What's Your Story with Jaime & Stan

What’s Your Story, Brent Osborn? Tanks, teamwork, and leading with purpose

Episode Summary

In this powerful and down-to-earth episode, we sit down with Brent Osborn, a former U.S. Army officer turned corporate leader and community mentor. Brent shares the pivotal moments of his life from leading a reconnaissance platoon in Iraq to working on Wall Street and coaching youth sports all while holding tightly to the values of trust, service, and resilience. Whether he’s making hard choices for the sake of family, mentoring at-risk youth, or reflecting on the lessons learned in combat, Brent brings a grounded and thoughtful perspective to what it means to lead with purpose in every chapter of life.

Episode Notes

In this powerful and down-to-earth episode, we sit down with Brent Osborn, a former U.S. Army officer turned corporate leader and community mentor. Brent shares the pivotal moments of his life from leading a reconnaissance platoon in Iraq to working on Wall Street and coaching youth sports all while holding tightly to the values of trust, service, and resilience.

Whether he’s making hard choices for the sake of family, mentoring at-risk youth, or reflecting on the lessons learned in combat, Brent brings a grounded and thoughtful perspective to what it means to lead with purpose in every chapter of life.

Key topics discussed

Military service and leadership

• Brent’s journey into the U.S. Army via an ROTC scholarship and his deployments to Korea and Iraq.
• What it was like to lead a platoon in high-pressure situations and the burden of responsibility for his team’s lives.
• How the military shaped his values around teamwork, trust, and mission-first leadership.

The transition to civilian life

• Leaving active duty and entering the corporate world at Lehman Brothers and later Fidelity Investments.
• The emotional and cultural adjustment from combat to corporate, and how he found new purpose outside the military.

Navigating difficult decisions

• Turning down a rare opportunity in special operations to prioritize being present for his family.
• Walking away from a long-standing job due to misalignment with leadership and finding the courage to start something new.

Community advocacy and mentorship

• Brent’s passion for coaching and community work through the Police Athletic League (PAL).
• How his own childhood and early mentors shaped his dedication to giving back and providing safe, positive environments for youth.

Parenting and passing on values

• As a father of four, Brent shares how he teaches his kids about resilience, kindness, and leadership through service.
• Why he believes strong relationships are the foundation for making a lasting impact.

Memorable quotes

“The military taught me to trust the person next to me, even if we didn’t see eye to eye.” – Brent Osborn
“The relationships you build at every stage of life are what truly matter.” – Brent Osborn
“Giving back isn’t just about helping others; it’s about growing yourself.” – Brent Osborn

Where to listen & watch:
YouTube: https://youtu.be/jj-Wwm0gcGw
Apple Podcasts: https://tinyurl.com/mtkxjcez
Spotify: https://tinyurl.com/yhkw24v7
Amazon Music: https://tinyurl.com/2hnfynpm

Connect with Brent:
Learn more about PAL: https://www.nationalpal.org/
Connect with Brent Osborn: https://www.linkedin.com/in/brent-osborn-cfa-84175/
Recommended book: Leaders Eat Last by Simon Sinek

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