Meet Jeremy Harper

We had the good fortune of connecting with Jeremy Harper and we’ve shared our conversation below.

Hi Jeremy, we’d love to hear more about how you thought about starting your own business?
Starting my own agency wasn’t a decision I made overnight—it was the natural next step in a journey that began more than a decade ago. I’ve been helping families plan vacations since 2013 while also working full-time as a high school teacher and softball coach. During that time, I was fortunate to build a successful travel business, booking millions in vacations (No I don’t make millions) and, more importantly, building lasting relationships with my clients.

Before becoming a travel advisor, I had the privilege of working as a Disney Cast Member. In 2020, I was honored to receive the Disney Legacy Award, one of the company’s highest recognitions for Cast Members. While I no longer work for Disney, the lessons I learned there about service, attention to detail, and creating meaningful experiences have stayed with me. Those principles continue to shape how I serve every client today, whether they’re traveling to a Disney destination or anywhere else in the world.

As my business grew, I realized I wanted the opportunity to build something that was truly my own. I wanted to create a brand that reflected my personality, my passion for travel, and the level of service I strive to provide. Launching Talking Umbrella Travel gives me the freedom to shape every part of the client experience while continuing to do what I love most—helping people create memories that will last a lifetime.

My background as a teacher has had a tremendous influence on how I approach travel planning. Just as every student learns differently, every traveler dreams differently. My job is to listen, understand what matters most to each client, and create a vacation that is uniquely theirs rather than offering a one-size-fits-all itinerary.

At the end of the day, this wasn’t about leaving something behind—it was about building on everything I’ve learned over the past twelve years. I’m incredibly grateful for the mentors and opportunities that helped me get here, and starting my own agency is simply the next chapter in a journey that’s always been about helping people experience the ENTIRE world… Including Walt Disney World

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
Travel has always been about people for me.

When I first entered the travel industry in 2013, I wasn’t simply looking for a career—I found an opportunity to help people create some of the most meaningful memories of their lives. Whether it’s a child’s first trip to Walt Disney World, a honeymoon, an anniversary cruise, or a once-in-a-lifetime European adventure, I’m honored every time a client trusts me with those moments.

What sets me apart is that I don’t see myself as someone who sells vacations. I see myself as someone who listens. Every family, every couple, and every traveler has a different story, a different budget, and a different dream. My goal is to understand what’s important to them and design a vacation that feels like it was created just for them.

Professionally, my journey has been anything but traditional. I’m a full-time high school teacher and softball coach, and I’ve built my travel business during evenings, weekends, summers, and every free moment in between. Those careers actually complement one another. Teaching has taught me patience, communication, and the importance of truly listening to people. Coaching has shown me how to adapt, solve problems under pressure, and always put the team first. Those same skills have become the foundation of how I serve my travel clients.

One of the most influential experiences of my career was working as a Disney Cast Member. I was honored to receive the Disney Legacy Award (Blue Name Tag), one of the company’s highest recognitions for Cast Members. While I no longer work for Disney, the principles I learned there—attention to detail, exceeding expectations, and making every guest feel valued—continue to shape the way I run my business today. I strive to make every client feel like they’re my only client.

Has it been easy? Not at all. Building a business while teaching full-time has meant sacrificing evenings, weekends, and vacations. There have been countless late nights answering emails after grading papers, planning dream vacations after softball games, and learning every aspect of running a business one step at a time. But every challenge has reinforced how much I love what I do.

Today, after helping clients plan vacations to destinations around the world, I’m excited to begin the next chapter by launching Talking Umbrella Travel as my own independent agency. It’s a dream that’s been years in the making.

If there’s one thing I want people to know about my brand, it’s this: Travel isn’t about checking destinations off a list—it’s about the stories we collect, the people we share them with, and the memories that stay with us long after we’ve unpacked our suitcases. My job is to help create those stories, one journey at a time. I’m not in the travel business. I’m in the memory-making business. I don’t book vacations—I help people write the stories they’ll be telling for the rest of their lives.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
As a travel advisor, I believe every destination has its own story. My favorite part is helping people discover it. If my best friend were visiting Southeast Louisiana for a week, I’d want them to experience more than just the sights—I would want them to experience the culture and the people that make this part of the country so special.

We’d start our mornings with beignets and coffee before exploring the French Quarter in New Orleans, taking in the architecture, the street musicians, and the incredible history around every corner. We’d spend time strolling through the Garden District, ride the St. Charles Avenue streetcar, and enjoy live jazz on Frenchmen Street after dinner.

Of course, no visit would be complete without great food. We’d have chargrilled oysters at Drago’s, a classic po’boy from a local favorite, fresh seafood along Lake Pontchartrain, and finish at least one evening with bread pudding or bananas foster. In Louisiana, every great memory seems to begin around a table.

I’d also take them beyond New Orleans. We’d spend a day exploring the small towns and scenic beauty of Tangipahoa Parish, visit local farmers markets, and, if the timing was right, catch one of our area’s incredible festivals. One of the things I love most about Louisiana is that there’s always a celebration happening somewhere.

If they enjoy the outdoors, we’d take a swamp tour to experience the beauty of our wetlands, learning about the wildlife and ecosystems that make this region unlike anywhere else in the country.

What I love most about traveling—and about sharing my own home—is that the best experiences usually aren’t the biggest attractions. They’re the conversations over dinner, the local musician you stumble upon, the hidden bakery someone recommends, or the sunset you weren’t expecting. Those are the moments people remember long after the vacation ends.

That’s actually how I approach planning travel for my clients. Anyone can book a hotel room. I want to help people discover the experiences they’ll still be talking about years later.

Who else deserves some credit and recognition?
I wouldn’t be where I am today without the support and encouragement of so many people over the years.

First and foremost, my wife and children deserves more credit than anyone. Starting a business while teaching full-time and coaching means there are plenty of evenings and weekends spent planning vacations, answering client questions, and working behind the scenes. They have been my biggest supporters, my sounding board, and the people who have encouraged me to chase this dream, even when it meant taking a leap into the unknown.

Professionally, I’m incredibly grateful to the mentors and agency owners I’ve had the privilege of working with since I entered the travel industry in 2013. Each one taught me something different about serving clients, building relationships, and growing a business. Those experiences laid the foundation for what has become Talking Umbrella Travel, and I wouldn’t be here without them.

I’d also give a shoutout to my students and athletes. That may sound a little unusual, but teaching and coaching have made me a better travel advisor. Every day, I learn the importance of listening, communicating, solving problems, and meeting people where they are. Those same skills are at the heart of planning a great vacation.

Finally, I’d like to recognize my clients. The fact that families have trusted me with some of the most important moments of their lives—their honeymoons, anniversaries, family vacations, and once-in-a-lifetime adventures—is something I’ll never take for granted. Their confidence in me has allowed this dream to grow from a side passion into my own agency, and for that I’ll always be grateful.

Website: https://www.talkingumbrellatravel.com

Instagram: @talkingumbrellatravel

Facebook: https://facebook.com/talkingumbrellatravel