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Tony Jefferson
Founder, TravelingSession.com
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About me

I’m Tony, a 21-year U.S. Air Force veteran, IT and cybersecurity professional, and founder of TravelingSession.com.

I spent most of my career overseas, living in Japan, Germany, and South Korea which gave me a lot of opportunities to travel. I noticed there was a gap between my favorite places and the places the media pushes.

That led me to create TravelingSession.com — The Social Platform for Personalized Travel Discovery.

When you look for places to travel online, is that recommendation you got meant for you, or are they recommending the same place to everyone. Most travel sites act like we're all the same.

TravelingSession.com is the social platform that helps you find destinations that match your travel style by connecting you with people who travel like you, because the best recommendations come from people who travel the way you do.

Our mission is to blend community and technology to guide one simple idea: Travel should be meaningful, intentional, and discerning.

A big part of what we’re building is also giving travel creators and experienced travelers a home for their content and travel history.

And I’m always interested in meeting people who are thinking about where travel discovery, social media, and AI are headed next.

Travel should be about the traveler, not the destination.

Why did you join the community?

I joined to meet more people who are shaping the travel industry — especially travel creators and influencers. I’m also looking for people who might be a great fit for our Featured Traveler program. I’m interested in learning from other people and finding ways to collaborate. If you’re a travel creator, influencer, photographer, blogger, frequent traveler, or someone with a great travel story, feel free to hit me up.

What is your favorite travel destination?

It’s a toss-up between Okinawa and Malta. Okinawa hits home because it was my first overseas post with the Air Force—it changed my perspective on everything. Malta? I just dig the vibe.

But to be real: I have a love/hate relationship with this question. It implies there’s one 'best' place. There isn't. Okinawa was perfect for me because of my specific Travel Style. That’s the philosophy behind TravelingSession.com. It shouldn't be about the destination; it should be about the traveler.

Where do you dream of traveling to?

Bora Bora. No long explanation need for this one. Either you get the appeal or you don’t—and honestly, that’s the whole point.
Travel is personal.

What was your first travel job?

I was in the US Air Force for 21 years, 11 years overseas. I lived in Okinawa, then up in Aomori Prefecture. Then Germany—just north of Trier—and Seoul for a year.

The best thing about living overseas is the proximity. Suddenly, the rest of the world feels a lot closer. A weekend trip to Brussels or a quick flight to Macau becomes normal. Living locally in those spots didn't just rack up miles; it taught me how to actually navigate the world.

What do you want to learn more about?

The psychology behind the booking.

I want to know exactly what makes the individual traveler tick. Why do they choose this spot over that one?

We are moving into a world where people are chasing meaningful experiences, not just photo ops. I want to go deep on that shift. The better we understand the why—the real human drivers behind the decisions—the better we can build the tools to help them find it."

Three words that describe why we should travel?

Travel is Self-Discovery

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