What makes covert operations so interesting, and even funny at times, is that things are purposely not what they seem.

I often find myself explaining to people that despite its ‘cool factor’, a covert operation isn’t just conducted for fun. It’s a tactical method for achieving very specific goals, and it can be expensive, risky and difficult to manage.

That being said, there’s still no denying the fact that once the operation is running properly, there are indeed many interesting, even funny, situations that can come up.

Let me give you just a tiny sampling of this.

Working with different clients

One of the things that makes the work of an external vendor so interesting is that you get to work for many different types of clients in many different environments. Variety, it’s been well said, is one of the spices of life.

I’ve had clients who came directly from intelligence agencies, and who knew exactly what kind of covert operations they wanted. I’ve also had clients that admittedly didn’t know the first thing about covert operations, and others that didn’t know the first thing about covert operations but claimed otherwise. It’s this latter category that tends to produce some of the funnier stories.

I had a production company client from Los Angeles that wanted a certain celebrity who was attending an event in San Francisco to receive covert protection. This, I was instructed, should take the form of a Secret Service-type close protection operator in a black suit with a pigtail earpiece. I had to explain that this was in fact a very overt form of protection, despite what my Hollywood client might be used to seeing in the movies.

On another occasion, I had a Silicon Valley client who needed six covert operators spread out at various locations in their headquarters. We started the operation early in the morning when my team met up at a coffee shop in the area. We then made our way into the headquarters’ loading dock where we were met by two of only seven people in the entire corporation that knew about our operation (except for one supervisor and one GSOC operator, even the campus security team didn’t know about us). The team got geard up in an internal room and each operator was discreetly escorted to their individual location.

At a certain point during the day, the corporate security director became upset about my operators not being in place. He had to be walked into each room and common area to have the operators discreetly pointed out to him. Despite the fact that all of them had extensive military and security backgrounds, I had specifically selected them based on age and appearance. Casually dressed with their laptops and coffee cups, they were so well embedded into the the techie environment that no one, including the man who had hired us, realized they were there.

Working with different operators

Just like I get to work for different types of clients, I also get to (or rather have to) employ different types of operators. As always, the mission and the environment dictate how you operate and who you should employ.

The reason why the above-mentioned operation went so well was because the operators were relatively young, white, Asian and Latino men and women who were dressed like hipsters and techies. In other operations that take place in other environments, different operators can be used. Political correctness simply has no place here.

The black middle aged operators I work with (both ex-cops with extensive undercover experience) simply can’t blend into a room of young tech workers. They can, however, make themselves invisible in the many downtown environments we often work in.

There’s the short, friendly, middle aged white lady who blends so perfectly into shareholders meetings that even I sometimes have a hard time spotting her. No one else in these meetings has the foggiest idea she’s carrying a concealed weapon and that she’s an ex-police lieutenant with thirty years of law enforcement experience, ten of which were spent as a SWAT operator.

As for large, serious-looking men with military, law enforcement and security backgrounds, it’s interesting to see who can blend into different environments despite their size, and who can’t. Those who can’t tend to be better suited for vehicular surveillance operations.

I’ve never managed any mobile vehicular operations but static ones (oftentimes overnight) are quite common. In these types of operations, it’s interesting to see who has less experience, and therefore needs more guidance, and who has years of experience and knows the drill.

I once managed a complex overnight operation where five operators were positioned in five different vehicles on different levels of an indoor parking lot. The operators had to remain unseen in their vehicles the entire night. Before the operation started, I met each operator at a different location a few blocks from where the operation was to take place in order to brief them and to give them some overnight provisions. These included snacks, water, energy drinks and a couple of empty Gatorade bottles.

Some of you already know why you’d need that last item. Gatorade bottles have larger rims which makes them ideal for “depositing” your fluids. Remember, we’re talking about an overnight covert operation where you don’t get any bathroom breaks. Also, when it’s dark and you reach for a bottle, the difference in shape helps you prevent accidentally drinking out of, or peeing into, the wrong bottle.

I had to explain this to the operators with less relevant experience. I remember one of them looking quite bemused as I was talking, thinking I must be joking. Explaining this to another operator however, an ex-Navy SEAL with years of PSD contract work in Afghanistan, earned me a different kind of bemused expression. This one for wasting my breath. I think his exact words to me were “This ain’t my first rodeo, kid.” We both had a good chuckle about it. I just had to make sure everyone was on the same page.

Interesting encounters

A few years ago, I was leading a covert operation that was meant to detect hostile surveillance and other pre-incident indicators around a large tech conference. As I was walking around a large dirt lot in the area of the conference, I saw a man enter the lot carrying a black plastic case. I continued walking a little longer to avoid any direct correlation and spotted a good static position further down the street next to some trees behind a small parking lot. Having seemingly stopped there to check my phone, I had a good distance from the individual (around 200 yards), a clear field of view and a few parked cars between us. The man had his back to me as he kept walking towards the middle of the large dirt lot.

I remember thinking “Please tell me that’s not what I think it is.” But sure enough, I saw the man stop, lay the case on the ground and open it up. He took a medium-sized item out of the case, laid it down on the ground and took out a smaller item which he held in both hands. He then took two steps back and the medium-sized item lifted off the ground. “You’ve got to be kidding me.”

I immediately reported that a drone was in the air, and gave the exact location of the drone operator. The lot was actually owned by the company in question and drones were strictly prohibited around the conference. No less than three uniformed security officers got to him within sixty seconds, which was when I walked away.

Despite the inclination to watch what happened next, there was no real benefit to my sticking around. My part was over. Also, if the individual were to put two and two together and realized that three uniformed security officers probably wouldn’t have triangulated on his exact location as quickly as they did without any help, he might have figured out that another operator was in play. On top of that, most of the uniformed security officers also didn’t know about our covert operation, and the few who did, didn’t know who I and my team members were. There was just no point in sticking around to allow someone observant to detect me.

Maybe an hour later, as I was walking a bit closer to the main entrance of the venue, I practically bumped right into my first cousin on the sidewalk. I had known that she worked for the company in question, but so did thousands of other people. The thought of accidentally bumping into her hadn’t come up (and wouldn’t have really changed much if it had). Unexpectedly bumping into people you know is just one of the things you have to accept when you live and work in the relatively small San Francisco Bay Area.

Still, it’s a strange feeling when your personal and professional worlds literally bump into each other on a Silicon Valley sidewalk.

There are celebrated stories of how trainees in clandestine agencies are purposely made to run into friends and family members during training in order to check if they can still hold onto their covers. In my case though, there would have been no point to such a thing. For one thing, I wasn’t exactly operating in enemy territory, and if anything, our unexpected meetup only helped me blend into the environment as we stood and chatted for a minute or two. Knowing what I do for a living, my cousin didn’t have to ask me what I was doing there, and just told me she was happy I was around that day.

Interestingly enough, I recently found myself on the opposite side of an accidental meetup. A friendly British acquaintance of mine who organizes security conferences around the world was attending the recent RSA conference in San Francisco. We decided to meet up at one of the high-end hotels downtown to discuss the possibility of my being a speaker at a future conference he was organizing.

The hotel was unsurprisingly full of RSA attendees and various side-events and meetings were happening there. As soon as I stepped into the lobby, I saw a local professional acquaintance of mine sitting alone on one of the sofas. We had worked together in the past but hadn’t seen each other for some time. He was there providing covert protection for an important Silicon Valley CEO (which was one of the reasons his position covered the entrance to the lobby).

There’s no denying the slight awkwardness of a situation like that but having both recognized each other, it would have been even more awkward to try to ignore one another afterwards. Besides, keeping him company, even if just for a few minutes, could help him better blend into the social environment he was in. So I joined him on the couch to wait for my British friend and we got a chance to catch up a bit.

The Russians…

Over ten years ago, I was in charge of a multiple-day protective operation that necessitated the continuous presence of an operator in a parked vehicle outside a high-end residence in San Francisco. I don’t usually consider operations like that covert, since there’s no real cover or concealment in play. Neighbors almost always start noticing it after a while, and without fail, so do the police patrol officers. For this reason, we always reach out to the SFPD beforehand to let them know about stuff like that (professional courtesy of this sort can sometimes be very useful and is always very appreciated).

When I went to conduct an advance before the operation, I realized that the residence in question was within two blocks of the very large and imposing Russian consulate (the same one that was subsequently shut down by the State Department in September 2017).

My points of contact for this operation were two jovial middle-aged corporate security directors who had previously retired from the FBI (the residence in question belonged to one of their corporate executives). I voiced my concerns about the fact that the Russians were sure to detect our continuous presence, and might mistakenly think we were there to surveill the consulate. I asked them how they suggest we handle this tricky situation but both of them just started laughing. “The russians aren’t going to bother you, kid. We used to post agents out there all the time back in the 80s, just to fuck with them.”

The operation went smoothly and just as they told me, the Russians indeed didn’t bother us.

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Go behind the scenes of corporate surveillance detection & covert special operations. Get a first-person account of actual covert operations I’ve participated in. Learn the secrets of the trade and discover a hidden world that’s all around you.

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