Over the course of his career he has opened a number of companies. The first company he started was while he was still in college. It was McKenna Venture Investments and it was based in New Orleans. He says that he came up with the money to start this company by doing medical exams on prisoners. This business, though, had most of the properties it owned when Hurricane Katrina turned New Orleans into a lake. He tried to recover by fixing up properties and selling them to people with low to moderate incomes. He decided to quit the industry, though, when mortgages were being issued to people with little to no income and not having to put any money down on the house they were buying.