Former NFL running back and University of Iowa Hawkeye Trevor Bowlers joins host Kaylee Williams to share his journey from immigrant kid in Guyana to professional athlete to founder and CEO of Letter B Global Technologies.
Trevor talks about the “impossible” moments that shaped him—from his father’s leap of faith moving their family to Canada, to grinding four years on the bench before finally starting for the Hawkeyes and earning a shot in the NFL. He connects those experiences to entrepreneurship, emphasizing belief in yourself, relentless preparation, and surviving in a world where someone is always being groomed to take your spot—just like in pro sports.
Bolgers transitioned from a Division I running back at the University of Iowa and NFL player for the Jacksonville Jaguars into a tech entrepreneur. Born in Guyana and raised in Alberta, Canada, Bolgers launched Letter B in 2008 during the financial crisis. Today, his 17-person team specializes in “cultural design,” building custom software and operating systems for manufacturing and business clients whose operational needs extend beyond standard off-the-shelf software.
Building Solutions Around Customer Culture
Letter B’s platform drives critical infrastructure, including an auto parts quoting engine that processes over two to three million quotes daily. Highlighting the mindset required to shift from professional athletics to enterprise software development, Bolgers stated, “I’m gonna say the first thing you need to understand is belief in yourself.” This human-centered focus shapes their hands-on internship program with local universities, giving young developers direct experience writing live production code rather than throwaway projects.
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Pivoting to Event Planning with Illuminate
Drawing from his work with youth sports organization Mid-America 7v7, Bolgers recently launched Illuminate (iPlan), a specialized event-planning platform featuring customizable project boards, internal budget tracking, and an AI form builder. Currently serving four paying clients, the platform cleans up fragmented spreadsheets and event logistics. Reflecting on the discipline required to pause development and build a formal go-to-market plan, Bolgers remarked, “I’ll have to say, we’re really excited because we’ve actually like been through this a few times now to know that we actually need to pause and develop the strategy.” When offering counsel to early-stage entrepreneurs, he offered straightforward advice: “If there’s something that you’re trying to figure out if you can do it or not, go do it.”