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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.”

How the Fort Collins Pig & The Plow Farmstead Bakery Became a Post-COVID Success Story

You may have read the popular Farming Fort Collins Blog turned online farm and ranch directory, turned e-zine, The Pig & The Plow: From the Field, but have you stopped by the Pig & Plow Farmstead Bakery and met the woman behind it all?  

Erica Glaze has been busy. After growing up in the fresh, local food scene of New England, she saw a need when she moved to this area back in 2003. “I worked for the Federal government for 3 years and the State for 10 years, but I’m not a good office person, I was ready for a change.” Her desire to connect people to good, local food was the catalyst behind the Farming Fort Collins Blog. The blog turned into an online farm and ranch directory in 2014, then the e-zine evolved to explore the local food scene more. In 2017 she bought her first oven and launched The Pig & The Plow Bakery out of a converted shipping container on her Farmstead.  

Erica connected with the Small Business Development Center through word of mouth and a mutual connection to an SBDC Consultant. “I took a start-up class and continued to move forward to figure out what was needed to take each next step.” She utilized the resources from the beginning and found a network of mentors. “I’m not afraid to raise my hand and ask for help. There are things you’re good at and things that don’t come naturally. With mentors it wasn’t just me, I had a huge network.”

READ — Modern Day Mentorship

The business consistently outgrew space after space. COVID could have devastated the business, but luckily Erica set it up right. “When COVID hit we had to stop our NOCO Meat Collective classes, the restaurants we supplied closed, and the Farmer’s Markets were halted. Luckily, we were already online and had a following. Within 24 hours we added other market partners to our website and continued selling.” COVID didn’t stop them from thinking about the future. In June of 2021, after outgrowing yet another space, they moved into the Colorado Feed & Grain in Timnath.  

The opportunity to move into their newest location at 140 Boardwalk Dr. in Fort Collins presented itself earlier this year and within two months was a done deal. The space was formerly a bakery but also includes a great area for retail. “My husband was always really supportive and handy. He bought me that first oven and built the shipping container. When we decided to move to our new location we knew he needed to be more involved, so he officially became part owner.” It only took three days to move and set up the shop. They opened on November 15th. 

The unique thing about the business is the attention to how they do things. “We’re not the only bakery in town, but we use local, organic ingredients to create a new twist on old classics.” One of Erica and her staff’s favorite parts of the business is exploring and blending food and culture to bring something new into the fold. No day is the same when you get to experiment and create.

READ — Rising Food Costs Create Unique Challenges for Hunger-Focused Agencies 

The future for The Pig & The Plow Bakery looks bright. She’s focusing on continuing to develop the community around the business. She loves building opportunities for collaboration and creating a place for people to come and grow. One thing she looks forward to is continuing to be a part of people’s special things, whether it’s baking goods for an occasion or as a treat. “We had a woman at the farmer’s market who saw our Danish bread and cried. She was homesick and so happy to see and experience something familiar.”  

Her advice for budding entrepreneurs is this: “Don’t waste your time figuring it all out on your own. Learn from other people’s mistakes. Find the experts and be open to expanding your network.” She also advises connecting with people in your industry, and not seeing them as just competition. “There’s room for everyone, the more we connect and help each other’s growth, it’s an awesome experience.”

She’s most proud of the business she built that continues to move forward. From a converted shipping container to having a great new space with the right equipment and a great team (The Pig & The Plow Bakery employs 1 full-time employee and 2 seasonal contractors), not to mention the people they’ve connected with along the way.

Since 1989, the Larimer Small Business Development Center Network (SBDC) has been dedicated to helping entrepreneurs and businesses start, grow and prosper through street-smart business education and assistance throughout Larimer County. 

We support the growth and resiliency of small businesses by providing free confidential business consulting, practical workshops & events, and connection to resources. Our consulting experts work in partnership to provide entrepreneurs with crucial information that can mean the difference between success and failure. Our vision is to be your premier, trusted choice for business consulting, training, and resources.