Work Hard, Play Hard

“A hobby a day keeps the doldrums away,” said Phyllis McGinley, the acclaimed Pulitzer Prize winning poet. Bill Gates seems to agree and turns to his favorite hobby of bridge, which he frequently plays with Warren Buffett. Martha Stewart has a serious scrapbook fetish, and Jim Clark, the mastermind behind Netscape, sails the seas on Hyperion, his 197-foot mast sailboat. At a time when most scramble to salvage their enterprises challenged by the economic climate, let us introduce you to five achievers who are as interested in their boardrooms as they are in leisurely pursuits.

Jess Jackson

For Jess Jackson, the wine entrepreneur behind the Kendall-Jackson empire, the line between work and pleasure is blurry at best. What some would consider hobbies have become professions for this Renaissance man, who considers family his biggest priority. A lawyer, winemaker, farmer, and horse breeder, Jackson is ranked 536th on Forbes’ World Billionaires list in 2010. Amazingly enough, Jackson has done exceptionally well in all layers of his multi-faceted career that kept bringing him back to winemaking. “When I take on an endeavor, I aim to be successful at it and put in the work necessary to achieve that,” Jess reveals. “At the same time, fate is not entirely in our hands, so a little bit of luck is always helpful.”

It was with that same verve it took to make his wine empire a success that Jackson applied himself to thoroughbred breeding and racing. “In 1938, my uncle took me to see Seabiscuit at Bay Meadows,” Jackson recalls with nostalgia. “It was the Depression, and the world needed a hero. Seabiscuit wasn’t perfectly conformed but he had real heart. That’s when it took hold in me.” Pending definition of success, Jackson, who today is the majority stakeholder in thoroughbred Curlin, has become as triumphant in breeding horses as he is in winemaking. Curlin has earned more than $10.5 million in total, making the thoroughbred the highest North American money earner, thanks to wins at the 2007 Preakness Stakes, the 2007 Breeders’ Cup Classic, and the 2008 Dubai World Cup. For all of Jackson’s efforts, presented him with the Sportsman of the Year 2008 Insider Award. Still, perhaps Jackson’s biggest passion has been the outdoors, which consequently labored his professional success. “As I moved through law and my various careers, I was always drawn back to the outdoors: hiking through the Sierras, going up to the Trinity Alps, driving through the vineyards of California,” Jackson admits. “In hindsight, I was—with no particular awareness of it—migrating back to my family’s farming roots.”