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In this Lessons episode, explore how strategic visibility and unconventional thinking can drive business growth. Discover how media exposure builds credibility and scales a brand. Understand how fast decisions with imperfect information create momentum. And uncover why defining risk appetite and managing internal threats is critical to long term success. You know, it's, it's interesting you keep mentioning your lack of basically business acumen, but yet you've built a successful company. You work with Fortune 50, Fortune 100 and you've probably marketed yourself a hell of a lot better than a lot of the people with 2000 person plus companies. Like how many of their CEOs have been on Rogan and, and, and Patrick David's podcast? And I'll throw myself in the mix even I'm not on that level yet. But I mean, but you know, so I'm seeing you're doing something. So what, what do you think consciously or maybe now subconsciously is just thinking through what do you think differentiated you when it came to building the business, building a personal brand, marketing yourself. Because all this and then, I mean you're on TV too. You've done some very strategic things that anybody else coming out of the agency, anybody else coming out of the military, FBI, even police force, they have a story to tell. Yay. You know, it's a little bit sexy, but I mean FBI is sexy. You're up high enough in the military, you do some cool shit. That's sexy too. You can build a brand around that. What made you different?
B
Yeah, I mean I think and some people have and they've done, they've done it very well. Yeah, you know what I kind of, I kind of blundered into. If we just look at the media appearances, if you just talk about doing talking head appearances for the news on, on national security issues or counterterrorism or whatever the topic may be, I kind of blended into it. I had moved from London to the east coast to set up an office. We had just taken our first investors and they BGR, which is a fantastic lobbying firm in Washington D.C. and so part of the agreement for the investment was open an office there with them co locate and at the time we were starting to build up a presence in Iraq. And this was early, early 2003, so very begin of our first incursion there. But we had been dealing with some of the infrastructure companies. And so the point of this story is one day Ed Rogers, great guy, terrific individual, part of BGR and the original founding partners, he came walking to my office, knocked on the door and said, hey, Fox News needs somebody to talk About Iraq, you know, head over there. It'll be fun. You got to be kidding me. So I made sure, you know, don't talk about anything stupid. But you can, you can, you can do it. And the agency's always been good with me that way. But so I went over, did the appearance and, and found out after the first couple that, you know, honestly, as long as you don't say anything stupid, you don't fall off your chair. Right. You know, the news networks need to fill up a lot of time, and I just happen to have a lot of, you know, experience and background in certain areas and, and was willing to go on and talk about that. And so some of the outlets, including Fox, they were very good. You know, they were very good to me. And, and they were. And then I discovered that I wasn't getting paid for any of it. But what they would do is they would put the company name on the bottom, like, you know, with, with the company and I, and once I realized that, then we were off to the races because, like I said earlier, there was no way we could have, as a startup, afforded that sort of marketing. It just wasn't going to happen. And so, you know, I, I was, I realized that, you know, that was an edge. Right. We had an opportunity there, and then everything else just sort of kind of fell into place, I suppose. Yeah.
A
No, I was going to say it's amazing how, you know, to, to have a good story, you just have to have a, a cool career, do something incredible and then speak about it. But you'd be surprised at how many people just don't feel comfortable leaning into that. And then you did.
B
Yeah, I mean, I think the agency, again, because of what I was doing in operations, and, you know, you do have a sometimes an overblown sense of, of confidence and, you know, so I think that that part of it never. And I, and I genuinely like talking about issues of the day. I, I spent a great deal of time focused on that. I have a, A lot of friends in a lot of different places, and we, we, we end up, you know, banging on about, you know, the, the current crises.
A
There's never, there's never a shortage of them, so.
B
There's never a shortage. And so it helps if you find it all interesting.
A
Right?
B
You can't, you can't fake that part of it. It's like, But I, I, you know, again, I think, you know, luck kind of fell into it again. And then, you know, once I realized that it was certainly beneficial, you know, it wasn't Like I was going to turn down opportunities.
A
Yeah, no, no, obviously another one of the rules that you mentioned, which I thought was interesting just in terms of velocity and getting shit done, it's, it's number four, it's get off the X. Yeah. What does that, what does that mean exactly? Where does that come from in an agency context? And then how does that translate into business startup, entrepreneurship?
B
Well, in an operational sense, you know, not just the agency, but military and other organizations, the, the X means is essentially an ambush site. So, I mean, a, you don't want to be on the ambush site to begin.
A
Yeah, fair.
B
The idea is you spend a lot of time training to recognize indicators of a potential ambush, right? And you know, but if you do get on the X, if you're unfortunate and for whatever reason you land on that spot, then you have to be able to get off the X, you have to get out of there, right? And in operational terms, that's a tough thing because everything starts locking up, right? And you're, you know, you start, you know, getting blinders and, you know, your hearing goes. And you know, in any, any difficult situation, right, you have to start relying on big muscle memory. And so that's again, why training is so important, why, you know, it's not enough just to do, you know, some training, you have to constantly review it. But anyway, the point is, in business, what it means is, I think, anyway, in my opinion, this is what, again, you know, there's no hard and fast, I suppose, to any of this, but from my perspective, it simply means knowing how to make decisions quickly with imperfect information, right? Because once you land in the, in the, from an operational perspective, right, you just gotta, you gotta take action, right? You don't have time to sit around and hope that you get all the data, you know, where, you know, where are all the hostile elements? What the hell is happening? You, you have to start making decisions, right? And it's the same in, in business, right? You, if you wait for all the data sets to come in, if you wait for all the analysis to be done on whatever it may be, something bad's going to happen, right? Or the competition's going to have your lunch, or you're going to lose the opportunity or your reputation is going to be damaged, whatever it might be. So it really comes down to how do you learn to. And also a lot of this is about how do you impart that ability to your personnel, to all the folks that are working with you to make these decisions.
A
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B
Yeah, there's, I mean, there's, there's, there's a lot of, there's a lot to this. It's, it's a fairly, I mean, part of it is not that complicated. Part of it is, you know, knowing your risk appetite, which is another, you know, element of.
A
I was actually curious about that one too. Only because I thought that business inherently comes with risk. So how do you not have a risk appetite if you're building something?
B
Well, you'd be surprised. And even, I mean, going back to, you know, the intel community. Look, intel organizations, which, you know, by definition are risk taking operations, they go through periods of time where they become risk averse. Right. It's because, you know, they've had blowback from, you know, some operation or they've gotten their ass kicked up on Capitol Hill too many times.
A
Yeah.
B
And so, you know, suddenly you've got a, a cycle where, you know, management is avoiding risks. And I've seen A couple of those cycles sweep through the agency over the years, and that's, it's a bad thing. But, and so you have to understand what, and when you're understanding what your risk appetite is, it also means you have to understand what your shareholders or your investors or your board of advisors risk appetite is. You have to understand what the client's risk appetite is for sure, when you're talking about, you know, working for them and providing, you know, strategic intelligence or guidance or due diligence or whatever it may be. And, you know, that's a, that's a key part of it and that informs a lot of other decisions that you make, including how do you, you know, again, make decisions with imperfect information.
A
Another, you know, when you're talking about risk appetite, I'm, I'm interested because you deal with businesses that are dealing with threats. So in a business landscape, advice for executives, CEOs, founders, what are the threats that you see really plaguing businesses right now? And I know there's, you know, there's specific examples that would not transcend every industry or every category. But you see, you see macro level. What are some things that people should think about?
B
Well, I think any company of any size, and it doesn't really matter how big it is because small businesses can, can be damaged quicker and faster and, you know, more broadly than, than large corporations at times from some of these. But the insider threat is always something that, that we end up talking about. And the insider threat can mean a variety of things, right? It, it can mean, it can mean within a pharmaceutical company, you've got somebody who has been recruited, developed by a competitor to provide, you know, intellectual property or key information regarding research and development. It could mean they could have been compromised by, you know, Chinese intelligence service. Right. I mean, that, that sounds, oh my God, that's spooky. But look, yeah, you know, that's happened to Dow, it's happened to dupont, it's happened to a wide variety of companies, right, where state sponsored intel services have targeted the private sector, gone after individuals who they've identified through the typical recruitment process or recruitment cycle and just, just like an intel service would and go after these individuals who can provide then inside information. Economic espionage, basically. So that, and so that's an example of an insider threat. You know, insider threat can also be, you know, a disgruntled employee who decides, you know, to do enormous damage because perhaps they work in it or wherever they may have access to very sensitive information. It could be an accounting issue in finance. So the insider Threat is something that companies need to be focused on. Cybersecurity is obviously a big buzzword and has been for a while. And that is a whole separate conversation in terms of the ability of companies to understand what those threats are, to stay on top of those threats, to understand how to respond, when to, when to incorporate outside law enforcement assistance. The FBI is working very hard now to try to establish better dialogue with the private sector so that they can better inform the private sector where these threats are coming from. And you know, and it's just, you know, the potential for damage to a company when we talk about, and you mentioned it early on, when you talk about like within operations or within the agency, failure to do the right thing can lead to, you know, death or, or serious, you know, goat rope. Then, you know, I think with the private sector, you know, you're talking about the, the crushing of a, of a, of a company. You're talking about the, you know, irreparable damage to a brand. You're talking about, you know, massive losses, layoffs. I mean, there's, there's all sorts of damage that can be done through companies not paying attention. I mean, look at, you know, svb, Silicon Valley bank. Probably not the best example of like that, that sort of insider threat that seemed more like it was a bunch of tools trying to make decisions that were completely inappropriate for also. Yeah, yeah, so there was. So, you know, you also have to worry about the insider tool thread, apparently.
A
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Episode: Lessons – 17 Years Undercover Then He Built a Business Empire | Mike Baker - Fmr CIA Officer & Portman Square Group CEO
Date: March 23, 2026
In this “Lessons” episode, Scott D. Clary interviews Mike Baker—a former CIA officer turned CEO of Portman Square Group. The conversation focuses on how Baker leveraged an unconventional career, strategic self-marketing, and operational experience to build a thriving business. Key themes include the value of visibility, making quick decisions with imperfect information, understanding risk in business, and recognizing internal threats.
Media Appearances as Unpaid Marketing
Being Authentic and Owning Your Story
Concept Origin: Operational and Business Translation
Importance of Training and Instilling Decisiveness
Insider Threats: The Often Overlooked Danger
Cybersecurity and Proactive Response
| Timestamp | Speaker | Quote | |-----------|---------|-------| | 02:48 | Mike Baker | "Once I realized that, then we were off to the races because… there was no way we could have, as a startup, afforded that sort of marketing… it just wasn't going to happen. That was an edge." | | 03:54 | Scott D. Clary | "You'd be surprised at how many people just don't feel comfortable leaning into that. And then you did." | | 04:43 | Mike Baker | "You can't fake that part of it… once I realized that it was certainly beneficial, it wasn't like I was going to turn down opportunities." | | 06:18 | Mike Baker | "It simply means knowing how to make decisions quickly with imperfect information… if you wait for all the data sets to come in… something bad's going to happen." | | 11:36 | Mike Baker | "Intel organizations… go through periods of time where they become risk averse. And that's, it's a bad thing." | | 13:07 | Mike Baker | "The insider threat is always something that… we end up talking about. And the insider threat can mean a variety of things..." | | 15:41 | Mike Baker | "You also have to worry about the insider tool threat, apparently." |
This episode distills major lessons from Mike Baker’s eclectic career, connecting lessons from covert operations to C-suite decision-making. Listeners gain tactical advice on self-promotion, quick decision-making, understanding organizational risk tolerance, and safeguarding against internal threats—applicable for entrepreneurs, executives, and anyone navigating high-stakes environments.