Executive Grind?

Maybe you’ve seen the grown-up on the skateboard before. He’s usually at Fleischmann’s Skate Park in Naples once a week with a couple of younger skaters in tow. They outshine him on the ramps—but not by much.

Unless you get close enough, you might not realize that the man sailing on the skateboard down the vertical half-pipe is Bill Thomas, vice president of the Collier Family Office, which handles the financial interests of Barron Collier’s descendents. The two younger skaters are his sons, and Bill Thomas, 48, is easily the oldest guy out there.

He has been skateboarding since he first stepped on a board at age five. It was a hobby he abandoned only briefly, when his sons were younger, but he took it up again when his Evan, 14, and Ryan, 12, gravitated to the sport around the same age their father had.

Now he and his sons skate together every week, in addition to their tae kwon do (all three are third-degree black belts) and the running he does with his wife, Heather.

The three skateboarders of the family even take vacations every year for what Thomas calls "a guys’ trip." He and his sons venture to Southern California to skate various parks, meet such legends of skateboarding as Mike McGill and the Z-Boys, and learn about the sport’s history.

"There’s a rush," says Thomas of his lifelong hobby. "There’s a Zen-like connection—this slowing of the body and the board and you’re gliding. It’s a wonderful, wonderful sport."