Interviews and Reviews

Navigating the Skies: An Interview with Barry Oberholzer

navigating the skies an interview with barry oberholzer

Helicopter Pilot, Entrepreneur & Humanitarian

Aviation specialist, Barry Oberholzer is a skilled helicopter pilot who has worked for various elite aviation companies. A global humanitarian and entrepreneur, he has worked in the United States, South Africa, and the Middle East. He attended the American Military University in 2012 and has studied at the University of South Africa as well. Barry Oberholzer is the author of the bestselling book, The Black Market Concierge.

What inspired your professional pursuits, in adolescence and as you grew into adulthood?

In my younger years, I was excited to play rugby professionally. That dream lasted for nearly a decade, and I represented the United States Eagles, attending the age group World Cup in Italy and Chile with the U.S. team. While in Italy, we visited the Air Force base as guests of the base’s commander, and I was selected to fly in an F14 trainer. It was a life-changing moment.

My professional sports pursuits were soon left behind for a career as a helicopter pilot and aviation consultant. A passion for aviation has always been there, even when I was playing rugby and from a young age, but once I’d gone up in F14, that was it for me. I knew I’d fly the rest of my life. Flying has informed my entire career. It led me to my experiences as a confidential informant, and it was vital to my philanthropic and service efforts.

How did your time as a confidential informant in the Middle East influence your humanitarian initiatives?

My time as a confidential informant was a surreal, immersive experience, unlike anything I’ve experienced since, and truly hard to describe to others who have not known the life. The primary directive in that space is to gather intelligence and deliver it to those who require it—any time, under any circumstance. That life and that role require engaging with various people, working with them and gaining trust, then gathering information to pass on. There’s a real element of danger and intrigue, and as a young, unmarried man, it was a really fulfilling, exciting career choice.

As I look back, I can identify these unimaginable risks and choices that often make me wonder what I was thinking, but in the moment, that life and work were what I wanted to be part of, what I was committed to. It was a constant adrenaline rush. I knew what I was doing would affect the greater good, but I was constantly at risk, and anything and everything could go wrong, at any moment.

My greater goal and higher purpose in it all? It was helping our government stop foreign groups from obtaining sensitive military equipment. Seeing how the rest of the world works, changes you. It gives you a new perspective and a drive to help, however, you can. That was the takeaway from my time as an informant—helping those whose lives are decimated by unmanaged power is vital.

Of the many hats you wear, personally and professionally, what are the most important?

I am a husband and a father, first and foremost. That part of my life is important and dear to me, and I keep it close, personal, and private. These personal aspects of my life drive the other bits. I am an entrepreneur and a pilot. That’s important. I’m a philanthropist, that’s just as important and absolutely informed by the work I’ve done, the skills I have, and the way I want my family to see that this world can be changed and can be helped. Looking back at my experiences, I’ve had the honor of working with people from all walks of life, all sectors, and from very extreme socio-economic backgrounds.

At the end of the day, working toward the greater good is key, and that requires resources, time, specialized talents, and money. I have been privileged to lend to efforts in the Middle East and other spaces around the globe, and I am committed to continuing efforts to make small changes with a big impact in any way I can.

Key Takeaways

  • Do what you can, when you can. Push when you can. Support when you can. Stand up, whenever you can. The world needs your focus on the greater good.
  • The skills you learn are more than just a paycheck. They’re a way to support a better world and level the playing field for others.
  • Celebrate the small wins, every single day. Those compounded wins are how we create big change.
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