When Barry Shevlin launched FlyUSA in early 2020, he wasn’t chasing headlines or a billion-dollar valuation. He was testing a theory. The longtime tech entrepreneur and pilot believed there was a better way to connect flyers with aircraft within an industry long overdue for modernization. Fast-forward five years, and FlyUSA has become one of the nation’s fastest-growing private aviation companies, landing at No. 45 on the 2025 Inc. 5000 list and generating upward of $80 million in annual revenue.
Shevlin’s success story is rooted in Tampa Bay, where he grew his previous company, IT services firm Vology, from a $1 million startup in 2002 to a $175 million powerhouse before selling it in 2019. “I’ve spent my entire career growing businesses,” he tells SFBW. “We created great opportunities for employees and families, and that’s fulfilling. FlyUSA has carried that same spirit—just at 30,000 feet.”
What began as a kitchen-table conversation evolved into a technology-enabled aviation firm with more than 2,000 retail clients, 100 employees, and 30 aircraft under management. FlyUSA’s business spans four divisions: on-demand retail charter, aircraft management, maintenance, and its certified air-taxi operations, which allow aircraft owners to charter their planes when not in use. That versatility has positioned the company as a top-to-bottom solution in private aviation.
For Shevlin, the spark came from frustration as much as fascination. As a CEO and pilot, he constantly fielded pitches from fractional-ownership and jet-card providers but found the industry’s sales playbook outdated. “It felt like everyone took the same shotgun approach—nationwide marketing, no personalization,” he says. “We wanted to build something more cost-effective, reliable, and easy to do business with.”
FlyUSA’s approach—responsive, personalized, and easy—became its calling card. What started as $300,000 in 2020 sales ballooned to $4 million the next year, then $10 million, $20 million, $40 million, and now nearly $80 million. Its client base spans Florida and beyond, with heavy traffic between Opa-locka, Palm Beach, and major hubs like Teterboro, N.J., and Tampa.
A key differentiator has been Shevlin’s use of technology. FlyUSA’s proprietary mobile app and digital infrastructure give clients real-time visibility, seamless booking, and control over every flight. “I’ve been shocked by how paper-based this industry still is,” he says. “We’re a technology-enabled business at heart. Everything we build is designed to improve both employee and customer experience.”
FlyUSA’s ambitions aren’t slowing down. By 2027, Shevlin aims to manage 50 aircraft and reach $150 million in revenue. The company also owns Clearwater Airpark (KCLW), giving it full control over maintenance, operations, and customer experience. That vertical integration—paired with a strong safety record and profitability—sets FlyUSA apart from flashier competitors chasing growth at all costs.
The company’s story also has a personal touch. Shevlin co-founded FlyUSA with his son-in-law, William Holtz, now its president and COO. “It’s been great watching him grow as a leader and executive,” Shevlin says. “We started this as a small project together, and it’s evolved into something special.”
Outside the cockpit, Shevlin and his wife, Kathy, are lifelong baseball fans who attend 30 to 40 games a year. The couple, who’ve built their businesses and family life in the Tampa Bay area, see FlyUSA not just as a company but as a community builder—one that connects people and possibilities across the friendly skies.
“The idea was simple,” Shevlin says. “We wanted to make private aviation more approachable, more personal, and more efficient. Everything else—growth, recognition, success—took care of itself.”
