Money / Mark Cuban Success Stories: What They Did in Their 20s Mark Cuban, Howard Schultz, Tim Allen, and others By Ruth Brown, Newser Staff Posted Mar 30, 2013 2:46 PM CDT Copied In this May 26, 2009 file photo, Mark Cuban, center, walks out of his federal hearing accompanied by members of his legal team at the Earle Cabell Federal Courthouse in Dallas. (AP Photo/Tony Gutierrez, file) Did all successful people spend their 20s studying, scrimping, and struggling their way to the American dream? Some, yes—but others were in jail or working retail, as Business Insider reveals in a roundup of what today's success stories were doing in their 20s: Investment shark and Dallas Mavericks owner Mark Cuban was a bartender and then a software retailer, sleeping on the floor of a three-bedroom apartment with six other people. Getting fired inspired him to start his first business. Starbucks CEO Howard Schultz was a salesperson at Xerox, yet to enter the coffee industry. "I learned more there than in college about the worlds of work and business," he wrote in Pour Your Heart Into It. Comedian Tim Allen was caught at an airport with over 650 grams of cocaine, and spent the next two years in prison. That forced him to make a change: "When I went to jail, reality hit so hard that it took my breath away," he said. Domestic guru Martha Stewart was a stockbroker on Wall Street. "I never considered myself an unequal and I think I got a very good education being a stockbroker," she said. For more examples, click here. (More Mark Cuban stories.) Report an error