LTG Vince Stewart Leaves Legacy of Service, Commitment to the Next Generation

Today, I’m speaking with retired Lieutenant General Vincent Stewart. General Stewart spent nearly four decades serving in the US Marine Corps, culminating in roles as the Director of the Defense Intelligence Agency and Deputy Commander of US Cyber Command. He retired in 2019 and founded Stewart Consulting Company. He also works in a number of advisory roles across the defense and intelligence space today.

We’re chatting with him today, because he was recently named as the recipient of this year’s William Oliver Baker Award from the Intelligence and National Security Alliance. The Baker Award was established in 1984 and recognizes some of the greatest leaders and innovators in the national security space. So thank you so much for joining me on the program today, General Stewart. I really appreciate it.

No, it is indeed my pleasure and looking forward to the conversation.

We’ll start with the most recent thing, and then we’ll make you go back to the recesses of your 40-year career. You spent your last tours at DIA and Cyber Command. Those are some pretty significant missions at a pretty significant time in kind of understanding what’s going on with cyber threats and cyberspace. Obviously, the DOD network, I used to work for the Army, so I understand the scope and scale of anything involving the military IT networks. It really becomes a very global threat. It’s a pretty big elephant to eat. So how did you go about tackling kind of the cyber threat vector in your last role? I know you had some pretty significant accomplishments there in the time that you were there, so talk a little bit about that mission.

The first thing I often tell folks is the threat is real. It is real from nation state, it’s real from criminals, it’s real from hacktivists, and we are all part of that attack surface. And so when you come to grips with the idea that the threat is real, you also quickly realize that we can’t do this on our own as individual, fighting the threat. So you have to have a comprehensive strategy for how you deal with the threats. How do you do it collaboratively, so it’s collective in defending our enterprise? We know that the threats are interested in the things that impact our way of life. So building the forces that can help us to understand the threat, counter the threat, and do it in a collaborative public-private partnership approach is absolutely essential.

And so we spent a good bit of time obviously in building that military capability, but more importantly for us is how do we share, collaborate, and have collective defense rather than point defense. And so there was a good bit of effort for us to do that sort of collaborative cooperative work. And if we do that well, we have a chance to be successful. If we don’t do that well, then we’re all at jeopardy, because as I said, we’re all part of the attack surface.

Somebody got a copy of my questions to you sir, because this is a perfect tie-in to what I was going to ask next as well. So I love talking to folks who have spent a career in the military and then pivot into the private sector. Do you see anything differently now being on the other side of it, out of uniform, but still working in this space?

Yeah, there are a couple of things that I find surprising. Although it is important at the executive, the C-suite, level to recognize the threat, it is probably not as refined in how you counter that threat. There’s an expectation, I think, in many cases that our government will solve this before my company becomes a target. So I’m always surprised that folks understand the vulnerability, understand the risk, but don’t build simple things like incident response plans to deal with when, not if the event occurs. And even some of the ones who have incident response plans have not exercised those incident response plans, so they’re going to be figuring this thing out when there is a crisis, which is probably not the best time to figure out how you counter the threat.

Now, more and more companies are hiring “cyber experts” to be on their boards. Some of them are doing a very good job of listening to some of these cyber experts, but some are simply, quite frankly, just checking the block. It becomes really important to be deliberate in our thinking in the corporate side. I don’t always see that. It’s really important to have a response plan. I don’t always see that. It’s really important to have those tabletop exercises that helps you to think about what happens in the first 10 minutes, in the first hour, who has authorities, what is the scope of their authorities, What’s your strategic communication plan? I don’t always see that. What I remind folks in the private sector is we simply in our government do not have the capacity to cover every possibility. The cavalry isn’t coming, so you better be prepared to fight the fight as best you can, at least in the early stages of crisis.

No, I love that. I think that’s great advice and feedback. There’s a ton more that’s going on today, probably than ever before, when it comes to information sharing, but there’s still a heavy commitment on companies and especially those that are working and partnering with the federal government in any capacity. But I know one of the things that NTSC has really pushed a ton recently, too, is that even if you’re not working directly for the federal government, you still have the obligation for cyber response. You should still know that you’re a potential victim of all of this. Certainly, foreign intelligence adversaries are after all of that tech as well. Do you have any thoughts around that? Even if you’re not in the defense industrial base per se, why do these cyber issues matter to you?

Even though it’s not in the defense industrial space, it is in the national security space. Economic impact in a banking sector, for instance, doesn’t sound like defense but will impact our national security. The risk, the things that we’re seeing where adversaries are targeting the healthcare system has an impact on all of us. You can’t find a direct line to defense effort, but it is all about the security of our nation in its broadest context, the economic implication, the information implication, the military implication, et cetera. So you don’t have to draw a direct line to defense, unless the line is defense in general of our nation and our wellbeing across all the elements of power. And so I try to convince folks that if I’m going after a defense entity, I may use any number of vectors to get to that entity, so I need strong defenses across our entire enterprise.

I warned you this is going to happen. We’ve touched on the end of your military career a little bit and your current career in the private sector. I want to go all the way back. You immigrated to the United States from Jamaica when you were 13. I think that’s significant. We get a ton of questions about that kind of stuff at clearance jobs, because a lot of people see the path into a national security career is one that’s not necessarily accessible to immigrants. The military specifically has always had a great track record, I think, of attracting immigrants into service. So I’d love to get a little bit on your perspective as an immigrant into the country and then joining the military and then again rising to kind of pretty much the highest levels within our intelligence community.

I had no military experience, no one in my family had ever served, but I wanted to do something to give back to my newly adopted country. When I came here, I found that I had significant opportunities, which is why we immigrated to the United States, tremendous opportunities here, warts and blemishes of this country. There is no other country on the face of the earth where the opportunities are present if you’re willing to go to work, if you’re willing to get an education and you’re willing to go to work, and you’re not bound by some of the historical baggage of this country.

When I went off to university, I went to Western Illinois University, which interestingly enough is the home of the Fighting Leathernecks. Much of my adult career, I’ve been a leatherneck either at the university or in the Marine Corps. I decided I wanted to do something to give back, to play my role as a citizen in this country. And so I looked at both the Army and the Marine Corps, and was convinced that in the Marine Corps I could contribute to something bigger than myself. The intent was to do it for three or four years and then leave the Marine Corps and do something else. Well, the opportunities continued to present itself to me in the Marine Corps, and there was one challenge after another that we were able to overcome the challenges, and in this case, I mean challenging opportunities, operational opportunities.

And the Marine Corps gave me some chance to go off and study some more and get a couple of master’s degrees. And then I woke up one day, and it was 38 years later, just putting one foot in front of the other and taking advantage of those great opportunities that presented itself. Never envisioned that I would have a clearance, never envisioned that I was going to join the intelligence community. I started off in the armor tank community. That’s what I wanted to do. Somewhere along the way, someone decided that the opportunity in the intelligence community was a good opportunity and that it all seemed to have worked out in the end.

Tanks to tech. Only in your US military. I love how the different career pivots get you there, and I love the way you phrased that with the next challenging opportunity. I think that comes up for a lot of people that do continue with a career in military service. It’s just because they see that next challenge, and obviously a ton of challenges, but things that are very worth tackling, and you had a lot of those in your career. So talk to me about having a career first, because you’ve had a few of those. Is it kind of strange to be in “groundbreaking” territory? Are you used to it now? Do you notice it as you’re going through, or are you at the point now where you can kind of reflect on your career and see how significant some of those things are?

I don’t remember who said this, and I’ll paraphrase, “Never look back as they might be gaining on you.” I’m waiting for the time when I can look back and revel in the accomplishments, but I’m not there yet. And I’m finding now even in the private sector that there are still some challenges out there that I’d like to help to overcome. One of the things, I suspect we’ll get to this at some point, we have to think our way through how we partner with other nations that share our values and our interests globally. I’ll leave that there, and then we’ll come back to it. But I’m still looking for challenges and opportunities, because that’s become the norm for me. I can’t imagine getting up at five or six in the morning and watching soap operas all day. So I’m still driven by the challenges that we face as a nation and the challenges we face on the international stage, and I want to continue to contribute to how we overcome some of these difficult tasks.

I’m still in it. I’m not yet looking backwards. You guys in this interview probably caused me to look more reflectively than I have in a long time, but there’s still so much work to be done in our nation and across the globe. So maybe when I actually retire, I stole a phrase from General Kip Ward, who says, “You’re not retired, you’re rewired.” And quite frankly, I’ve taken the uniform off, but I still work probably as much if not more than I did when I was on active duty, and I work more because I don’t have a staff to turn to.

Hey, that’s key too. Man, to have to leave that military community and staff behind. That’s significant. So talk to me a little bit the current challenges facing the US. What would you consider some of the most significant challenges facing the US today?

We have competitors who are determined to be the dominant force in the future. Our traditional partners are wrestling with where to lay their bets. Do they continue with the United States, or do they partner with others who are rising or trying to revitalize their power? We generally don’t appear to have a coherent strategy for dealing with this. We have become so divided that we can’t agree on simple things. I’m not even sure we can agree on what our values are or what our interests are globally.

In the absence of a integrated coherent strategy to deal with our competitors, we are at risk. Where do we fit precisely in the INDO/PACOM region? Where do we fit in the Middle East? How do we lead effectively the globe? As much as people will have negative things to say about the United States, the globe is watching, nation states are watching our behavior and our action and they’re taking their cues from us. So we have to live our core values, we have to be clear in terms of our international interests. We are still arguably the leaders of the free world, and we’ve got to stand up and act as leaders, and I’m not always sure that we’re doing that. And part of that is because we are so divided as a nation where everything becomes a political issue, a partisan issue as opposed to an issue that’s in the interest of the United States.

Sorry. You could get me going on this one for a long time.

Well, you talked a little bit before about, and I did love this, you’re not looking back, you’re looking ahead, because you know don’t anybody to be able to catch up with you. But I do want to reflect maybe a little bit on do you have key achievements or accomplishments in your career that you consider really significant or milestones that you’ve been really proud of?

I had a unique opportunity as an intelligence officer to run a large combat outpost, camp Fallujah during the heights of the conflict there in Iraq. To have a military installation in the heart of the Sunni insurgency, to run that facility, to manage portion of the battle space, to have in excess of 4,000 people under my care, and to be effective in not only running the installation but engaging with the locals around the installation, I would argue that that’s probably one of my most satisfying accomplishments. We took care of the people, we made sure that they were ready for their combat missions, and we brought most everybody back home. So I feel really good about that.

I think my experience at DIA, I often describe it as a PhD in leadership and management. You have a very diverse workforce spread across the globe. I used to get the question, what is the DIA culture? And you quickly realize you’ve got operators, you’ve got analysts, you’ve got folks at different combatant commands, you got the different services. So you’re trying to blend a really, really diverse set of folks into a coherent culture, so one of the things that you call your values that you want everybody to buy into. And so that was for me an incredible challenge, both in leadership and management, to at least get everybody comfortable with who we are and what we believe.

So those are probably the two biggest highlights towards the end of my career. Close behind that is watching how we grew as a cyber unit from the concept of cyber operations through training the force to employing the force to watching them mature from a distance. So those are probably the big three, as I’m forced to look back, that I had learned a lot from and maybe are proudest of.

I love that. And you’ve talked a lot about different kind of aspects of your career that definitely tie in to mentorship. I’m sure at different points in your career, you had opportunities to be mentored and have had opportunities to mentor others. Can you kind of talk about that experience, maybe some mentors in your career or how mentorship has played a factor? I know that’s a big element of INSA as they’re trying to really energize the next generation of intelligence leadership. So talk about mentorship in your career.

I was very fortunate. I had from the early part of my career the opportunity to command and lead Marines as a young, really just a brand new captain. So I had an opportunity to lead at, I think, every rank that I attained. And so it was for me, the first part of this is how as a leader you inspire and empower people to bring their best every day. And then from that, who do you turn to, either as an example, and I’ll mention a couple examples, or you turn to mentor as you try to impart some of your values to the next generation. I remember General Officer Cliff Stanley was not a mentor, but what a great example. Everything you heard about Cliff Stanley said, “That’s who I want to be. And so it was always good to be around someone like that, who set the example of what excellence in leadership really looks like.

And then I had the good fortune probably later in my career than I had hoped to have some terrific mentors, who spent quality time with me telling me what was important for my personal development and career progression. And I made it in a point to reach back. And if we talk about reaching back or looking back, probably one of the things I’m most proud of is what some folks affectionately call the Stewart Tree, where I have had the opportunity to reach back to some young men and women and mentor and guide them and demand excellence of them. My mentees have to read, they have to write, they have to present themselves in such a way that when the curtains come up, they’re ready. They’re carrying our reputation as part of this group.

And I look back now and there are a number of young men primarily who are now general officers, who I consider part of the Stewart Tree. Mentorship, reaching back, pulling someone up, helping them to be successful, giving them the pathway, the recipe for success, particularly for those who have been underrepresented, because they don’t have access and they don’t get to see what right looks like very often. So I’m a huge fan of both helping people to achieve.

And the other side of this, well there are a couple parts. One, coaching, mentoring and sponsoring, because I was the beneficiary of someone who called ahead and said, “Put Vince Stewart in a particular job, because he’ll get it done.” And he sponsored me with my next commander, who arguably saved my career, because when I was frustrated and thought about resigning, he would not allow me to resign. And shortly thereafter I got promoted. So coaching individuals, mentoring and guiding them, giving them the roadmap to success and sponsoring them in their next assignments are absolutely critical components that I believe in strongly.

I love that. That was my favorite part of the interview so far. I think that’s so key that I love the Stewart Tree analogy. I think we all need to be building our career trees, absolutely. I think most of us get to a point where we’ve tried to quit a job at least once. If we haven’t, we’re probably not trying hard enough. We haven’t gotten frustrated enough. But you have to have that person that kind of encourages you to keep going even when you’re in that really tough assignment or at that spot that seems impassable.

There were jobs that I wanted that I thought, “Wow, this would really be cool to do,” and I pushed really hard to try to get it. And to have a mentor say, “No, that’s not the right job.” And I look back now and think had I taken some of those really cool jobs that I wanted, I maybe would’ve retired as a colonel. But because someone pointed me in the right direction, the rest, as they say, is history. But I didn’t know any better. I wanted a cool job.

Some of the growth jobs aren’t the cool jobs, sadly enough. Well, I want to talk a little bit about the Baker Award. I really love that award because it has been awarded to so many different individuals over the years and shows kind of the breadth of intelligence, so members of Congress, former CIA directors, cabinet secretaries. Why is the intelligence community include all of these different actors, and how do you see that as really important to us accomplishing our objectives that all of those people play a role and that all of them are working together?

Yeah, actually you’ve hit it, but let me back out just a little bit. I almost fell out of my chair when Tish Long called and told me I was selected because of the incredible heroes before me. And when I say you hit it, we’ve all played a role in this community, whether it’s in the legislative, ensuring that we have the right legal framework, legislative framework for how we do business, how do we ensure that we have proper oversight in this space? Just driving development, the continued development of our intelligence community, the continued professionalization of our intelligence community, the continued drive to ensure that we are well positioned to deal with all of the threats and challenges in the world.

This is team sport. And so cutting across all the diverse entities and individuals seems absolutely appropriate. And gosh, what heroes that have done this before me had this opportunity before me. And I tell folks now, much like the medals and ribbons and devices that I wore on my uniform, I wore them, but so many other people earned them for me. It was the team and the people who I had the pleasure of leading and who were supportive of me that got me to this place. And I can’t take a whole lot of credit except for not screwing it up too badly.

I love it. Well, you kind of touched on this already, but yeah, kind of talk about that, the feeling that you had, knowing that you’ve a achieved this award or been granted it. You talked about your initial reaction. Now that you’ve had time to reflect on it.

Yeah, I’m still trying to process that, because there’s so much more that I think I can and maybe should be doing to truly earn it. I recognize the things that I contributed has had an impact, but when I compared some of the others, I know I’ve got a whole lot more to do to truly feel like I’ve earned it. I’m honored, I’m humbled, I am in many cases overwhelmed. Maybe I am too harsh a judge on my accomplishments, but I’m going to use this hopefully as an opportunity to do more, so that in retrospect, I will feel better about all the different ways I’ve contributed to the success of our community. So I’m not quite basking in the glory just yet.

Well, anyway, that’s probably a good sign. That’s what the community wants and needs, and maybe that’s a new pivot point for awards like this, saying, “Hey, this isn’t saying you might not have even accomplished your most significant things yet, but you’ve accomplished a ton, enough worth recognizing, and now we get to pivot and move on to the next significant threat or accomplishment. And we continue to have more of those certainly in this community, I think we know.

I think that’s fair. Like I said, I’m probably in some ways too harsh a grader. I know if I were to look back, I could probably point to some really good milestones. I’m not ready to rest. And so this may be a springboard for some other opportunities to continue to contribute to the community.

Lindy Kyzer:

Vincent Stewart:

Lindy Kyzer:

I know I used to have all of my time. On that, thank you so much, General Stewart, for your time. Go to www.insaonline.org to learn more about the Baker Award dinner, which is happening later this year, and we are really looking forward to that opportunity to celebrate all of your accomplishments, general Stewart, which certainly are significant in our community, is excited to recognize. Again, in the IC, a lot of your successes are classified, as we very much know, so the opportunity to kind of recognize a career of service, even one that’s very far from over, that has had really a lot of important milestones is certainly worth doing, and we’re looking forward to doing that at the Baker dinner.

Thank you, and thank all the folks who voted for me, and I’m really looking forward to June 9th, I think it is, and let’s have a party.