Cracking the Corporate Code: Turning Military Skills into Cyber Success

In this episode of Exit Buddy: Veteran Stories to Guide You, Kathleen and Rachel sit down with Army veteran and West Point grad Bryson Bort, who went from feeling “complete ignorance and sheer terror” in terms of military transition, to successfully building multiple cybersecurity companies and a nonprofit. From a global commodity manager who didn’t know what an RFP was, to an IT asset manager, to the creator of a global CMDB that actually worked, to offensive cyber in the intelligence community, Bryson shows how curiosity and tying your work to dollar value can open doors you never knew existed. He also delivers some tough‑love truths: why you need to stop sacrificing yourself for the mission in profit‑driven environments, what risk in entrepreneurship really looks like, and how networking and reputation can turn even your missteps into momentum.

Chapters

• 02:09 – Meet Bryson: Choosing West Point Over MIT
• 04:50 – Medically Discharged & First Civilian Interviews
• 06:30 – “What’s an RFP?” Alone, Unqualified, and Learning Fast
• 09:06 – Back to Tech as IT Asset Manager & CMDB Builder
• 10:30 – Cracking the Corporate Code with the CFO
• 11:57 – State, DIA, Special Forces & Googling “What’s a CTO?”
• 13:40 – Building an Offensive Cyber Unit at the Tip of the Spear
• 14:55 – Tough-Love Truth: Stop Sacrificing Yourself for the Mission
• 15:31 – From Napkin Sketch to Launching GRIMM
• 17:59 – Rethinking Risk & Failure in Entrepreneurship
• 20:57 – Co‑Founding ICS Village & Giving Back to the Community
• 22:08 – Network, Ask Questions & Fix Your Resume

Key Takeaways

• Tie Your Work to Dollars: In corporate environments, showing financial impact keeps projects alive through leadership changes and budget cuts. Bryson’s global CMDB didn’t simply survive because it was technically elegant; it survived because he could show hard dollar savings to the CFO.
• Stop Sacrificing Yourself for the Mission: Bryson’s wake-up call to veterans in the civilian, profit‑driven world is, if you’re yoked to the mission at the expense of your health and family, someone else is profiting from your sacrifice. You are allowed to set boundaries.
• Entrepreneurial Risk Is Often Lower Than You Think: For professionals with strong reputations, starting a consultancy is usually a measured risk. Worst case? You build a bigger network, deepen your expertise, and become more valuable when you step back into a traditional role.
• Network Your Way into Clarity: If you don’t know what civilian job fits your MOS—or if you even want that path—conversations are your intel‑gathering. Each coffee chat narrows the options, sharpens your resume, and reveals opportunities that never get posted.
• You Already Know How to Figure Things Out: From West Point to Signal Corps to offensive cyber, Bryson kept succeeding in jobs he didn’t initially understand by doing what veterans do best: figuring it out under pressure, seeking guidance, and taking ownership.

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Transcript

Bryson Bort 00:00 I took the first civilian job I was offered. I was so afraid. Between West Point and the army, I felt institutionalized. It felt like leaving jail and you're thinking, I don't know what the real world is like, because you're in this bubble.

Kathleen Smith 00:14 Welcome to Exit Buddy: Veteran Stories to Guide You. This podcast shines a light on the real struggles and triumphs of veterans navigating life after the military.

Rachel Bozeman 00:23 In each episode, we dive into heartfelt stories of resilience, setbacks, a little humor, and growth as veterans transition and find new purpose in civilian life. And here for the journey, we're your hosts. I'm Rachel.

Kathleen Smith 00:39 And I'm Kathleen. If you're looking for inspiration, practical advice, or just a reminder that you're not alone in your transition, Exit Buddy is here to help you thrive beyond the uniform. Enjoy today's story from our next honorary Exit Buddy. It's always so much fun to be in this studio, and I am so excited about today's guest, because when I started this podcast, Bryson was one of the people I definitely wanted to have be part of our podcast. And as usual, whenever I ask something of Bryson, his first response is yes, Kathleen, and I so appreciate that. So just a little background, in case there's a few of you out there that don't know Bryson. He's a former Army officer who studied Computer Science at West Point and then went on to build not one, not two, but multiple cybersecurity companies, including GRIMM and SCYTHE. He is also the co-founder of ICS Village, a nonprofit focused on protecting our nation's critical infrastructure. And I think I have just touched the iceberg of the many things that are Bryson's depth of knowledge and his passion for giving back to the community. So welcome to the studio, Bryson.

Bryson Bort 01:49 Just like the answer is always yes to any question, anything that you need, Kathleen, my resume is the opposite where I can't say no.

Rachel Bozeman 01:58 So tell us a little bit about your origin story. How did you first start in the military? What transitioned into all of the companies that have been created and everything in between? Tell us more.

Bryson Bort 02:09 I wanted to go to the army when I was in high school. I briefly flirted with, I think, the dream that everybody has of wanting to be a jet pilot. Who wouldn't? And it just didn't seem to fit. And so I knew all the way as a junior that I wanted to go to West Point, and I wanted to be an army officer. And the reason that I did is because the army and the leadership is all around people. I had a scholarship to MIT, but I chose West Point again, going back to the fact that I wanted to serve coming out of it. And I consider myself a frustrated philosophy major. I did computer science because I had to choose my major, 97 or 98 so the .com era is taking off. Folks are talking about how to be a part of that. What would be after your career? And that's also why I branched Signal Corps. I wanted to branch armor, but the colonel pulled me aside. I was actually the first full time brigade Information Security Officer. So you can imagine these things 30 years ago. We have networks. We have computers at West Point, but the security thing is always going to be what follows, just like what we see in our industry today. And so I was the first one where they were like, Hey, we need a cadet who's marshaling the security resources of the Corps. And so because of that, they came and hunted me down and were like, You need to go in the Signal Corps. This isn't an option for you. And I was like, Yeah, but tanks are so much more fun. And the colonel was like, Well, when you get out of the Army, what skills do you think you're going to harvest from being an armor officer versus being a Signal Corps officer to transitioning into the civilian world? I was like, oh, huh, I thought of that. So okay, I guess I'll go Signal Corps. So that's what brought me into the Signal Corps in the army, and I served, and I got hurt during the war, and got out as a captain, and I took the first civilian job I was offered. I was so afraid. Between West Point and the army, I felt institutionalized. It felt like leaving jail and you're thinking, I don't know what the real world is like, because you're in this bubble. And it was the Lucas group. It's one of these companies that specializes in grabbing Junior military officers and just running them through a funnel of interviews, and you don't even know who you're gonna be interviewing with. I walked into one place, and it was General Dynamics, and they were looking for a deputy program manager for ammunitions in the war. And I'm like, Okay, I can't wear armor because I'm injured, and so I don't know what I'm doing with that one. And it was the last interview of the day. I did eight that day. And shortly after, actually in the interview, because the job was global commodity manager, I was being recruited to be a global commodities manager for a global aerospace and defense company. And so we did commercial and military aircraft. So if you've been on an aircraft, this may make you feel good, this may make you feel bad. I would hide a part of that. So any plane you've been on, I helped build the power supplies and the subcontract assemblies. But back to this interview. I said I don't even know what that job title is, and so they spent the entire interview convincing me that maybe I would be qualified for this. And I'm like, There's no way I'm qualified. I don't even know the job. I don't know anything about this. And then as I was driving back with my wife at the time, back to post, I got the phone call and they're like, Hey, we're offering you a job. And I was just so elated, in hindsight, that really speaks to the desperation that you're going to hire someone who's clearly not qualified, doesn't know what they're doing, but you're just going to make it happen. And I did that for a year, and then got back into the IT side of the house. I'm the only person I know that has actually built a fully functioning global configuration management database, the CMDB that actually worked. I never talked about that, because it takes away from my elite hacker cred. But yeah, I was an ITIL master who really did that side of the house before I got recruited up to Washington, DC in oh seven, and that's where I got to the intelligence community, and that's what ultimately led to my path into cybersecurity.

Kathleen Smith 06:15 So obviously, you overcame many different challenges and sort of misconceptions or preconceptions about what it was going to be like through your transition. And do you remember some of the things going through your head?

Bryson Bort 06:30 Because I got hurt and was medically discharged, I kind of was the first of the class and the first of many of my peers to go into the civilian world, what I would say at the time, back in 2004 is complete ignorance and sheer terror. That's all I had. I had no prep, I had no idea what I was doing. I was just grateful that these folks even got me interviews. And I took the first job that I was given, even though I was eminently unqualified. And you think this part eventually has a feel good story there where it works out, but I was not qualified. And even worse than that, my boss was in England, and all of the other folks on my team were also all in England. So I was by myself at the time, in Clearwater, Florida, not knowing my job, not knowing anything. And when I say I don't know my job, I'll never forget this moment, because right in the military, if you give me enough direction, I'll figure it out. That's what we're trained to do. And I couldn't get enough direction. And I remember my boss being like, well, just send out an RFP. I'm like, What is that? I don't know what an RFP is. And she's like, it's a request for proposal. I mean, was it an acronym definition? I still don't know what that is. And we're a multi billion dollar company, and I'm in charge of hundreds of millions of things. If you feel better or worse about flying on a plane now it's I can't help that. But I was like, maybe there's a template. Surely there's got to be something for some random guy to be going and telling the whole supply chain what to do on something. That's where I started. And it wasn't until I first had my first meeting with human resources. So I discovered it's not on your side that I managed to get a coach, which was one of the other team members. And I was just like, I want to work with Andy. And that was what saved me. I got to shadow Andy. I watched what he did. I learned again. If you give us the instruction, you give us the chance, we'll figure it out. That's what we do. And so that's where I had to go and align that for myself, to go have the company give that. And then I was successful.

Rachel Bozeman 08:36 Thank you for sharing that. And it certainly breaks my little recruiter heart to hear hey, come take a job, and you're like, I don't know what this job is, but sure, I can do it. But now I wanted to get to the good part of the story, if you will. So you worked the job. You did the one that you may not have known what you were doing, but you did the darn thing. How did you get back into your passion? How did you get back into the tech side of the world?

Bryson Bort 09:06 Well, that story is going to sound very similar, so it's still a good one. Let's hear it. There was a job inside the company for an IT Asset Manager. And I didn't know what that was, either, but I was ready to get back into it. I'm ready to do computers again. And I'd mastered the job. I was successful as a global commodity manager. I made a difference. We did what we needed to do, but it wasn't I wasn't passionate about it. I did get Lean Six Sigma, and I got a lot of exposure to those kinds of things. And so I saw this job posting, and I remember I went and met with the director, and what I didn't know very much he knew even less. So I was like, All right, here's a chance for me to teach myself yet another thing, because I know more than he does. And so that's how I got that piece. And then, because of the success of the CMDB, which took four years to deploy globally. And one of the biggest things I did, and I think this is really important for folks in the technology fields to hear, is how I was successful with that project was not the technical stuff. What I did is I tied the project directly into the CFO at the top of the company, and I was able to show dollar savings from what we were doing. They didn't care about the security, they didn't care about asset integrity. They didn't care about any of that. And the other thing that I didn't realize that gave me is because four years is a long time. Think about all of the changes in the company and leadership and management and all of that stuff, and my project was able to survive through all those changes because I had the ultimate metric of dollars, which nobody else in that side of the organization was able to figure out. This is the challenge we still have in security, is how are we seen as not a cost center, and tying back into that. So I got a reputation for that. And then when I got recruited to Washington, DC, it was based off of that. And so then I was a part of the programs that did all of the technological refresh for every embassy, every consulate in the State Department around the world, which is a really cool program called Get them. We did a similar thing for the Defense Intelligence Agency, and then we did some special forces work in Africa, and that was great, except I didn't feel that guy was getting the support that I was looking for out of the job. So there was an executive in the group who had just become the CTO for everything, for the whole company. And this is, again, I'm not making this up. I googled what CTO was because I didn't know what a CTO was. I'm sure everyone's laughing now, like You dummy, if he can do it, anybody could do it. This again. This was, like, 20 years ago. A CTO was a new thing. Nobody knew what a CTO was, let alone me. So I googled it. I'm like, I still don't know what it is. And I went met with him, because I wasn't trying to interview for a job. There wasn't even a job position, which I think is the thing that's relevant here, is a lot of these things happen, not because they ever get posted. I went met with Mike, and I was just like, hey, I'm not happy. I'm looking at jumping ship. And he's just like, come work with me. And I was like, What is a CTO? And that was, again, this was another job where I had a boss who just gave me the autonomy to go and learn it, to do it. And I got huge corporate, big company projects. And my claim to fame there was, I structured the R and D program for the entire company. So I built this R and D process and program, and ultimately that program, one of the biggest parts of the program was the offensive cyber group, which was so secretive at the time, we like as a country, we didn't even acknowledge we were doing that kind of work. And so I was just like, well, that's the coolest thing ever. And the next thing I knew, they recruited me. And again, same kind of thing. I'm down there, and I don't know what this is, right? I have the background in it, but this is truly the tip of the spear. This is the edge of very few people in the world even knew how to do this stuff, let alone me, who knew nothing. And I came in and righted the ship, and the next thing I knew, I was in charge of everything, and I got to grow that whole unit, and it was the best job I ever had. But eventually we became so successful that I spent more time sitting around cheap wooden tables you see in government arguing with staff not to screw over my people. And I was just like, I don't want to do this anymore. But I didn't know what I wanted to do. I was just this is the mission. I love the mission. And I think, like a lot of us, you stay committed to the mission. Well, I'm gonna really slap every all the listeners across the face on this one, because I know all of the gentle slap, a gentle it's not a gentle, no, it is not a gentle slap. Rachel, I am slapping them so their eyes roll into the back of their head, and the sticks we call Gibbs slap. Stop sacrificing yourself for the mission all the time. It doesn't last. You can't do it. You will break.

Kathleen Smith 14:06 You will break. Your support of the mission is still a great passion, but you can't do it at the sake of your health.

Bryson Bort 14:14 Especially not in the civilian world, correct? And because this is a profit-driven environment, so while you're sitting there being yoked to a mission, there's somebody who's profiting from that, right? But at the end of the day, you can't be so blind to just mission, mission, mission, that you forget yourself, you forget your family. It doesn't work. And so that's where I was in that space where I was staying at something I wasn't happy with. It wasn't fun anymore. I wasn't doing cool things in the field. I was just doing spreadsheets and arguing. It wasn't, I was a senior executive. Imagine that boring. And so it was this guy named Brad who encouraged me. He's like, why don't you start your own thing?

Kathleen Smith 14:55 I was just gonna ask, let's talk about that. Let's talk about this jump. Let's talk about, yeah, you know, other entrepreneur, yeah. I mean, some of us become entrepreneurs because they don't think that they're talented in anything else. Some of us get tired of the corporate world and think that we have a really great idea. But there's a lot to go into that, because you can fail. There's really high failure rates, but you haven't failed. But let's tell everyone about your decision to leave the boring tech world or government tech world and start your own thing.

Bryson Bort 15:31 So I'm gonna disagree. I don't think that there's as much failure in entrepreneurship as people think. And we're gonna get to that, because that's the first thing everybody goes to their head, what if I fail? Look at the risk. I can't afford it. And I was in that same boat in 2012 I was like, I'm not gonna start my own company. That's scary. It's terrifying. And then I started to think about it, and I was like, Well, I had someone to encourage me. So find folks who are going to encourage you. Build your support group around it. One of the things. So I teach entrepreneurship. I debuted it six years ago a class six years ago at DEF CON, because I realized I'd see all these nerds who were all doing all the tech work, but they had no idea how companies worked and how that affected them, and they were frustrated with it. So even if you don't want to start your own company, learning how to start a company and how to run a company will make you better at your job and understanding everything that is happening. So just like in the military, you don't do anything alone, and entrepreneurship even more so. You need that support network to get you there, and then when you go into it, you need to have the buy in and support of your family and your friends, because you're going to disappear. It's hard work, and it is a 24/7 job, not because you're literally working 24/7 but because you're going to be mentally captive 24/7 thinking about this idea, and when you get employees, oh my gosh, right, the same way we take care of our soldiers. It's even more in this regard, because you're also responsible for the paycheck now. So when they complain about the that part, which we always complain about the army, because none of our pay ever was right and everything was always messed up, well, guess what? That's you now. You're a big army, and you're doing it, so you're going to be thinking about it 24/7, so with Brad's encouragement, I sat and drew on a napkin an idea that I wanted to do, and January 2013 is when I launched. GRIMM was my nickname in the intelligence community, so it seemed like a good name to keep Bryson's consultancy sounded kind of douchey. So I went with GRIMM, and I started by myself, and I can remember this 13 years ago, almost the day, sitting there staring at a coffee table with a phone and a laptop going, huh? Day one, I went from being really important on Friday to being really nobody today. Maybe I should call some people. Is that how you get work? You start calling people put the shingle out. And that was the start of GRIMM.

Kathleen Smith 17:59 Great advice as far as your entrepreneurial venture, and yes, I agree with you. It really depends on who it is and how they prepare themselves for that entrepreneurial venture, other than not going alone having a mentor. Can you talk a little bit about what veterans should think about if they're doing an entrepreneurial venture, if they have a family?

Bryson Bort 18:19 Great. So this gets back to risk. First, it comes down to money, right? Money is the lifeblood of an idea. You got to have that covered the starting your own company is taking the bet on yourself. And that was what I told myself, was like, Look, I had this high opinion of myself. Clearly, I don't know what I'm doing, and I keep succeeding. So let's let the market decide if I'm as good as I think I am, and let's see how it goes back to risk and failure. The reason I said I don't think the risk and failure is as bad as people think about it is most folks are going to start consultancies. So there's two kinds of businesses, services, product services are people based an hour of work, roughly, is worth an hour of pay product, whatever somebody pays after you built something that reaches that level. So consultancy is a much easier thing. You're going to start a consultancy when you are known for what you do. This is something you're an expert in. You can't be just somebody else on the line being like, Oh, I'm going to do just jump out, start my own consultancy. Like, who's going to hire you for what reason? Right? They're hiring you. They're hiring your reputation. And so the reason I say there's not as much risk is because that reputation, if you've achieved that, people are naturally going to be coming to you. But let's say it doesn't work out. But what does that mean? Well, first of all, during that whole time, you are going to have built a much larger network than you ever did inside the job, because that's the job, right? You're making calls, you're expanding your network, you're going and meeting people that you didn't go meet before you're doing these projects. So your reputation and the knowledge of people who know who you are is going to increase, which means when you go, Hey, this isn't working out. I'm ready to go back into the machine. Guess what? That's gonna be really easy to do, because you're now an even bigger commodity than you were beforehand. Like, to me, that's the worst way out. As long as you're fiscally conservative, you have this all button down with your family. The worst case scenario is essentially, like, you could pay and go to college, or you can pay and invest in yourself and build all of this professional network that now is what you do. I mean, Kathleen, the reason you're good at what you do is your professional network. You built that because you have been an entrepreneur.

Kathleen Smith 20:33 One quick question before I cut Rachel off. Tell us a little bit about why you started ICS Village, and I've noticed this sort of trend among some of our veterans, who are entrepreneurs. They always do something that's giving back to the community on top of their entrepreneurial ventures. So just a quick share of that, and why you did that?

Bryson Bort 20:57 I first visited DEF CON, I would say 09 and 10. And I think it was probably around 2012, or 13, that I first started to see the villages. I helped the car hacking village stand up. I worked with a couple of other ones. And it was a group of OT engineers that had gone and scrounged together and built the first version of the ICS village. And then Tom Van Norman, essentially, was the guy who took all that and by himself, was trying to keep it going. And I can't remember his 2015 or 2016 I remember I'm at DEF CON with Tom and the ICS village there's not a lot. And I was like, Tom, what's going on? He's like, the only reason we're even here is because GRIMM sponsored us. Without you, we had no money. And I was like, Oh, I have an idea. And so I went back to him, said, what if you and I co founded a nonprofit? So we built an organization around this. So this could be more than just this. This could be a year round thing, and we can make a big difference. Tom agreed. And so the 501 c3, is that's the birth of the ICS Village with Tom. By the way, Tom's also a vet. He's an Air Force vet. Awesome.

Rachel Bozeman 22:08 Well, I think I'm gonna take us back to the beginning. So we've picked up so many good nuggets of just advice. I love the kind of cracking the corporate code, getting good with finance. Very well done, my friend, very well done. And just kind of the enlightenment on entrepreneurship and all of the goodness. But for those that might be at that point in their career where they're going to transition out of the military, is there any other advice that you would give to them as they start this new transition?

Bryson Bort 22:37 Network, network, network. Common theme. I mean, relationships are what make everything work, and also, okay, actually, I've got one. So folks are sort of like, they struggle with the resume. And part of the reason they struggle with the resume is because they don't know what they're going for. Because why would you I don't know the civilian jobs. I know my MOS. That's easy. I was given an MOS done. I don't have to think about it. Now, there's all these options, what is the MOS equivalent? For me? I'm sure there's probably something where you can look up MOS to civilian job titles, but that may not even be what you want. You might be like, You know what? I've had enough of this. The army bro educated me. I don't want to do this anymore. I want to go do something else, right? So that's again, where networking can help. You don't have to have it all figured out. And I think a lot of folks hold back from engaging or asking for help or questions, because they're like, Well, I don't know enough, and I don't look stupid. That's okay. This is the same way we do intelligence. You have a little bit of an idea, and you talk to somebody about it. They're like, oh well. And they might add, and give you a little more context, you're like, well, now I understand a bit more. And even better, they're going to know somebody you don't know. You're like, Oh, okay. And they're going to introduce you to that person. And so you iterate these conversations, from starting from nothing to a little to suddenly, you have a better idea of what's possible and what you can do and what those jobs are. And now back to those awful resumes that every vet creates to start with. This is where Kathleen and Rachel are laughing because they know they've seen them, and I started to write. Now you know what to look for. It's easier to tailor your resume appropriately to that, because you have the goal and you have the direction that's driving you, and you earned it naturally, organically, by networking that way.

Kathleen Smith 24:24 And on that note, I'm going to say thank you, Bryson. I know you're extremely pulled in so many different directions, but I really knew that you would want to share your story with our veteran community and really provide them the inspiration that they need to get over this next little hurdle and onto finding their passion. So thank you again for joining us. Thank you. I so appreciated my friend Bryson joining us today, and I was so appreciative of his information about hey, sometimes you might not know what it is, but you have the guidance from your military background to figure out and research and meet people and ask questions, and even if you don't have direction, you can still find stuff.

Rachel Bozeman 25:12 I loved two things, and they're both start with the same letter, you know, I love a good theme, Kathleen. I loved his curiosity behind everything it was, I don't know. So I just found a resource, whether it was Google, whether it was a human like, I don't know what a CTO is, but instead of letting that hold him back, he said, I'll find a way. And I liked his creativity, just like, Okay, let's do this. And really just continued to kind of persevere through it. And I really did appreciate that he broke the corporate code, and I think he shared it out there for all of you, make friends with finance, show your value, and you too, my friends, can be uber successful in all things that you do. So thanks so much for listening. We so appreciate you. Make sure that you go out there and follow for more episodes and subscribe to our LinkedIn newsletter, you're going to find a lot of great information in there, and also the links to every single one of our shows. So until next time, peace out, exit buddies.

Kathleen Smith 26:11 Bye, everyone.