When he first started boating, he did not see African-Americans captaining boats on the Chesapeake. However, he and his brothers were very skilled boaters and Wooley could drive a boat before he had a car driving license.
An IT professional by trade, Wooley knew from an early age that you needed to make a certain amount of money to afford the lifestyle of sustaining and owning a boat. The first boat he ever bought was a fifty-fifty investment with his father.
This boat, purchased from a dentist, was appropriately named The Tooth Fairy. I saw a couple black boat ownersβpleasure boat ownersβbut not maintaining a living as an entrepreneur that worked five to seven days a week on the water.
It was not until I became older that I understood there were black watermen on the Chesapeake Bay, a place where I fished all my life. However, now Wooley has found himself as one of those entrepreneurs on the Chesapeake Bay. Transitioning out of IT, he started a business in the late s, working as an independent maritime consultant.
Wooley also joined Airbnb and advertised his boat as a two-bedroom, one-bathroom floating condo, and began accepting clients, just to test the waters. He sees himself as a 21st century watermen. Learn more about the history of African-Americans on the Chesapeake Bay. Time to share! Please leave comments that are respectful and constructive.
