Real Lessons a 30-Year Private Investigation Career Taught Us

In this episode

What does 30 years in the investigative industry look like? Oscar Santamaria shares the personal story of how he entered the field in 1992 after failing the bar exam and taking a “part-time” surveillance gig. Thirty years later, he and Francois discuss how their characters were forged in the “wild west” era of South Florida. They emphasize that while gear changes, the “human element”—integrity, persistence, a

How do professional mistakes shape an investigator’s character? In a moment of candid transparency, Oscar shares a story from his early days when he overstepped his bounds by attempting to translate a legal mediation. The result was a hilariously disastrous linguistic error that taught him a lifelong lesson in professional specialization. This segment highlights the hosts’ commitment to honesty and why they believe admitting mistakes is the first step toward true expertise.

Can a ruse be the difference between success and failure? The hosts recount a high-stakes child custody case that took them from the heat of Florida to the cold of Harrisburg, Pennsylvania. They detail the grit required for a “trash pull”—coordinating with local sanitation to retrieve physical evidence of a court violation. They also update the “AI Challenge,” explaining why the Toyota Corolla is the new king of blendability and why the modern cell phone has finally retired the traditional key fob camera.

What You Will Learn In This Episode

01
The Value of 30 Years of Experience: Oscar reflects on his journey starting in July 1992, highlighting how the industry has shifted from the aftermath of Hurricane Andrew to the AI-driven landscape of today.
02
Humility as a Professional Asset: One of the most important lessons in an investigator’s career is knowing when to admit you aren’t the right person for a specific task, as shown in Oscar’s humbling “translation” story.
03
Agility Over Size in Fleet Selection: In the latest AI Challenge, the Toyota Corolla emerged as the superior choice for South Florida surveillance due to its commonality and superior maneuvering in tight residential areas.

Francois McKinnon: Welcome to the Miami PI Chronicles podcast where the world of private investigation comes alive. Joining me is Francois McKinnon of McKinnon Investigative Group and Oscar Santamaria of Optimum Investigations as they tap into their combined 60 plus years of experience in the industry. From real-life cases to insider tips, they bring the stories, insights, and expertise that only seasoned pros can provide. So sit back, listen, and enjoy the show. Hey Oscar, welcome back to the show. Episode 31. How do you feel this week?

Oscar Santamaria: I’m doing well. I’m doing well. How about yourself, Francois?

Francois McKinnon: Everything is going well. We’re excited. We’re getting emails from listeners and the show is really carrying on. It’s kind of insane. I know that we’ve had people reach out to you this week.

Oscar Santamaria: I actually did. You know what? I want to do two shout outs. One to a gentleman by the name of Oscar Rosa. He’s a renowned private investigator from Spain and the host of a podcast called Loco del Fondo, Historias de Detectives de Verdad. He comes from a long range of private investigators and we absolutely love what he’s doing. This man has passion for the private investigative industry. I mean, he dedicates hours and hours a week on his show.

Francois McKinnon: Yeah, I was quite surprised, Oscar, how many hours he dedicates to the podcast.

Oscar Santamaria: But he has a passion like I’ve never seen in my life. And for all of our Spanish listeners, I encourage you to take a listen. Again, the podcast name is Loco del Fondo, Historias de Detectives de Verdad. Also, I would like to thank one of our absolutely best listeners.

Francois McKinnon: Our favorite. Our favorite.

Oscar Santamaria: Yes. We affectionately refer to her as Marlene from Asheville. She’s actually from Florida. I’ve known her since I was 13 years old. Very good friends with her family. And she is always on us about why is your show late? Why isn’t there? She’s not even a private investigator. And yet she like really cracks the whip on us.

Francois McKinnon: And oh, yeah, she puts us in our place, Oscar. Yeah.

Oscar Santamaria: You know, every everybody should have a fan and a friend like Marlene from Asheville. So Marlene, if you’re listening, thank you. You know, I appreciate you not only as a friend, but also as our number one fan.

Francois McKinnon: Yep, I agree. And we love Marlene and her husband, Joe. Everything. These people are wonderful. I wanted to give a shout out, Oscar, to Bob Scarservant in Waynesville. This guy is the guy every time I fly anywhere because I live so far away from the airport, you can’t get any service. There’s no Ubers or Lyft around to get a ride to the airport. This guy picks me up at five o’clock in the morning on time. When my plane gets there, I make one phone call. He’s one minute away. So his company is called Bob Scarservant and his phone number is 619-318-6990. So if anybody needs a ride to the airport, the doctor’s office, hospital in Asheville, please give Bob a call. He’s your guy.

Oscar Santamaria: Marlene, I hope you’re listening.

Francois McKinnon: Yes, Marlene, because Marlene goes on. She always uses Uber.

Oscar Santamaria: She does. She lives way where Ubers don’t go either. So Bob Scarservant.

Francois McKinnon: Oscar Rosa is also a professor at the University of Madrid. So being as passionate as he is with the private investigation thing, I believe you told me that his siblings are also private investigators and his father was a private investigator.

Oscar Santamaria: I think so, yes. And he’s running the agency, I think, for years. And, you know, it’s a little bit different in Spain than it is here. They’re not allowed to carry weapons. And I don’t believe that they do criminal type of investigations. I could be wrong, but I think that we’re going to have him on the show in maybe a month or so. And and I think it’s going to be a very good interview. The man, like I said, has got passion that I have never seen before. I mean, it kind of like makes me feel like I’m slacking on the passion game. We got to pick it up. We have to.

Francois McKinnon: Well, listen, I think it’s always stimulating to see somebody that passionate that spend so much time preparing for their podcast and the show and investigations. We’re going to we’ll have him on the show and then we can ask him how different it is from here, because I see that he went to two American universities. So his English might be it must be up to par. So we’ll we’ll try to have him on the show and we’ll keep you guys posted.

Oscar Santamaria: Yes. Looking forward to that. And as well, we’re looking at other interviews of, you know, some very accomplished private investigators. And we’re trying to line those up. And hopefully we’ll have that settled in the next couple of weeks. And it’ll be quite insightful.

Francois McKinnon: So we’ve had a lot of feedback from our last guest, Mark Hurwitz, and a lot of people enjoyed his interview last week and on episode 30 and also told us that to get other PIs that are located in Miami, Ft. Lauderdale, in our area, you know.

Oscar Santamaria: Yeah, we definitely will. I got a lot of positive feedback from that interview as well and the other ones we’ve done. I’d like to have Mark back only because, you know, we kind of glossed over his experience at the CIA. I know, you know, there might be some things he can’t talk about, but that would be pretty fascinating. I know that he bought up a lot of terms that the people in the CIA use. Like he mentioned, he runs his company like a CIA station. I’d like to really understand what that means. And then I think also he talked a lot about street craft. That’s like a term that I really never heard about. So, you know, there’s just some things I would like to touch base on him and we’d love to have him back sometime.

Francois McKinnon: Did you start watching The Americans?

Oscar Santamaria: I did. I did. How do you like it? Oh my God, I cannot get, you know what? Philip. I cannot get past Keri Russell. I mean, I knew she was in something before, but damn, I didn’t think she did anything since like the 90s. And I watched this and wow, she’s a really good actress. That’s a good show. I’ve only gotten to episode one, but I’m going to continue to watch it. I mean, you guys talk very highly of it.

Francois McKinnon: Oh yeah. Well, to get back to your point about the street crafts, these are like the oldest undercover agents tricks to pass on a dead drop or something. And, you know, back then there were no cell phones. So they have to use pay phones, but the CIA could locate every pay phone that a phone call was made from. But by the time they show up, nobody would be there. Yeah. Right. So you’re going to see throughout the show that they have some really cool stuff and the way also that they set up people, you know, when they want to get rid of somebody, they set them up real bad and then they get caught doing something horrible. So the way they manipulate, like the CIA does as well, but the way they manipulate in the intelligence world, manipulate people and turn them to be your assets for your government is pretty cool. So I think you’re going to see a lot of that in the show and it’s very neat and very educational.

Oscar Santamaria: Yeah. I spoke with some other people about it and I don’t think anybody said a negative thing about that show. Funny enough, when you mentioned that, years ago I had a PI friend of mine that was talking about, he accepted a case from a gentleman that was also, I don’t know, ex-FBI, CIA, one of those. And the guy didn’t want to send him an email or anything. He actually told him, you know, there was a dumpster behind this restaurant and there would be a folder with all the information taped to the bottom of the dumpster. And, you know, I kind of thought it was a little ridiculous, but it was used. I mean, I guess that’s, you know, I guess, I don’t know what the reasons were. It seemed like it was a pretty cut and dry case, but that’s the way he wanted to do it.

Francois McKinnon: So I guess- Is he a private investigator now?

Oscar Santamaria: He is a private investigator now. Wow.

Francois McKinnon: That must be hard to meet clients. You know, I’ll meet you by the dumpster on 6th Street.

Oscar Santamaria: No, he didn’t meet him. He had like the whole information there and, you know, like in an envelope taped to the bottom. I thought, I’ve never heard of that before.

Francois McKinnon: So- That’s a little too much. Yeah. Unless you’re, is that for a background check, a dossier or something?

Oscar Santamaria: Was that, no, it was a surveillance. And I don’t know what the whole thing about it was, but, you know, I thought it was a little overkill, but who knows? Maybe he had a reason for it. Who am I to judge? Exactly.

Francois McKinnon: Some people are very careful.

Oscar Santamaria: So I don’t know, Francois, if you’ve been noticing how quickly time goes by. You know, I’m driving through some places. Obviously, you know, when you’re a Miami private investigator, you’re always driving through locations and you’re always like, you know, I work there and there and there and there. But there’s so many changes that are happening to the city that I grew up in and it’s going by fast.

Francois McKinnon: Dude, I was in Miami, what, 10 days ago? And everywhere I drive, I go, oh, I did a surveillance there. I did a surveillance there. I did a surveillance there. And 30 some years have passed and we’re still in the game. You know, I had a big case with the client that lost some very expensive jewelry. So I was able to go to Miami and apply enough pressure for them to realize that this jewelry was never sent. So working on that right now. And what was I going to tell you? How did you, how did you start? What made you want to become a private investigator? I forget.

Oscar Santamaria: You know what? It kind of just happened. I always kind of wanted to be a private investigator. It’s one of the things, a police officer, a private investigator, maybe a fireman. There was a little bit of a time when I wanted to be a lawyer until I miserably failed the bar exam. So I graduated college. I taught for a little while. I really wasn’t knowing what I wanted to do. And my sister happens to be an attorney and she worked next to these private investigators and they were looking for a part-time surveillance investigator. And my sister said, Hey, my brother’s, you know, might be interested in that. So I did that. And that was back in like July, 1992.

Francois McKinnon: Look at you remembering the dates.

Oscar Santamaria: You are getting old. You know, the only reason I remember that is because shortly thereafter, Hurricane Andrew happened and then it really disrupted the profession. And I was at, I was quickly out of a job for several months. And after starting a new career, I was like, can I at least keep the badge? So he called me back about four or five months later. I continued to do that for a agency and we did that in 1995. So this will be my 30th year. And I’ve been doing a lot of reflecting, you know, when I started, things weren’t always smooth sailing. I didn’t know what jobs to take on when we first started.

Francois McKinnon: Have you realized anything from that?

Oscar Santamaria: I absolutely did. One thing that I learned about those days is, is never take a job that you really aren’t qualified to do. And I learned that pretty early on. You know, when you’re a private investigator, you kind of want to do everything just because, you know, you want to get as many clients as possible. So some of the things that I did was, you know, obviously surveillance statements. I did things like personal injury case signups for people too injured to go to a law firm, property damage photos and stuff. And one day this client asked me to, to translate a mediation that it was, you know, they were so far apart. He didn’t, he didn’t really want to spend the money for a translator. It was so, it was so short notice. He said, we’re so far apart. I don’t even think you’re going to be asked any questions. And I was like, look, man, you know, I can speak Spanish. I understand it, but I’m, I’m in no way a translator. He’s like, again, you know, it’s going to be very simple questions. Do not worry about this. And I said, all right.

Francois McKinnon: So what was the case about?

Oscar Santamaria: So this guy was injured, falling on, he was on an escalator and he, and the escalator suddenly stopped and then he fell forward and like it was halfway down. So, you know, everything started off pretty good. The, the mediator, you know, asked me how the incident occurred and you know, what his injuries, what injuries he sustained as a result. I was able to get through that pretty easy. He asked me several other questions and I was able to, and I was able to get through all those and I was beginning to feel quite comfortable actually. Oh, this isn’t so bad. Maybe I’ll just, I’ll just maybe incorporate this into, you know, as a career. And then he asked me this question that really at that point I shamed my client. I shamed my client’s client. I shamed myself. I shamed my family. I shamed the entire legal profession. And I, and I, and I, I shamed translators, you know, the world over. And, and I would like to take this opportunity to just say sorry. And I have never done an official translating. Now, you know, I do my little things, you know, for statements and stuff I can get around that, but I will never for legal purposes ever in my life, Francois, listen to me, be hired as a translator. So.

Francois McKinnon: I know a little bit about this story, but share it with our listeners because, and build it up because I, I was in my car the other day. I was laughing so hard. I was crying. I couldn’t see the road.

Oscar Santamaria: So after he told me, you know, you know, just a few questions that I was good. He, he asked me, okay, aside from, aside from his neck, his head, his knees, his wrist, that he claims that are almost completely healed. He’s also claiming a loss of consortium relating to the damage to a medical device he had inserted a few years ago. Everything started off fine until we got to the medical terminology, and I realized I was out of my element. It shamed everyone in the room. It was a terrifying experience.

Francois McKinnon: You’re not doing that anymore. No. And you know, but some good did come out of it. I told a friend the story and he ended up canceling his own translation gig the next day. It was not my shining moment for sure. I still have nightmares about it.

Oscar Santamaria: Listen, man, after 30 something years of doing this, there’s always some weird stuff that we did. Originally when we had jobs, we wanted to do everything. And sometimes, like you said, we weren’t prepared or equipped to do them. So we had to, we had to, to, uh, to improvise back then. Remember?

Francois McKinnon: Yeah. Listen, with experience, you learn a lot. And, you know, those were the days that, uh, you know, my, you think you can do it all. And obviously that’s not the case. At least I didn’t laugh because that would have been very bad. Usually when I get nervous, I start laughing. We’ve done some stuff that, I don’t know, for me, for some reason it worked out, but I’ve certainly done some stuff that I, back then, I’m talking about 30 years ago, I didn’t know what the hell I was doing. And I worked with you all the time. We had that crazy case that we got to travel. We got to go places. Remember when we’re in Pennsylvania in the mountains?

Oscar Santamaria: We were in Harrisburg. Yeah. I remember the turnstile doors and the hotel with the scorching water. We went for a drink at a local bar. And just being friendly, Francois, you started talking with a guy sitting beside us.

Francois McKinnon: And he said his father owned the local garbage company. So my eyes lit up. I looked at you, you were in immediately. And then we asked them if they could go and pick up that garbage and we’d pay them. Which they did. And the garbage actually came in very handy for that child custody case.

Oscar Santamaria: We had one hell of a setup, right? We pretended that we were limo drivers after the Superbowl. We were loose and having fun, and the subject came and joined us in the pool. She started ordering drinks herself, which she was not supposed to. I went to the front desk and got her room receipt that showed detailed billing for alcohol. Then after she checked out, we went to her room and documented all the beer cans in the trash to prove she violated the court order. It was licensed surveillance taken to the next level.

Francois McKinnon: We put the trash in a FedEx box and sent it back to Florida. We opened it on a tripod and documented every single thing. It stacked like a son of a gun. That case went on for about a year and a half. Every single weekend for a year and a half. That was a lot of money back then. We did one hell of a bang up job. I think it sharpened our game back then because we were constantly on the job and we had to learn as we went.

Oscar Santamaria: And I wanted to tell investigators in South Florida or anywhere that if they want to be a guest, they can email us at miamipichronicles at gmail.com. We also have our AI challenge results. We pitted the 2025 Toyota Camry against the 2025 Toyota Corolla. Who do you think wins?

Francois McKinnon: I say the Corolla. What are the results?

Oscar Santamaria: For the 2025 Corolla, it’s smaller, more common, and easier to blend in. It’s more agile and better for tight spaces. Based on that, it looks like the Camry was defeated. We now have a new champion for surveillance vehicles. We also pitted covert cameras against one another. What makes a better covert camera: a key fob or a cell phone?

Francois McKinnon: I would go with the cell phone. Everyone is walking around with one anyway. It’s less suspicious.

Oscar Santamaria: AI agrees. The cell phone has far superior video quality and better low light performance. It’s my go-to thing now. It’s so much easier than downloading from a key fob to a computer. You can send the evidence directly to the client.

Francois McKinnon: On that note, we’re going to call it a show. I look forward to next week, buddy. For all of your investigative needs and a free consultation, please call the McKinnon Investigative Group at 954-513-7414. That’s 954-513-7414.

Oscar Santamaria: See you next week, Francois.

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