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Gina Osborne
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Rachel Yucatel
Today on Misunderstood with Rachel Yucatel.
Gina Osborne
As a girl in her 20s, I was chasing spies literally across Europe and BMWs and Audis and undercover and Mercedes.
Rachel Yucatel
You are an assistant special agent in charge of the FBI. What was it like breaking into that world?
Gina Osborne
I got into the FBI in 1996. I was definitely in quote unquote, a man's world. And then when I rose up through the ranks, I was still, you know, more often than not the only woman in the room of the high level executives. And when you look at China, Iran, North Korea and Russia, 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. I did a lot in my law enforcement career. There was a 200 million dollar contracts with three law enforcement agencies and I found that they weren't doing what they were to be doing. And I wound up going to the inspector general and I was fired. When you choose that hill that you're willing to die on, sometimes that hill chooses you.
Rachel Yucatel
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. My guest today knows that moment very well. Gina Osborne spent nearly three decades inside some of the most male dominated, high stakes stakes institutions in the country. First in the U. S Army counterintelligence, then Rising to one of the highest leadership roles a woman can hold. In the FBI, she led counter terrorism teams, cybercrime investigations, organized crime units. Work where fear is real, consequences are permanent, and leadership isn't theoretical. And yet, even at that level, Gina wasn't immune to being misunderstood. Because when a woman leads with certainty and instead of softness, when she speaks plainly, instead of performing likability, when she refuses to apologize for authority, the narrative shifts. She's no longer strong. She's too much. She's difficult. She's labeled a mean girl. In a system that rewards silence and compliance. This episode isn't about climbing the ladder. It's actually about questioning who built it and who was never meant for it. We talk about what fearless leadership actually looks like. Not the Instagram version, but leading while scared, unpopular, and under scrutiny. We unpack why insecure systems punish women who don't play along, how internalized competition shows up in high pressure environments, and why explaining yourself to people committed to misunderstanding you is a losing game. Gina now hosts her own podcast called Making Maverick Moves, where she challenges outdated leadership models and pushes for something more honest, more human, and more effective. This conversation is for anyone who's ever been told to tone it down, anyone who's watched less capable leadership rise because it felt safer, and anyone who's ready to stop leaning in and start taking the damn seat. This is Gina Osborne, and this is Misunderstood. Gina, thank you so much for joining me today on Misunderstood. It's such a pleasure to have you here, especially on. With your background on the morning that the announcement of Diddy's, you know, what's happening with him has just come out. So can we actually start by talking about that? It looks like he beat the most serious charge, but he was found guilty on two of five of the charges. Can you walk me through that?
Gina Osborne
Yes. So the racketeering and the sex trafficking, he did not. He was not found guilty, but on the transportation across state lines for prostitution, he was. So I think that's going to significantly decrease any sort of jail time that he was looking at.
Rachel Yucatel
Do you think there's a chance he might get out very soon?
Gina Osborne
Well, the judge is looking at that today. I think the judge has planned to make a decision on that today. I think it's very likely because I think he's already been in jail for about a year, and I don't know how much time he's looking at, but he may even get out and have time served and. And that could be the end of that. So it'll be interesting to see, see what the sentencing looks like for him.
Rachel Yucatel
Wow. This will be very interesting, needless to say. All right, so you have such an extensive background, which I already alluded to in my intro, but I would like to hear from you and give me an idea of how you even got into this. Tell me about your childhood. What did you want to be? Did you know you would ever get into something that had to do with law enforcement, army stuff, like counter terrorism, like all that stuff?
Gina Osborne
Well, 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. So I'm going to date myself, you know, the CIA versus the KGB and, and all of these spy things. That was something that absolutely fascinated me. And I wanted to work for the CIA. And in my second year of college, I had run out of money. I was going to a community college. I didn't know how I was going to make it to a four year university to get my degree. I was a cocktail waitress at a comedy club. And one night I was at college and I'm sitting in the library and a young man came up and started talking to me and telling me about the Army's counterintelligence program, how I can live overseas, how I can, you know, have the condos, everything. Private Benjamin. Right. And so the next day I went down to the army recruiter and I signed up. And about nine months later, I was eating dirt at Fort Jackson, South Carolina in basic training.
Rachel Yucatel
Oh my gosh. And did you absolutely love it? And were you learning all these new things you never thought you would, or were you like, this is a mistake?
Gina Osborne
No. Well, going through basic training, my dad was a Marine, and so I kind of was raised like a boy. I think the biggest joke that God played on my dad was giving him two girls. And so my sister went into construction and I went into the Army. So the, the basic training wasn't that drastic for me because I kind of grew up with that. But yeah, I was very, very fortunate the way that it went because I wound up my first assignment was in Belgium, which, funny enough, that's where Private Benjamin was assigned at the Supreme Headquarters, Allied Powers Europe. And then the next three and a half years I was in Frankfurt, Germany, and I was assigned to this special that investigated the highest profile espionage cases. So as a girl in her 20s, I was chasing spies literally across Europe and BMWs and Audis and undercover and Mercedes. And it was just really, really a fascinating time. In history.
Rachel Yucatel
Oh my gosh. So you are an assistant Special Agent in charge of the FBI, which is one of the highest positions a woman can hold in that space. What was it like breaking into that world?
Gina Osborne
Well, I was the assistant Special Agent in charge of cyber and computer forensics in the LA office. So. So yeah, I, I was in the military from 87 to 92 and then I got into the FBI in 1996. And back then about 14% of all of the special agents were women. So there weren't a whole lot of us out there. And so, yeah, it was interesting. I mean, I was definitely in quote unquote, a man's world, working in a male dominated field. My first assignment was working Asian organized crime in Little Saigon here in Orange County, California on an all male task force. So yeah, so being the only woman woman in the room, I definitely got used to it. And then when I rose up through the ranks as an executive, even right before I retired, I was still, you know, more often than not the only woman in the room of the high level executives. So, yeah, you definitely get used to it.
Rachel Yucatel
At what point in your career did you realize that, like being good at your job wasn't necessarily enough? There was a lot of perception going on. You had to sort of perform at a different level.
Gina Osborne
You know, early on I had that perfectionism where I felt everything I had to do had to be 10 times better than the men or else, blah, blah, blah. But as I became more experienced, I realized that all that was was in my head and I was just holding myself back. So, you know, 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. As I look back, if I put more pressure on myself than was necessary because I was competent, I was good at what I did and I was accepted in the workplace. So. So really the pressures I put on myself were totally, completely unnecessary. Wow.
Rachel Yucatel
But do you think, I mean, to be accepted, I think is pretty, you know, that's not necessarily how it always works. I feel like sometimes men would tend to, or other people in general, men, women, whatever, would tend to undercut you. Women because they're jealous, men because they just think they can do it better. And you were doing these jobs that were pretty exceptional. You know, do you find that that is a normal thing that you see that, that people just accept that or they give you a harder time as a woman?
Gina Osborne
Well, I think, I think. Let's go back to my Childhood a little bit when my parents got a divorce when I was young and my mom was left with my sister and me to take care of. And she had been a hairdresser before she got married. And so 13 years later, she's got these two young kids and she wound up choosing to go into real estate, which was really, really risky in the 1970s because not a lot of women were doing real estate number one. And you know, here she, she, it was a commission based situation and she wasn't getting alimony. So, so my mom went out there and in her first year selling houses that were $35,000 a piece, she wound up making it into the million dollar club by selling over a million dollars in property. So I think I had a really, really great role model and we never really had that in our house. And it was funny, when I was in the army and basic training, I got pull out of bed in the middle of the night to go paint the first sergeant's office, something that happened from time to time. And one of the other women in my platoon started talking about the glass ceiling. And that was something that I didn't even know about. And so, so really I think that if we buy into all of these things that we're supposedly told or we learn, that really slows us down. But I think maybe I had blinders on because I was so busy doing my job as great as I can, creating these really, really, that I didn't have the time and the energy that would put into really doubting myself.
Rachel Yucatel
Yeah, yeah. Well, you obviously have so many lessons that you can teach from being in those positions, which I do want to get into. But I want to go back to talking about a little bit about your experience because it's so fun. You were talking about investigating espionage at the end of the Cold War. Right. What were some of the biggest threats that you were tracking? And how do you think the espionage test tactics have changed since then?
Gina Osborne
Oh my gosh. Well, back then it was before it was with the Soviet Union. Right. We knew who our, who our enemy was before, you know, the wall came down actually. And so, so the, and then, remember, we didn't have cell phones, we didn't have all of the technology that we have today. So those, you know, Cold War tactics that the Soviets use, the dead drops and you know, all of those things that was he in the 80s, which was actually the decade of the spy. So the biggest case that I worked while I was there and the case agent on the case was my role model who was A woman. It was the Albert Sombilay case where during Desert Storm, all of his unit were over in Kuwait blowing the Scuds out of this, you know, into the sky. And. And he was back in Bombholter Germany trying to sell troop deployment information where his. His. His people were. So it was a really fascinating time to follow him. And we did a sting operation and got him into a hotel room. He thought that he was meeting with the Middle Eastern entity, and he sold his soul for $3,000 and wound up getting 34 years in prison.
Rachel Yucatel
Oh, no way. I mean, I feel like this could be. This is what movies are made of.
Gina Osborne
Oh, my gosh. And I was across the street from. In his housing community. I was in an apartment across the street, and they had told me it was nightt. And they told me that they were going to arrest him at the gate, coming on to his. His housing complex. Right. And so I'm, like, so disappointed because I had been locked up in this apartment for a week, you know, and I was just waiting because to be able to see an actual spy get arrested is something that. That's all I wanted. So I was looking in the distance thinking, okay, maybe I could see some lights or something or hear a siren. And instead he pulled up in front of his house, and that's where they wound up arresting him. So. So, yeah, that was one of the. The two top moments of my law enforcement career to actually be able to see someone who had been, you know, committing espionage get arrested.
Rachel Yucatel
Oh, my God. Amazing. Let's talk about your time in Los Angeles. What kind of cyber threats were you seeing that the public had no idea about?
Gina Osborne
Oh, gosh. So computer intrusions, national security, computer intrusions. One of the big cases that. That was the hack of Sony Pictures in 2014 by North Korea. And that was really fascinating because North Korea used psychological warfare against Sony Pictures. And to remind everyone what it was all about, there was a movie called the Interview. And I think it was Seth Rogen and James Franco. And at the end of the movie, I don't want to spoil it for anyone, but they depicted the Supreme Leader of North Korea in a very, very, very unpleas. And so the North Koreans were not happy about that. And so, yeah, so one day, it was like, I think the Monday before Thanksgiving in 2014, all of the Sony Pictures employees come to work around the world, and they see a skull and crossbones on their computer. Their network had been completely compromised, and all of their information on their network had been taken. And about every Two or three days, they were putting out different batches of things that had been on their network, like emails from the top people at Sony saying not very nice things and employee information, their Social Security numbers, HIPAA information. So it was really fascinating to see how this computer intrusion turned into this absolute catastrophic event on US soil. So it just goes to show what they're capable of, of.
Rachel Yucatel
You know, it's funny, in watching just shows on Netflix, I mean, Grey's Anatomy and the Resident, they're both, you know, obviously surrounding hospitals. They both talk about the networks being hacked and somebody asking for $10 million ransom to turn on the computers Again, I mean, do these things really happen as much as they're showing them?
Gina Osborne
Oh, yeah. In fact, I think they happen more because companies don't want it to get out that these things are happening. So, yes, in fact, Iran, they had attacked or tried to attack a hospital. I mean, you. We would see it all the time with regard to the ransomwares, the business email compromise where, you know, they go, they identify who the financial person is and a big corporation and they, you know, get into the system and make it look like an email going from the CEO to the financial person saying, hey, I need you to, to, you know, get $10 million over here. But we have to do it right now because blah, blah, blah, and people are doing it and if they do it voluntarily, they don't get that money back. But the FBI is, if you report it to the FBI within a really short amount of time, the FBI may be able to get that money back. But, you know, if it's been a couple of days, then, you know, forget about it. But, yeah, that happens all the time. And then I was also in charge of the Crimes Against Children program for seven years, and that was really near and dear to my heart because it is a whole nother world that we don't want to think about. But 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. And so that was a really great time.
Rachel Yucatel
Meaning, like sex trafficking and stuff like that.
Gina Osborne
So sex trafficking, but also, you know, with the child pornography, you would be surprised at how many predators are out there trying to get our children. And there were cases here and all across, you know, the country where you hear about, you know, these, these little girls falling in love with some predator, and then the predator comes and picks them up and. And it's just a horrible story.
Rachel Yucatel
Yeah, we all used to see it on To Catch a Predator. Remember that show?
Gina Osborne
Yeah, I loved that show. That show, yeah, yeah. Do you remember the episode where the guy showed it up with his five year old kid? Did you see that episode? Oh my gosh.
Rachel Yucatel
I had Chris Hansen on my show and we talked all about stuff like that. Yeah, I mean, it's fascinating. And now he has his own network, but people like feel like they don't really believe that that stuff happens. It happens all the time.
Gina Osborne
It happens all the time. Yeah.
Rachel Yucatel
And the one thing I wanted to go back to a series again, another stupid show that I'm watching that I just finished called Zero Day. I don't know if you're familiar with the this, it's about a cyber hack that happens and it happens for one minute, I guess, throughout the entire, all of the nation. And it turns off everything from lights to transportation. So airplanes go down, cars get hit, trains hit each other, and there was like, you know, 3,500 deaths within this one minute. And it happened internally. It was, you know, they thought it was Russia and it ends up being an internal thing. But is that something that should keep people up at night, that something like this could happen? It's more than just somebody wanting money from turning down the software at a healthcare center. It could be bigger than that. Is there something that keeps you up at night still?
Gina Osborne
For sure, yeah. If our critical infrastructure is attacked through a cyber attack, absolutely. It could happen. It has happened. I mean, there are a lot of different incidents of it happening. When you look at China, Iran, North Korea and Russia, I mean, it's not that they just have a few people sitting in a room doing this. They have armies of people who are doing this all day, every day, trying to get into our systems. Because really, when you think of the next major war that's going to happen, I mean, what's the best way to drop us to our knees is to take out our power, take out our water, and you know, create a kinetic attack where you're right, trains run into each other. It is very, very, very real. And, and it, I mean, I don't want to keep everybody up at night, but it is definitely a real threat.
Rachel Yucatel
What if I.
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Gina Osborne
Wow.
Rachel Yucatel
And being in that department, is it something that we are very aware of and some people, a huge team of people are also working to keep them out.
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Gina Osborne
Yeah. So, yeah. So the military, they have their cyber program. The FBI has their cyber program. So. And I was very, very fortunate to work with some of the best people in the business. These amazing chess players, you know, what I. What I would call them. And so we're very, very fortunate to have such really talented people working on our side. But again, there are adversaries trying to get into our systems as we speak. So we really have to be village vigil. What I would always tell people, and I still tell people, is you're only as strong as your weakest link. So if you've got an employee who is, you know, gets an email and then they decide to click on that link, that's how you get the malicious software into your system. So we really have to be careful about, you know, who we're. Who we're interacting with. Make sure that they are the people who are sending us these emails. But really think twice before you click on a link, because that's where it all begins, Right?
Rachel Yucatel
Right. There's a term that the Navy SEALs use called easy day. And looking back at your FBI career, what was the most high stakes or high pressure operation you were part of and how did you find that you could lead through it and the lessons that you learned from it?
Gina Osborne
Gosh. You know. You know what's funny is of all of the time that I spent 28 years in law enforcement, between the military and the FBI, I would say the most violence and the most, most chaos and crisis and change that I dealt with when I was the chief safety and security Officer at LA Metro, I saw more violence in my first week at la Metro on our system than I did in my entire 28 year career. So what I do when I'm speaking, I do keynote speaking as well as training. And, you know, there are three things that you do when you're leading through chaos, Cris and change. And this is one thing that I implemented when I got to LA Metro. The first thing we had to do was get the water out of the boat. I came in right after the pandemic. At the end of the pandemic, 2022, there had been no fair enforcement or code of conduct enforcement on the system for two solid years. The unhoused were sheltering on the system. There were so many. It was Mad Max, you know, beyond Thunderdome. That's what the system was. And, you know, we just had to keep our eye on the ball and go get the water out of the boat. And that's kind of triaging to, you know, stop the bleeding. So you have to do that, you have to surround yourself with a great team. That's really, really important. Because the last thing that you want to do when you're dealing with a crisis is to have somebody who is adding more crisis and chaos into your team. So you want those people to be sitting in the next room while you're, you know, surrounded by your team and, and really having that vision as to what it's going to look like when you, you've made that change. But you really have to get the buy in from all of the people around you to be able to make that change happen. And so those are the three things that I tell people, you know, when they're leading through a crisis. You can do it, but you can't be concerned about, you know, getting your holes fixed in the boat, painting the boat, putting accessories on your beautiful boat, get the water out of the boat first, and then that's when you can build and make things better.
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Rachel Yucatel
I love that you talk a lot about fearless leadership. Not the absence of fear, but action despite it. Can you talk about a time where you led when you were pretty terrified, but you got through it?
Gina Osborne
Gosh, you know, all the time. And that's, you know, that's what I, when I talk about making maverick moves, that maverick move in order to get to your breakthrough success, you know, 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. And I kind of talk about how, you know, like in the FBI, when we go and we do an arrest warrant, okay, so we're out there at O Dark 30. We've done our homework. We know who lives there in the house. We know what the house looks like. We know what we're going to do once we get into the house. House. And then we stack up, you know, a bunch of agents get together and then we're heading towards the door. And there is a point where there's no turning back. Right. You don't have that option. You're going through that door and you don't know if the suspect is asleep upstairs in bed or laying in weight with a gun pointed at the door. So that's when you go through anyway. And that's what I tell entrepreneurs and other people who want that breakthrough success is that you have to believe in yourself enough to know that, trained, that you know what you're doing and what you. You believe that you're going to make it through. And then if you get on the other side of the door and have to deal with a threat or, or something that doesn't go as planned, you have that ability to pivot. So a lot of people don't make it through that door to the breakthrough success because they stop. But when you present it to yourself, like, okay, I don't have the option not to stop. I'm going to go through no matter what. What, that's when we find our breakthrough success.
Rachel Yucatel
Yeah. Yeah. I want to talk about women and leadership because I know you talk a lot about that. What inspired your philosophy that mean girls don't make leaders?
Gina Osborne
You know, that. That came up. I wrote an article on LinkedIn about that. And I had just been at my friend's house in Arizona. The lady that I spoke about, the case agent on the Albert Sambilay case, she was 10. She's 10 years older than I was. I am. She was in the military during the time when we had the women Army Corps. Okay, right. So, you know, she, she is definitely a trailblazer. And so I went. She had a surgery and I went to take care of her. But then she introduced me to her other friend who was the first female paratrooper in the army, and she has dementia. And so my friend was. Had gone to Georgia, picked her up, put her into a care facility near her, and had planned to take care of her for the rest of her life. And then as I was leaving this experience and really recognizing, you know, what, this is what sisterhood is all about, you know, willing to have your back. And these are the women who came before me who, who made sure that, you know, my road was a little bit more clear for me to walk through. And then someone had reached out to me and told me about how she was getting ready to leave this agency that she' with because of this mean girl gang. And it really got me thinking about how, you know, it is a luxury for these women to have these mean girl gangs. And really, I mean, it's kind of akin to the old boys network. Right? The mean girl gang is based on imposter syndrome insecurity and really, really poor leadership because they feel like they have to put people down in order to make themselves look better. But, but all of the women who come before you, they did not do what they did in order to make it easier for you just so that you can tear other women down. So yeah, so I wrote that article because we really have to get back to that sisterhood because it doesn't serve anybody. All it does is take away all of the hard work. And believe me, I saw a lot in my career and my friend saw a lot in her career. And so in order to pay homage to the people who made your road a little easier, we need to be better.
Rachel Yucatel
Yeah. What are your thoughts on, I mean, listen, as a female working with a lot of males, I find that I always have to be very careful of my tone because people won't hear what I'm saying, they'll just hear my tone. Whereas if it was a man talking, he would be seen as powerful and smart and all these different things. Like I'm, I know you've run into this. So, so like, how can women lead unapologetically without being seen as difficult or bitchy? You know, all these words that people want to use.
Gina Osborne
Right. But is, is there evidence of all of this or is this what we're telling ourselves? Because believe me, I am a six foot blonde. I am a force to be reckoned with when I'm out there working with men. And yes, did I experience that? You know, back the 80s and the 90s for sure. But what I learned was you need to take me for who I, you know, if you have an ego problem that you can't, you are intimidated by me. That's not my problem. So I think we just really need to look for the. Because we have these assumptions about, okay, this is why they're treating me in this way. But is it, you know, and are we holding ourselves back, maintaining that thought process? Well, it's me, I need to be nicer. I can't be blah, blah, blah, blah, blah, you're a badass. Rachel, you can act however you want. So that's, you know, we just have to, you know, look at those assumptions and look, okay, is there evidence about this or is this just their problem? And am I accommodating them or changing the way I do things just so that they can feel better?
Rachel Yucatel
I think that's a really good point because I think most people would be, like, say the opposite almost when you're right. I mean, if you. You take your job seriously, you know, you're good at it. It's like, you know, just be that person, be that babe and like, you know, that's their problem if they can't handle how you handle work and how you get shit done, so.
Gina Osborne
Right.
Rachel Yucatel
I love that you just said that.
Gina Osborne
Yeah. But we also have to be collaborative and, you know, and we also have to take other people's opinions. So if. If this happens all the time, then maybe we need to reflect and say, okay, maybe I need to take a different approach. But again, we don't want to automatically think that or put that in our brain and start thinking about it, because otherwise that's just going to slow us down.
Rachel Yucatel
Yeah. What do you think systems of power get wrong about how leadership should look, especially for women?
Gina Osborne
So when I. Yeah, so I think what we get wrong is thinking that our superpowers aren't enough. So I'll tell you. So I got into cyber. I have no computer skills. Really aptitude, we'll say I do have cyber certifications, but, I mean. And I wound up getting into cyber because I was on the FBI's inspection staff, and I raised my hand and volunteered to inspect the cyber program. And then all of a sudden, because I was the only one who volunteered, I wound up doing all of them. And then that gave me subject matter expertise on prior and things like that. But when I became the assistant special agent in charge for cyber and computer forensics, I showed up. And because I had learned from mostly men, I had this lead from the front mentality for leadership. But then I found, as I'm surrounded by all of these cyber geniuses, that I would lead from the front and nobody was following me. And so I thought, okay, well, you know, technology expertise is currency here, and I have nothing. So that was really when I started to lead authenticity authentically. I started to have to take inventory. Okay, well, what are my superpowers? I'm great at communication, solving problems, getting money. You know, there I have all of these things, and I think a lot of us. And once I started leading with those things, that's when the squad supervisors and their agents started coming to me because I had something to offer them. So I always tell women, look at your superpowers and instead of focusing on what you're not getting good at, for me it's patience. I have no patience whatsoever. No matter how much time I spend on having more patience, I'm never going to be the most patient person in the world. But if I really focus on the things that I am good at, that's where I'm going to shine and I'm going to create my leadership behind the things that I'm really good at. So, so what I tell women, you know, find out what your superpowers are, get really, really good at those. And, and that, that's, that's going to be the basis from your leadership for your leadership.
Rachel Yucatel
Yeah, I feel like a lot of women get tripped up with people that are committed to just not understanding us right or not understanding where we're going to. Why is it important to stop explaining ourselves to these people that are committed to misunderstanding what, who we are and what we're doing?
Gina Osborne
Because all it does is slow us down. All it does is slow us down. So if you are constantly trying to appease other people, people think of all of the energy that goes into that and then of course someone's going to say something and then you're going to get mad and then you're going to call all your friends and say, hey, did you hear what so and so said to me? And then you're going to be up all night plotting that person's demise. I mean, think of all that energy that you just spent when you could be working on whatever projects you're working on to make your next maverick move. Right, right. So I think we really have to take inventory as to what are we spending our time and energy bemoaning. And put that aside, put it in a box, you can come back to it later. But right now focus on where you want to find your breakthrough success and don't let anything derail you.
Rachel Yucatel
What is something you wish more young women knew about rising through male dominated spaces?
Gina Osborne
It's not about them. You know, I mean I think we really make a lot of stuff about ourselves and the injustice of it it all. But if it's, if we look at it as this is business and how do I fit into this business and how am I going to be successful in this business? And there's a great book called the Four Agreements, I'm sure you've heard of it. Where yeah, yeah. Where they talk about, he talks about being, you know, taking things personally is like the most selfish thing that you could possibly do. And again, when we do that, and we all do, you know, from time to time, time, all that is, is just that energy draw that's taking it away from us having breakthrough success.
Rachel Yucatel
Yeah. Can you tell people about your podcast? Making maverick moves?
Gina Osborne
Yes, making maverick moves. So again, you know, a maverick move is when you're afraid, but you go forward anyway. And my first guest was the LA City fire chief. And I remarkably, I had interviewed her before the fires and I think I talked to in, in November and I asked her, I said, so what? Tell me about a maverick move that you've made. First female fire chief in the city of Los Angeles. Remarkable individual, remarkable human. And she said, gina, my maverick move, I'm doing it right now because I don't have the resources to do my job. And so fast forward to the fires where she went out and really made her maverick move by, by calling out the mayor about how, you know, she had the. There she's not getting the funding that she needs in order to be able to fight these fires. And then two day before, two days before I launched my podcast, she was fired. So I understand, you know, those are the type of people that I want to talk to because I want people to learn from, you know what, there are consequences from making maverick moves, but sometimes, you know, when you choose that hill that you're willing to die on, sometimes that hill chooses you. So. And that's what makes make us remarkable. So that's why I want to. I bring people onto my podcast who talk about, you know, the maverick moves that they make and, you know, the things that are getting in their way and the things that they do in order to, to push through. And I just want to inspire people and really continue my service to help people get to where they want to go.
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Rachel Yucatel
So in that same vein, what would you say is your. Is one of your biggest maverick moves that you've done? In your life?
Gina Osborne
You know, I think just, you know, I did a lot in my law enforcement career, but what got me fired from LA Metro was the fact that I found law enforcement. There was a $200 million contracts with three law enforcement agencies, and I found that they weren't doing what they were supposed to be doing. And I wound up going to the inspector doing general and I was fired after that. So, so, yeah, so that was a hill that I was willing to die on because after I got fired, I wound up, they, LA Metro had this big surge in crime and stabbings and shootings. It was just horrible. And, you know, speaking out to, to help LA Metro get their own police department, because that's something that I'd worked on for, for two years before that. So, you know, that was definitely I, you know, I, I, I talked about the hill you're willing to die on, but that was the hill I was willing to die on because, you know, that position was really a calling for me just as much as my law enforcement career, because you have riders who are dependent on the transportation system and it being safe, as well as those frontline employees, those bus operators who are getting assaulted. And so, so, yeah, so I definitely found out what the consequences were of doing that. But I think it's made me a stronger person and it really put me on this maverick move, you know, point that I'm, that I'm, I'm really pursuing just because, because we can all do that. It's just, you know, we have to understand that consequences come with it, right?
Rachel Yucatel
Absolutely. What a story. In all your experience and all the things you kind of know that we don't know are there, what, what threats are real right now that the average person might not be thinking about? I know we talked about cyber threats, but is there something that we, we don't, we're like, not even aware that we should be nervous about?
Gina Osborne
Well, I think, you know, I had, I just had a guest on my podcast and we talked about bullying and we talked a little bit about cyberbullying. You know, I think given cell phone, giving cell phones to kids is, is a threat. And I think parents are really not looking at it from a perspective that, that you need to have an agreement with your kids and make them sign an agreement when you hand over the cell phone, which means they know that this cell phone does not belong to them. It belongs to the parents. They have to. There's a code of conduct on the cell phone because so many times, I mean, you would never allow some strange person to come into your child's bedroom alone with them while you're home. You know, we're doing that by allowing them to have access to all of these chat rooms and all media. So there are so many dangers for kids, you know, not to mention the predators, but also the bullying and also, you know, trying to look so great on social media. So that's one thing that parents should really be aware of, that they really need to dial back on this free for all that we're having with these kids and these electronic devices because they're really a danger to our kids.
Rachel Yucatel
I mean it's so true. I have a 13 year old and like when I try to take her phone away, it's like she turns into a terror to Dactyl. It's like she's so committed to this phone. That's the only way she can connect with anything, anyone. I mean she could barely get through a meal without, you know, just from having a normal conversation. So now I've made it this rule that like we have to have a conversation and you know, As a typical 13 year old kid, she like kicks her head back. She's like, oh my God, like I'm stabbing her by saying have a normal conversation. How was your, your day? You know, it's like being a terrorist to her. So it is funny. But you know, she goes on, what are these games? Roblox or something? And she does now tell me, you know, she's interacting with people. She's like, oh yeah, I know mom, that's not another 13 year old kid. It's like some person in Ghana somewhere. She's like, I'm fully aware. I mean it's made her grow up faster. But I almost thought it was a good thing when TikTok almost disappeared. Was it TikTok that almost disappeared? And then, you know, I get asked all the time by random people to be calling our senators and things being passed here in Florida about not letting kids bring phones into schools up to a certain age. And I sign all these things and it never happens and no one cares. So it just seems very odd to me that people all agree that these phones are totally dangerous, but no one really does anything about it. And the kids, they're so used to it from when they're babies that they just, they really don't see how it's terrible. You know, they don't get it. So it's a very uphill battle. It's really hard and, and I don't even know how you fix it. I really don't but it is very, very scary, for sure.
Gina Osborne
Yeah, it, it is. And when, I mean, I've unfortunately seen the really, really dark side of it where kids have committed suicide as a result of someone they fall in love with who winds up being a 40 year old man. And this happens and that happens, you know, the bullying aspect of it. But yeah, we really, really, you know, I highly recommend putting monitors, checking up, making sure your kids know that you're checking on them. And I know, but by the time they're 13, it might be, you know, a big shift if we decide to start doing this now. But, but, you know, before you give your kid that cell phone, make sure that there are their ground rules and they understand those ground rules because, yeah, I mean, our kids there, there is definitely threats. And having worked crimes against children for seven years, I can tell you that they're real.
Rachel Yucatel
Yeah. And again, I had a guy on about sex trafficking and people think this is something that happens like in other countries, not ours. Or, you know, you go to Las Vegas and you see all the signs, but in the stalls of the bathrooms. But you kind of don't assume it has anything to do with you. And he was like, no, this is you, these are your kids, these are, these are people, you know, and it is the biggest threat and no one knows it. And he thought that that was, he was saying that was the scariest thing. What are you still learning about leadership even now?
Gina Osborne
Gosh, you know, implementing your vision as a leader, it just has so many moving parts. But what I've learned as a leader leader is that you really have to get that buy in and empower your people. You hear so much about micromanagement or, you know, when you're the boss, you want it done a certain way, but all that does is rob that creativity from your people and it doesn't empower them to want to do great things. And really, when you look at the great things that are happening in this world, I can tell you, nine times out of 10, they're going to be coming from a team of people, people whose leader empowered them to do these great things. And that's how I lead and that's how, I mean, I didn't always lead that way because of course, you know, when you're a brand new leader, you're going to micromanage and you want to make sure that, you know, nothing goes wrong. But even, you know, when I look back on my career, especially with the FBI, what my legacy is, my legacy were these young supervisors coming up behind Me that I allowed them to make mistakes and, you know, they wanted to do something their way. I may, you know, give them, okay, well, maybe let's think about what happens if you do it this way. But they were intent on doing it that way and they wind up in a rabbit hole. Right. And then I'm there to help them out of the rabbit hole. It's so important to. And that's how you learn, you know, you learn through mistakes. So as leaders, we have to be, you know, understanding that sometimes mistakes are going to be made. We can't, you know, create, create such a standard that we're going to stifle people. But if we empower our people as leaders, that's how we're going to find our great success.
Rachel Yucatel
Yeah. And just because our show is called Misunderstood, what do you think has been the most misunderstood thing about you throughout your career or your journey?
Gina Osborne
Gosh, what has been the most misunderstood? You know, I mean, it probably goes back to what we were talking about, you know, from the beginning. Leading, being in the military and learning how to lead from the front and then intimidating other people. But again, you know, I think you learn that that's not my, that's not my problem. That's their problem. Okay. So, yeah, so I think, you know, being, being ag, because believe me, I've been called it all the B word, you know, aggressive, you know, too assertive to this, to that. But again, you know, you just have to leave it behind because that, again, that's their problem, that's not mine. My problem.
Rachel Yucatel
Okay, you do speaking engagements. You're a TEDx speaker. Talk a little bit about where people can, can listen to some of your, your speeches.
Gina Osborne
Yes. Well, so I keynote, so go to gina l.osborne.com. i've got a sizzle reel that can show you of my speaking topics. And I really enjoy speaking to women's groups to empower them to be the, the best leaders they can, can be. That's. I love women in cyber because they're such unicorns, right? Because there are so few women, you know, engineers and, and women who are working in the cyber industry. I just spoke at the, at this World Cyber Women and Cyber conference and it was just really a lot of fun to, to see these women because that, yeah, they're definitely unicorns and I love to see how they solve their problems and, and, and get through their days and, and, and lead and be successful. So that's a lot of fun.
Rachel Yucatel
And making Maverick Moves comes out every Monday. Tell people where they can find your Podcast.
Gina Osborne
Yes. You can find us on Apple Spotify, your favorite podcast provider. We're also on YouTube and we have our shorts on TikTok.
Rachel Yucatel
Amazing. And do you have any upcoming guests that are exciting we should know about?
Gina Osborne
Yes. Gosh. My, my bullying. My, my maverick mom, who she's coming out next week, she was really intense because her son was bullied. And she made the maverick move of putting out a letter to all of the parents of the kids who were bullying her son out on social media. And it was a beautiful story because an MMA fight owner, he owns a studio, reaches out to her, reached out to her and said, hey, I want, you know, to give your son his power back and gave him free lessons. It's just a really beautiful story.
Rachel Yucatel
I just got chills. That's amazing.
Gina Osborne
Yeah. And then I have, for being in Orange county, we have the Housewives of Orange county and Tamara Judge. She had this blue peel. I don't know if the Bravo universe is aware of it, but I had her plastic surgeon talking about that blue peel and all of the controversy that she went through to show the world how she was healing. So. So he's really fascinating, too.
Rachel Yucatel
Oh, amazing. I love it. Okay, well, I'll have to listen. I appreciate you. I think you're great and I cannot wait to see, you know, one of your talks coming up. And hopefully I actually have a couple people I can, I can think of off the top of my head who you should have on your show because they are making maverick moves. So we will be.
Gina Osborne
I would love that. Please send them my way.
Rachel Yucatel
I will. Gina, it's been a pleasure. Thank you so much.
Gina Osborne
Thank you. Foreign.
Rachel Yucatel
Thank you so much for listening to Misunderstood. I'm your host, Rachel Yukatel. Please be sure to subscribe to the show and give us a five star rating and review. You can support the show by joining our patreon@patreon.com misunderstood with Rachel Yukatel. Do you have ideas for the show or want to reach out, email us@infomisunderstoodpodcastmail.com that's spelled M I S S. Understood. Thank you so much and I'll see you next time.
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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.
“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)
“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)
“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)
“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)
“North Korea used psychological warfare against Sony Pictures...all of their information...had been taken” (15:26)
“Companies don't want it to get out that these things are happening.” (17:24)
“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)
“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)
“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)
“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)
“Are we holding ourselves back, maintaining that thought process?...You’re a badass, Rachel, you can act however you want.” (33:42–34:52)
“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)
“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)
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)
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)
“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)
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