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Tony Jefferson
Founder, TravelingSession.com
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About me

Most platforms give generic travel recommendations. TravelingSession.com helps you find destinations that match your Travel Style & connect with people who travel like you.

I'm introducing TravelingSession.com, The Social Platform for Personalized Travel Discovery, built on the belief that "Travel Should Be About the Traveler, Not the Destination."

My mission is to blend community and technology to create more intentional and meaningful travel experiences, all guided by a simple promise: To make travel more personal, intimate, and discerning.

Always down to connect with DMOs, brands, and creators who are tired of the cookie-cutter travel advice.

Why did you join the community?

Simple: You have to be where the innovators are. I’m building a platform that challenges the 'generic' status quo of the travel industry. You can’t do that in a silo. I joined to connect with the DMOs, creators, and tech leaders who understand that the future of travel is personalized, not one-size-fits-all. I’m looking for partners who see where the industry is going and want to get there first.

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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