On the Right Stack - Episode 11 - Benjamin Bressler, Regional Airline Pilot

In this episode of On the Right Stack, Jason steps away from technology to tell a story about dreams. His guest, Benjamin Bressler, recently became a pilot for a regional airline, capping a goal he first set at age ten. Benjamin walks through the training hurdles, a failed first check ride, and the financial and personal sacrifices that came with chasing an expensive dream. He describes the shock of the job offer, his first takeoff, and the imposter syndrome of walking through the terminal in uniform. A grounded reminder that persistence pays off.

What is On the Right Stack?

On the Right Stack is a podcast for business leaders, executives, and technology decision-makers who want to cut through the noise and build technology strategies that actually work. Each episode features candid conversations with seasoned operators, CTOs, CISOs, and CEOs sharing hard-won insights on tech strategy, transformation, and leadership. We don’t talk about technology for technology’s sake — we talk about the decisions that move businesses forward. Hosted by Right Stack Advisors, where smarter technology decisions start.