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Alan Henderson on Gen Z leadership, AI‑powered governance, and why a 25‑year‑old esports founder thinks city government should run like a startup.
There is a particular kind of clarity that arrives after loss — the kind that strips away politeness and replaces it with purpose. For Alan Henderson, that clarity came in 2022, three months before his 22nd birthday, when lupus took his mother. What followed was not a retreat into grief but an acceleration into action: navigating hospital bureaucracies, disability attorneys, insurance networks, mortgage payments, and the suffocating realisation that the systems designed to help his family were instead grinding it down.
"I felt powerless against a system that is just way bigger than you," Henderson told me during our conversation on The World's Mayor Experience. That single sentence carries the weight of thousands of Tampa residents who share the same frustration — with housing they cannot afford, transit systems that strand them, and a city government that speaks in jargon rather than solutions.
Henderson is now 25. He is running for mayor of Tampa in 2027, and his platform reads less like a political manifesto and more like a product roadmap for a city that desperately needs a software update. His campaign slogan — "Building the Tampa of Tomorrow Today!" — is backed by a 30+ page policy guide structured around four pillars, each targeting a structural failure that Tampa residents know intimately.
I have spent years exploring what it means to wield power through surrender rather than coercion — the ancient principle that real authority flows not from grasping but from releasing. Henderson's campaign embodies this paradox. He is a young man with no political machine, no Super PAC money, and no inherited influence — and that absence of entanglement is precisely what makes his platform hold together.
This article presents the full scope of that conversation, supplemented by Henderson's published policy documents, biographical records, and independent analysis. It is written for the resident who wants details, the policy student who wants frameworks, and the search engine that wants the truth.
Alan Henderson's public life began at age nine, performing in commercials and promotional material for Disney in Florida. By high school, his attention had shifted to screens of a different kind: he launched a YouTube channel within the GTA 5 roleplay community that attracted nearly 70,000 subscribers in under a year. When the roleplay scene lost its appeal, Henderson pivoted — founding Dilemma Esports, a professional esports organisation that has since grown to over 100,000 subscribers and secured a partnership with Champion Apparel in 2019.
The accolades followed. The Tampa Bay Times named him one of the city's top 25 entrepreneurs under 25. Florida's CEO Monthly designated him "Most Influential CEO of the Year" in 2022. Henderson built a verifiable track record in business before he ever mentioned the word "government."
But it was his mother's death that reoriented everything. Henderson described the experience during our interview as a crash course in systems failure: "At 19, I got confronted with hospital networks and insurance and disability attorneys and a whole world… it gave me the ability to recognise that there are a lot of people who feel powerless against things that are out of their control."
He is now supplementing that lived experience with formal study at Harvard Kennedy School and drawing on his internship at McKinsey & Company, where he encountered the rejection of the "expert mentality" — the dangerous assumption that the way things have always been done is the best way.
If you're the smartest person in the room, then you're probably in the wrong room.
— Alan Henderson, citing his McKinsey internshipJoshua T. Berglan interviews Alan Henderson (11 Feb 2026, 68 min). Split-screen broadcast covering CitySync, vacancy taxes, modular housing, AI traffic management, police accountability, and microtransit. Full transcript available below.
Available on Apple Podcasts, Spotify, and all major platforms. Runtime: approx. 68 minutes.
The centrepiece of Henderson's governance philosophy is the CitySync Initiative™ — a proposed unified digital platform that would consolidate every resident-facing city service into a single hub. In Henderson's framing, if you can track an Uber Eats delivery, you should be able to track a garbage truck. If your bank sends push notifications, your city should send neighbourhood safety alerts.
"A lot of this tech already exists and performs really well," Henderson explained. "It's just about — can we position it in a way so it's actually useful to the population?" The proposed features include AI-generated transcripts of city council meetings in plain language, real-time voting records, smart digital forms with 24/7 assistance, issue-tracking dashboards, and a City Hall LED board that illuminates as campaign promises are fulfilled.
I pressed Henderson on government technology's notorious failure rate. His response was telling: "I want to run Tampa not like a corporate bureaucracy, but like a startup. Underpromise and overdeliver. Don't put all your eggs in one basket." He described a pilot-first methodology — test at the neighbourhood level, measure against defined KPIs, and pivot or eliminate what does not work.
Among his proposed day-one executive orders is a moratorium on all public surveillance technology — including facial recognition, data fusion, and social-media scraping — until full transparency protocols and public hearings are established. "If you are going to incorporate it, the public needs to be made aware," he said. "It can't be something that's done without full transparency on the impacts of the algorithm."
This dual commitment — to technological adoption and civil-liberties protection — echoes the tension I explored in The Meek Warhorse : the idea that the most powerful systems are not those that seize control, but those that earn trust through voluntary restraint. Henderson's CitySync does not demand citizen compliance. It offers radical transparency and lets the data speak.
The most headline-generating proposal is a vacancy tax of 1–3% on long-term empty investor-owned residential units. Henderson frames this as modest and data-justified: "Our numbers show somewhere close to 13% of the city is just out-of-state companies owning properties and doing nothing with them." Revenue would fund RMAP (rent subsidies for qualifying households) and HRRP (a home repair and renovation programme).
When I characterised this as a bold move against the real estate lobby, Henderson did not flinch: "I don't think it's much of a penalty to say, sure, you can do it — but if you're going to hoard housing during a housing crisis, you probably should have to pay just a little bit for that advantage."
His second major initiative is modular housing at a target cost under USD 700 per month(approximately EUR 645 / GBP 555). He addressed the stigma directly: "When your challenge is you can't build houses fast enough, when you do build them they're not cheap enough, and you need them to be resilient to storms — you look at modularism as a solution." He cited Florida's Live Local Act, which allows affordable housing meeting certain standards to bypass permitting and council approvals, as the framework for rapid deployment.
Additional proposals include slumlord enforcement, mixed-income workforce housing, smart impact fee reform, and neighbourhood solar microgrids that reduce both utility bills and grid vulnerability — critical for a hurricane-prone Gulf Coast city with nearly 30,000 residents on waiting lists for housing.
Henderson's transportation philosophy is captured in a single line from his policy guide: "You shouldn't need a car to belong in this city." The goal is not to eliminate driving but to make alternatives — walking, cycling, ride-sharing, public transit — genuinely competitive.
The most technologically ambitious proposal is AI-powered traffic signals that respond dynamically to congestion and prioritise emergency vehicles. Henderson also plans to expand Tampa's existing Dash programme — currently a downtown-only subsidised ride-share service — citywide. He framed this as economic double duty: "People who need opportunities for work get it, and people who need to get to and from their work also get it."
Microtransit shuttles would fill the last-mile gap. Henderson described concrete pilot routes: large parking structures to the downtown arena, USF campus to the city core. Protected bike lanes with reflective guardrails, dedicated mobility hubs with shaded seating and bike locks, and toll-free express lanes for buses and first responders round out the plan.
There is a deeper truth in Henderson's mobility vision that resonates with what Nathaniel Allenby described on this programme when he spoke about cycling 28,000 miles (45,000 km) across ten countries: the radical discovery that freedom is not about owning a vehicle but about having the option to move through the world on your own terms. Henderson is not proposing an anti-car utopia. He is proposing that Tampa residents deserve the same menu of choices that residents of Amsterdam, Tokyo, or Copenhagen take for granted.
Henderson rejects the false binary between "more cops" and "defund the police." His answer to my direct question was immediate: "I also do believe in hiring more police because I do ultimately want the city to be safe. But when you bring on more police officers, you have to also think about how you can elevate the standard of engagement."
The technology component is specific: Tampa PD already uses Axon body cameras with real-time AI analysis — earpiece-connected systems that provide officers with legal guidance on scene and transcribe conversations. Henderson's proposal is to extend that infrastructure to flag deviations from protocol, for misconduct and for commendable behaviour. "All I want to do is flag when they deviate from that blueprint. If we have all the tools in place to recognise it, we should at least talk about it."
He proposes making the next police chief selection a public process, accountable directly to residents. On-scene camera teams would document interactions to build trust through transparency.
Beyond policing, the pillar includes expanded mental-health co-responder teams, city-funded therapy resources, a Tampa PD Youth Explorer Programme, K–12 career pathways into trades and public service, "quiet zones" like butterfly gardens and wellness parks, and — critically for a Gulf Coast city — a disaster and climate preparedness plan featuring solar-powered shelters, flood infrastructure, and citywide satellite Wi-Fi for crisis communication.
Henderson's youth programming carries particular weight for me. My own mission through the global changemakers we feature on this platform — from Princess Abumbi Prudence rebuilding youth futures in Cameroon's conflict zones to climate activists in Nigeria — has always been rooted in one conviction: the most effective crime prevention programme ever invented is a young person who believes they have a future worth protecting. Henderson's platform reflects that same conviction, localised for Tampa.
I have interviewed heads of state, climate activists from the Bafut Kingdom in Cameroon, youth leaders from Lagos to Louisville, and displaced workers navigating Industry 5.0. I have built the frameworks — Media Company in a Box , Failure to Framework , The Bridge to Media Empowerment — that help voiceless communities turn their stories into sovereignty. I say this not to credential-stack but to establish a baseline: I have sat across from enough leaders to know the difference between someone performing vision and someone carrying it.
Alan Henderson carries it.
What struck me most was not the technology — though the CitySync concept is one of the most coherent digital-government proposals I have encountered from a municipal candidate. What struck me was his refusal to be ideologically captured. In an era where candidates perform loyalty to a tribe, Henderson answered every question with systems thinking. His vacancy tax is not "anti-business" rhetoric; it is a supply-side correction backed by local ownership data. His police reform is not abolitionist posturing; it is an extension of technology Tampa PD already deploys. His modular housing advocacy leverages existing state legislation that most Tampa residents do not know exists.
I wrote recently about the ancient concept of praus — the meek warhorse, power under control. The Greek military did not destroy a wild stallion's strength; they trained it to respond to the rider's command. Henderson's candidacy is a civic expression of that same principle. He possesses the energy and aggression of youth — the thumos that drives founders and builders — but he has willingly submitted it to the discipline of data, community input, and institutional guardrails. That is not weakness. That is the most dangerous form of strength in politics: a leader who does not need the office to validate his identity.
Political analyst Tara Newsom of St. Pete College has publicly noted the "uphill battle" Henderson faces against more seasoned candidates. That assessment is correct conventionally. But I have spent my career watching conventional assessments fail when they collide with authentic narrative — what I call the dominion of the surrendered. Henderson's story — caregiver, entrepreneur, systems thinker, son of Tampa — is not manufactured. It is lived.
My professional assessment: whether or not Henderson wins in 2027, the CitySync model, the vacancy-tax framework, and the AI-accountability policing proposal deserve serious study by every mid-size city. This is not a campaign built on vibes. It is a blueprint. And blueprints outlast elections.
[00:00:00] Joshua T. Berglan: Ladies and gentlemen, and the misfits who refuse to stay in their lanes, welcome to The World's Mayor Experience. I'm your host, Joshua T. Berglan. For the new listeners, let me give you the lay of the land. We do not do small talk here. We do real talk. We strip away the corporate veneer and the media spin to get to the marrow of the human experience. I stand here as a man who has battled dissociative identity disorder and who navigates the world on the autism spectrum. But today you're going to see something else. You might see me shaking. It's not just in my hands. It's in my neck, my head, in my entire body. You might hear the struggle in my speech. These are not just tremors. This is my body reacting to the world in a way most people can't imagine.
[00:01:17] Joshua T. Berglan: I feel every frequency whether it is an electronic signal, human energy, or the raw power of mother nature herself. It surges through me in a very supernatural way. It is painful and is definitely exhausting and it's a daily battle just to speak into the microphone. But I refuse to hide it. These are not weaknesses. These are my credentials. Because when you have been broken by the system and when you feel the weight of the world literally vibrating in your bones, you learn to build something better. We talk a lot on this show about shadow prisons, the cages society puts us in. But I don't just talk about breaking out. I provide the keys.
[00:02:22] Joshua T. Berglan: And for those of you who are done consuming and you're ready to start creating, if you want to build a brand that is cancellation-proof and a legacy that outlives you, I invite you to work with me. As the Omni-Media Architect, I help visionaries weaponize their story to serve the world. You can find all the details at joshuatberglan.com. But today, today we're looking at the face of the future. We are speaking with a young man who isn't waiting for permission to change the world. He looked at his city, saw the cracks, and decided to fill them not with concrete, but with code, compassion, and a whole new paradigm.
[00:03:36] Joshua T. Berglan: He knows how to build communities in the digital age. But when tragedy struck, when he lost his mother to lupus and saw firsthand how the systems failed her, he didn't just grieve — he mobilized. He is running for mayor of Tampa in 2027 with a platform that reads like a blueprint for a smart city with heart. He calls it "Building the Tampa of Tomorrow Today." He is fighting for Access Over Authority, People Over Portfolios, Mobility Over Mayhem, Safety Over Soundbites.
[00:04:53] Joshua T. Berglan: Ladies and gentlemen, however else you identify, please help me welcome the candidate who is redefining what leadership looks like — Mr. Alan Henderson.
Alan Henderson: Wow. I am doing so well, and thank you for such a thoughtful introduction. How are you?
Joshua T. Berglan: I am excited to interview you, for sure. I love your vision. It is disruptive in every sense of the word.
[00:05:45] Joshua T. Berglan: What are you grateful for today, and why?
Alan Henderson: I'd say lately I've been extremely grateful for opportunities like this one and for a city that has been open to giving me the space to put my ideas out there. Because I really do care about how we grow and how we make progress for the people who live here. Coming out of kind of nowhere without a massive political background, but a background that I think is respectable and competitive in this race, I just feel blessed that age hasn't been an inhibiting factor, race hasn't been an inhibiting factor to people taking my ideas seriously.
[00:06:59] Joshua T. Berglan: You've built an empire in esports with Dilemma Esports. Gamers are problem solvers. They optimise. They strategise and they hate lag. How does the gamer mindset translate to running a city?
Alan Henderson: I'm actually a pretty bad gamer myself. But I fell in love with the business side of esports pretty early. I liken esports a lot to politics, actually — you have a brand or a narrative that you're trying to support, but then also so many different interests that you're trying to weigh at the same time. The players have a certain standard, coaches have responsibilities, marketers on the team — and then managing the budgets, travel, logistics. I realised a lot of those skills carried over pretty well with running a campaign.
[00:08:08] Joshua T. Berglan: You lost your mother to lupus in 2022. You said that experience showed you how local systems fail people. Can you take us back to that time?
Alan Henderson: Losing Mum was something that was really tough on me and my family. It required me — I was her oldest son — to kind of step up and grow up pretty quickly. The major takeaway was just really feeling powerless against a system that is just way bigger than you. At 19, I got confronted with hospital networks and insurance and disability attorneys and a whole world. But it gave me skills I carry to this day. It gave me a sense of resilience. And ultimately the ability to recognise that there are a lot of people who feel powerless against things that are out of their control. And our city government doesn't have to be one of them.
[00:10:25] Joshua T. Berglan: The establishment is going to use being 25 against you. What does a 25-year-old see that a 60-year-old career politician is blind to?
Alan Henderson: A lot of my age is rooted in seeing opportunities where other people see problems. I took an internship at McKinsey and one of the ideas they tried to drive home is getting rid of an expert mentality — if you're the smartest person in the room, you're probably in the wrong room. Being able to not have any previous agenda has given me the space to really just listen to what the residents want and try to translate it into policy that actually gets things done. When I look at the mayor's role — too young for what? A lot of the actual role is managing relationships with stakeholders, pulling together people to take ideas off of paper. The mayor's role ends up being less the specialist and more of the generalist.
[00:15:26] Joshua T. Berglan: You want to create CitySync — a digital hub for everything from potholes to voting records. Government tech is notoriously awful. How do you bring Silicon Valley efficiency to City Hall?
Alan Henderson: Our idea for CitySync is to take data we are presumably already collecting but just activate it and make it resident-facing. On the simple level, it's transcript analysis for city council meetings. But also internally having transcripts for every single department meeting so we can sync them up and find opportunities and bottlenecks. If you can track your Uber Eats order, maybe you should be able to see when the next garbage truck is coming. I want to run Tampa not like a corporate bureaucracy, but like a startup — continuously trying to prove value. If the model doesn't work, I'm not someone that's going to sit on it and keep throwing money at it. We'll fix it or pivot.
[00:19:51] Joshua T. Berglan: People are scared of AI. How do you use AI to empower citizens rather than monitor them?
Alan Henderson: A lot of the people who are afraid of this technology — their intuition is correct. Great power comes great responsibility. We're already seeing it leveraged in useful ways and in ways that are of disservice to the public, like creating misinformation at the highest levels of government. I actually just published a list of day-one executive orders, and one of them is a moratorium on all public surveillance — facial scanning IDs, data fusion, social media scraping. If you are going to incorporate it, the public needs to be made aware. You need public hearings. And then just being explicit about what the risks are, what the potential gains are. There should be some really strict guardrails to keep people safe.
[00:28:07] Joshua T. Berglan: You're proposing a vacancy tax on long-term empty investor-owned units. That is a bold move. Is housing a human right or an asset class?
Alan Henderson: I believe housing is a human right. When you're talking about a two-billion-dollar budget and a resident pool of around 400,000 people, there's really no excuse to have people living on the streets. The vacancy tax is modest — in the range of 1 to 3%. Our numbers show somewhere close to 13% of the city is just out-of-state companies owning properties and doing nothing with it. If you're going to hoard housing during a housing crisis, you probably should have to pay just a little bit for that advantage. All of those dollars will be spent on building more places for people to live.
[00:33:10] Joshua T. Berglan: People hear "modular" and they think trailer park. Paint the picture.
Alan Henderson: When your challenge is you can't build houses fast enough, when you do build them they're not cheap enough, and you need them to be resilient to storms — you look at modularism as a solution. These are homes built faster, that cost less, where you're activating the local workforces. Florida has the Live Local Act — if you're building to a certain affordability standard, you can bypass permitting and council approvals. The growing list of people who need homes in Tampa is a little under 30,000 and only expected to keep growing.
[00:36:20] Joshua T. Berglan: You talk about microtransit shuttles for the last mile. How do you make them reliable enough that people trust them to get to work?
Alan Henderson: Our goal with microtransit is to supplement the main bus system. We also have this programme called Dash that we can expand citywide — people can get much cheaper rides. Or adding bike locks to bus stations. Just simple upgrades that make options other than driving a little bit more compelling. We would pilot neighbourhood level, pilot small before we scale.
[00:42:28] Joshua T. Berglan: Critics will say we need more cops, not therapists. What is the data that proves prevention is better than punishment?
Alan Henderson: I also do believe in hiring more police. But punishing crime is great — what's even better is making sure there's no crime that happened in the first place. Being proactive in preventing it, by understanding who are the most likely offenders — in our city, it's typically young people — and thinking about what are the conditions that create this type of crime. If you can leverage that information correctly, you can put in place incentive structures that stop people from wanting to engage in those behaviours in the first place.
[00:49:12] Joshua T. Berglan: You're proposing AI to flag both misconduct and commendable behaviour in the police force. Police unions are powerful. How do you get them on board?
Alan Henderson: Tampa already uses Axon body cams providing real-time AI analysis of active crime scenes. It has an earpiece connected so officers can ask policy questions about the law, it's transcribing the conversation. It's basically giving them a blueprint for how to do things correctly. All I want to do is flag when they deviate from that blueprint. Tampa PD should know I'm going to have their back — we're going to build the trust together. But it means holding each other accountable. The next mayor will have an opportunity to select a new police chief. I want that process to be public.
[00:52:16] Joshua T. Berglan: One of the things sticking out is I don't know your political party. Your answers are so common sense. Where did your political ideology come from?
Alan Henderson: A lot of it came from personal experiences and conversations with residents. I've always been a systems thinker. It's funny you said it's radical — I often think it would be radical to not do these things. I ultimately just want to be a really thoughtful steward of what we would inherit. I think we just came back from years of divisiveness. If you had a candidate trying to be thoughtful about what you say, trying to find consensus and be a bridge builder — that would be a useful thing to have in 2027.
[00:54:38] Joshua T. Berglan: If you could enact one global law regarding smart cities, what would it be?
Alan Henderson: Almost certainly something to do with civil liberties and data protection. Establishing the ethical guardrails for this technology. So whatever the impacts, it's not happening in the dark. Whether or not cities decide to lean into tech will be up to residents to choose. But if they do, it should be really clear what the rules of engagement are, so nobody's being taken advantage of.
[00:57:08] Joshua T. Berglan: There's a 19-year-old listening who feels powerless. What do you say to them?
Alan Henderson: Look, I get it. I can understand why they would be disenchanted. But people generations before me fought very hard for their right to participate. And the one thing we know about rights is that if you don't use them, you will lose them. If there was ever an opportunity to stand up for yourself — now is the time. Things aren't anticipated to get easier unless the people watching this decide to do the work. Go out and be decisive and vote for the people who are saying things that will improve your life.
[00:59:23] Joshua T. Berglan: One raw, unfiltered truth about the state of our cities?
Alan Henderson: The lack of expertise that exists in our broader government. The egos that run municipalities — afraid to be wrong, afraid to get feedback. So many missed opportunities because politics has crept into what should be routine civil work. Maybe you don't need the politician who has decades of government. Maybe what you need is a teacher, or someone who's lived in the trenches, who's seen the community's gains and deficits up close. That's the kind of person you want advocating on your behalf.
[01:02:04] Joshua T. Berglan: Paint a picture. It's 2030, three years into your term. What does a Tuesday morning look like for a single mother living in your city?
Alan Henderson: I want my administration to be defined by opportunities and access. If you need childcare on the weekends, you can trust you have that opportunity. If you need to get around Tampa and can't drive, I want you to request a ride on your phone or check where the buses are. If an emergency happens and you call 911, I want record-breaking response times. I qualify these changes as simple but significant. They take Tampa away from just being a great place to be and make it an incredible place to live — to build families, to pursue the full extent of your dreams.
[01:05:35] Alan Henderson: I'm someone who was born in Tampa and I've been fortunate enough to see both sides of our city. I've seen all the great things — the happy hours and rooftop bars and sunsets that are amazing. But I've also seen up close the very real challenges that a lot of residents face. The way we bridge that gap is not by continuing to elect the same politicians. I believe in practical, well-researched policy positions that I'm willing to negotiate in public view. Are we going to be the city that continues to invest in image, or are we going to go for a change? 2027 is the time for us to elect different. Support my campaign at hendersonfortampa.org.
[01:08:34] — End of Broadcast —
Blueprints for a Purposeful Tomorrow
