The Code To Winning - RETIRED FBI AGENT FOR 26 YEARS & PRIVATE INVESTIGATOR || TOM SIMON || EPISODE 030

Episode Date: June 10, 2025

🎙️ INSIDE THE MIND OF AN FBI SPECIAL AGENT: Uncovering Fraud, Lies & Truth Episode [030] | The Code To Winning In this gripping episode, we sit down with Tom Simon, a former FBI Special Agent with over 26 years of elite investigative experience.   From cracking high-profile fraud cases to mastering the art of interrogation at the CIA Interview & Interrogation School, Tom shares exclusive, behind-the-scenes insights into the world of financial crime, federal investigations, and private intelligence work.   🔍 What You’ll Learn in This Episode: *What the FBI really does behind closed doors and how it differs from the CIA *How Tom helped take down major investment fraud schemes, embezzlers, and romance scammers *The most shocking high-profile cases he worked on during his FBI career *His elite interrogation techniques and how he got career criminals to confess What it’s like now as a Licensed Private Investigator & Forensic Accountant.   Tom is not only a decorated investigator but also a CPA, expert witness, and highly sought-after private consultant for cases involving forensic accounting, internal controls, due diligence, and FBI referrals. If you’ve ever been curious about the real world of federal agents, financial crime, and the psychological warfare behind confessions — this episode is unmissable.

In 1995, when I turned 25 years old, I became an FBI special agent, went away to the FBI Academy for training in Quantico, Virginia. The FBI and the CIA interact to share information and hand cases off to one another. If we have someone who's mixed up with a terrorist organization here in the U.S. And we have intelligence that they're heading over to South Africa, for example. At that point, we'd probably reach out for the CIA and let them know that this individual is headed back to Africa. And they need to be monitored and investigated. Persuasion is of utmost importance, especially when you're an FBI special agent. What are some of the things that you looked at when you were trying to negotiate or try and convince the client or somebody to do something that you were there meant to do?

I think empathy is important. By that, I don't mean sympathy, right? I'm not saying that I feel sorry for a bad guy. But I think the ability to look at the world through their eyes and understand what their motivations are and kind of play to that goes a long way toward persuading. someone to giving you a confession when it's against their self-interest to do so, and to understand that people, that no one is the villain in their own life story. People don't look at themselves as being bad guys. When someone does something bad, they see themselves just reacting to the circumstances of their lives. So I think that understanding and getting into their mindset and

kind of building that rapport with them and coming at people with a non-judgmental attitude goes a long way to persuading them, in my case, persuading them to confess to the crimes they've committed. The Code 2 winning insights you need today to seize the world tomorrow. Today we have an amazing guest, a real treat. I'm going to give you a brief introduction of our guest today. He's actually a retired FBI agent, an FBI agent, a special agent for 26 years, and right now a private investigator year in the Sunshine State of Florida. Without further ado, ladies and gentlemen, our special guest today, Tom Simon. Great to be having this today.

KT is so great to be here. Thank you so much for having me. Awesome stuff. Thank you very much for coming in. Like I said, I have been seeing a lot of your content on social media. It's been very exciting to see a lot of the stuff and the experiences and the stories

that you've come across as well. And so when I got the opportunity to be in Florida, I was like reaching out to Simon, you were top of the list as well. So I'm grateful the opportunity for you. Well, I'm so thrilled to be here. I've seen so many of your clips online and you're really good at what you do. Awesome. I appreciate that so much. I want to kind of just, you know, dive and I have so many questions I want to ask you regarding this topic.

I want to actually figure out, like, how did you start, you know, your journey to becoming an FBI agent? And how was that, like, at the beginning? Well, I wanted to be an FBI agent ever since I was a little kid, probably for all the wrong reasons, right? Me reading Marvel comic books and watching action movies. I thought I'd be spending a lot of time jumping off moving trains. And the reality was the job was very satisfying, but it was a lot of. lot in very different ways. So what you quickly learn when you're young in high school is that you need to get good grade, stay away from drugs, crimes, and criminals, and then go to college. And so it was unclear to me what I should major in college. And at the time, the two big majors

that the FBI was looking for was accounting, and they wanted people to go to law school, if possible. I wasn't crazy about school. I didn't like school at all. And so I learned that accounting is a four-year degree. Law school would be a four-year degree plus three years of law school. So I took the path of least resistance, majored in accounting, did that for three years, working for a big accounting firm called KPMG. And then in 1995, when I turned 25 years old, I became an FBI special agent, went away to the FBI Academy for training in Quantico, Virginia. Okay. And when you got your accounting degree, was that in Florida? Which state was that? I went to Clemson University in South Carolina. It's a big football school. I was about to say I know Clemson are very, very good in football, and they pretty do well.

They've been doing well for the past five or six years as well. Yeah, they're sort of one of these kind of schools that's probably primarily known for football, second for academics. I wasn't a football player. But an accounting degree is like you're learning a trade, like it's a refrigerator repair or a carpentry. You're learning how to do something. And so I walked away having the skills to be an accountant. And then I passed the CPA exam, which is the certification for becoming a certified public accountant. And so your experience with a big fork.

So for instance, in my example, when I graduate in BYU, I end up before then I did an intern, in New York and it was exciting. I was with Bloomberg. In matter of fact, I was one of the 40 interns to actually meet Michael Bloomberg at that point in time in my experience. You working in the Big 4, KPMG, how did that kind of like lead towards you, going towards the FBI or what skills do you gain over there as well? Sure. Well, first of all, you're dating yourself or maybe dating me because back when I was there, it was the Big Six. And Arthur Anderson went by the way inside Cooper's and Libran merged with Price Waterhouse. Those things have happened, but now it is the big four.

For me, you know, it taught me how to put on a suit and go to work and be a professional. It taught me how money flows in and out of organizations because it started in the audit practice there. And so I got to kind of understand businesses and how they work and how the accounting systems in these businesses worked. By the time I had done that for about two years, they started a forensic and investigative services practices, conducting fraud investigations for clients who had problems. And I was able to get into that practice, which, oddly enough, is what I'm doing now as a private investigator. And so it was kind of a nice hedge for me,

because I know the FBI is a long shot for any applicant, no matter how good or bad you are. And so for me, it was just in case the FBI didn't come through, I could be a professional financial crimes investigator for the rest of my life, which is all I ever really wanted to do anyway. Awesome. And I've always been curious.

I know probably some of the guests are curious out there. and what would you say the difference between the CIA and the FBI, if you don't mind me asking that? That's a fair question. Okay, so think of it this way. The FBI is a criminal investigative agency based here in the U.S. The CIA does not conduct investigations. It's not what they do. They have no criminal authority.

You cannot be arrested by the CIA. The FBI also has a national security mandate to identify and catch or monitor spies who are here in the United States, collecting intelligence for foreign nations, the Chinese, the Russians, etc. Whereas the CIA, they're overseas spying on behalf of the U.S.

So on the national security side, you can think of it as the FBI being the spy catchers and the CIA being the spies overseas. The CIA has no mandate and doesn't operate inside the U.S. And is there, do you guys have certain jurisdiction over? Because I don't know, I'm giving examples from the movies I've watched

where you'll end up getting like NYPD doing an investigation. Then FBI rock up. with their black suits and they're like, you know, so they'll take it over from there. Then the NYPD are so absurd. They're like, oh, no, no, why they want to do this? I feel like FBI have jurisdiction over pretty much the United States, all 50 states as well in its territories. But then where do you guys draw the line?

Like, is it you take over, you know, situations or investigations beyond, like your jurisdiction? How does that work? That stereotype that Hollywood has implanted in your brain and the brains of probably what I think is probably 300 million Americans, that the FBI is somehow taking cases from the locals stealing their cases is my big pet peeve. That has never happened in 120 years of the FBI's existence. There are federal crimes and there are state crimes. And there's very little overlap between the two. The police will investigate local crimes. The FBI will investigate federal crimes.

Quite often, while the police are investigating a crime, they'll say that they could use FBI assistance and they'll call us in and will collaborate with the local police like the NYPD and work together to work the case up. Or oftentimes the police, especially in the financial crimes arena, will say, you know, we don't have the time or resources to deal with a complex financial crime. We're busy keeping people safe on the streets. Would you mind taking this from us? And we'll be happy to take those cases and work those up federally. That stereotype that I think everyone got from the movie Die Hard when the terrorists took over the building and the police were doing a perfectly fine job. And then the FBI came in, pushed them aside and mucked it all up. But boy, oh boy,

has that implanted in people's minds because they think the FBI does that. My father is 80 years old. He loves this TV show called SWAT. And so I sat down with him to watch SWAT, even though I don't like watching police. Is he snipes? Is that one? No, maybe perhaps in the movie, but there's an actual TV show called SWAT on like CBS. Not a show.

I've only seen one episode. But gosh darn it, that one episode I sat down to watch with my old man, sure enough, the police were doing a great job with this hostage situation. And the FBI came and took it over. And I was like, oh, I can't even escape it with my own father. but it doesn't happen in real life. It never, ever happens. It's only really damaging, though, to the FBI's reputation

when you're dealing with police in some small town who don't normally deal with the FBI who have that stereotype in their minds from Hollywood. And you have to spend a lot of time and effort winning those police officers over and letting them know that we have nothing but respect for them and we're not coming to screw anything up. We're here to understand their investigation

and collaborate with them. And so I've had to do that dozens of times in my career. but boy, oh boy, that stereotype has a real lasting effect on people. I'm grateful for you debunking that because that's the perception I actually even had to this day until you debunked there because we just had the thought that, hey, listen, they have jurisdiction and they can just take cases over as well. I thought that's like that. It's never ever happened in 120 years that I've ever seen.

And the thing to think about, okay, federal cases are inherently are interstate, right? There needs to be interstate transportation of stolen property or someone, using interstate wires or the U.S. mail system. So right away, we're solving a problem that the police really don't have the wherewithal to investigate interstate crimes because it's difficult for them to go over to Los Angeles when they're in New York to conduct interviews on a case. The FBI happens to be everywhere so we can do that. Also crimes on federal reservations of some kind,

whether someone chooses to commit a crime on Pentagon grounds or military-based grounds or in a national park. You know, it's federal land, so it becomes a federal. crime at that point. And that's basically it. Unless it's a counterterrorism matter or national security issue, those are the crimes that the FBI works, but no one really is interested in taking a case from the New York Police Department. And if an FBI agent did, the New York Police Department would probably thank them, because unfortunately, KG, there's plenty of crime to go around. Wow. Thank you so much for sharing that. And I know you mentioned earlier on with the whole CIA

being more like in foreign, because when I did my history, because we studied a lot of of the history of the Cold War, the Vietnam, JFK with the Bay of Pigs, their creation of the CIA and so forth. So like I did that actually before I even came to America. Part of our history was starting the Cold War. However, now, obviously you guys are more like jurisdiction of the United States. If there is like a case of somebody leading back to the United States, that the CIA end up like connecting and working with you guys and then the FBI takes over the minute the person lands in the United States. That's exactly how it works, KG.

In the FBI and the CIA interact to share information and hand cases off to one another. If we have someone who's mixed up with a terrorist organization here in the U.S. And we have intelligence that they're heading over to South Africa, for example. At that point, we'd probably reach out for the CIA and let them know that this individual is headed back to Africa and they need to be monitored and investigated, oftentimes with the cooperation of local authorities in that foreign country. And that's what really fell apart pre-9-11, right? the information sharing between the FBI and the CIA was problematic. It was stovepiped.

And there's an argument to be made that they may have costed people's lives back in 2001. And the mandate we got from on top, from up high, was that we need to stop that. We need to stop stovepiping information and begin pushing information out to the intelligence community and receiving information from them so we can help keep Americans safe. And that's what we have done. The FBI implemented that by hiring hundreds of intelligence analysts whose sole job is to write up intelligence products and push those out to the intelligence community

to make sure we're covered and not stovepiping information like we're protecting it for ourselves. Okay. And then what do they look for when they try to recruit an FBI? Because I feel like I don't know any FBI ages. I think you're probably the second one I knew. The other one I spoke to about is the private, I mean, is the negotiator as well.

So I've always viewed FBI as like a very classified kind of position. Well, I mean, again, I keep my word, we're criminal investigators as well. So the criminal side of the house, which is pretty much what I mostly worked on, I had some national security cases. All those cases come out in open court, and the agents are there in open court testifying, and anyone can sit in the back of the courtroom and watches. So we're really not hiding in the shadows the way a national security agent might want to. So I think that's another stereotype, is that somehow we can never tell anybody what we do for a living.

I was always very transparent about what I did for a living, And I was often on television speaking on behalf of the FBI. So the idea of me kind of lying to my next door neighbor and telling him that I'm a civil engineer just didn't make any sense. No, no, no, no, no. Sorry, not lying per se. More like nobody like knows. I don't know an FBI agent. Like I thought it was more like you, not even being discreet per se,

but just like I felt like it was just a classified position where only like 10 people are in there. You know what I'm saying? Yeah, I mean, so we're a nation of probably 350 million people right now and there's 12,000 FBI special agents. So the odds of someone knowing a special agent is probably slim. And the people you know casually from the gym or you're playing tennis, maybe not just mention what they do for a living.

So kind of like you're never more than a few feet away from a spider at any given point in the U.S. You're probably no more than a few blocks away from an FBI. Okay. Okay. And one of the things I also noticed, and I've been seeing a bit more, because now I'm being more aware because I travel so much. And then I realize that the FBI, there's also agents like in a state level, right? Or is it all federally?

Because you'll see an FBI like, I saw a compound electrician the FBI for like Idaho or something like it. Or is that just? Well, sure, no. I mean, the FBI has 55 field offices scattered throughout the United States and pretty much the 55 biggest cities of the U.S. and then if there's a good bit of distance between two offices, they'll have a satellite office. For example, we have a Jacksonville office of the FBI, but Tallahassee is the state capital of Florida. That's three hours away from Jacksonville. We need to have FBI agents there, one, to investigate the crimes and two, to respond in case something happens.

So we have a satellite office of the Jacksonville office located in Tallahassee. So when you start taking a look at those small resident agencies, there's hundreds of FBI offices scattered throughout the U.S. And so, but this will report to D.C. even though, like, it's... Well, DC is our headquarters, but, you know, I was an agent in the field for 26 years. I never, there's no investigations happening at headquarters. Headquarters has an administrative function only, you know, basically getting funding for the FBI and kind of keeping track of the programs and reporting to Congress and the president, things like that.

So I never really had a whole lot of interaction with headquarters because I was in the field conducting investigations because I never went to headquarters. I went 26 years without a promotion, and so I was never clawing my way up, that bureaucratic ladder where headquarters was a factor in my life. People always ask me about the new FBI director. Is he good, is he bad? I said, listen, I served under five different FBI directors,

and it never mattered a bit to me who they were. And with the FBI director, I know the president's got certain jurisdiction. I'm more in the financial economics. That was my field, so I follow stuff, like when Yellen was the federal chief. chair to Jerome Powell. Like, that's more like my field. I understand, like, you know, we studied that.

And I know this president can end up nominating, but can he, he can fire and hire, like, an FBI director. It's a little different with, like, a federal chair. Right. The FBI director is a political appointment of the president. Now, we had the original director of the FBI. It was a guy named Jay Edgar Hoover, who served forever, like 40 years, like way too long. And, you know, ended up kind of losing his mind, a lot of corruption issues, or

of bias and prejudice. I mean, he formed a great law enforcement agency, but by the end, by the 1970s, he was losing his marbles. And, um, and so then after he died, and it became important that the FBI have kind of a check and balance against that happening. And so the way they did it, though, to keep it non-political, is to make the FBI director appointed by the president, approved by the Senate, and then he serves a 10-year term, with the idea being that he's going to serve with it under at least two presidents. Because it's supposed to be very non-political position. Now, what's happened lately, though, is President Trump was not happy with Director James Comey and fired him, which the President can do for any reason at all or no reason at all.

He's still a presidential appointee. Then he instilled a guy by the name of Christopher Ray as director, who served under a good bit of the First Trump administration under the entirety of the Biden administration, but then Trump was unhappy with his performance when he was re-elected, and he has since placed a director in there named Cash Patel, who, again, unless a president does that he, unless a president, decides to remove him, will be serving a 10-year term as FBI director. You clarified that pretty well. I appreciate that. I had a question I wanted to ask you. This is, it was more of a controversial take. And I don't even know how true the story was. I read a lot of articles, and it's one of the things that came about and I read about it.

It's about, it was a disaster that actually happened within the federal borough where one investigator was trying to find a Russian leak within the department, and it turns out that he was the spy for Russia. Is that a true story? The FBI has had a couple of people agents in my position spying for Russia. The most prominent one that you're probably thinking about is a guy named Robert Hansen. That's his name, yes. Robert Hansen, back in 2000, it was discovered through an internal FBI investigation,

had been spying and providing secrets to the Russians for probably 10 or 15 years of his career. He, the FBI eventually caught him using a sting operation and undercover pretending to be a Russian handler and had him drop off secrets and then the FBI arrested him when he was making the drop off of those secrets. It was a terrible day for the FBI, right? One of our own decided to go over and work for our enemy. And so, you know, Robert Hansen was investigated by the FBI. He ended up getting life in prison and he died. in prison a year or two ago. And so absolute shame on the FBI's face, for one, not catching him

and two, allowing it to happen again. And they implemented security procedures. After that point on, for every five years during my career, I was polygraphed and interrogated by FBI agents, as every other agent was, to make sure I wasn't a national security threat working for a foreign power. And one of the things I do like about the whole situation is how transparent the federal Baru have been with like the mistakes that they've made and things that have come out as well. So everything has been very transparent to the American public. Nothing has been like hidden. Of course classified stuff are, but like for the most part, like they're being transparent

with the mishaps and mistakes that they're, that. The thing that people need to understand is that in the world of law enforcement and intelligence gathering, there's a lot of room to make mistakes. And so you need to be forgiving of the ones that aren't, don't have massive, you know, a blast radius, but you need to like stamp down really hard. When it comes to someone committing an act of treason or corruption, you can't forgive them, pat him on the shoulder. The cover-up is always worse than the crime in those situations. I love that so much. I love that. I want to touch on, I would say today, an average American is probably a little hesitant on just trusting any form of law enforcement or political ecclesiast.

a political leader or just people that have jurisdiction over them, what would you say to those people that are just very hesitant to trust like just people in power? Well, you know, I don't think people should trust people in power. And I don't think people should inherently trust the FBI because the FBI says anything. The FBI, when they make criminal allegations in the government in general, has a burden of proof to bring that case into an open courtroom and establish what the evidence is of someone's wrongdoing. So if I'm sitting there kind of, you know, on television, hootin and hollering about what a bad guy somebody is,

you don't need to believe me. I would rather you're not. I like the idea of a skeptical public. But I'd like you to watch that court case and see how it plays out once we present our evidence in the courtroom, which is where it should be presented, not on Instagram. Tom, you're very good at these answers. I appreciate that. You have good questions. Now, before I kind of go into more questions, I wanted to figure out what would separate a state case and a federal case? Can you give an example of those two as well? Sure. Okay.

Let's go bank robbery. Banks are federally, the deposits in any U.S. bank are federally insured by the FDIC. So you go into a bank, you stick a gun in the teller's ear, you take money from that teller and you drive away fast. That's a federal crime because you've stolen from a federally insured financial institution. However, you go to the liquor store next door, you stick a gun in that liquor store owner's ear and you walk away with probably twice as much money and drive away. that's not a federally insured institution. The FBI has no dog in that fight, and that's a police matter. But then if you were to see it yourself as an FBI agent,

can you like arrest the person or do you have no jurisdiction? Where do you draw the line? The FBI legal guidelines say that if an FBI agent is witnessed to a felony and has the ability to stop it in progress and effectuate an arrest and hold that person until the police come, then you can do that. It's very different, though, than me getting road rage because I see someone driving like an idiot, well, I'm on my way to work at the FBI, right?

In theory, I guess I have the lights in my car. I can pull that person over and put the handcuffs on them, but then what the hell do I do with them, right? The FBI doesn't have a traffic court. All of stuff. I love all these stories, and one of the things that really just stuck out is I watch your page. Matter of fact, I actually have like an alert on your profile

whenever you post like me. Everyone should, KJ. This should be mandatory. It should be baked into the Instagram. No, because you've not just that. Not only are you like, at storytelling, not only are you great at like stories. I'm one of those people that I just, I love hearing like based, like my favorite movies are based on a true story, like situations

like catch me if you can. Yeah. You know what I'm saying? And like stuff like it, not that I'm supporting the crime, it's just that it's like, how did this person get away with so much? It's staggering, isn't it? And it's just fascinating because he, he faked to be a pilot. He faked everything, but he was, he just seemed like there was always one step, beheaded, it could hardly be caught, but that seemed like it was a FBI kind of case for them to like investigate in, right? Well, again, the story of Frank Abagnale from Catch Me, if you can, is really the story of a bank defraudder, right?

It's a guy who's creating counterfeit checks and trying to negotiate those checks. Again, you're messing with the banking system at that point, and you're inviting FBI attention. Awesome. Now, now to go into these questions that I also prepared, and I want to kind of dive in and talk about, What was the psychological shift that you did going from an FBI special agent to becoming a private investigator today? When I stopped being an FBI agent and became a private investigator, I needed shift from having my loyalties be to the U.S. Constitution and that burden of proof that every FBI agent must meet in a criminal case to client service. My clients have a problem when I'm a private investigator, and my job is to advocate for them and advise them about what to do about that problem. very different burden of proof, very different focus.

A crime victim when I'm the FBI agent is not my client. As someone who's deserving of compassion and kindness, but they're functionally a witness in my case. When I'm a private investigator, it's all about the client and what questions do they have that they need answered by the private investigators? So it's a real customer service mindset as opposed to a loyalty to the Constitution and a patriotic mindset. And what kind of clients hire you and what would be a private

investigate an issue. Sure. A typical client will hire me because they have been ripped off in a financial crime of some kind. They're a small business that has an embezzlement, meaning an employee has stolen money from them, or they're a person who made an investment that turned out to be a fraud. They're trying to get their money back is their first priority, and if they can't get their money back, they want this case investigated by the FBI. Now, any citizen can call the FBI and say, help, help, I've been robbed, but the problem is the FBI is just drinking from a fire hose of complaints all the time, right? We have 350 million Americans, 12,000 FBI agents. They need to pick their battles. So what I do on behalf of the client is I investigate the fraud, that's pretty much

what I did for the FBI, and I create an FBI referral report. I will often then go to the bad guy and let them know that my client has hired me to investigate this fraud. I think it might be in your best interest to pay back my client. Sometimes they do. I can be very persuasive, KG. But if I fail in that mission, then I take this case and I shepherd it to my former colleagues at the FBI in a very organized report with all the evidence tabbed for them, and I presented to them as a potential case that they may want to work. And oftentimes, they choose to open up those cases and investigate them themselves and the bad guy who should have paid back my client when I asked them too nicely ends up in an orange jumpsuit and an

order of restitution, meaning they need to pay my client back through the garnishment of wages when they get out of prison. That's sort of the core of my business. I do lots of other things, to including expert witness testimony, public speaking, training. I'll do background checks for women who don't want to end up in the trunk of a car when they meet the men of their dreams on Bumble, stuff like that as well. But most of my time, money, and effort is on financial crime investigations with a client focus. I'm glad you kind of touched on that. Before my perception as well of a private investigator, I was, I know you're probably

judging me of how small-minded it was. I just had the perception. Private investigator is, my wife is cheating on me right now. I need to find out if it's cheating on me. And those guys out there doing the whole investigation. Surveillance. Surveillance, tracking the car doing whatever.

And then all of a sudden gets exposed. And then it's just like this dramatic scenery. And it's like, oh, no, you didn't do that to them? And I'm glued to the screen. Like the whole cheetah's scene. That's what my perception of the problem. I've done that. I mean, I've done that.

And when I was, especially when I was starting out in 2021, I took a lot of cases like that. I now spend a lot of time and effort. And I get probably 50 calls a month from people wanting that kind of service. And I'll hand them off to somebody who's a better surveillance agent than I am, who's cheaper if that's what they really want. But I spend a lot of time talking those people out of it. And here's why.

One, if you think your spouse is cheating on you to such an extent that you're going to pay an expensive private eye like me to follow them around, you're probably right. Two, in the state of Florida, it probably doesn't really matter if they're cheating or not because if you're getting a divorce, you're going to split it 50-50. It's not like you get more money if you're married to a real jerk. But also, the client needs to, so you're going to be paying a private investigator, a good bit of money to follow this person around. Normally, that's not going to happen for more than an eight-hour shift. I found that my clients were very, very bad at choosing the eight-hour shift that they thought their spouse was going to be cheating on them.

Like, okay, do you want me to go from four to midnight? What day of the week do you want me to go to follow him around? And where am I starting from? I'm starting from his work? Am I starting from his home? And the client's never really sure. they have this feeling in their gut that it's happening, but they're not really good at saying when it's going to happen.

And then I'll say to them, okay, do you think he's going to be having sex in a public park on a picnic blanket? Or do you think he's going to go somewhere private to do it? She's like, well, he'd probably go somewhere private. And I go, well, how am I going to see that, right? I'm not going to be able to access the apartment that he walks into in an apartment building or the office or wherever this is happening. And so I'm not really sure I'm even in the best case scenario

going to be able to get you the proof that you want. So now we're talking about the client spending thousands of dollars for me to like sit and watch a door that's not going to open or a car that's not driving while the guy's inside watching baseball on a Saturday night while his wife's out of town because that just happens to be the night that he's not cheating. And so the client walks away disappointing because they spend a fortune because they're paying for my time, whether I'm successful or not. And then they just have a bad taste in their mouth about my agency. I don't want to be in that kind of work. I want my clients to have some possibility of success. and closure and get the answers they need. And I think surveillance is a real lousy way to do that.

And I'm sure any private investigator that's watching this is frustrated with me kind of sharing this dirty little secret because everyone's making a lot of money doing these spousal surveillances. But nine times on it, their batting average is terrible. The idea that these guys are going to actually see an act of infidelity during a surveillance from a car is slim to none. And how legal even is it for them to actually have like cameras? Oh, well, no, you can't, I mean,

you can't, a private investigator can't install a camera in someone's house without their permission. And without wiretapping as well, you can't do that. No, you know, I mean, no private investigator is going to be able to wiretap someone's phone. You give me someone's phone records because you have a shared cell phone account and you want me to identify these 10 numbers and who he's calling. That's a reasonable thing. I can get you answers to that. But the idea that I'm going to be able to for eight hours, follow this person around and you're going to guess correctly what those eight hour period is, I'm not interested in having disappointed clients.

That's all you're asking for. So I hand those off to different PIs to do the work. Oh, awesome. Again, it's the bread and butter of most private investigative agencies. There's a disconnect for me because I want, before I even accept a client, to have some reasonable expectation of success for them. And then how, I want to read this question specifically because I felt I wanted to like, kind of like elaborate on it in depth.

It says how do rules of engagement and engagement and ethical boundaries change when you're no longer backed by the federal authority? I think with that the big thing would be the liability. So I carried a gun every day for 26 years as an FBI agent, knowing that if I was in a shooting, a good shoot, right? And I'm not running off half-cocked, just shooting people because the line's really long of McDonald's, but a shooting with a, you know, in a dangerous situation that the U.S. Department of Justice, the FBI and the law enforcement world is going to have my back.

will defend me in court if I need to, if they need to, and I had total faith that the government's not going to leave me hanging out to dry. As a private investigator, if I get involved in a shooting, I'm going to wind up in handcuffs, even if it was a righteous shoot in the back of a police car, needing to establish my proof and probably being sued by the guy I shot, possibly being charged with a crime for using my weapon in the line of duty. Again, even if it's a good shoot, and then the burden of proof is upon me. So, you know, as a result, I carry back. private liability insurance now. But you need to be more judicious when you don't have the backing of the federal government in that use of force. How dangerous is it, though? Because I know you

mentioned earlier on, like, if somebody comes to you, you can come to you as a private investigator or the country as a client to a private investigator and you go and approach the bad guy. And you know, like, now that you're not backed and you're approaching the bad guy, aren't you putting yourself in a vulnerable and dangerous position? Because you don't know what the bad guy actually has in his military arsenal or like may be able to retaliate, maybe they feel like they're provoked as well. So I know you're very good at persuading, but how do you create a rather safer environment

to try and protect yourself as well in that situation? Well, I mean, at some point you're accepting some amount of risk, right? It's a risky job. That's why I charge what I charge. And but, you know, we're also in a nation, again, with 350 million people and about 700 million guns, many of whom are concentrated here in Florida, which is a constitutional carry state,

meaning that anyone can carry a gun in Florida as long as you're not a convicted felon without any kind of license or training. And so you just assume that everybody there is carrying a weapon. And so then at that point, you're kind of relying on the strength of your personality, the strength of your training, and maybe you set up a situation

where if you're going to meet someone, you're meeting them in a public place. It's hot here in Florida, so people aren't often wearing suits like you and I are. They're underdressed, and so you make sure that you have your weapon on you and you hope that they're not going to pull out their weapon. So far I've been fortunate. I've had a couple hairy situations, but none of them that have escalated to that level of violence.

Interesting. Interesting. I know that you're very good at persuading. And I know obviously the skill just gets better over time, considering that you were there for 26 years. Persuasion is of utmost importance, especially when you're an FBI special agent. What are some of the things that you looked at when you were trying to negotiate or try and convince the client or somebody to do something that they were meant to do? I think empathy is important. And by that, I don't mean sympathy, right? I'm not saying that I feel sorry for a bad guy. But I think the ability to look at the world through their eyes

and understand what their motivations are and kind of play to that goes a long way toward persuading someone to giving you a confession when it's against their self-interest to do so. And to understand that people, that no one is the villain in their own life story. People don't look at themselves as being bad guys. When someone does something bad, they see that. themselves is just reacting to the circumstances of their lives. So I think that understanding and getting into their mindset and kind of building that rapport with them

and coming at people with a non-judgmental attitude goes a long way to persuading them, in my case, persuading them to confess to the crimes they've committed. Isn't that hard though sometimes because they're automatically defensive thinking that, listen, you're just trying to get your way to confess, but I've watched some of those stuff because I don't know why I watched like some of these crime stories when you see somebody killing somebody, and then they're in the room. And, like, it's not FBI. It's just like a local authority. And sometimes they confess, but sometimes, like, the approach is a little aggressive.

Like, you got to tell us, you killed your friend, Karen. You killed your friend, Karen. I'm like, she's not going to break. I would say that's a mistake, that approach. I went to the FBI interrogation school. I went to the CIA interrogation school, and I've traveled around the world, training foreign governments and foreign law enforcement on how to do it better. And it's all really based on empathy, again, which is very.

very different than sympathy, right? Like, let's say you were sitting across the table from a child molester, a guy who did the worst things you can imagine to a child. Do you have sympathy for that person? Absolutely not. No, but are you able to step outside of your own ego and try to see the world through their eyes and try to understand the rationalizations that happen in their mind

that allow them to do such a monstrous act? It will be hard to do that, I'll be honest. Which is why you train yourself to do that, right? So what is it, let's drill down on this, in the worst case scenario, someone who's done horrible things to children. What are they telling themselves, right? They're telling themselves they have a compulsion, that they can't stop, that they have this attraction to children, that they wish they could flip a switch in their brain and be normal. They're telling themselves all of these things. Maybe they're even lying to themselves and saying these children are trying to seduce him.

I don't believe these things, but I'm allowed to actually play with those ideas in my conversation with him to get him to confess to me. even though it's against his self-interest to do so. And that's the difference between empathy and sympathy. Wow. Now that you put it that way, it's hard, I know, because I absolutely, under no circumstances, if I had a child, would be able forgiving or even, like, think of it, like, non-emotionally regarding that

I'd just probably want to just get my hands on that person and just... Agreed, but you're misunderstanding that the job of the FBI agent or any investigator, is not to punish them, is to find out the truth and get down to what actually happened. And that way you can bring that truth to a prosecutor and to a judge and a jury one day and explain what happened. The thing to understand is that the investigator's job, whether it's a private investigator or an FBI agent, is not to punish the subject.

It's to get to the truth. You find out what happened by using all the tools you have in your toolbox and get that documented, whether it's an audio recording or a report, and get that to the attorneys, the prosecutors, the judge. judge the jury, and all you're doing is collecting the truth. You're not judge jury and executioner. This is not a Marvel comic book. I love that. And I appreciate that. I feel like it's a, it's a career path and a special position that requires people to fully invest in because sometimes it can become a little mentally draining, I would assume, for other people. Without question, yeah.

Because I've seen people in law enforcement. Everything I'm saying is just more like a local jurisdiction, never the FBI. You see a lot of them when they retire because of just the mental stability that they incurred and the pain that they've witnessed and the stuff that they've seen that some end up in a state of depression as well.

Do you think that has ever affected a lot of people in the FBI regarding situations and the mental stability of them? I think without question that law enforcement is very stressful. You're constantly dealing with the absolute worst of society

and that takes your toll on you, which is why any law enforcement agency worth a dam has an employee assistance program. You need to have enough self-care to go to those people and say, listen, I need to speak to a counselor. I need to talk to somebody, whether it's a chaplain, whether it's a psychologist, whether it's a shrink, and work your way past those things. I advocate talk therapy. You know, it doesn't necessarily even have to be a formalized relationship with a health care professional. It could be a friend or a mentor.

But you can't keep these things bottled up, or you're going to end up having a heart attack at age 50. And how do you balance it out? How do you, like, try and bring that down for yourself? I think professionalism is the key to everything. realizing that your job is not to punish anyone, your job is to get down to the truth, and you're working toward a greater good here. You also need to recognize, again, that we're a very big nation with lots and lots of people. And just because we are wallowing in the muck, that doesn't mean that everyone out there is a bad guy. And as a private investigator right now,

obviously in the state of fraud and also 50 states based here, have you ever encountered a situation where you or that a client has approached you with that you perhaps felt that you wish you had the badge to back you? I think that happens every day and where it really manifests itself the most is doing a knock and talk where you need to collect evidence, you're going to knock on someone's door to their house. Now when they would come to the door and I was an FBI special agent, I would show them my badge and credentials. I would say, hi, my name's Tom Simon. I'm an FBI special agent. I'm investigating such and such and such. I was wondering if you could help me out and answer a few questions because we're really trying to make sure we can get to the bottom of this and and blah,

blah, blah, blah. And so the FBI, even though we've had some bad media over the past few years, is still pretty beloved by the actual public. And so once you're no longer an FBI agent, you kind of lose that. You lose the ability to have the badge and the credentials and the goodwill that the FBI has fostered for the past 120 years working on your behalf. As a private investigator, I still do a lot of knocks and talks and interviews, but I need to kind of rely on the strength of my own personality, whatever charm I can muster up and try to build rapport with them, so they'll answer my questions because there's no authority behind my knocking anymore. And just to follow up on that,

has there ever been a situation similar to what you did in the FBI? Just following up on that question, they actually have had to deal as a private investigator. Something very similar that, oh, my gosh, I just did that thing within my 26 years. Oh, all the time, because, again, what I'm really doing right now is conducting financial crime investigations on behalf of clients who were ripped off,

as opposed to financial crime investigations on behalf of the U.S. government. And honestly, my cases right now often culminate in me packaging it up and handing it off to the FBI to bring it across the finish line because I can't arrest anybody anymore. But it's really the investigative process is very much the same. Just the authority I have is now diminished.

Now I want to ask a certain question. What is the most morally complicated situation or case that you've worked on? And how did that ever question your judgment when you worked on it? I had a case where the subject to the investigation was a woman named Capua. It was in Hawaii at the time. She was a very nice woman who did a Ponzi scheme and ripped off like a million dollars from people that she knew. So looking at it from the outside, you think, I'm like, heaven, she's a monster. And that she spent the money on herself largely and paying people back to create the illusion of investment returns.

Because that's what a Ponzi scheme is, right? I'm taking money from you, and then I'm giving you a little bit of your own money back to create the illusion of investment returns. But once I scratched the surface, I realized that Capua was doing this because she herself had been victimized in a Ponzi scheme. She met a guy who happened to be in prison at the time, who was a con man, who convinced her that he was this great commodities trader. And that if he gave her, you know, and that he could double her money every 90 days or whatever the promise was. But she didn't have any money to invest with him. So she lied to her friends and family that she was going to be trading commodities because she had been. trained in that, but she wasn't telling them the important fact that they, that she was actually

giving their money to a man who was in prison and his wife who was out. It was a big, messy, case. But the bottom line is that Capua was not born to be a con artist. She went into this thinking that she could make money for herself and for her friends and family. And when I finally confronted her and she got a criminal defense attorney, he basically turned her over to me and said, okay, we want you to co-in-ordered her to cooperate with me. against the real bad guy, the con artist who tricked her into doing this Ponzi scheme. And so she cooperated with me, and she was fantastic. She gave me, we met for hours, she was a lovely person,

she felt terrible about the people who lost money and her fraud, but she had done something wrong. She had lied to people to steal money from them. And so I show up at her sentencing, and I made it perfectly clear to the judge and probation and anybody who wanted to know that she was really a victim of circumstances and that she had done something wrong, but she had, in my mind, very much redeemed herself

by cooperating with the FBI against a much bigger criminal. And the judge still threw the book at her, and she ended up going to prison. And I felt bad about that because she made a bad, terrible mistake and had a moral lapse, but she wasn't a con artist.

She didn't go into this with the intention of harming others. I want to just add on that. And I noticed, like I said, most of the stuff I love watching, It's always based on like true stories, true crime and stuff like that. And I was fascinating. You probably know these two stories. And I'll just kind of like give a brief overview of them.

But it's a story of a Russian girl named Anna Davely. Yeah, yeah. I watched the TV, the Netflix show. Anna Delvey. Yeah, Anna Delvey. And so, you know, just for the viewers out there, just a brief introduction of who she was. She was a Russian girl who came from, I think, Russian and German parents. year in the United States

and with obviously good intentions to try and live a certain lifestyle end up like defrauding a lot of investors in portraying herself to be a very, very wealthy Russian girl inheriting from a billionaire and so forth as well and another story of a lady

in in California and her story is also very sad because she was a straight-A student and what happened is she wanted to try and like create the first blood sample Oh sure

the um, gosh, what, Elizabeth? Elizabeth. What was her name? Not Elizabeth Smart, Elizabeth. Something like that, right? Yes. And I noticed with all these... What was the name of her company? I wish I could have been a blood work thing, but... Right.

But you know what I'm talking about. Yeah, finish your thought about that, though. What were your thoughts about that? My thoughts, because, and people often think I'm playing the devil's advocate in this, but I looked at her situation, straight a student, she always wanted to change the world. She was in that class of the Mark Zuckerbergs, all like the founders and stuff. And what happened is that like there was no reading when they were trying to get like, when they were in Europe trying to like convince like clients to try and like funding this thing. And then they made that one specific switch where they cheated the system by creating a certain narrative

or like an answer for the situation they were looking for. And what turned out to be one lie end up becoming multiple lies and multiple lies. And then before you know what you're in the cycle where you keep trying to rationalize because you did a one big lie, but all the intention to want to do was change the world. And so when we play the devil's advocate and we see in the eyes, obviously I'm just playing devil's advocate, but you're an FBI negotiator, you understand and you're seeing through their own lens that these people actually see things different to what we as people see it. Can you add on those two stories, please?

Sure. Well, regarding Anadelvia, I'm probably a lot less sympathetic to her than you are. Her whole thing, she had very much a fake it till you make it kind of worldview where she was going to lie to people. all about ego for her, right? Anna Delvey wanted to be a big shot. She wanted to be a socialized. She wanted to be kind of the it girl in her friend group. And she funded that by like just stealing

money from the people who loved her. I don't have a ton of sympathy for her. I mean, she's paid her debt to society. She's going to end up being deported before it's all over. And she was terrible on dancing with the stars. So, so. You have to add that in. With Elizabeth Holmes of Theranos,

I think you're probably on the right track, where she probably truly did intend to have a test that would answer all the questions and solve a lot of health problems. But once that blood test was proven to not work, the idea of pushing forward, lying about whether it's successful, and then taking money from investors on the basis of that, I believe that's more of a function of Elizabeth Holmes' ego rather than some good intentions. So I'd push back against your supposition that these two are just victims of circumstances. How do you deal with situations where they start believing in their own lives? Because I feel like in situations such as this, you know, with Elizabeth Holmes,

if they portrayed that Netflix series apparently was as accurate as it could be, she actually started believing in rationalizing, saying, hey, listen, I've already been molested. And so it'll be okay. It'll be okay. It'll be okay. Just keep moving forward. Right.

The thing to understand about con artists is that they're very good liars, but they're also very good at lying to themselves and rationalizing their behavior in their minds, which is why when I interrogate them, I'm not doing these giant global moral judgments about whether they're smart people or good people, about whether their business has value. I drill down on the specifics.

You know, I want to get really granular with them in my interrogations and say things like, okay, but when you weren't making enough money to pay the investors, you began to pay them back with their own money. Is that correct? And then oftentimes will say, yeah, I did that. And I go, but I'm assuming what you're going to tell me is that that was a temporary measure until the company started making money. Yes.

And I go, but do you do understand that the definition of a Ponzi scheme is paying investors with their own money and the money of other investors rather than with the profit, that you're making in your business or investment program. You understand that as the definition, don't you? And they go, yes. And I go, well, then can you understand why someone looking at this from the outside might see what you did as being a Ponzi scheme? And they'll go, well, yeah, I guess now I do see that. And so if you address the conduct and not their character, you can get that confession and get them to admit to the conduct

as opposed to them turning their weapon on themselves and saying, oh, my God, Tom, I am a bad person. No one will ever admit that. it's yeah by the way I'm not I'm not playing I'm busting your chops I just laid the viewers now I'm not condoning and accepting their actions I just wanted to say that everyone was just so against the whole situation like oh my gosh it's so even I'm like she thought what she was doing was correct it's wrong what she did oh yeah but in her eyes she was just trying to like do good and she thought it was going to be okay but that's true with everybody right Again, no criminal sees themselves as the villain in their own life story, right?

Think of it this way. Here's a good analogy. You're driving to work. Someone cuts you off in traffic. You honk your horn. Maybe you give them the finger. But in your mind, that's a bad person. You know everything you need to know about that person and how horrible they are during that one little time of interaction.

The next day, you're running late. You're going to be recording a podcast with an FBI, former guy. And you're running a little bit late. You cut someone off in traffic because you're really trying to make that deadline. Are you a bad person in your mind? No. You're reacting to the circumstances of your life. And that's the way criminals see themselves is that I wasn't a bad person.

I was reacting to the circumstances of my life. And if you could understand that about everyone, when they do something wrong or do something bad, you're going to be a better interrogator, you're going to be a better investigator, and you're going to be a better person. These are nuggets. These are golden nuggets. Can we go for another three hours till? I'm down. We got to catch your flight, though.

What are the tools that you guys use to interrogate? Because, again, I think the reason, I'm glad you're debunking all these myths that I keep giving out of, like, waterboarding and putting people upside down, dunking them in the water. Speak now. If they ever hold your peace. Let's talk about that. Let's drill down on that a little bit because there is a perception that, and in developing countries, it's very common for the police to use torture. or physicality to get someone to confess. But let's talk about what is the purpose of an interrogation.

Are we trying to get them to confess? Are we trying to get them to tell us the truth? Because I can tie you to that chair, KG, and probably burn you with cigarettes, and you'll tell me you're the queen of Mars. But it ain't necessarily so. I want you to tell me the truth, and there's tools to do that that don't involve violence or intimidation

or making someone feel scared. But how? It's through empathy, through understanding that no one is the, the villain in their own life story, and I'm going to say to you, an interview is a question and answer. An interrogation is a monologue where I'm talking and you're listening. And what I'm going to be saying to you in that monologue is that I know that you're not a bad person, KG, and I know that you are probably feeling tremendous financial stress. I've met the worst people in the world, child molesters, serial killers, bank robbers, and you're not that person.

I don't see you as a bad person, but I think you were reacting to the circumstances of your life when you stole that money from the cash register. I think that was going on. I think you probably had some serious financial stress in your life that was causing you to do that. But I don't know. Maybe you were taking that money to party, buy cocaine,

go to the strip club. I just don't know. So my question to you, KG, is, did you take that money from the cash register because you wanted to party? Or did you take that money from the cash register because you were experiencing tremendous, financial stress and you intended to pay it back one day. Which is it? Boom. All right. That was a 10 second

example and that's not probably just like the surface value of how you guys actually go into this thing. But that's the trick, right? It's a non-judgmental approach. It's not threatening. It's understanding that they don't see themselves as a bad guy and in getting them to admit to the conduct by explaining the rationale for what they did as opposed to, you know, tell me you did it, tell me you did it, tell me you did it. You just end up in a cul-de-sac there. You go nowhere. And you see, with my, I've done sales for six years, and it's obviously, it's nowhere near the level of negotiating and,

and empathizing and so forth. It's just, obviously, there's a lot of skills that we learn in terms of body language, a tone of voice, eye contact, reading the situation, preempting, getting them something of building value as well. And I just feel like FBI, the academies, is a completely different ballgame because the example you've made right now is a little different because now I was actually even like instead of having my shoulders up like why tell me and like just naturally I started leaning back and I'm like wow like maybe maybe I just needed something you know fundamentally people want to be understood and so if you truly try to understand their perspective people are going to talk to you what's the detail from one of your wildest cases that still haunts you today I have a handful of cases that still haunt me even after all these years

One of them is the, and it wasn't my case, I was just on the team of agents investigating it. It was the disappearance of two little girls, the Luke sisters. They were ages like five and seven. They were waiting for the school bus one morning, and they never got on the school bus. They disappeared, and never to be seen or heard from again. FBI agents, like including myself, went out there to investigate the case. And, you know, we ended up doing landfill searches, digging through the garbage, looking for these girls. We had search parties walking through the woods, looking for these girls.

and technically we never solved the case, but we actually did solve it. We knew exactly who took those girls. We know exactly that he killed those girls, and we know exactly why. But we never found the bodies of those girls. And as a result of us not having the evidence enough to prove it, because it's almost impossible to prove a murder without the bodies, that man walks free to this day, and that haunts me every single day. But how do you know he did it?

We had substantial evidence that he did it. I can't really get into the details of the case because it's technically still an open investigation because the girls haven't been found and this gentleman hasn't been charged, but we're going on a decade later and they haven't. And so we had enough proof that we are metaphysically certain at the FBI.

Who did this crime? Absolutely no question in our minds. And the only thing we would need at this point is to find those girls. And we never did. What could get him arrested, though? Is that the final piece? I know the instant till proven guilty and in situations where people are still guilty and walking free,

there has to be something that can be done like in the legal system to try and like bring them down. Yeah, find the girls. Find the girls. I mean, you know, you don't even need at this point the, I mean, whatever physical evidence could be found through whatever remains are still there now, you know, over a decade later would be useful. But, you know, prove that the girls are in fact dead. Okay. That's sad. I empathize for, it's the dad that that killed the girls. I'm not saying who killed them.

Okay. I'm not looking to be a defendant in a civil suit. The government failed to arise to its burden of proof. That's on us, right? But the, you know, that's what we do. We rise to our burden of proof or we don't. We don't arrest people unless we can prove it in court. Glad you, glad for elaborating on that.

And I want to try and ask, have you ever walked away from a case because the truth was too dangerous to reveal? I wouldn't say we ever walked away from a case, but let me tell you a story and we'll see if this kind of falls into that broader category. When I was a relatively new agent, I had a case of a $250,000 embezzlement from an insurance company from an employee named Johnny. Very unsophisticated embezzlement. Johnny was stealing checks from the insurance company, writing them to himself, depositing those checks in his bank. account and then recording them in the accounting records of the insurance company as if they were to pay the bills of the company. Makes sense? Easy fraud, nothing to it. I was getting ready to go interrogate Johnny and get the confession from him. And then two very burly old agents from our organized crime,

our mafia squad in Chicago came to me and said, hey, are you investigating a guy named Johnny? And I go, yeah, I was going to head out and talk to him in another couple of days. They were come in the office. So I'm sitting there with the organized crime guys, and these guys were like, you know, like 50-year-old. This is the 90s. They were smoking cigarettes in the office. None of the rules applied to these guys. They've been investigating the Chicago Mafia for years. And they explained to me that they had a wiretap up and Johnny was all over the wiretap. It turned out Johnny was a low-level mobster. He was a bookmaker who would take bets from people and then with the mafia and then like pay out those bets or not pay out those bets. Johnny had gotten himself in trouble with his mob

bosses by placing too many sports bets with his mob bosses, pretending they were coming from people when in fact Johnny was a degenerate gambler and losing his own money to the mob. Now the problem when you bet on sports with the mafia, unlike one of these betting apps, is that the mafia will grant you credit, where you don't have to necessarily pay them up. But if you fail to pay them on the back end after losing that bet, then you get put on a loan shark juice loan and things like that. So Johnny was tied up in that. And his losses to the sports. sports betting and his payments of this coincided perfectly with the instances of embezzlement in my case. He was embezzling money to pay off the mafia to pay his gambling debts. You get the background there?

Okay. But they were nervous that if I went to Johnny and brought this case against him, it was going to spoil the wiretaps that they had up now. Because when you arrest somebody, you owe them and their attorney's discovery, which is basically all the evidence we have at them. The FBI at that point had dozens of hours of tape of Johnny speaking to his mob bosses and the people inside the mafia with whom he owed the money. What happens if we arrest Johnny and I have to turn over those tapes? We burned the wire. At that point, the wiretap of the mafia will be known those mobsters will throw their phones in the Chicago River and we lose the ability to monitor them. So we didn't walk away from the case against Johnny, but it got delayed like a year and a half

where until the wiretap was taken down and they began doing the takedowns of the mafia guys who got captured on that, then I could bring my case against Johnny because we didn't want my little fraud case to spoil a giant enterprise investigation against this racketeering organization known as the Chicago Mafia.

Meanwhile, so for that two-year period, I'm getting calls from the victim, this insurance company saying, when are you going to bring charges against this Johnny guy? And I had to make up, like, well, there's a lot of issues. We're still trying to get some financial records together. I'm kind of tap-dance. for them, not telling them that we have this wiretap on the mob that would be compromised if we

actually brought the case against Johnny. It all ended up fine. Johnny ended up pleading guilty and going to prison for three or four years, and the Chicago mob pretty much doesn't exist anymore due to that wiretap in other cases. Wow. But, you know, my little case could have had insane ramifications had I pushed forward with it without respecting the bigger case of the mafia in Chicago being dismantled by those guys. Which goes again to what you've been stressed. on the entire episode, you have to put away your ego sometimes and look at the bigger picture in situations as well. I mean, right.

While I wanted credit for a job well done and I like the idea of completing a case, it's not like I get to keep the license plate teammates in prison, so it's no big deal to me. I don't, you know, I wasn't getting paid. Now I get paid for succeeding with my clients. When you're an FBI agent, you're getting paid for doing your best. And then in situations like that and other situations like we spoke about earlier on with the two kids that were murdered, how do you maintain, like, emotional, um, intelligence or like just like sensitivity in situations like that try and like you know those traumatic

experiences and matter of fact i'm going to ask it a little better how do you maintain emotional boundaries when dealing with sensitive or traumatic content every single day well again i think you just need to talk to the people in your lives you need to understand what your role as the investigator is right it's not our job to punish and it's our job to find out what happened and report the truth warts and all and um if you're having psychological difficult If it involves something with kids, maybe you give your kids a little longer hug that day when you come home from work. Maybe you, you know, you talk to the people in your life. If you need to talk to someone professional, again, the FBI has an employee assistance program, as does every law enforcement agency at this point, where they're set up to, there's, without stigma, they'll give you someone to talk to. And so you can't keep that stuff bottled up. That's why people have heart attacks at age 45.

Awesome. And I want to ask you this, what was the most, like, interesting? I wouldn't see. hard, I wouldn't say difficult, I wouldn't say complicated. Just an interesting situation that you wouldn't go across day to day in the FBI that you had to like resolve your federal Peru as well. I need to think that through. If you're asking me what my favorite case is, that's like picking out your favorite child, right?

You love them all in their different ways. My most interesting case, again, I worked a lot of the same case again and again and again just with different characters in it, right? I mostly did financial crimes. So I had a lot of different embezzlements. I've probably seen every single way that a person can steal from their employer. I've worked a lot of investment fraud, so I've probably seen every single way someone can steal from investors.

But as a result of working those kind of high volume, low-impact financial crimes, I became very, very good at interview and interrogation. I'm able to get confessions from people because I've had my 10,000 hours. I've done this again and again and again. So I began getting brought in on other people's cases to get the confession on difficult cases. We had a case in Florida. A woman fell off the balcony of her carnival cruise ship in her cabin to her death. And it was suspected, but we didn't know at the time that it was her boyfriend who might have actually pushed her or thrown her over the balcony, whereas he was claiming that she just

accidentally fell off the balcony, even though the railing went up to your chest. And so with the limited evidence we had, I got to sit down and interview that, interrogate that guy, and talk to him and at the end of about a 45-minute conversation, he admitted that he picked her up like Thanos by her throat and threw her over because she was annoying him. Hmm. And that guy's in prison right now for a murder. And so things like that I look at as gratifying, not as an ego boost for me, but because I was able to bring justice to the family of this poor, poor woman who went on a cruise

with the wrong boyfriend. Powerful. Absolutely powerful. In situations such as that, I know... I don't know. From the movies I've watched and the series, I've watched situations like the mafia that are sending drugs inside, and the drug, the cartels and all that.

I know when you watch movies, they always say never under no circumstances break towards, like, the United States law enforcement. And I've seen people in those movies, they'd rather die than to confess what happened because they feel like the repercussions of returning back to the cartels is far greater than them actually even confessing as well. Have you ever come across situations where people just did not break at all or even like confess to what they did? I had situations where people opted invoked their right to an attorney in during, while I'm interviewing them and chose to not speak to me,

which is fine. That's certainly they're right. And so therefore you don't get the confession and you just have to work a little harder to get the evidence to make the case without the confession. Which is no big deal, right? I wouldn't be interviewing them if we didn't have evidence against them. Thanks for answering these questions. Is there a gut feeling you developed over the years that you now trust more than any hard evidence? Yeah. Are you familiar with the work of Malcolm Gladwell?

No. Okay, so he's a journalist. I think he was a New Yorker journalist, but he likes writing about social science things. And he wrote a book called Blink about how people who were experts at something from having done it for a long time can kind of evaluate things trusting their instincts, their gut instincts.

Like someone who's a art forgery expert can just look at a painting and see something in the brushstrokes that maybe you or I can't see and say that's a fake Picasso, not a real Picasso. And then he wrote another book called Outliers where he discussed the concept of the 10,000 hours, that after 10,000 hours of doing the same thing

again and again and again, you develop an expertise in that. And I think that really feeds into the blink, the ability to, you know, where the Beatles got their start playing in a strip club in Hamburg, Germany, and they became playing like Chuck Berry covers, and they did that for 10,000 hours, and they became so good with their instruments that they could produce the greatest music ever known to ma'am. That type of thing. And so I think that over time, I become really, really good at detecting deception in somebody,

detecting if they're lying to me. And I think of an example. I get a call from an attorney in Hawaii when I was, working there as an FBI agent saying got a weird situation where my I have a client whose daughter said that she was kidnapped and brought to a hotel room in in in in in in Wiki key and the guy and I oh my God was she sexually assaulted and he goes no that's what's weird the guy just talked to her for an hour then it sounds like he got cold feet and let her go and she's hysterical she called her mom her mom called me and I go I need to talk to this girl right away bring this girl in sitting down

I'm talking to her. She's 18, 19 years old college kid. And she tells me the story of what happened. And, you know, this guy, like, picked her up off the, this guy like basically dragged her in the street to an elevator, brought her up to a hotel room, sat her down in a chair, and then it sounded like he was going to assault her, but he got cold feet and didn't. And they literally just talked for a while, and then he let her go. And she was telling me the story, and I couldn't think of anything worse, right? I couldn't think of anything more awful than like being a teenage girl who had experienced something like that. But something inside me, and she was showing no outward signs of deception that I was trained to recognize.

You know, they train us and stuff like that. But ultimately, I just felt in my heart there's something about her story that I didn't believe. But I didn't, it wasn't enough for me to jump down her throat and call her a liar, which I'm happy to do if I'm certain someone's lying to me. But I said to her, I said, listen, there's something about this whole thing you're not telling me. And then I just sat there and be quiet. And I think investigators need to harness silence as a tool. Because if you and I sat here staring at each other silently, you're going to want to fill that dead space by talking. And that's what she started to do.

She started talking and she said that she made the whole thing up because she was cutting class and her mom found out and she baked this crazy story up and it spun out of control and now she's in a room talking to an FBI and none of this actually happened. And I said, listen, I go, no harm, no foul. We didn't really marshal any resources other than me in this thing. I was a dumb 19-year-old kid once. You need to level with your mom that this never happened and kind of make peace. But you just dodged a bullet because it had this thing escalated, and I got people out there pulling surveillance tape from the hotel and the Honolulu Police Department doing door-to-door searches and the press conference to show a picture of this pretend guy. Then you would have

been down a road that we couldn't turn back from. But right now it's just me. I'm a very compassionate man. Go in sin no more. And so I cut her loose. But there was nothing about that that any book could have identified as to what she was doing that made me feel that she wasn't telling the truth, other than the fact that her story was just so odd that I just had to trust my instincts on it and confront her in a very gentle way. And she copped to the fact that she had made it all up.

It's sad. And it reminds me that I've come across a lot of stories where you see, like a potential football player rising to prospectively in the draft, comes across a girl, not interested, no more wants to go for another girl, that one claims that one's raped him, and then it leads to one case before you know it he's in prison. And in the situation, I'm like,

this is more often than not. Why did they end up in prison if there was no substantial evidence to try and, like, show that this football player did not even rape or look at or touch his girl, but then the evidence was like they just, contruted to the fact that he needs to go to prison for 15 years. Like those stories are very sad every time I come across them. Why don't they conduct enough evidence like law enforcement for that?

Well, I can't speak to any specific case that you're aware of that I'm not. I mean, I think it'd be crazy to think that every accusation of an assault like that is true. And in thinking that, and likewise, you can't assume that everything is false, which is why it's so important that we have evidence and that the government's forced to rise to its burden of proof at trial and have a jury of 12 come to. a consensus that he did this. The jury is emotional sometimes, right? I'm not saying that every jury gets it right every time, but that's the system that we have,

and it's the best system we have until someone comes up with something better. I'm going to ask one controversial question. You don't have to answer it. It's not part of the thing. But you just give me guilty or not guilty. Okay? About whom? O.J. Simpson.

Okay. I'll give you that. O.J. Simpson killed Nicole Brown Simpson and the gentleman. However, I do not believe the government succeeded. rising to its burden of proof. There was enough reasonable doubt that the jury got it right by finding him not guilty, although he actually did in fact kill that woman. Right? Because there's two different things. There's what happened

and then can the government prove what happened? Those are very two different metrics. But the glove did not fit. Again, I am totally open to the idea that the government failed to rise to its burden of proof and the jury got it right. I am not open to the idea that he didn't kill those people. The man

is a double murderer. But he deserves to be free of that double murder because the government didn't prove it. I'm interested to know, was there a rule that you broke during the investigation, and were you glad that you did it? Okay. So I have a story that I think addresses that issue. I had this FBI agents all have informants.

They call them confidential human sources right now, but they're people in the community who funnel information to the FBI to kind of build up our intelligence source. I had this informant named Annie, who was really good at pretending to be a 13-year-old girl online. And so we utilized her, took out an ad on, rather we posted an ad in a website saying that she was a 13-year-old girl and wanted to lose her virginity. We did this to attract child predators. And so we did. We got a child predator to meet Annie at a park bench and a Sunday afternoon, told him to bring condoms so

he could deflower this 13-year-old girl. And Annie's playing it straight with him. And of course, when he arrives, he wasn't there to meet Annie. He met me. And so me and my partner, we got to confession from him and basically cut him loose because we needed to present it to the prosecutors. I got chewed out for running what they called an undercover operation without the proper authority. And they're not wrong about that. Because anytime someone is pretending to be someone they're not at the request of the U.S. government is technically an undercover operation. And so I got in trouble for that.

And the federal prosecutor refused to prosecute the case because of this. But the guy we got the confession from was in the U.S. Navy. So I brought this case to the U.S. Navy and they prosecuted him in federal court and he went to prison. And as a result of me breaking the rules and doing this operation, a child predator is now off the streets. Oh my gosh. That's amazing news to year. I'm glad to hear that it's exciting to hear that these predators are kind of, and there's a lot of operations that are working towards getting people on the ground railroad,

all these different stuff that I think it's O-U-R operations underground railroad or something like that. Many of these things are actually helping people. people get these predators out the street. So I'm glad you mentioned that story. I often ask this question to all our guests towards the end. Obviously our podcast is called the code to winning insights you need a day to seize the world tomorrow. You shared something very, very insightful. I'm excited for those episodes to drop as well. In your personal definition, what does it mean to be winning? In order to be winning, you need to be able to look at yourself in the mirror when you're an old man like me at age 55 and say, did my life matter? And when you're a former FBI agent, you never

really have to ask that question because the job that you did and the life that you had matters. Love that so much. Tom, if you could look at the camera and let our guests, our guests, our guests, know where they could get a hold of you, if they want to contact you, email or whatever it may be, social media. My website is Simon Investigations.com, and I'm also on social media, TikTok and Instagram primarily under the name Simon Investigations. If anyone out there's looking for a private investigator or know someone who is, I would really appreciate your referrals Likewise, you should follow me on social media because I do two to three minute crime stories

every single day from an FBI perspective. Also, if you're part of a group or an organization that needs a public speaker, like a keynote speaker for a convention or a meeting, please contact me through my website. Thank you so much and be cool. The co-winning insights you need a day to seize the world tomorrow.

Retired FBI agent and private investigator, Tom Simon. Thank you so much for coming to the studio. Thank you so much for having me.