Episode 30

With Tra WIlliams

When Tra Williams first set foot in Florida, he never imagined he would one day lead the state’s largest network of commercial driver-training schools. Fresh off selling his mechanical-contracting business in Connecticut, Williams acquired a single CDL academy in Winter Haven in 2020. He wasn’t impressed by what he found—but he was captivated by its potential.

Within weeks, Williams told his new instructors, “I bought this company for what it could be, not what it was.” His vision caught fire against the backdrop of a nationwide driver shortage. As two-year truckers began commanding six-figure salaries, Williams forged a partnership with the State College of Florida, earning the governor’s backing to replicate his model statewide. By mid-2024, Fleet Force had grown to ten campuses—from Fort Lauderdale to Panama City—and trained over 3,000 drivers that year alone.

Williams attributes his rapid growth to an unshakeable culture of gratitude and accountability. He insists that every team member, whether in Orlando or Pensacola, embody “joyful words in a thankful heart” and “collective trust through individual reliability.” On day one, he laid down a simple rule: you’re either “in or out” of the company’s values. This clarity allowed him to build a cohesive workforce spread across 500 miles—where instructors know their students by name and show up at 7 AM without fail.

Despite never holding a CDL himself, Williams leads through servant leadership. He recalls a performance review where his mentor reminded him, “Not everybody thinks the way you do—invite input.” Today, he practices that lesson by empowering veteran operators to manage their campuses, rarely losing sleep over whether they’ll rise to the challenge. He believes intuition, honed by years of running businesses, guides his decisions as much as spreadsheets and metrics.

Work-life balance for Williams isn’t a trade-off but a harmony: morning workouts, a quiet cup of coffee, and time for family and faith fuel his productivity at the office. “If there’s a fire,” he admits, “my routine goes out the window—but on most days, that time is sacred.”

Not content to stop at driver training, Williams is already piloting a tech startup called ParkPro. Described as “Airbnb meets Uber for truck parking,” the platform connects truckers—who are legally required to rest but often find no space—with vacant lots nationwide. With one parking spot available for every eleven trucks, ParkPro could unlock America’s vast, underused parking landscape.

Looking back, Williams marvels at how a childhood spent selling roadside produce and ceramics instilled in him an entrepreneurial instinct he once took for granted. Today, his story offers a roadmap for aspiring founders: define your values, invest in culture, trust your gut, and—above all—bet on what could be, not just what is.

When Tra Williams first set foot in Florida, he never imagined he would one day lead the state’s largest network of commercial driver-training schools. Fresh off selling his mechanical-contracting business in Connecticut, Williams acquired a single CDL academy in Winter Haven in 2020. He wasn’t impressed by what he found—but he was captivated by its potential.

Within weeks, Williams told his new instructors, “I bought this company for what it could be, not what it was.” His vision caught fire against the backdrop of a nationwide driver shortage. As two-year truckers began commanding six-figure salaries, Williams forged a partnership with the State College of Florida, earning the governor’s backing to replicate his model statewide. By mid-2024, Fleet Force had grown to ten campuses—from Fort Lauderdale to Panama City—and trained over 3,000 drivers that year alone.

Williams attributes his rapid growth to an unshakeable culture of gratitude and accountability. He insists that every team member, whether in Orlando or Pensacola, embody “joyful words in a thankful heart” and “collective trust through individual reliability.” On day one, he laid down a simple rule: you’re either “in or out” of the company’s values. This clarity allowed him to build a cohesive workforce spread across 500 miles—where instructors know their students by name and show up at 7 AM without fail.

Despite never holding a CDL himself, Williams leads through servant leadership. He recalls a performance review where his mentor reminded him, “Not everybody thinks the way you do—invite input.” Today, he practices that lesson by empowering veteran operators to manage their campuses, rarely losing sleep over whether they’ll rise to the challenge. He believes intuition, honed by years of running businesses, guides his decisions as much as spreadsheets and metrics.

Work-life balance for Williams isn’t a trade-off but a harmony: morning workouts, a quiet cup of coffee, and time for family and faith fuel his productivity at the office. “If there’s a fire,” he admits, “my routine goes out the window—but on most days, that time is sacred.”

Not content to stop at driver training, Williams is already piloting a tech startup called ParkPro. Described as “Airbnb meets Uber for truck parking,” the platform connects truckers—who are legally required to rest but often find no space—with vacant lots nationwide. With one parking spot available for every eleven trucks, ParkPro could unlock America’s vast, underused parking landscape.

Looking back, Williams marvels at how a childhood spent selling roadside produce and ceramics instilled in him an entrepreneurial instinct he once took for granted. Today, his story offers a roadmap for aspiring founders: define your values, invest in culture, trust your gut, and—above all—bet on what could be, not just what is.

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