We recently had the chance to connect with Tony Jefferson and have shared our conversation below.
Tony, a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: Have you ever been glad you didn’t act fast?
It’s not so much that I’m glad I didn’t act fast — it’s that I had to learn when to go fast. For a while, entrepreneurship was being sold as this flashy, high-speed game — raise capital quickly, scale fast, make money overnight. But I realized, it’s hard to go fast when you’re playing the guessing game. Going fast without a clear vision will probably do more harm than good.
There were definitely opportunities early on where I could’ve chased quick revenue, but it would’ve pulled focus from the bigger vision. I could’ve gone after funding, too, but that might’ve meant losing control of the company before it was ready.
What I’ve learned is that before you hit the gas, you’ve got to be crystal clear on where you’re going. Once the vision is locked in and the plan is solid, then it’s time to move fast — with intent and purpose.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Tony Jefferson, founder of TravelingSession.com. While serving 21 years in the Air Force, I had the chance to live and travel all over the world. I kept noticing that my favorite trips weren’t the popular places you hear about all of the time. They were often hidden gems I had never heard of. It’s not that the popular destinations are bad places to visit, but there are places that just better fit my vibe.
That’s what led me to build Traveling Session. It’s a social platform that helps people discover places that actually fit their travel style. Places that are right from them, not just trending. I believe travel should be about the traveler, not the destination.
Most travel platforms just push what’s popular, which funnels a ton of people to the same handful of destinations. We’re different. We’re about the people. We help travelers connect through real experiences and honest reviews so it’s not just about going somewhere — it’s about going somewhere that’s right for you.
Right now, I’m focused on growing the community and improving our personalization features so we can make travel discovery more human again. It’s been a long journey getting here, but I’m proud of what we’re building and the kind of travelers we’re attracting — people who care about authenticity, culture, and connection.
Amazing, so let’s take a moment to go back in time. What did you believe about yourself as a child that you no longer believe?
Growing up, I believed the formula for success was simple: go to school, get a job, work hard, and make money. I saw a lot of people who do very well using this model, but something didn’t quite sit right with me. I never saw anyone living the life I wanted to live.
Back then, entrepreneurship wasn’t really something people talked about, so when I started my own company, I had to learn a lot from scratch. But honestly, what I had to unlearn turned out to be just as important.
I had to learn that cash isn’t always king — ownership and assets give you way more leverage than money ever could.
I had to learn that time is limited — if your only income comes from trading time for money, there’s always a ceiling on what you can earn. And you’re just one illness, natural disaster, or market downturn away from losing that source of income.
And probably the biggest one: spend money to buy back your time. You can save a few dollars doing everything yourself, but that’s not how you grow. You can’t make CEO money doing minimum-wage tasks.
Was there ever a time you almost gave up?
Oh yeah — I had to learn early that entrepreneurship is not for the weak.
I remember one night I bricked the platform hard — that’s nerd talk for breaking a computer so bad it’s basically a paperweight. I couldn’t access the front end or the back end. I couldn’t even remote into the server. I’m a pretty resilient person, but for someone with a tech background, that one hurt. I shut the door to my office and didn’t go back in for two days.
Public Service Announcement: never, ever run new code on your live production website.
Once I pulled myself together, it took a few days to get everything back up and running. The very first thing I did after that? I moved everything to a managed server and hired a developer. Best money I ever spent.
Even though I have a tech background, I realized my job isn’t to be the technician — it’s to grow the company. Lesson learned.
Sure, so let’s go deeper into your values and how you think. Is the public version of you the real you?
It wasn’t always, but it is now.
When I was in the military, they had a clear definition of what a “perfect Airman” looked like — and to be successful, you had to fit that mold. You didn’t get to choose how you talked, how you dressed, or even how you cut your hair. They told you what your principles were, what your core values were. In a way, it was easy, because they told you exactly who they thought you were supposed to be.
Even growing up, parents and teachers try to shape you into what they think a productive member of society looks like.
Entrepreneurship, though, is a completely different world. I didn’t realize how much of an introspective journey it would be. The hard part is that there’s no one to tell you who you’re supposed to be — and no one really warns you how much of you shows up in your company.
I struggled with that early on, and it showed. I tried to mold myself into what I thought a “perfect entrepreneur” should be. But it doesn’t work that way. You have to figure out who you are, lean into your strengths, and get comfortable with your weaknesses.
Once I figured that part out, everything else just started clicking. It’s hard to explain, but I haven’t met too many successful entrepreneurs who haven’t had that same exact aha moment.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. Are you doing what you were born to do—or what you were told to do?
I think I’m doing what I was born to do — at least, it feels like it.
My only real stresses come from my own impatience and occasional procrastination. The company’s gaining traction, the work is challenging enough to keep me fully engaged, and I’m still obsessed with it enough that I honestly can’t remember the last time I felt burnout.
My wife usually has to come drag me out of the office long before I feel like stopping.
I don’t really know how to gauge whether I’m “doing what I was born to do” or not, but I can tell you this — I’m doing what I want to do, and that feels pretty good.
Contact Info:
- Website: https://travelingsession.com/
- Instagram: https://www.instagram.com/travelingsession/
- Linkedin: https://www.linkedin.com/in/tony-jefferson-traveling-session/
- Twitter: https://twitter.com/Travel_Session
- Facebook: https://www.facebook.com/travelingsession/
- Youtube: https://www.youtube.com/@TravelingSession
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