Bob Gourley on Operational Intelligence for Strategic Decision-making

Informing your decisions with intelligence analysis and.

Insight brought to you by the team@ooda loop.com hi, everybody. Welcome to Oodacast. I'm Jen Hoare. I'm not a co founder of OODA, but I'm here with one. I'm here with the venerable Bob Gourley, who has kindly allowed me to take the seat again. The Barbara Walters seat, as I jokingly referred to it after I interviewed Matt DeVoe to apply the same interview treatment to Bob and learn more about his fascinating career, his expertise that he brings to clients at ooda, his interests, and an opportunity to get to know one of the voices you probably hear every week when you tune into oodacast. So thank you, Bob, for having me.

Oh, thanks for this.

I'm going to welcome you to your own show.

Thank you. I look forward to this.

Bob, I wanted to start by asking you, a lot of folks who are listening to this podcast know you. Maybe there are others who don't, but I'd like to learn about your career, which is so multifaceted. You've been in the private sector, government in various capacities. What do you consider the main thread, the one thing that is a constant throughout all of the chapters of your career and the different roles you've had?

That's an interesting question. And if you, if you ask it that way, one thing rises to the surface in my mind, and that is in my formative years as a young Navy intelligence officer, my career path was one we called operational intelligence. That's bringing together all of the data from every source you can get your hands on and trying to figure out a dynamic situation. What is an adversary doing and how do you know that? Based on every source of information, including information that could be just flat wrong, or it could be an adversary that's trying to deceive you. So that thread has stuck with me through all other aspects of my career, no matter what I've been doing. I've been in these positions where I need to sort out a lot of complex, ambiguous information and come up with assessments on what's going on.

That's really interesting. In light of all of the different chapters you've had, what do you consider yourself best at and what do you consider yourself? Not to say that you have weaknesses because everyone knows you're perfect. But what do you consider to be something that you've always been working on to get better at?

Well, you know, I would say that the answer to that may have changed over time as I've matured and I find some capabilities I Have, they're far better. Now I can put things in a longer context, but others, maybe I'm not as sharp, you know, and maybe I need to start taking prevagen to, you know, keep my edge up. But I would say at this stage in my career, the things I still really think I'm good at are taking in a lot of information and, and picking out the right kernels and filtering and correlating and coming up with things I need to drive decisions. Now I would also say that's something I'm very bad at. It's something you can never be good enough at. You need to keep learning. What are your trusted sources of information? How do you know they're trusted? And is something you trusted yesterday still trustable today? And how does it fit with everything else going on?

What do you do to get better at that discipline and all of the areas that you're always trying to work on? What are your tools and approaches that work best for you to improve?

Well, that's tough because it's hard to say what objective metrics are in that area. But I tell myself that if there's some things I can do to keep current, for example, reading books, and not just books about what's happening today, or books about technology, that's important, but books on ancient history and books on the humanities and the liberal arts and things like that, I believe help. Something else I really think helps is staying in practice, continuing to think and engage in complex issues. So nothing kind of goes to waste. And I see myself never stopping that, always trying to learn new things. Now there's other things I do just for fun, and I tell myself it's helpful, but I'm not sure if it is really or not. I love learning new technologies and that includes new programming languages. I'm not saying I'm good at it. You would not want to come to me to be your developer, but I like opening up a new programming language and working through an example or two and getting the hello world, then telling myself that oh, I'm young again.

That's great. Something that when we first met, that I appreciated about you and that we continue to talk about through our work together is the fusion and collaboration of what I jokingly call the more old fashioned methods of intelligence collection, such as human intelligence, talking to sources, cultivating smart people in your network to help teach you and advance what you know. What do you see as the. What are some examples in your career where the more old fashioned traditional methods have interacted with the highly technical?

Well, when I First started my career, you know, I didn't really know what was going on, but I would read books and articles and there was a debate at the time because President Carter had decided to reduce the amount of human that the CIA did. And a director of CIA, Stansfield Turner, a retired admiral, really slashed the humeant forces. Now I was just an ensign right after that happened. I didn't understand the impact, but I did understand that they thought technology would do it all for us. We, we had satellites, for example, that could detect where a ship was when it turned on its radar. These Navy satellites, we call them ELIM satellites for electronic intelligence. And that was critically important to us. And I guess the Stansfield Turner model was all we need is that technical information and we'll know what the bad guys are up to. But it turns out that wasn't true. You really need people who can gather insights from human beings and that doesn't have to all be the deeply secret covert stuff. Even just talking to people or reading newspapers and having linguists who can read in the language of another culture you want to understand is so critically important. I don't know if we ever really recovered from that slashing of hument, although we certainly tried. And in the ramp up to the war on terror there was lots of investment in that, but it takes decades to build back that capability.

Very interesting. Both you and Matt have this deep appreciation for that fusion of the human intelligence capability with the highly technical and analytical part of things. I wanted, speaking of ooda, I wanted to hear a little bit from your perspective about the co founding. Well, the founding of which you are co founder of ooda. So tell us a little bit about your inspiration for OODA along with Matt and also how you met Matt.

Okay, yeah, so let me start there because when I was in the Navy I wanted to write and I would publish articles every now and then. And sometimes I would have bosses that asked me to do that. They wanted a new joint concept written about and they wanted an article put in a proceedings magazine with the Naval Institute, for example. So I would write that. I was very happy to. And then I went to Marine Corps Command and Staff after an afloat job at 7th Fleet. And there you have to write, so you got to do a master's thesis and all this other stuff. And I published a few articles and I met a very interesting professor named Dan Keel. Dan was studying and talking and writing about information warfare at National Defense University. And he had created a contest called the Sun Tzu Information Warfare Contest. And he had been Running that for several years. He encouraged me to submit a paper to it and I won. And so I was very excited about that. Well, it turns out Matt devoe had won the year before, so that's how we first heard of each other. And so ran into him in those circles writing about information warfare. And then I was later named to be the Director of Intelligence for the Joint Task Force for Computer Network Defense. This is the first cyber comm at dod. And my job was figure out what.

All the bad guys are doing and.

Get the right intelligence to our decision makers. So I was on the team that's raising defenses. Matt was on the red teams, working under contract to others to penetrate dod. So he was out doing things like hacking satellites and hacking aircraft carriers. And so I got to work with him there too. And he really helped bring this hacking community to us and help build trust based relationships between communities that had never worked together before.

So I worked with Matt a lot through the decades after that. Separate careers, but staying in touch.

And the founding of ooda, what was the genesis of how to make it as unique as it is and what it offers clients?

Well, we had been doing more and more work together through the years. I would be a sub to him or he would be a sub to me. And we team on things and do stuff. So we already knew we could work together and we had already been publishing stuff. He had created this OODA Loop site about a decade ago. I created a CTO Vision site about a decade ago and we had already been tracking what each other were doing there. So it almost became just a natural conversation. How do we bring all of this stuff together? And once we kind of made those decisions that we wanted to do this and bring the best of his experience and my experience together, we had to think, what do we call this thing? And OODA is what kept coming back to us. And we thought, not everybody knows what the OODA acronym is. And it might mean whenever we have a new client, we're going to have to do some explaining. But we decided to do that anyway because it is such a great decision model and it's a great homage to this guy, Colonel John Boyd, who created the OODA Loop concept. So we decided to stick with them.

Something that OODA provides and you specifically nurture is connection, networking, introductions and encouragement, which you do through the podcast, through the various meetups. Now, unfortunately, virtually, what contributed to making you such a connector and networker, where does that come from? Because you seem to do it pretty naturally and quite prolifically.

Well, thanks for saying that because I never felt that. I always felt like it was kind of. I forced myself to do it. I'm really an introvert who's much more comfortable being alone or with people I've already met. But through the years I've had to interact and speak at conferences or build events or bring teams together. So I certainly do that and I realize the power and I love doing things like this because it forces me out of my shell now and it gets me meeting people and talking to people and gives me an excuse to really interact and grow and learn because people are what it's all about and it's those connections between individuals right now. When I was the Chief Technology Officer at Defense Intelligence Agency, I used to joke that I love people and technology, just not in that order.

Really.

It is all about the humans. No matter whether you're in a government organization or a commercial organization or academia, it's all about the people really driving things.

Well, interestingly, you've managed to get people to interact over technology. I mean, at the core of OODA are some really formative discussions about developments in challenges to and challenges of technology. And you've got a network of people that meet to talk about the important issues and their consequences and to meet each other to do business. I think another facet that comes out of that is mentorship. And I wanted to ask you about your mentors. Who are they, if not by name, then by description? And what do you carry with you even today in practice from what you've learned from your mentors?

I've been so lucky to have some fantastic mentors and leaders, some of which are not with us anymore. There was a man who died far too young of cancer, four star Admiral Archie Clemens, who really had a huge impact on me and my career as a very young officer at an intelligence center. He called me one night. He was a 06, almost 07. They called it a Commodore. He's in charge of all the submarines in the area and he wanted to ask me a specific question. Is this Chinese sub going to deploy? Because if it is, I'm putting two submarines on it. So as a young kid, this is a big decision and it's late at night. I can't turn to my boss and I, I just told him, I said, here's the data I have, I think it's going to deploy, but I want to call my boss at home. And he said, you do that, but while I'm calling my boss, he's already deploying his subs. And that was the first time I met this guy, Archie Clemens, so he's a real man of action. Later, I worked for him at a place called 7th Fleet in Japan. He was the three star admiral in charge of 7th Fleet. And I saw him consume intelligence in ways that just were really impressive. He was thriving on information and intelligence. We would say things to him as intel officers, and he would then turn to his operations officer and direct him to do stuff, which made that director of operations kind of mad at us. But, you know, I just. It's the three star telling him, not me. A big example was 1996. China had announced it was. It could. It was going to launch missiles around Taiwan. And it put up areas in the sea where they said, it's too dangerous for any ship to be here. We're launching missiles just all around Taiwan. So we were responding, and we had an aircraft carrier coming into the area. And the admiral asked my boss, Eric Myers, an intelligence officer, what he thought the situation was. And I remember it to this day because Eric said, well, I've talked to the CIA, I've talked to dia, I've talked to the Office of Naval Intelligence, I've talked to the CIA on the ground, at the embassy. And everybody tells me they don't know what China's going to do, but they all tell me that they know you're already moving an aircraft carrier down, and they expect that. And then Eric added this. He said, but if you bring a second aircraft carrier, they're not expecting that. If you bring the Nimitz back from the Persian Gulf, they. They will be surprised. So then Admiral Clemens immediately turns to his N3 and says, Bring the Nimitz back from the Persian Gulf. The N3 said, I can't. He doesn't work for us anymore. And Admiral Clemens said, I don't care. Bring it back. And it's really ended up changing the world because Admiral Clemens did get his aircraft carrier. It's as if Eric Myers, the intelligence officer, was really in charge because he's providing the right info to Archie Clements. And that kind of story stuck with me. Great leaders thrive on info, and they take action on it.

Have you had an aircraft carrier moment like that where you've had to make a bold decision based on intelligence you've been given? You don't have to share details. You can't. But have you had a moment like that or moments like that in your career?

Yes. Big and small. I think all of us have those in. You know, when you make a lot of decisions and you feel good about making the right decision and it really changed things. Maybe one I can talk about is this Operation Moonlight Maze. Back to this joint task force for Computer Network Defense. Something was going on. Somebody was stealing secrets from unclassified networks from the Department of Energy, from Department of Defense, from academia and from several other places. No, it was scientific and technical info and people wondered who it was. And the FBI was in charge of the investigation and they were studying and collecting info and nobody knew. The JTF stood up. And so now I'm in charge of the intel support to that operation. I talked to some other old mentors, I should say mentors, not old. Rich Haver was a famous civilian in the Navy Intelligence and then Joint Intelligence community who was also a bit of a historian. Bill Studeman, a four star admiral who was acting director of CIA and he was the director of NSA for a while. And I talked to those guys and I told them what was going on and what was being stolen. They directed me to read some old historical archives that described how the Soviets collected technical information. And as I read these stuff from humint. So again, it's, you know, the way spies had told us about this, it matched up perfectly with this moonlight maze. So I pulled together more information, did more collection, and made an assessment that really made the FBI mad because their view was this is a law enforcement investigation. If you're interfering with an investigation that's illegal, you could get arrested. They're in charge and they have to collect evidence because this may go to court one day. Well, as I pulled stuff together and was able to say, okay, we're pretty confident that this is Russia. You're not taking them to court. It caused conversations in the White House, in the Oval Office, and it caused big decisions between deputy directors at the Department of Defense and Department of Justice level. And it resulted in an outcome where Department of Defense said, continue your law enforcement investigation, but there are serious national security implications here too. And it really changed the course of that activity.

Wow.

I asked this question of Matt, and I have to pose it to you as a technologist, what do you consider the greatest technological innovation of our lifetime so far?

I'd say it is our interconnected digital technology. Technology, our interconnected digital infrastructure, I think is the way William Gibson first described cyberspace. So it's the global grid, it's the Internet. You know, Gibson would later call it something else, an even broader definition. He called cyberspace a consensual hallucination shared by billions.

But really, to me, it is.

I mean, that's, I like that Expansive kind of thing because it fuels the imagination. What is this thing we have built, but really it's our interconnected it that we call the Internet is something we'll never turn back from. It's here forever.

Matt said the same thing. So I need to ask a tougher question next time. What are you most optimistic about when it comes to technology and how it's used and how it can be used for good?

You know, I think my optimism comes from the fact that we humans are still in charge and are innovating and creating and driving this thing. There's, you know, I have to be an optimist as a security guy because if you're not, you become a pessimist. There's so much that can go wrong, but I see so much good in different areas. For example, biotech, we're all in the midst of this horrible pandemic and so many lives have been lost and the economy's been disrupted, but there's now so much investment, not just in finding treatments and cures and vaccines, but in biotech overall. It's going to change our life for the better. Once we get through all this, I think the next 10 years will be the decade of biotech and I'm very excited about that. And infotech contributes to that. It couldn't have been done without info tech and this global Internet. But biotech is about to take off.

That's very consoling as well as insightful because that, and that shows kind of the expansive thinking about the applications of technology and where it can really affect our lives in a protracted or somewhat slow at times, but meaningful and beneficial way. I have to ask what technology or what developments that you see in our world now worry you most?

You know, I also worry about biology.

And biotech and the pandemic is something that did not take us by surprise, but caught us flat footed. And we need to realize that this can happen again and again.

And this one I'm really sure the right scenario is this was an accident. It was not man made. There's a lot that went wrong because of humans, but I think this came from nature in this horrible wet market area that, you know, crowds too many of these animals together. But the next one might be man made. We're at that level of our science and technology and the laboratories exist that can do that kind of thing. So that worries me.

At the risk of talking about both the positive and the negative concurrently, the election is coming up in a couple of weeks. What worries you from a technical perspective, from a cybersecurity perspective about the election, if anything?

Well, I think it's all, you know, we talked about the human element being so important. I guess what worries me is not just the technical thing. I mean, I don't believe that adversaries will have any success in really shaping the election through cyber attack. It could certainly sow disruption. But I have another worry that might transcend that, and that is whoever WINS the election, 50% of the people are going to be mad about that. Our own country is being pulled in just so many different ways. And if you have 50% of the people angry at the other 50%, will it cause violence? And I just hate thinking these thoughts, but we need to think about them. And that violence, will it include cyber attacks and violations of privacy and other malicious use of technologies like that?

In which case it's truly a domestic threat, or the worry that you have would be generated from within. We're not talking about a foreign adversary there that could create this concern that worries you.

That's correct.

Wanted to ask, because you've obviously successfully co founded OODA with Matt and you've been an entrepreneur for a while in other capacities, what advice do you have for entrepreneurs? What's hard, what's easy?

You know, I think my advice comes from history, including ancient history. If you read the really exciting history, it's always groups that oppose each other trying to reach some objective. And the winner is always the one that is persistent. You need more than persistence. You need the ability to spot what's going on and maneuver. And you know, that's where the OODA concept came from, this ability to make decisions in dynamic environments. But the persistence is key. And that persistence, that tenacity, the never giving up, is the thing that makes you successful. Unless you're born rich, which a lot of folks are, or you're lucky enough to get the right education, you know, even then you need persistence. But everybody else, it's just critical. You get nowhere without persistence. And now also think of the cyber security and cyber attackers. The cyber attackers that win are the ones with persistence. And that's whether you're a good guy on a red team or a bad guy trying to steal secrets. You got to have that persistence. And the good defenders, you always have to be on guard. You have to be persistent. I think to the entrepreneurs of today, I think that's the number one trait to cultivate. If you find you have this great idea and you get into it and then you just kind of like, eh, maybe not. Well, maybe entrepreneurship isn't for you, it's not for everybody.

That's true. And I think a subset of what you just shared is the ability and willingness to face rejection and not see it as a deterrent. And that is really, at the end, heart of persistence to defy that and to believe in what you're doing and believing there's a place in the marketplace for it.

Right.

I wanted to ask you, of course, as you often do of your guests, about what you're reading, but I want to be a little more specific, which is, what have you read in the past, say, six to 12 months, good, bad or neutral that has really stuck with you? And why?

Well, a couple things. One, years ago, I read this book, the Black Swan by Nicholas Nassim Taleb, and you probably read that, too. What a great book. Everybody has read the Black Swan. And, you know, the concept of, you know, people in Europe used to think it's impossible to have a black swan. And it was even used as an expression. It's like, oh, that's a black swan, meaning it doesn't exist until the black swans were discovered in Australia. And then, you know, it's that kind of surprise. Well, he wrote this whole book about how we fool ourselves and how we don't understand risk. And when the pandemic hit, I thought I got to reread that, and I did. I'm so glad I did. And then I read another one of his twice, which is fooled by randomness. So I just reread that, and I would highly recommend that to anybody. He talks about human nature and the way our brain works and how we want to think, we understand things. It's just natural. What you may be looking at, though, could just be random patterns and you make some sense out of it when you shouldn't be. So both. Those are fantastic books I reread at the beginning of the pandemic, and I'm glad I did.

What are you looking to read next?

Well.

Another friend just recommended to me a book called Win Bigley, and it's by Scott Adams, the creator of Dilbert. And Bigley is a Trump word. And he wrote this kind of describing Trump's way of influence and persuasion and how he uses those in negotiations and in influence and getting people to think his way. And like him or not, he's a persuasive individual. And so I'm definitely going to read Think Bigly by Scott Adams.

Very interesting. Maybe wait until after the election for that or. You're digging into that already.

Yeah, I think it's probably next up on the queue. I just finished let's see, T Minus AI by Michael Kanan, who is an Air Force captain who helped shape Air Force AI work. And I gotta tell you, he's just really a great writer, and it's stuff that I think we may already know, but he explains it so well. He's really, really well done.

Wow, that's interesting. Well, I have a guest question. I've turned to our friend Matt Devoe, who knows you well, who has worked with you for a while. And I said to Matt, what would you like to know about Bob that you still don't. You still haven't learned about him?

And.

And he wanted to know, would you rather live in a Neuromancer or Snow Crash future? And for our audience, please describe, for those of us, myself included, the nuance of those two things. I looked it up, and I understand it's part of the cyberpunk genre of literature, and I'd love your take on that genre as well as these alternative futures, presuming they're binary.

Yeah, what a great question, because he's forcing me into this binary answer of thinking through both of those universes, neither.

One of which I really like.

Snow Crash, though, is such a great book that describes a world that in many ways, we're living in now. Now, this book was written, I think, in the mid-90s, like 92 or 94. And he describes a place where you can order a car just like that, and it comes to you, and pizza delivery is like a premier job. The gig economy is what it's all about. So this is, you know, decades ago he's talking about the gig economy, but it's a very dystopian world also, and it's tough to get along and tough to survive, and everything's a fight and a struggle, and that part I don't like very much about it. Neuromancer is very technologically enabled, and there's a blending of technology and humanity and an ability to carry data around in your head for others, for pay. And it's just so connected. And there is Internet. If I had to pick, I would say the Neuromancer world, and I would run towards jobs in that Neuromancer world, where I'm just connected to the whole.

Grid and plugged in with everything and.

Participating fully in cyberspace.

Well, I'm glad you committed to an answer, because I can understand the shades of preference for both or turning away from both. I want to practice what I preach, which is that I end every interview with what else do you think is important to share with the world about Bob Gourley that I haven't already asked?

Oh, I would say something I wish everybody realized is that I love connecting with people on social media. You know, LinkedIn is a great way to connect and I like helping people out who need some advice or assistance or a connection. If there's someone who's earlier in their career and they want me to look at a resume or give them a recommendation to another place, I love doing that kind of stuff. If it's people later in their career, I'm glad to do that for them too. So that's one thing I'd say. I really like feeling like I'm helping people out and if I can help someone in a career decision, that's really wonderful.

That's wonderful. And it's so important and effective when people of like mind and interests can meet each other and keep each other in mind as they go along in their careers and with the people they meet. And having that thoughtfulness really does a lot of good and can be really helpful in getting people to their next thing that they may not have imagined. Thank you, Bob. This was really interesting to learn more about you. I appreciate being able to be a part of the oodacast staff of interviewers and I look forward to the next OODA event, whether it's network event or training or another oodacast episode. Thank you so much. Thanks everybody for tuning in. Stay healthy, stay safe.

All right.

Thanks Jen.

Thanks Bob. Thanks for listening to this OODA Loop production. For the latest analysis on cybersecurity technology and global risks, please visit www.ooda loop.com.