Highest Office Held: US House of Representatives, Maryland

Hindsight being 20/20, it's hard to believe that starting a company that sold pagers in the 1990s was a bad idea. As an ex-NBA star and former Maryland Congressman, Tom McMillen wasn't used to failure. His pager company, McMillen Communications Corp., changed all that.

The company quickly went under and was forced to file for bankruptcy. On the day that they filed Chapter 11, they also attempted to change the name of the company to shield McMillen's future reputation. McMillen had another company, creatively named American Beeper Associates, which went under on the same exact day. The total liabilities between the two companies totaled over half-a-million dollars.