JEFF SHEPPARD always beat the odds. He wasn't good enough as a junior guard at Atlanta's McIntosh High to make the state all-star team, but a year later he landed a scholarship to play at his dream school, Kentucky. In his first three seasons with the Wildcats, Sheppard, a 6'3", 185-pound guard, averaged just 5.9 points, but in 1998 he was the Final Four's Most Outstanding Player. Led by Sheppard's 16 points, Kentucky came from 10 points down in the first half to beat Utah 78--69 in the NCAA championship game.
But Sheppard's next long shot—a successful pro career—ultimately did not work out. After graduating with a degree in math education, he played one season with the Atlanta Hawks, averaging 2.2 points a game. He then played in Italy for two years, but he quit the game after the Sept. 11 terrorist attacks. He settled down in London, Ky., with his wife, Stacey. (The former Stacey Reed also played basketball for Kentucky and is seventh on the school's career scoring list.)
After trying pharmaceutical sales for a year, Sheppard decided to bring his experience in basketball to his next venture. In 2003 he and Stacey started a clothing company called 15inc., which sells corporate and sports apparel with custom logos. The company is based out of a 7,000-foot warehouse near the home where the Sheppards live with their eight-year-old daughter, Madison, and four-year-old son, Reed.
Sheppard, now 33, also does motivational speaking, coaches clinics and is a sales director for WazooSports.com, a website launched last October that broadcasts Kentucky high school football and basketball games online and on cable. "Nobody is doing good-quality broadcasts of high-profile prep school events," he says. "It's the next horizon right now."