The Hunter Webb Interview (Harrisburg, PA)
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HARRISBURG, PA -- Hunter Webb is an American medicare agent and businessman from Harrisburg, Pennsylvania.
He's currently an independent medicare agent at Health 360 Concierge, while having prior experience in the supply chain industry and content creation world.
Tyreese Smith caught up with Webb in an interview on navigating the healthcare industry, personal growth and evolution in modern times.
Hunter Webb Feature:
Hunter, how’s everything man? Welcome to the platform. I haven’t done this in months, so this might be a bit rusty but the world still spins. Tell us about yourself; Who is Hunter Webb?
"To give a brief introduction, my name is Hunter Webb, and I work as a Medicare agent serving the local community. I was born and raised in Harrisburg (Pennsylvania), and this role has given me the opportunity to build a deeper connection with the people in and around the area, while providing a service that genuinely impacts their lives."
"I’m still relatively new to the field with about eight months of experience, but in that short time I’ve learned a lot about communication, business operations, and what it means to be a self-starter and take ownership of your own path. I got started in Medicare through my fiancée’s (Kennedy Miller at CBS 21) mom, who also works in the industry. Before entering this space, I spent a period of time moving between different jobs. Working at UPS, doing door-to-door solar sales, and serving in restaurants. During that time, my fiancée encouraged me to look into health insurance and Medicare as a potential career path. After connecting with her mom and a few experienced agents, I started to understand the structure of the industry and the impact it has on people’s lives. The more I learned, the more it made sense. Not just as a career opportunity, but as a way to combine entrepreneurship with meaningful, community-based work."
"Since then, I’ve found a strong sense of direction in it. It’s challenging, but it’s also rewarding to build something of my own while helping people navigate an important part of their lives."
I’ve known you for almost a decade now, but you’ve always had an entrepreneurial mindset. No matter if it was creating a wave or leading others, you always knew how to work through a process. Even if it was for the love of the game. How does entrepreneurship hold near and dear to your heart?
"That’s right we go way back. We knew each other throughout school, but really got close in high school, especially senior year. Whether it was inside jokes at track practice, hiking up Shock Rock, or just talking about music, we always found a way to have a good time. It’s interesting looking back and seeing how far we’ve come from being kids with no real direction yet."
"I’d say entrepreneurship has always been part of me," Webb continued. "Even if I didn’t recognize it at the time. I’m naturally more introverted, so I wouldn’t have pictured myself running a business or being someone people rely on in a professional sense. But life tends to shape you through experience more than expectation. When I was around 14, I asked my parents for a phone, and they told me if I wanted one, I’d have to earn it myself. At first, I couldn’t even get a traditional job because of age restrictions, so I started finding small ways to make money. Mowing lawns, walking dogs, shoveling snow, and even painting a neighbor’s house. That was really my first exposure to working for myself, and I remember how rewarding it felt to earn something through effort. Later on, in 2023, I started a small business running Facebook ads for local business owners. I taught myself through YouTube and courses, set everything up, and tried to structure it like a real operation. While it didn’t end up working out due to difficulty acquiring clients, it taught me a lot about execution, consistency, and the reality of building something from scratch.
Looking back, I think the biggest gap wasn’t effort—it was guidance. I didn’t really have a mentor in that space, and I was trying to figure everything out on my own. In my current role as a Medicare agent, that’s been completely different. I’ve been fortunate to have experienced mentors who actually guide me and help me navigate challenges as they come. If I had to give one piece of advice to anyone trying to build something, it would be simple: find people who are already where you want to be, and don’t be afraid to ask questions. Most people are more willing to help than you think, as long as you approach them with respect and intention."
Why is it important that we take care of our health as human beings?
"Health is often described as wealth for good reason. When we take care of our physical and mental health, we maintain the ability to live freely. Pursuing our goals, working, building relationships, and experiencing life without unnecessary limitations. Good health gives us independence and flexibility in how we move through the world.
On the other hand, when our health declines, our options become more restricted. Even simple daily activities can become difficult, and it can limit our ability to work, travel, or spend time with the people we care about. Mental health is as important, as it shapes how we think, feel, and respond to life’s challenges. In that sense, protecting our health isn’t about avoiding illness. It’s about preserving freedom, stability, and the ability to fully participate in life."
We understand that you’re also a content creator who pops up from time-to-time to drop heat. Everybody knows there is a process behind it, though. Taking some time to dissect the science, how do you see propaganda vs marketing in selling an idea?
"When I look at propaganda versus marketing, I see them on a spectrum rather than as completely separate things. Both are ultimately about influencing how people think, or feel about an idea, product, or message. The difference comes down to intent and transparency.
A lot of modern marketing, especially in digital spaces, leans heavily into emotional persuasion. Instead of focusing on what a product actually does, it often sells a feeling; Status, Confidence, Belonging, or Escape. In that sense, some marketing starts to resemble propaganda because it can shape perception more than it informs decision-making. As a content creator, I try to be intentional about that line. My process is less about pushing a reaction and more about presenting an angle, or idea that people can think about critically. I think good content should guide attention and not control it. At the same time, I also think audiences today have more responsibility than ever. With how much content we consume daily, it’s important to recognize when something is trying to influence emotion versus when it’s actually providing substance. Being able to identify that difference is what keeps people from being passively influenced.
Ultimately, I see marketing as a tool—it can be used responsibly to communicate value, or it can drift into manipulation if it relies too heavily on emotional distortion without substance behind it."
You have experience in being in front of the camera from years past. I can relate to this as I got bored, put together some ideas and began to open up to the public again. Talk to me, Webb, how was your experience in photography?
"I wouldn’t say I have extensive modeling experience. The moments that I did step into that space taught me a lot about confidence and putting myself out there. Especially as someone who’s naturally more introverted.
The first time was during a high school fashion show. I was wearing something I normally wouldn’t choose for myself. I remember being genuinely nervous walking out in front of everyone. But, once I did it and heard the applause, it felt like I broke through a mental barrier. It showed me that a lot of the fear was built up in my head more than anything. I had a similar experience when I went to New York for an introductory photoshoot with a modeling agency. They had me posing out on the street against brick walls, poles, and everyday city backdrops with people walking by. It felt very exposed, and at first I was definitely uncomfortable. But, once I settled into it, I realized that confidence isn’t about feeling ready, it’s about being willing to step into situations where you’re not. I’ve noticed that in other areas of my life as well. Whether it was speaking in church, participating in skits during Boy Scouts, or leading meetings as a supervisor at UPS, the initial nerves have always been the hardest part. Once you get past that, you realize you’re more capable than you thought.
Even though I’m not actively modeling now, I still respect the power of photography. A single photo can capture emotion, confidence, and identity without saying a word. And for me, those experiences weren’t just about modeling—they were about learning how to be comfortable being uncomfortable, and that’s something I still carry with me today."
The 21st Century has been an interesting time for humanity. Through digital technological advancements, the rise of a globalized network and adaptability. The biggest thing that comes to mind is the internet, while social media and now artificial intelligence are playing a part as well. How do you view the digital world from your lens?
"The digital world today is almost overwhelming in how much it offers. There’s an endless stream of information, content, and opinions. It’s easy to get lost in it. I think most people, myself included, have experienced that through things like mindless scrolling.
At the same time, that same abundance creates a level of opportunity that’s never really existed before. We now have access to tools, platforms, and audiences that used to be out of reach. In a way, everyone is a few clicks away, and if you understand how to communicate effectively, you have the ability to reach and impact people at scale. I also see the digital world as both an extension of real life and a world of its own. It reflects who you are, but it also gives you the ability to shape how you’re perceived. You can use it to express your authentic self, or you can build an image. In many cases, people are doing a mix of both. Because of that, I think it’s important to be intentional about your presence. How you present yourself, what you engage with, and even who you surround yourself with digitally because that environment influences your reality like your circle does.
Artificial intelligence is another layer of that. I see it as a powerful tool that can enhance productivity, creativity, and problem-solving whether that’s generating ideas, automating tasks, improving customer experiences, or supporting areas like healthcare and education. However, it’s still very new. There are real concerns around ethics, misinformation, and environmental impact, so it’s something that needs to be developed and used responsibly.
Overall, I think it all comes down to awareness and intention. The digital world can either distract you, or empower you. If you’re passive, it’s easy to get pulled in different directions. But if you’re intentional, it becomes a tool for learning, creating, and building something meaningful. I try to approach it with that mindset. Using it to grow and create value, rather than just consume."
How do you establish a work-life balance?
"For me, work-life balance is about setting boundaries, but also being realistic about when things need extra attention. I try to stay pretty structured during the day. When I’m working? I’m locked in and focused. When I’m off? I try to actually step away and not keep my mind half in work mode.
On a normal day, I’ll handle client work and anything I need to get done earlier in the day, then give myself time later to unwind. Spending time with my fiancée, being outside, or doing something that helps me reset. I’ve learned that if I don’t actually disconnect, I don’t really recharge.
That being said, I don’t think balance is always perfect. There are definitely times where work needs more attention when larger tasks arise, or things get busy. I’m okay with that, I just try not to let it become constant. At the end of the day, it’s less about splitting everything evenly and more about making sure I’m actually present in whatever I’m doing. Working when it’s time to work and resting when it’s time to rest."
Representation plays a huge part as human beings. Through how we dress, speech, our etiquette, while additionally for some of us having to break barriers. Why is standing out so crucial to maneuver in life?
"Representation plays a quiet, but constant role in how we move through the world. Whether we realize it or not, we are always being interpreted. By how we speak, how we carry ourselves, and now even by how we exist digitally. I’m not heavily active on social media outside of work, but even that absence is still a form of presence. In today’s world, you’re always being 'read' in some way. Over time, I’ve learned that you can shape your reputation, but it only holds weight if it’s rooted in something real. The more you try to manufacture an image that doesn’t match who you actually are, the more effort it takes to maintain it. Eventually, that tension will show. Authenticity is what makes a reputation sustainable.
As for standing out, I don’t think it always comes from being loud or different in obvious ways. Sometimes it’s much quieter than that. It can be choosing to actually listen when someone speaks instead of waiting to respond. It can be offering help when there’s nothing in it for you. It can be carrying yourself with a level of intention in spaces where most people are operating on autopilot.
In that sense, standing out isn’t really about attention. It’s about presence. The impact you leave on people without trying to force it. Ironically, the less you try to perform it, the more real it becomes."
A lot to be thankful for at this point in life. You’ve sacrificed a lot in your early 20’s to stay ahead of the game. Not many take on leadership roles at a young age let alone don’t know where to begin. What has been the driving force in leading you to become the person that you are today?
"I’m really thankful for where I’m at in life right now, and I don’t take it for granted. I’ve been fortunate to grow up around people who guided me in different ways. Through family, church, and work experiences. Each of those environments shaped a part of who I am today.
A lot of my drive comes from reflection. I’ve learned that real growth usually happens when you put yourself in uncomfortable situations, and choose to figure things out anyway. The earlier you’re willing to do that, the more you start to grow through it. I’ve also come to value effort over everything else. People say 'high risk, high reward,' but I see it more as high effort, high reward. Consistency and discipline are what actually move you forward over time.
As for leadership, I believe we can be influenced into it as well as develop it on our own through experience. I’m grateful for the people who put that battery in my back early on, and over time I’ve learned that leadership really comes from repetition. Stepping up even when you’re unsure and building confidence through action.
At this point, I’m just trying to stay grounded, keep learning, and move with intention, while appreciating the people and experiences that got me here."
Thank you Hunter for taking the time to talk to me today. Do you have any words of encouragement or motivation for people? Any last words?
"I’d just say be authentic to who you are. The more genuine you are, the easier it is for the right people. The ones who actually relate to you will find you and connect with you in a real way.
I also encourage you to take care of your mental health. Don’t ignore signs of stress or burnout when they show up. Work will always be there, but if your mental health starts slipping, it’s a lot harder to recover from that than it is to take a step back when you need to.
Don’t overlook the small wins. Every step forward matters more than it seems in the moment. Every task finished, every day you show up, every bit of progress is stacking toward something bigger. Slow motion is better than no motion, and that’s what really matters day-to-day.
Lastly, don’t be afraid to ask for guidance. It takes humility, but it’s one of the fastest ways to set yourself up for long-term success. You don’t lose anything by asking. You only gain clarity, direction, and understanding. At the end of the day, it’s not about having it all figured out right now, it’s about staying true to yourself while you figure it out.
Thank you for having me!"
Hunter Webb
Business Page: https://www.facebook.com/hunterdoesmedicare
LinkedIn: https://www.linkedin.com/in/hunterknowsmedicare/
Email: hunter@health360pro.com
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