— My father was a professional gambler. I’m an entrepreneur. However, the biggest risk taken by my family came from my wife Karen, a Catholic school principal who grew up on a dairy farm.
She didn’t win the lottery, but she won a professional jackpot. Starting in July, she will be president of the Ursuline Academy in New Orleans, one of the most prestigious private schools in the country.
Founded in 1727, the Ursuline Academy is the oldest Catholic School and also the oldest all-girls school in the United States. It has incredibly impressive alumni, with several nationally and internationally famous graduates.
Karen wasn’t looking for a new job. When the headhunters first called, her reaction wasn’t positive. We were just married in June, she loved her current job, never lived outside Kentucky and was finishing her doctorate.
Her biggest concern was me. My structured settlement business operates nationally and my writing internationally, thanks to my syndicated column and Huffington Post contributions, but I am as deeply rooted in the legal, business and media communities in Kentucky as anyone can be.
A fear was that moving from Kentucky would damage my career. I love New Orleans and have been there many times, but have few clients in the area.
I happen to love Louisiana history. My high school civics teacher, Dick Maile, was an All-American basketball player at LSU and started me on a fascination that continues 40 years later. My friend and former New York Times reporter Gary Rivlin (who wrote a must-read book about payday lending called Broke USA) is writing a book about post-Katrina New Orleans and told me I would love living there.
Being the son of a gambler and an entrepreneur taught me one thing: the biggest risk in life is not taking one.