From Burns Steakhouse to City Hall: The Unconventional Path of Tampa’s Youngest Mayoral Hopeful - Alan Henderson

In this inspiring 30‑minute conversation, hosts Sharmin Prince and Mitzy Dadoun sit down with Alan Henderson after a short guided breath‑work session. Alan shares how his unconventional path—from founding a company at 16 while working at Burns Steakhouse, to caring for his ailing mother, to running for mayor—has shaped his leadership style, his commitment to active listening, and his bold vision for a more affordable, safe, and inclusive Tampa.

Sharmin Prince
Welcome to the Transforming Lives panel podcast. I'm one of your hosts, Sharmin Prince.

Mitzy Dadoun
And I'm your other host, Mitzy Dadoun. And we have our guest with us, Alan Henderson, who we will introduce a little bit more after we do some breath work.

Sharmin Prince
Great. Thank you, Mitzy. Now, if you would just take a moment with me, if you're comfortable and you can close your eyes, you can do so. but take a deep breath in through your nose and hold that breath and exhale, let it go through your mouth.

Again, deep breath in and out. In, And out. Another deep breath in. And hold this breath for a moment and feel it.

And as you exhale, just let go of everything that didn't serve you today. And take another deep breath in. and let go of the plans that you have for the remainder of the evening so that you can be grounded and centered with us for the next 30 minutes. Thank you so much for joining us for that deep breathing exercise.

Now I want you to meet our guests, Alan Henderson, a 24 year old entrepreneur and community advocate, exploring a run for mayor of Tampa. His journey is one of resilience from founding his first company at 16 to becoming a caregiver for his mother, an experience that forged his deep commitment to service. He's a nationally recognized innovator and is now channeling his entrepreneurial spirit into a vision for a more affordable, safe, and inclusive Tampa. Welcome to the Transforming Lives, Alan.

 Alan Henderson
Thank you very, very much for the thoughtful introduction and for having me. I truly appreciate

Sharmin Prince
it. Is there anything you would like to add? to your bio?

 Alan Henderson
No, I think that was a really great introduction. I think you touched on a lot of the core themes I'm excited to talk about. Of course, my journey is unconventional, but I hope that it allows people to maybe see the potential in their own unconventional journey and step up and get involved with what's important to them.

Sharmin Prince
Beautiful. In your bio, you mention that you founded your first company at age 16 while working at Burns Steakhouse. What did those early years of balancing work, school, and entrepreneurship teach you?

 Alan Henderson
I appreciate that. It taught me a lot about If you know anything about Burns, we say here the legendary Burns Steakhouse in our city because they have a pretty high standard, a pretty high culture. And so very early, I kind of knew what it meant to show up early and work really late and put a lot of effort into the product that you're trying to build. It taught me about how to compartmentalize, right?

How to, um, set high standards and then just work at it continuously. Um, and because it also all happened to be things I was passionate about. Um, you know, my, my company, you say company at 16, it really starts as a community before anything else. And so because it was something that I was passionate about, um, it taught me to spend time curating and spend time focusing on final product and it's something I carry with me to this day.

Sharmin Prince
And where did you get the drive, the motivation to start a company at 16? Because most people are in high school and not thinking about entrepreneurship and You were in school, you're working, and then you're creating your own business. Where did that drive come from? I

 Alan Henderson
have to give essentially all the credit to my parents. from a very young age invested time and energy in just believing in me. I went through a lot of phases as a kid, you know, and so I'm not sure that it was always financially convenient or, you know, but they supported me through it is my point. And they were encouraging And so as you try things at a young age and you get out, I really, I probably started my first business, uh, when I was closer to like 13 or 14, uh, selling pictures for my brother's football team to the parents.

And so that journey started with, you know, the Christmas before that season, asking for a camera, you know, telling me, I think I want to get into photography. Um, it turned into, you know, maybe photography classes in Tampa. Uh, and eventually it turned into, you know, selling those pictures. So definitely my parents believing in me.

And supporting Dream Jump from the onset gave me the room to kind of learn and explore and to keep building.

Sharmin Prince
Wow.

Mitzy Dadoun
And I mean, I'm really curious. I mean, 24, you're running for mayor. How did your journey take you to the point where you are now running for mayor?

 Alan Henderson
That's a great question. Like I said, it's certainly unconventional. It's a career and a life outside of politics, but I would say of being affected by the system that I want to try to fix. You know, I've seen, especially as my mom started to get a little sicker, I've seen what it's like to try to work against a system that feels so much bigger than you and feeling powerless against it.

For me, it turned into a motivator. It turned into, you know, something that said, all right, I have these skills that have allowed me to deal with tough times, it allowed me to compartmentalize, it allowed me to empathize with others really well. And I feel like where we are in our city, where we are in Tampa, the city is looking for someone who can listen. The city is looking for someone who can understand the challenges of what it's like to live here.

You know, we're dealing with a lot of issues that a lot of growing cities experience, you know, traffic, congestion, a lack of opportunities, and feeling like you're getting priced out. And so taking that really lived experience, that resident experience of fighting big systems and leading through it, I think is what could really benefit our city right now.

Sharmin Prince
Thank you for sharing that. What specific experience being the caregiver to your mom which by the way, before I continue, I need to commend you on that because it's not often you hear or meet a 24 year old who has been a caregiver to their mom. Was there a specific experience that motivated you to say, you know what, I think I need to become a change maker in this city. And in order for me to do that, I have to be in city hall.

 Alan Henderson
I appreciate that question. It's likely a variety of experiences to be truthful. One of the early ones I can tell you, I mean, it just starts with having to take over things so quickly. You know, as she, my mom was the sort of, my dad would call her the glue to our family.

Right. So she was managing bills. managing insurance, healthcare, you know, kind of doing it all in silent as she's sick. And, you know, we as kids didn't really experience the full extent of it until we kind of got hit with it all.

And so someone had to kind of step up and take over everything from medications to schedules and appointments, you know, dealing with Tico on the phone because they want to cut the power off. And it's just a lot to have hit you all very, very quickly. And so I had to not only learn how to heal myself, learn how to protect myself and grow through that, but I also have people underneath me that were counting on me to, um, be there for, for the company, the team we're building. I'll be there for my family.

And one of the experiences that made me ultimately realize that, well, maybe I did pick up a little bit of, um, sort of acumen throughout the journey was by the time the funeral happened, we had this family provider, family funeral home, essentially, that everybody goes to. And for some reason in our family, it's like if you do things a certain way for a certain amount of time, that's just how it is. And nobody really seems to question it. And so, you know, we go there and I think the director was essentially assuming it was a done deal.

shake hands, he hands us the bill of goods. And I'm looking and I'm like, they're charging us for the miles we drive, they're charging us for the weight of the casket. It's just a bunch of just extra fees. And I knew that that likely wasn't the best investment for us.

And I knew that even my mom would have wanted me to do a little deeper research than that. And so I had to take a leap of faith and say to my family, say to the pastor and everybody there, we're probably not going to sign anything today. Let us go do more research and we'll get back." And I could feel the weight of that decision making it on behalf of the family right there in the moment. But I knew that that was the right case and so we found a funeral home in Tampa and the service was beautiful.

The service was truly beautiful and probably saved us about, funerals are expensive so it saved us a considerable amount of money but the point is it took really leaning on the experience of understanding what matters to her, fighting for what's important for my family, and being courageous about it to get what we wanted. And I think that those kind of values translate really well in City Hall. Great.

Mitzy Dadoun
Yeah, I think that when you mentioned that sort of just that not accepting the status quo, and even though we were the youngest having a voice and speaking up. and saying, you know, this feels off, and so let's take a breath and re-examine. And, you know, so often, especially in government,

 Alan Henderson
it

Mitzy Dadoun
happens that, well, this is the way we've always done it, so we're just going to keep doing it this way. And it's like, yes, but if it's broken, then the way we've always done it isn't just the thing to continue with. And it's, as you say, hard to push against when there's a lot of others that say, well, this is how it's always been.

 Alan Henderson
Exactly right. And I figured I'm not tied to any political systems. You know, my experience is building communities in Tampa, networking deeply in Tampa, seeing both sides of the city, as I like to call it. And running on that kind of conviction, I think is going to be way more relevant to solving issues than decades of experience being in and of the system.

Sharmin Prince
I love your path and thinking about being a candidate with your unique path. And I didn't mention this in your bio, an actor with this need,

Mitzy Dadoun
an

Sharmin Prince
entrepreneur. caregiver to your mother, the experience that you just shared. In that moment when there is grief, a vulnerable moment where persons really capitalize on taking advantage of the grieving family, you stood up and you're like, no, this is not what we're going to do and made a decision to break traditions and customs in the family, it's a remarkable quality for a mayor of a community or of a city.

With that in mind and all the rules that I listed, what skills are you using to promote yourself and, again, your rivals?

 Alan Henderson
Certainly. I would say one of the skills that have helped me the most, without a doubt, is actively listening to the people around me and then trying to deeply empathize with their experience beyond what they're trying to portray but the actual person beneath the exterior. And it's a skill that over the years has opened so many doors for me. It's allowed me to travel the world.

It's allowed people who maybe otherwise wouldn't have believed in me, but because I'm actually listening to what they're saying and I'm listening to the advice that they're giving. These are CEOs in our city. These are chief executives who in any other world really wouldn't be interested in lending their time, I'm sure. But it's because I'm deeply focused and committed to understanding them and what they're going through.

And skills have translated to my teams as well. Being able to actively listen to their concerns and invite them into building with us has allowed me to scale really smart teams. You know, honor students at our local universities, business owners, entrepreneurs, We call it the Tomorrow Team, our sort of expert panel. These are seasoned professionals, multi-year professionals.

And I take into our conversations the same degree of active listening I take into community halls and town hall sessions, just to focus on understanding their problems, understanding the feedback they give us, and running with it.

Sharmin Prince
Well, active listening is a developed skill. So I'm curious. because you mentioned that a lot and I know it's a developed skill. So where did you learn that active listening is an important skill when you're serving humanity or truth for service to humanity?

And how have you honed in, developed and now It's a part of who you are.

 Alan Henderson
I appreciate that, and that's sort of what I was thinking about as you're asking it, is it's always sort of been a part of who I am, I suppose, growing up. You know, as an actor, you know, with Disney especially, you're pretty high standard, so you're always kind of listening to specific cues. You know, hey, can you smile more during this line? You have to actively listen.

And then over the years, that shaped into, especially like a single mom that got sick. You're listening to really specific instructions on dosage or medication. You're listening to specific instructions on physical therapy, that sort of thing. And so over the years, it's just sort of been a skill that I've seen when I apply it to my teams and I apply it to my own personal life and the people I care about.

And just truly just listening to the things that they're saying to you, it resolves for a lot of bandwidth. You can save a lot of energy and kind of curate a lot of alignment just by listening to the people you care about. Um, and so maybe it was a slower burn, if you will, but it sort of got me to where I am today. And now it's a skill that I can't even imagine facing life without.

Mitzy Dadoun
You know, when a lot of people think of politicians. I would think that one of the biggest lacking skills that I see in most politicians is active listening and hearing what people are saying. So I think that in and of itself sets you so far apart

 Alan Henderson
and

Mitzy Dadoun
above and beyond probably 99% of all politicians, whether they be local, state, federal, you know, that's the foundation of everything to build on.

 Alan Henderson
I appreciate it. And I know how serious it is, especially when you're wanting to run a city. And if, you know, when we start to serve, especially as a young leader, uh, that kind of feedback is invaluable. And the way I've always seen it is if you are serious in your commitments, if the things you're running on are the type of city and foundation, you actually want to curate.

I don't know any serious leader that wouldn't want feedback that wouldn't want to actively listen to concerns. And so they can work on it. Right. And so it is a stark contrast to a lot of politicians that we've seen, but it's also what is fueling the desire to get in the race, to sort of be the change that you want to see, right?

Mitzy Dadoun
And one of the other obvious sort of questions is, you know, you're relatively young compared to a lot of other people who enter into politics. And in a lot of ways, I'm sure that that is, that opens a lot of doors and it makes a lot of other doors harder to get in because of it. Can you elaborate a little bit about sort of how you're dealing with that aspect?

 Alan Henderson
It's really, yeah, I definitely think, like you said, it's opened a lot of doors and it's sort of raised pretty important questions that require me to answer and require our campaign to address thoughtfully. Generally, it's been the city has been pretty receptive. I would actually say the most surprising part was how quickly that became a non relevant factor. I think that at first we were very excited.

I'm one of the youngest candidates in our city's history. And so at first, it was something that we were really excited about loud and proud. And then we started to realize, Oh, okay, Tampa is taking our campaign very seriously. And for mayor, it's an important role.

And so A lot of the conversation they started with, oh, you're young, you know, what's your favorite food? What's your favorite color? Now it's how are you going to solve the challenges in our city? And so that shift, it was it was short lived.

The kind of excitement, I suppose, of being the youngest candidate. But I like that it's open. What I really value is that other young people can sort of see themselves in our campaign and can step up and face their experiences. to lead their own lives, to do something impactful in their own journeys.

And so that's something I still value a lot. And I think that our core audience in the campaign are gonna be people that I can hopefully inspire with that theme.

Sharmin Prince
As an entrepreneur, you're used to moving quickly and being the decision maker and ensuring things happen. and getting the results in order to get the results and the desired outcome. But people often criticize the government or even the city for being too slow and having all these red tape and bureaucracy in order to get a decision. How would you apply your startup mindset to ensure delivery of your promise, the promises that you've made to your constituents, and make it more efficient and effective?

 Alan Henderson
I love this question because part of my favorite thing about leadership is getting into the weeds and the different cultures of each department so you can lead it effectively. Our approach looks like starting small, right? Not trying to bet everything on one particular approach. Build it in pilots and scale it as you ensure it's effective with the city's input.

And so when you're starting with not how do you change the entire city overnight, but how do you change one specific deliverable or how do you account for one specific outcome? And then my job as a leader is to go into meetings with the city attorneys and accountants and planners and to work with them and say, this is the outcome that we want to achieve. What are the steps in between? How do we get there?

And what can we do today and tomorrow to be one step closer to it? And it looks like just having honest conversations that look similar to that. And I think that when you're working from that approach, and you're honest with the community, and I see that you're really trying to make an effort, I think that what we'll get through the end of that will be far more productive than what we've had leading to.

Sharmin Prince
Excellent. I love your approach where you're focusing on, how can I put that? There is a specific area And you're going to be working on that area and then develop. And it sounds like this is my assumption from what you're saying that if that doesn't work, we have a strategy that we're going to implement as a followup.

So great strategy, but I read that you about expanding affordable housing. I'm in New York city worked in. the homeless and formerly homeless sector. So I understand the importance of affordable housing and how are you going to put a modern or use your generational impact to ensure that the expansion of affordable housing in Tampa is intergenerational?

 Alan Henderson
Oh, what an amazing question. Because it sort of also talks about a question that I spend a lot of time thinking about, which is what sort of impact do you ultimately want to have on the city? Do you want to get your name on the side of some building? Or do you want to be in the libraries?

And for me, consistently, the impact I want to leave is that intergenerational reprioritization. of the people who live here, recognizing housing as sort of a non-starter, as a right, a human right. I don't know how you can have a competent city when residents every day are increasingly sleeping on the streets. And so what our approach looks like is changing how we procure some of these housing.

I think that continuing to try to invest in the same strategies is going to lead to sort of the same outcomes. And so I'm a big fan of modularism and creative retrofitting. We've seen hotels be reformed into affordable spaces. There's viable models all across the country, all across the world, that I think would work really great in Tampa.

But it all begins with, again, staying outcome-oriented, being receptive to new designs. And I think that if A mayor can introduce this kind of thinking can be bold and maybe say we can have a few neighborhoods that might not have to look all like the rest of the neighborhoods, but if they're obtainable, that's a great option for the city to have. And so just being kind of unafraid to open that seal, I think will invite a lot more creativity and culture over the years as well.

Mitzy Dadoun
That sounds like a great way to look at it. Because as you say, there's so many buildings that as the world has evolved and changed buildings that were once full are now empty and figuring out how to repurpose them and use them for housing is a fabulous way to help, you know, improve the area too, because then it's not just an empty building sitting there. Who are some of the leaders, business owners, influencers that you liked the way that they've sort of approached things and that helped you build your style, so to speak?

 Alan Henderson
Oh, I love this because it's a really personal list. Everything from authors to, you know, leaders in history that have also kind of stood up in their own journeys, stood up for what they believed in. and worked really hard to achieve it. So I could give you a probably pretty exhaustive list.

But I'll tell you one of the more recent ones that inspired me. He's a professor. I study at Harvard, the Kennedy School. And he's a professor there, and he's an author.

And we were talking about imposter syndrome. And I'm telling him, like, I understand how City Hall works very well. I take very detailed notes during city council. And when I go out and talk with residents, I understand deeply the conversations and the issues that are impacting them.

And I carry that with me. And I'm also 24. And every conversation that I have, I feel like I end up leaving it with so many more questions and so much more that I want to learn. And so I'm telling him that it makes me feel capable in so many ways.

But it also reminds me of, you know, the audacity of the role and what we want to accomplish. And he reminded me, and it stuck with me, that is a sign of someone who cares about the word. And that there will always be more to learn. There will always be more to integrate yourself with.

But the fact that you don't enter it feeling like you know it all is a great starting place for transformative change. And so there's a variety of stories and conversations similar to that trend that just from watching how they've carried the weight, you know, President Obama, I think, is historic. Martin Luther King, Rosa Parks, Toni Morrison, an author I was reading recently. I mean, just I could go on and on and on about just leaders who have just carried the things they valued with them and it's manifested in their work.

Sharmin Prince
I want to follow that, but because of time, because I love your list of leaders, but I like that the first person you mentioned is a professor. So there is that intellectual foundation that is important also to serve the community. along with your personal experiences. You've been recognized on the list of like 25 on the 25 Titan and 100.

But what does being a Titan means to you in the context of community leadership? Not just business successes, but being an advocate and now a mayoral candidate for Tampa?

 Alan Henderson
Thank you for that question. It's funny because that is largely how I see the value and the acknowledgement is through the lens of what it could mean for the community and what it can mean for the impact I hope to have across Tampa. Titan, in that sense for me, looks like someone who is unapologetically willing to stand up for things they value and unapologetically be themselves and trust their experiences and trust the outcomes that their experience will bring for them. You know, I see Titan as sort of a forger path, if you will.

And I hope that I'm able to forge paths for people along their journeys as well.

Mitzy Dadoun
even

 Alan Henderson
if it's a little different. Sorry, please.

Mitzy Dadoun
Oh, no. Alan, so how can people find you, get more information, see what your policies and who you are and what you stand for? What's the best way for them to get that information?

 Alan Henderson
I would hope, and thank you for asking, I would hope that they visit our website at hendersonfortampa.org. I share this, you know, our opponents, they're going to be running to the tune of about $3 million or so. It's going to be a very expensive race. Um, you know, but somebody reminded me of a story, uh, about, uh, a guy with just two shoes and he knocked on every door in Florida and, you know, the theme is that he won his race.

Uh, and so my goal is to build a team of people who see the vision, who also believe in a city that creates opportunities, uh, and not obstacles in their journeys. And so if that resonates Hendersonfortampa.org, uh, I'm looking forward to your support.

Mitzy Dadoun
Okay, excellent. And now for some wrap by our questions from Charmin to wrap

 Alan Henderson
us up. Let's do it. Let's do

Sharmin Prince
it. Tea or coffee?

 Alan Henderson
Oh, coffee. Good coffee doesn't hurt.

Sharmin Prince
Your best lessons you learned from Burns Steakhouse?

 Alan Henderson
Ah, work hard. Work hard. They work really hard there.

Sharmin Prince
One word your mom would have used to describe you?

 Alan Henderson
Wow. That's a good one. Empathetic, hopefully.

Sharmin Prince
Your go-to order at Tampa local spot.

 Alan Henderson
Ooh, go-to order. A cafe con leche doesn't hurt. It's very Cuban vibes.

Sharmin Prince
The most important skill you learned as a caregiver.

 Alan Henderson
Most important, I think patience, truly patience. That and active listening, like I said, we're big ones.

Sharmin Prince
Entrepreneurial trait most needed in government?

 Alan Henderson
Oh, good question. I would say agility. I would say agility and focus. Just the ability to kind of get things done, not taking no for an answer and being able to maneuver government.

Sharmin Prince
biggest advantage of being a younger candidate?

 Alan Henderson
Oh, no, I mean, no political baggage is great. I mean, I'm learning so much about politics and I'm like, thank goodness I'm not a career politician. It's an intense field, intense game, but the part that I love about the job is the ability to actually make change happen and not get caught up in the weeds. So just not having any of that tied to me is great, really freeing.

Sharmin Prince
Your superpower.

 Alan Henderson
Absolutely.

Sharmin Prince
What's your superpower?

 Alan Henderson
Oh, I would say seeing people, if that makes sense. Being able to really, truly see and value the unique energy and perspective they bring to a challenge. Our, our goals, um, seeing them for who they are has been incredibly fulfilling, even for myself.

Sharmin Prince
As an innovator. a piece of outdated tech that City Hall still uses?

 Alan Henderson
Oh, great question. Probably one of the things that we're focused on innovating starting day one is how we leverage data in Tampa. You know, we outsource a lot of studies and a lot of times we get so caught up in bureaucracy, even just repaying for studies that we did, you know, just two years ago, it's kind of a mess. And so I think that we can simplify a lot of it.

by putting a lot of city services front and center for residents, making it really clear and easy to understand and to navigate their government, I think is a great starting place for Tampa.

Sharmin Prince
Final question. Finish this sentence. Tampa's greatest asset is in its

 Alan Henderson
people. Absolutely it's people no doubt about it and I think the next best thing we can do the next best thing the next mayor can do is reflect back the opportunity and the potential and open doors for its residents that's how we will unlock the Tampa of tomorrow today.

Mitzy Dadoun
Thank you so much for joining us today Alan I know that everybody's going to get a lot of great information and can you give us how to find you again one last time?

 Alan Henderson
Absolutely. HendersonforTampa.org and at Henderson for Tampa on all social media. Thank you guys so much. I appreciate your

Mitzy Dadoun
time. Thank you.