Stay in the know. Subscribe to Currents

3 Keys to Being Your Own Boss: Brand-Building, Work Ethic, Relationships

3 Mins read

As a former owner of 33 Orangetheory Fitness (OTF) gyms, I had the unique perspective of looking at our operations from a larger global sense as well as the individual gym challenges.

As the brand grew, so did the boutique fitness concept and the competition. OTF corporate did an excellent job of changing and developing the type of workouts in addition to the brand, keeping it interesting for clients. At the local level, our job was to follow the directions of corporate but also to enhance the client experience by creating a fun and compelling culture. We wanted to ensure that friendships and values were made to help retain clients.

COVID created a different set of challenges for the entire fitness industry, and many of the larger gym models did not survive. Again, OTF adapted, utilizing mask and non-mask classes with fewer members per class. We added air-cleansing equipment and spaced the classes so a heavy-duty cleansing could occur. As COVID began to decline, we focused heavily on the marketing of the product and assured clients it was safe to return to the gym.

I’ve built 14 companies, sold eight, and still have four in operation. I often consider myself one of the luckiest country boys on the planet. While “luck” always is a factor, I have truly found that the longer and harder I work, the luckier I get. Work/life balance is difficult at this stage in your life. Working 12-plus hours a day can certainly cause trauma and drama at home, so I learned to work around my schedule. I never missed Friday night dinner at home with the family and date night with my wife on Saturday night.

With my children, I chose to participate in their activities. In the case of my boys, I coached 17 seasons of some sort of young kid’s sports. I was always at the weekly practices and the games, followed by a meal and a hug, and then back to work. With my daughter, it was all about attending her events, such as singing, dance classes, and theater (plays). Then there was a meal—sometimes—but always a hug and then back to work. There is certainly a sacrifice in all this, but the reward of being successful and ensuring my family’s financial future made it all worthwhile.

One final factor ensuring my entrepreneurial journey was a success was relationships. Your entire future as “your own boss” is highly contingent upon the relationships you create along the way. Whether it be with partners, investors, vendors, bankers, employees, or even your competition, relationships will be one key factor defining your success. Yes, you are your own boss, but you will never achieve that final level of prosperity without these key relationships that will help you down various paths and with choices you will need to make to achieve your financial dream.

As I move forward into my next business chapter with three operating businesses and one public board seat, I have chosen a different path for my next “home run” in the pet space—specifically dogs. Factually, people spend more money on their pets than themselves. A new franchise emerged called Scenthound, which specializes in dog health, care, and grooming.

One of the biggest lessons I’ve learned in the franchise world is not to just buy a franchise; instead, buy a territory with multiple locations. In the case of Scenthound, I met with them at their corporate headquarters and was blown away by the infrastructure and support. They were definitely “the goods.” This led to a territorial discussion that allowed me the opportunity to secure three territories and an option on two more for a total of potentially 25 locations. And so, after a brief rest following the Orangetheory Fitness exit, we are off and running again.

James Harold Webb (, author of Redneck Resilience: A Country Boy’s Journey To Prosperity, is an investor, philanthropist, and successful multi-business owner. Webb began his entrepreneurial journey in the health industry as the owner of several companies focused on outpatient medical imaging, pain management, and laboratory services. Following successful exits from those companies, Webb shifted his focus to the franchise world and developed, owned, and oversaw the management of 33 Orangetheory Fitness® gyms, which he sold in 2019. He is now a franchise partner with Scenthound, a dog wellness company.

Related posts

17 Digital Marketing Budget Allocation Tips for Small Businesses

9 Mins read
Navigating the complexities of digital marketing can be daunting for small businesses, especially when it comes to budget allocation. To offer guidance,…

Shift the Tide: High-Performance Habits for Small Business Mastery

6 Mins read
The best version of your business is just a routine change away. Sounds simple, right? But altering those routines could be the…

Three Regulatory Issues Business Owners Should Be Watching

4 Mins read
Whether it be AI and data privacy, wage and hour laws, mandated retirement programs, or any number of other federal, state, and…