EPISODE · Oct 29, 2025 · 1H 3M
Gina L. Osborn on Rebrands, Resilience, and Results
from Conversations with Rich Bennett · host Rich Bennett / Gina L. Osborn
Retired FBI Assistant Special Agent in Charge Gina L. Osborn takes us from Cold War counterintelligence in Europe to leading one of the largest FBI cyber & counterterrorism programs in Los Angeles—including the response to the 2014 Sony Pictures hack. She shares how “Maverick moves” and servant leadership shaped her teams, why she blew the whistle at LA Metro, and what it really takes to break barriers in male-dominated fields. If you want real-world lessons on courage, culture, and leading through crisis, this one delivers. Sponsored by American Auto Repair Guest Bio: Gina L. Osborn is a retired FBI Assistant Special Agent in Charge and former U.S. Army counterintelligence special agent. She led major organized crime, counterterrorism, and cyber operations in Southern California (including the Sony hack response), later serving as Chief Safety & Security Officer at LA Metro. Gina is a TEDx speaker, leadership mentor, and host of the Making Maverick Moves podcast, where she champions bold, authentic leadership.Main Topics: · Cold War origins: Army counterintelligence, undercover work across Europe· Transition to the FBI: Little Saigon organized crime → post-9/11 counterterrorism· Building/leading cyber squads; responding to the Sony Pictures (2014) attack· Evolving from “lead from the front” to servant leadership for technical teams· LA Metro chapter: contracts, accountability, getting fired—then public advocacy that sparked change· Defining “Maverick moves”: the door metaphor, deciding which hills are worth it· Women in leadership: rewriting the stories we tell ourselves; ignoring “they”· Public speaking/TEDx: preparation, constraints (memorization, “stay on the X”), and takeaways· Rebranding a show: Lead Like a Lady → Making Maverick Moves and audience shifts· Mentorship legacy; longevity and caring for the future you (shout-out to Gina’s mom) Resources mentioned: · Making Maverick Moves (podcast) — rebranded from Lead Like a Lady· GinaLOsborn.com (stated as “Gina L Osborn dot com” in the show)· Gina on LinkedIn, YouTube, TikTok (per guest plug)· Sony Pictures hack (2014) — case context referenced· LA Metro (security, policing discussion)· Episode Sponsor: American Auto Repair· Supporter: Full Circle Boards· Supporter: Sincerely Sawyer Photography Send us Fan MailCelebrate the Magic of Words in Bel Air, Maryland!https://bookfairatbelair.org/American Auto Repair Sales & ServicesAmerican Auto Repair & Performance was founded on the basic idea that everyone deserves respect. It Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the showRate & Review on Apple Podcasts Follow the Conversations with Rich Bennett podcast on Social Media:Facebook – Conversations with Rich Bennett Facebook Group (Join the conversation) – Conversations with Rich Bennett podcast group | FacebookTwitter – Conversations with Rich Bennett Instagram – @conversationswithrichbennettTikTok – CWRB (@conversationsrichbennett) | TikTokSponsors, Affiliates, and ways we pay the bills:Hosted on BuzzsproutSquadCastSubscribe by Email
What this episode covers
Retired FBI Assistant Special Agent in Charge Gina L. Osborn takes us from Cold War counterintelligence in Europe to leading one of the largest FBI cyber & counterterrorism programs in Los Angeles—including the response to the 2014 Sony Pictures hack. She shares how “Maverick moves” and servant leadership shaped her teams, why she blew the whistle at LA Metro, and what it really takes to break barriers in male-dominated fields. If you want real-world lessons on courage, culture, and leadi...
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Gina L. Osborn on Rebrands, Resilience, and Results
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