Groupon co-founder Eric Lefkofsky got his start in business with a failed scheme to create and market a mascot to the University of Michigan:

Then in the late 1980s a group of University of Michigan students, Adam Blumenkranz, Eric Lefkofsky and David Kaufman, attempted to create a mascot on the university's behalf, a lovable creature known as Willy the Wolverine.
Willy was the result of six rounds of market research, Blumenkranz told the Michigan Daily at the time. What resulted was a friendly-looking mix of a bear and a wolf who wore a Block M sweater.
Administrators had little interest in a mascot, Fielding Yost's live-wolverine experiment be damned. Then-athletic director Jack Weidenbach refused to take meetings with pro-Willy students and told the Michigan Daily that U-M wasn't interested, period.
Undeterred, the entrepreneurs obtained trademarks for Willy the Wolverine and started selling paraphernalia with the mascot's likeness.
Expanding the Michigan tradition wasn't the students' only motivation: they were in it for the money, which is why they invested in the trademark and in market research. Their plan was to sell merchandise in the short-term, building a fanbase for Willy before selling him to the University to serve as the official, on-the-field mascot.
Willy didn't take long to rise to an impressive stature on campus. Blumenkranz and company arranged it so that Willy served as the grand marshal of the 1989 homecoming parade in Bo Schembechler's last as head coach. The 1990 Campus Directory was released under Willy's name, and the mascot posed on the front cover alongside the cheerleading squad.
"Don't be silly, work with Willy" read classified ads that appeared in the Michigan Daily, seeking student account executives.

Luckily, the thing was too cheeseball to ever take off. But Groupon seems to be doing fine.