Michael started his first company, Roberts-Roberts & Associates in 1974 with his brother, Steve, as a business consulting and construction management firm. Roberts Companies now consist of television broadcasting properties, real estate development entities, a restaurant chain and interest in Acme Communication (TV stations). In 2000, the brothers sold their Roberts Wireless Communications Company for more than $280 million worth of stock in Alamosa PCS Holdings, Inc. A Sprint PCS service reseller for most of Missouri. Roberts' company was Sprint's first black-owned affiliate. Roberts has owned over 25 companies with revenue over $10 million excluding the telecom operations.