Episode Overview

Title: Fearless: Former FBI Leader Gina L. Osborn on Power, Labels & Leadership
Podcast: Miss Understood with Rachel Uchitel
Guest: Gina L. Osborn – Former FBI Assistant Special Agent in Charge, Army Counterintelligence, Leadership Speaker, Host of “Making Maverick Moves”
Release Date: December 22, 2025

This episode dives deeply into what it means to be a woman in high-powered, male-dominated environments—in Gina Osborn’s case, the U.S. Army and the FBI. Rachel Uchitel and Gina discuss fearless leadership, how women are labeled and misunderstood as they gain power, the realities of cyber threats, combating imposter syndrome, “mean girls” in the workplace, and how to challenge systems that weren’t designed for everyone. Gina shares personal stories, actionable leadership advice, and hard truths about the risks and rewards of speaking up.

Key Discussion Points & Insights

1. Women in Power: Admired vs. Threatening (02:20)

• Rachel frames the episode by addressing the phenomenon where women’s competence is initially admired but later viewed as threatening:

  “There is a very specific moment that happens to women in positions of power. It's the moment when competence stops being admired and starts being threatening...when a woman leads with certainty instead of softness...the narrative shifts.” (02:20)

• Gina’s career—spanning Army counterintelligence to the FBI—exemplifies navigating spaces where women are often “the only one in the room.”

2. Early Inspiration and Breaking Into Law Enforcement (06:18)

• Gina was fascinated by espionage from a young age, wanting to become an “international woman of intrigue.”

  “As a young child and a teenager, I always say that I wanted to be this international woman of intrigue. I was absolutely fascinated with everything that was going on in the Cold War.” (06:18)

• A chance encounter at a college library led her to the Army’s counterintelligence program, setting her on the path to law enforcement.

3. Navigating the ‘Man’s World’ of the FBI (09:47)

• Gina entered the FBI in 1996 when only 14% of agents were women.
• Being “the only woman in the room” was her norm in both the Army and the FBI.
• Early perfectionism gave way to realizing that internalized pressure was often self-imposed:

  “The things that we say in our heads, those types of stereotypes, I think that we're giving them to ourselves because the voices in our heads are the loudest.” (09:47)

4. Powerful Role Models and Defying the Glass Ceiling (11:05)

• Gina credits her mother for modeling fearless risk-taking, entering real estate in the 1970s, and underscoring, “If we buy into all of these things that we're supposedly told or we learn, that really slows us down.” (11:05)

5. Espionage: Then & Now (13:03)

• Gina recalls chasing spies across Europe in her 20s.
• Describes working on a major espionage sting during Desert Storm, leading to the arrest of Albert Sombilay.

  “It was a really fascinating time to follow him...he sold his soul for $3,000 and wound up getting 34 years in prison.” (13:03-14:22)

Notable Segments & Timely Topics

Cyber Threats: Sony Hack, Ransomware, Crimes Against Children (15:26–21:31)

• Gina led the LA FBI’s cyber and computer forensics unit, working high-profile incidents like the 2014 hack of Sony Pictures by North Korea.

  “North Korea used psychological warfare against Sony Pictures...all of their information...had been taken” (15:26)

• Cyber attacks on hospitals and corporations happen more often than the public realizes, often undisclosed due to reputational risk.

  “Companies don't want it to get out that these things are happening.” (17:24)

• Organized threats from nation states (China, Iran, North Korea, Russia) are a daily reality.

  “They have armies of people who are doing this all day, every day, trying to get into our systems...the next major war that's going to happen is to take out our power, take out our water. It is very, very real.” (20:36)

Crimes Against Children

• Gina led the Crimes Against Children program for seven years.

  “There are FBI agents and analysts working this day in and day out looking at this material that would just wreck all of us if we ever saw any of it. And they save kids every day.” (17:24–18:50)

• The threat of predators targeting kids online is constant and pervasive.

Leadership, Gender, and Systems of Power

Turning Fear into Action (Lead, Even When Scared) (28:45–30:40)

• Gina shares how fear never really disappears:

  “That's when you come up against a door and you may be afraid, you may be intimidated, you may be confused, but you push through anyway…there is a point where there's no turning back...that's when you go through anyway.” (28:59)

• Practical advice for leading through chaos and change (e.g., with LA Metro):
  • Triaging the urgent (“get the water out of the boat first”)
  • Surround yourself with a good team
  • Get buy-in for your vision

Women Undermining Women: The Mean Girl Phenomenon (30:51)

• Gina notes that ‘mean girl gangs’ are “a luxury” that undermine decades of progress, often stemming from insecurity and imposter syndrome.

  “They feel like they have to put people down in order to make themselves look better...in order to pay homage to the people who made your road a little easier, we need to be better.” (30:51–33:11)

Unapologetic Leadership & Tone Policing (33:11–34:52)

• Rachel highlights how women are often judged for tone, not content.
• Gina challenges women to examine whether negative perceptions are real or internal:

  “Are we holding ourselves back, maintaining that thought process?...You’re a badass, Rachel, you can act however you want.” (33:42–34:52)

Finding and Using Your Superpowers (35:41–37:55)

• Gina realized that trying to lead like the men around her didn’t work; authentic leadership means identifying and using your own strengths.

  “Look at your superpowers and instead of focusing on what you're not good at...that’s going to be the basis for your leadership.” (37:55)

Stop Explaining Yourself (38:12–39:05)

• On not wasting energy convincing those “committed to misunderstanding you”:

  “All it does is slow us down...think of all of the energy that you just spent when you could be working on whatever projects you're working on to make your next maverick move.” (38:12)

Advice to Women Entering Male-Dominated Fields (39:13)

• Don’t take setbacks personally; it’s about the business, not individual slight.

  “Taking things personally is like the most selfish thing that you could possibly do...all that is, is just that energy draw that's taking it away from us having breakthrough success.” (39:13)

Memorable Quotes

• On Fearless Leadership:

  “Fearless leadership is not the absence of fear, but action despite it.” (28:45–28:59)

• On Leading Unapologetically:

  “If you have an ego problem that you can't, you are intimidated by me. That's not my problem.” (33:42–34:52)

• On Maverick Moves:

  “A maverick move is when you're afraid, but you go forward anyway.” (40:01)

• On the Consequences of Speaking Up:

  “Sometimes the hill you’re willing to die on, chooses you.” (42:20 & 40:01)

Practical Takeaways

• Cybersecurity: Be vigilant—"you're only as strong as your weakest link." Don’t click suspicious emails, and organizations must build a culture of cyber-awareness. (26:00)
• Parenting & Online Safety: Treat giving your child a phone as a privilege with boundaries, not a right; monitor and set rules to protect kids from predators and bullying. (44:18–47:16)
• Leadership:
  • Lead authentically by identifying and amplifying your strengths.
  • Don't waste energy on critics determined to misunderstand you.
  • Empower your teams—great outcomes come from teams, not solo efforts.

Notable & Memorable Moments with Timestamps

• Gina’s “spy chase” in BMWs and Audis through Europe — (01:08 & 06:18)
• Description of 2014 Sony Pictures hack by North Korea — (15:26–17:03)
• Reflections on the threats of large-scale cyber attacks and national infrastructure vulnerability — (20:36–21:31)
• Stories about crimes against children—why vigilance is crucial for parents — (18:50–19:18)
• Gina’s own firing for whistleblowing at LA Metro—when standing up means sacrifice — (42:20–44:01)
• The importance of letting go of the need to explain yourself to people who won’t listen — (38:12–39:05)
• Mean girl phenomenon: why women must help— not hurt—each other — (30:51–33:11)

About Gina’s Podcast and Ongoing Work

• Making Maverick Moves: Features guests who have pursued breakthrough actions, often at personal risk, to create meaningful change.

  “There are consequences for making maverick moves, but sometimes...when you choose that hill that you're willing to die on, sometimes that hill chooses you.” (40:01–42:20)

• Upcoming Guests: Stories on bullying, plastic surgery controversy, future leaders in business and public safety.

Final Wisdom

• Leadership is about empowering others—especially young leaders, by letting them make mistakes safely and learn from them.
• Advocacy for children online: The biggest threat to kids may be lurking in their phones, and parents need to act, not just worry.
• Most misunderstood thing about Gina: “Being aggressive, because believe me, I've been called it all...but again, that's their problem, that's not mine.” (50:30–51:11)

For more:

• Gina L. Osborn’s podcast “Making Maverick Moves” (Apple Podcasts, Spotify, YouTube)
• Speaking engagements: ginalosborn.com