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Floyd’s 99 Barbershop: From Sports Concessions to Clippers — the Story of the O’Brien Brothers’ Successful Pivot

When Paul, Rob and Bill O’Brien opened the first Floyd’s 99 Barbershop in Denver in 2001, none of the brothers had ever cut anyone’s hair, much less tried to do a shave with a straight razor. They were just looking for a new business plan that was not dependent on professional sports. 

The siblings owned Observ Inc., short for O’Brien Services, a concessions company that is a subcontractor in sports stadiums, most notably Coors Field. “There was a baseball strike in 1994,” says Floyd’s co-founder Bill O’Brien, who works on finances and store design. “In 1999 they were threatening to have another strike. We looked to diversify to something else.”

They evaluated several options, and decided they would do well in the hair business. The idea, Bill says, was to start a mid-priced barbershop that appealed to men who wanted more service than the bargain-priced chains like Great Clips and Fantastic Sams, but who did not want to spend the money or time for an upscale salon experience. Floyd’s 99 Barbershop is the mid-priced option that offers a complimentary shoulder massage after each service and a music-filled “amplified environment” with rock ‘n’ roll-themed décor.

Floyd’s 99 Barbershop

The brothers started Floyd’s in 1999 but did not open the first location, on 11th and Broadway, until 2001. “We found it hard to get landlords to get what our concept was,” Bill says. “They would say, ‘Oh, a barbershop.’ Old-school barbers were dying off.” 

Nostalgia played a role in the company name. That inspiration, as many might suspect, was the fictional character Floyd the Barber on the 1960s television sitcom “The Andy Griffith Show.” There already were about a dozen Floyd’s Barbershops in towns across the country, which Bill says were owned by various men named Floyd, so the new business added “99” to the name to differentiate itself.

The brothers opened the second location on East Colfax Avenue, and the third on Leetsdale Drive. They opened more locations, and began franchising around the fifth year in operation. “We were getting a lot of interest,” says co-founder Paul O’Brien, who works with franchising and real estate. “People were calling us.”

Anne O’Brien, one of their sisters, opened a Floyd’s 99 Barbershop in Maryland, where the family of eight siblings grew up. That location stayed open for five years, but then she declined to renew the lease when the rent increased. A franchisee that the brothers knew through friends opened locations in Dallas. “That’s not that uncommon, to open with friends and family at first,” Paul says. A Boulder-based franchisee, Jay Palmer, opened locations in Colorado and Kentucky. Today there are 130 locations in 15 states.

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The pandemic affected the haircutting industry. In the early months of COVID, depending on the area, stores closed and re-opened multiple times. When stores re-opened, safety protocols limited how many customers could be served at a time. “We had to get through that,” Paul says. “We did get PPP [Paycheck Protection Program funds], which helped us a lot.”

READ: How small businesses can prepare for success in a post-pandemic world

Today 70 percent of Floyd’s 99 Barbershops are corporate-owned. Paul says that percentage will decrease as more franchisees join the system. The brand is looking for multi-unit owners who live in the territories where they want to open barbershops. “It’s so important for the stylists and barbers to have a connection to who they work for,” Paul says. The clientele is still mostly men, and the most popular service is a haircut and a shave with a straight razor.

There are approximately 1,200 corporate employees. For corporate and for franchise locations, the challenge now is hiring and retaining talent. Barbers and stylists left the industry or went out on their own during the pandemic, or tried the hairstyling version of entrepreneurship, which is to rent a chair or a booth in a salon. The good news, Paul says, is barber and hairstyling schools are full, so new graduates should be available in the next year or so.

To attract new and experienced hairstylists and barbers, Floyd’s 99 Barbershop offers medical insurance and a prescription drug plan that includes insulin. Diabetes is a cause that the company does much fundraising for, and its charity of choice is the Juvenile Diabetes Research Foundation (JDRF). Paul’s daughter was diagnosed with Type 1 diabetes more than 10 years ago.

Floyd’s 99 Barbershop

Neighborhoods change, and several of the locations have closed and relocated. The Colfax store is now located farther east, and a large Floyd’s on Champa Street on the 16th Street Mall relocated to a spot near Union Station. Floyd’s corporate office is in Greenwood Village.

Running a business is not new to the O’Brien family. Their mother owned a successful insurance company in Maryland. Rob, who works on company culture and operations, and Paul are still involved in Observ. All three brothers are still involved in Floyd’s. The three agree on about 95 percent of business decisions ranging from price changes to locations.

“It was a lot of sweat and tears to get to where we are,” Bill says. “We talk to each other at least every other day, or every day, which has been great.”