Hindsight: What Nine Entrepreneurs Wish They'd Known

Ron Simpson, founder of Play N Trade
Age: 43
Industry: Video games
Number of employees: 40 corporate employees
When it all began: 2000

What he would change, if he could: Simpson, who got his entrepreneurial start in the jewelry business, says he would have implemented his Area Developer sales program sooner. "The speed with which Area Developers can sell, open and support stores turned out to be faster than the way we got it done in the early days with only five employees. They give you a sense of scale that cannot be achieved with limited resources, and it's great to have a face in the local communities across the country talking about your brand."

	Ron Simpson

Michael Ilitch, founder of Little Caesar Enterprises, Inc.
Age: 78
Industry: Restaurant
Number of employees: About 10,000 full- and part-time
When it all began: 1959

What he would change, if he could: For Ilitch, whose company also owns the Detroit Tigers and the Detroit Red Wings, the best move he's made was marrying his wife. He and his wife, Marian, have worked side by side for almost 50 years, building their pizza empire. As for his worst move, Ilitch says he's sure he's had more than one, but doesn't regret them. "I don't think I would have done anything differently. There were certainly some failures and many successes along the way, but I always enjoyed learning from all the ups and downs."

	Michael Ilitch

Annette Cook, founder of Barefoot Dreams
Age: 43
Industry: Retail
Number of employees: About 30
When it all began: 1994

What she would change, if she could: "If I could turn back time, I would have gotten more help, sooner," says Cook. The Barefoot Dreams creator found herself overwhelmed in 2003 when Oprah featured her line of cozy robes, throws and baby apparel as one of her favorite things. At the time, Cook was a stay-at-home mom, pregnant with her third child and operating Barefoot Dreams by herself.

"I didn't delegate enough, I did it all myself," she says. So after making Oprah's list, Cook found herself overwhelmed and understaffed. "Operations could have run a lot more smoothly if I had a top management team in place when that happened." Cook's employee roster has expanded, and her husband, Stan, is more involved with the company on a daily basis, allowing Cook to work remotely and focus on the company's future.

	Annette Cook