Michael Sheppard, the founder and managing partner of IronwoodDrive Financial Group, didn't come from a background in finance. He went to school to become an electrical engineer, and was later signed as an undrafted free agent by the Tampa Bay Buccaneers. However, when football didn't pan out, Sheppard turned his attention to the financial services industry, where he is one of a very small minority of African-Americans in his field.