When Bill, Rob and Paul O’Brien opened the doors of the first Floyd’s 99 Barbershop in Denver in 2001, they did it with no background in hair, and no guarantee their gamble would work out.
After building a successful sports concessions company from their base in the Colorado Rockies, the brothers wanted to move away from depending on other people’s stadiums and schedules, but quickly ruled out restaurants and bars. Then Rob called Bill with an idea – what about a barbershop?
“We wanted something that we felt like we owned, that we could control the destiny,” Rob said.
Bill thought it was crazy, but after going to a few franchise conferences and hair brand presentations, he saw there was room for something new.
Building a Brand
The first Floyd’s was in an empty Denver building beside one of the city’s hottest nightclubs. The idea for the shop still existed more in the brothers’ heads than on paper, but they knew this was the right location. With foot traffic and big windows that exposed the energy inside, it gave them visibility.
Needing a hook that pulled clients in, the new shop took inspiration from live music, with Bill coming up with an idea to plaster the walls with a collage of music posters. Soon the shop was full of images of Elvis, the Beatles and other contemporary artists that connected hair trends with music culture.
That promise of “old school new style” was baked into every decision. After opening the doors, the O’Brien boys added touches that felt both nostalgic and fresh, like a hot-lather neck shave that soon became a defining ritual for clients.
Floyd’s occupied the space between high-end salons and budget chains, offering expert cuts, value and an efficient experience that still felt indulgent. Crucially, it was “for everyone”: men, women, kids, long hair, fades, colour and texture. That let stylists fill the shop with kids, grandparents and clients of every age – exactly the generational mix the founders wanted.
“The most important thing is the person in the chair right that minute. Give them your 100 percent. That is how you grow the business,” said Bill.
It worked. Within nine months of opening, the brothers had another three Denver shops in operation. Cut to 2026, and Floyd’s 99 Barbershop has 144 locations across 19 states. The success of the brand is testament to the brothers’ guiding philosophy that a vibrant culture and workplace are just as important as great haircuts.
“We thought if we could create a place where people really like to work, our staff would become our clients, and then they would take care of the clients in the chair,” Bill said.
People First, Always
Floyd’s most powerful chapter is not national expansion or celebrity clients. It’s the people in the shops and the lives built around the brand.
The O’Brien brothers core value is “people first,” backed by concrete decisions. From the beginning, for example, they offered health insurance and have also created the Floyd’s Family Care Fund, supported by a percentage of every service and product sold. Employees facing hardship can apply for up to $2,500, more than once if necessary.
“We wanted people to have careers here,” Bill said.
Another cause became central after Paul’s daughter was diagnosed with type one diabetes. The diagnosis gave focus to the brothers’ charitable giving. Since then, Floyd’s has raised more than $2 million for diabetes research.
The Next 25
The brothers are clear about the future of their brand: Floyd’s will remain for everyone, rooted in music and focused on the people in and behind the chair.
“There can be as many Floyd’s as can be great Floyd’s 99 Barbershops,” said Rob. “It’s not how many we open, it is how many cool places we build with cool people.”
For Paul, the future means moving from defence to offence. After COVID and the industry shifts that followed, the focus is education, training and opportunity. “We want to create the best place to be, for our people and our clients,” he said. “That is what will carry us into the next 25 years.”
The Floyd’s story returns to three brothers who sold cotton candy in stadiums and decided to build something of their own. One haircut at a time, they turned a Denver corner shop into a national brand that still feels like a local original.
“Floyd’s means everything to me. It’s who I am. It’s what we do. When I’m awake, that’s what I am thinking about,” said Bill.