Episode Summary

Title: Inventing the Journey: Tony Jefferson on Building a Travel Platform from the Ground Up

In this powerful episode of Battlefield to Business, retired Air Force Master Sergeant Tony Jefferson takes us through his entrepreneurial evolution—from military structure to building a personalized travel tech platform, Traveling Session.

With over two decades in service, mostly overseas, Tony always had a passion for discovering new places. But transitioning from cybersecurity to startup founder was anything but linear. He candidly shares how he went from failing out of college to finding purpose through travel, learning to code, building a business with zero blueprint, and growing from each stumble along the way.

We dive into:

• How military life prepared (and didn’t prepare) him for entrepreneurship
• The massive mindset shift from orders to ownership
• The importance of self-awareness and personality testing
• Why following your passion isn’t enough—you also have to solve a real problem
• The challenges of being an inventor with no roadmap, and learning to outsource and pivot
• Building a platform that recommends destinations based on who you are as a traveler
• Redefining success beyond income—toward happiness, freedom, and family

Whether you're in uniform, out of uniform, or dreaming about your next chapter—Tony's journey will light a fire under your feet and remind you that you're not starting over. You're building something new.

Explore Traveling Session: https://travelingsession.com