In the early ‘90s, a baseball strike interrupted the O’Brien brothers’ concessions business, Observ Inc. In the late ‘90s, another strike loomed. “We said we should diversify and look at different businesses,” Bill O’Brien said. “We thought the hair business was the right business for us.”
In 2001, brothers Bill, Paul and Rob O’Brien opened the first Floyd’s 99 Barbershop. The brand has since grown to 133 salons in 15 states, 56 of which are franchised. The brothers wanted to create a space for customers to get their hair cut and styled that didn’t cost an arm and a leg and was a bit nicer than the run-of-the-mill barbershop.