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Alan Henderson is in the Rotation
Alan Henderson is a 24-year-old entrepreneur, lifelong Hillsborough County resident, and candidate for Mayor of Tampa. Born in Tampa and a graduate of Brandon High School, Alan has spent his life growing up with the same challenges and opportunities that shape many of the people he now hopes to serve.
He’s not a career politician — he’s someone who’s built things from the ground up.
As the founder of multiple award-winning companies, including Dilemma Esports & Entertainment and The Dilemma Exhibit, Alan has generated over 23 million impressions across his platforms, helped create jobs in the city, and led marketing campaigns that brought in over 7 figures of ARR on behalf of local and national clients.
Now, he’s applying that same energy and focus to public service.
Alan is currently pursuing 10 professional certificates from Harvard University's Kennedy School of government, covering topics like U.S. Public Policy, Social Policy, Contract Law, and the Foundations of the American Constitution. His education is rooted in a desire to deeply understand how systems work — and how to make them work better for real people.
He’s been invited to serve on boards like the Forbes Communications Council, the National Small Business Association, and his local credit union — not just because of titles, but because of how he shows up: with ideas, urgency, and respect for the responsibility of leadership.
Alan has been recognized as one of Tampa Bay’s 25 Under 25, named Most Influential CEO by CEO Monthly, and nominated for the Titan 100, which honors the region’s top executives.
His campaign isn’t just about politics — it’s about people.
Alan is running for mayor because he believes Tampa deserves a city that listens, that builds boldly, and that finally delivers on the promises made to its residents. He’s walked through personal loss, financial struggle, and rapid growth — and through it all, he’s learned how to lead with humility, resilience, and vision.
He’s not just asking for a title. He’s asking for a chance to prove that leadership can look different — and that it can come from someone who never stopped believing in this city.
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By Suncoast NORMLAlan Henderson is a 24-year-old entrepreneur, lifelong Hillsborough County resident, and candidate for Mayor of Tampa. Born in Tampa and a graduate of Brandon High School, Alan has spent his life growing up with the same challenges and opportunities that shape many of the people he now hopes to serve.
He’s not a career politician — he’s someone who’s built things from the ground up.
As the founder of multiple award-winning companies, including Dilemma Esports & Entertainment and The Dilemma Exhibit, Alan has generated over 23 million impressions across his platforms, helped create jobs in the city, and led marketing campaigns that brought in over 7 figures of ARR on behalf of local and national clients.
Now, he’s applying that same energy and focus to public service.
Alan is currently pursuing 10 professional certificates from Harvard University's Kennedy School of government, covering topics like U.S. Public Policy, Social Policy, Contract Law, and the Foundations of the American Constitution. His education is rooted in a desire to deeply understand how systems work — and how to make them work better for real people.
He’s been invited to serve on boards like the Forbes Communications Council, the National Small Business Association, and his local credit union — not just because of titles, but because of how he shows up: with ideas, urgency, and respect for the responsibility of leadership.
Alan has been recognized as one of Tampa Bay’s 25 Under 25, named Most Influential CEO by CEO Monthly, and nominated for the Titan 100, which honors the region’s top executives.
His campaign isn’t just about politics — it’s about people.
Alan is running for mayor because he believes Tampa deserves a city that listens, that builds boldly, and that finally delivers on the promises made to its residents. He’s walked through personal loss, financial struggle, and rapid growth — and through it all, he’s learned how to lead with humility, resilience, and vision.
He’s not just asking for a title. He’s asking for a chance to prove that leadership can look different — and that it can come from someone who never stopped believing in this city.