From FBI to Fearless | Gina L. Osborn's Story
05/12/25 • 54 min
Follow Gina!: https://www.instagram.com/ginalosborn/
Picture the resolve it takes to track Soviet spies across Cold‐War Europe, then rise through the ranks of one of the world’s premier law‐enforcement agency—only to step onto a TEDx stage and turn those lessons into a talk that moves strangers to act. That constellation of careers belongs to Gina L. Osborn. Gina’s sister, Lisa Osborn, guides today’s conversation. For three decades Gina has served country and community, proving that duty and daring are not mutually exclusive. In this episode you’ll hear Gina’s most gripping field stories and, more importantly, the frameworks she uses to turn adversity into advantage—tools you can apply to elevate your own life and career. If you’ve ever been told to stay in your lane and felt the instinct to build a brand‐new highway instead, this conversation is for you.
00:00 – From Cold War to TEDx: Meet Gina L. Osborn
03:48 – Her first Maverick Move at 16
06:39 – A stranger in the library changed her life forever
09:55 – Getting into the FBI during a hiring freeze
14:07 – Her first big case: crashing an organized crime ring
18:49 – Life at FBI HQ & inspecting field offices
22:56 – Inside the Sony hack investigation (North Korea)
30:55 – The real story behind LA Metro's safety crisis
36:56 – Fired for telling the truth—what happened next
39:37 – Fighting for Metro’s own police force
42:58 – Rebuilding after the fallout: TEDx, podcast & purpose
51:29 – How to make your own Maverick Move
Follow Gina!: https://www.instagram.com/ginalosborn/
Picture the resolve it takes to track Soviet spies across Cold‐War Europe, then rise through the ranks of one of the world’s premier law‐enforcement agency—only to step onto a TEDx stage and turn those lessons into a talk that moves strangers to act. That constellation of careers belongs to Gina L. Osborn. Gina’s sister, Lisa Osborn, guides today’s conversation. For three decades Gina has served country and community, proving that duty and daring are not mutually exclusive. In this episode you’ll hear Gina’s most gripping field stories and, more importantly, the frameworks she uses to turn adversity into advantage—tools you can apply to elevate your own life and career. If you’ve ever been told to stay in your lane and felt the instinct to build a brand‐new highway instead, this conversation is for you.
00:00 – From Cold War to TEDx: Meet Gina L. Osborn
03:48 – Her first Maverick Move at 16
06:39 – A stranger in the library changed her life forever
09:55 – Getting into the FBI during a hiring freeze
14:07 – Her first big case: crashing an organized crime ring
18:49 – Life at FBI HQ & inspecting field offices
22:56 – Inside the Sony hack investigation (North Korea)
30:55 – The real story behind LA Metro's safety crisis
36:56 – Fired for telling the truth—what happened next
39:37 – Fighting for Metro’s own police force
42:58 – Rebuilding after the fallout: TEDx, podcast & purpose
51:29 – How to make your own Maverick Move
Previous Episode
Build Your Port Before Your Ship Comes In
In this Power Moves and Leadership Lessons episode, we're talking about a lesson that separates the Mavericks from the Masses: It doesn't matter if your ship comes in if your port isn't built to dock it. You've heard the saying, "You're ship will come in." That sounds great, right? But here's the real question: When that ship arrives, will you be ready? Opportunities don't wait for you to get ready. It shows up, and if you don't have the foundation, the skills, and the mindset in place beforehand, that ship will sail right past you. So today, we're breaking down why preparation is everything, how your port protects you in the storms of life, and I'll give you three powerful ways to build your port NOW so you're ready when your moment arrives.
Next Episode
Purpose, Reinvented: Leading with Heart, Healing with Work | Bonnie Pomish, CEO of Working Wardrobes
Follow Gina: https://www.instagram.com/ginalosborn/
A powerful conversation on second chances, purpose, and building dignity through workforce reentry. What does it take to follow in the footsteps of a legendary founder — and make the mission your own? In this inspiring episode, Bonnie Pomish, CEO of Working Wardrobes, shares her bold journey of stepping into leadership with authenticity, compassion, and courage. From empowering veterans and formerly incarcerated individuals to redefining perfectionism and building a values-driven team, Bonnie reveals what it truly means to lead with heart. If you've ever struggled with self-doubt, leadership identity, or finding your purpose — this conversation is for you.
🔗 Donate or get involved with Working Wardrobes: https://www.workingwardrobes.org
Timestamps:
00:00 – Intro: Who is Bonnie Pomish?
02:02 – The mission of Working Wardrobes
04:15 – Serving veterans and translating military skills
06:22 – Parallels between reentry from military & incarceration
07:24 – Succeeding founder Jerry Rosen & "wearing your own shoes"
12:04 – Leading with vulnerability and strengths-based leadership
20:55 – Being a recovering perfectionist & embracing 1% growth
23:06 – Learning through failure and trusting team members
34:16 – What a vulnerable workplace culture looks like
37:54 – Advice for future leaders: be a good human
43:04 – Ways to support Working Wardrobes (time, talent, treasure)
47:25 – Bonnie’s biggest maverick move: moving to CA with no plan
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