Cheston Syma has spent more than 20 years building his Sport Clips Haircuts franchise, starting with two locations in 2004. The founder and CEO of Wheelhouse Partners now operates stores in Texas, Oklahoma, Illinois, Utah and Wisconsin. In 2026, he received the Logan Trophy, Sport Clips’ highest franchisee honor, named for founder Gordon Logan. The International Franchise Association also recognized him as a 2026 Franchisee of the Year.
Syma joined the Marines out of high school and spent six years on active duty. He served in the infantry, where he became a platoon sergeant and a primary marksmanship instructor for his unit. He was then accepted into the Marine Security Guard program and guarded U.S. embassies in cities including London and Port-au-Prince. After the Corps, he earned a business finance degree from the University of Houston. Not long after buying his first two Sport Clips stores, he went back overseas as a State Department and CIA security contractor in Iraq and Afghanistan.
The experience that shaped Syma's approach to business most was learning to lead people under pressure. He sees a direct connection between the Marines and managing a franchise workforce, even if the consequences are different.
“In a war zone, it is paramount to know your Marines, and now as a franchise, the same goes for my employees. In a war zone, it is a matter of life or death. The stakes are not the same now, but the skills still translate,” Syma said in an earlier interview with 1851 Franchise.
Syma now oversees more than 400 employees across his businesses. His expectations for the managers at Wheelhouse come from the leaders he encountered in the Marines, both good and bad.
“I expect my leaders to always lead from the front, which means leading by example. Do not ask others to do what you are not willing to do yourself. To this day, I will clean toilets and the floor around the toilet to show I am also there to serve the customers, not myself,” Syma told Franchising.com.
Syma thinks franchise owners spend too much time teaching managers how to run a business and not enough time teaching them how to lead people. He and his senior team hold leadership classes for the managers running his stores. His approach is to “train the trainer, trust but verify.” District managers control their schedules and are accountable for results, while every employee has the personal cell numbers of the leadership team, including Syma.
Maintaining those relationships has become more challenging as the business has grown. When he operated fewer stores, Syma knew every employee by name. With more than 400 people now, he works most closely with his district managers and a handful of team members, relying on weekly calls and regular store visits to stay connected to the broader workforce.
Syma spent years managing his first two Sport Clips locations from Baghdad and Kabul, relying on the managers back home to run the stores. That experience mirrors the brand's manager-led model. Sport Clips franchisees, known as Team Leaders, hire store managers to oversee daily operations while focusing on coaching those managers and building their teams.
“Veterans have done that job before, usually under a lot more pressure. Cheston is what it looks like when someone brings that training into our system,” said Brent Greenwood, vice president of development for Sport Clips and a United States Air Force Veteran himself.
The brand says veterans account for more than 15% of its system. Qualified veterans receive a 20% discount on the initial franchise fee. The commitment goes back to the brand’s beginning. Founder Gordon Logan is an Air Force veteran, and bringing veterans into ownership has been part of Sport Clips since he started it.
While Sport Clips offers incentives to help veterans enter franchising, Syma cautions that owning a business still requires a significant commitment. The first few years can mean long hours, and he believes veterans need to bring the same discipline to franchise ownership that they developed in the military. If they aren't willing to do that, he says, a corporate job may be a better fit. He also encourages veterans to stick with the franchise's playbook rather than try to reinvent the business.
“Following a system. Franchises are proven, and if you follow the model, your success rate will be much higher. Just like in the Marines, you cannot try to go rogue and reinvent the wheel,” Syma told 1851 Franchise.
Over 22 years, Syma has grown from two stores in Katy, Texas, to more than 40 locations across five states. His responsibilities have changed considerably since he managed stores from overseas, but he still follows the leadership principles he learned in the Marines, including leading by example and trusting the people he's trained.
Ready to start your franchise ownership journey? Join us on Dec. 1, 2026, at 9:30 a.m. CT. Sign up for the webinar here.
To find out more information on costs to buy this franchise, please visit https://1851franchise.com/sport-clips.
Sport Clips
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Marine veteran Cheston Syma opened his first two Sport Clips locations in 2004. In 2026, he won the brand’s Logan Trophy and was named an IFA Franchisee of the Year.
Cheston Syma has spent more than 20 years building his Sport Clips Haircuts franchise, starting with two locations in 2004. The founder and CEO of Wheelhouse Partners now operates stores in Texas, Oklahoma, Illinois, Utah and Wisconsin. In 2026, he received the Logan Trophy, Sport Clips’ highest franchisee honor, named for founder Gordon Logan. The International Franchise Association also recognized him as a 2026 Franchisee of the Year.
Syma joined the Marines out of high school and spent six years on active duty. He served in the infantry, where he became a platoon sergeant and a primary marksmanship instructor for his unit. He was then accepted into the Marine Security Guard program and guarded U.S. embassies in cities including London and Port-au-Prince. After the Corps, he earned a business finance degree from the University of Houston. Not long after buying his first two Sport Clips stores, he went back overseas as a State Department and CIA security contractor in Iraq and Afghanistan.
The experience that shaped Syma's approach to business most was learning to lead people under pressure. He sees a direct connection between the Marines and managing a franchise workforce, even if the consequences are different.
“In a war zone, it is paramount to know your Marines, and now as a franchise, the same goes for my employees. In a war zone, it is a matter of life or death. The stakes are not the same now, but the skills still translate,” Syma said in an earlier interview with 1851 Franchise.
Syma now oversees more than 400 employees across his businesses. His expectations for the managers at Wheelhouse come from the leaders he encountered in the Marines, both good and bad.
“I expect my leaders to always lead from the front, which means leading by example. Do not ask others to do what you are not willing to do yourself. To this day, I will clean toilets and the floor around the toilet to show I am also there to serve the customers, not myself,” Syma told Franchising.com.
Syma thinks franchise owners spend too much time teaching managers how to run a business and not enough time teaching them how to lead people. He and his senior team hold leadership classes for the managers running his stores. His approach is to “train the trainer, trust but verify.” District managers control their schedules and are accountable for results, while every employee has the personal cell numbers of the leadership team, including Syma.
Maintaining those relationships has become more challenging as the business has grown. When he operated fewer stores, Syma knew every employee by name. With more than 400 people now, he works most closely with his district managers and a handful of team members, relying on weekly calls and regular store visits to stay connected to the broader workforce.
Syma spent years managing his first two Sport Clips locations from Baghdad and Kabul, relying on the managers back home to run the stores. That experience mirrors the brand's manager-led model. Sport Clips franchisees, known as Team Leaders, hire store managers to oversee daily operations while focusing on coaching those managers and building their teams.
“Veterans have done that job before, usually under a lot more pressure. Cheston is what it looks like when someone brings that training into our system,” said Brent Greenwood, vice president of development for Sport Clips and a United States Air Force Veteran himself.
The brand says veterans account for more than 15% of its system. Qualified veterans receive a 20% discount on the initial franchise fee. The commitment goes back to the brand’s beginning. Founder Gordon Logan is an Air Force veteran, and bringing veterans into ownership has been part of Sport Clips since he started it.
While Sport Clips offers incentives to help veterans enter franchising, Syma cautions that owning a business still requires a significant commitment. The first few years can mean long hours, and he believes veterans need to bring the same discipline to franchise ownership that they developed in the military. If they aren't willing to do that, he says, a corporate job may be a better fit. He also encourages veterans to stick with the franchise's playbook rather than try to reinvent the business.
“Following a system. Franchises are proven, and if you follow the model, your success rate will be much higher. Just like in the Marines, you cannot try to go rogue and reinvent the wheel,” Syma told 1851 Franchise.
Over 22 years, Syma has grown from two stores in Katy, Texas, to more than 40 locations across five states. His responsibilities have changed considerably since he managed stores from overseas, but he still follows the leadership principles he learned in the Marines, including leading by example and trusting the people he's trained.
Ready to start your franchise ownership journey? Join us on Dec. 1, 2026, at 9:30 a.m. CT. Sign up for the webinar here.
To find out more information on costs to buy this franchise, please visit https://1851franchise.com/sport-clips.
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