after 42 years of swimming, forcing himself to breathe on both sides, rather than just to his right. A year later, on Sept. 4, 2013, he completed the swim.

Upping the ante: Once Bellini reached his goal, he decided he wanted to complete the grand slam. “I want to and need to force myself to face fear all the time,” Bellini says. His scariest swim was the Catalina Channel, in great white shark-infested waters, where swimmers are dropped at the beach to start at midnight. On Sept. 3, 2014, with three hours to spare, Bellini achieved his goal of completing all four swims in one year. Next, he hopes to swim the length of Loch Ness and the straight of Gibraltar.

Competitive advantage: “There's a high correlation of CEOs in high performing stressful jobs and what they do in their free time outside,” Bellini says. Bellini's next BHAG is to spend a week in the wilderness with only the bare essentials to survive. He also wants to complete the Iditarod. “I'm in the idea stage right now,” he says, “Because I don't want to get to the bottom of the list.”