Buckle Down & Break Through: From Devil Dog to Cyber Champion

Join Kathleen Smith and Rachel Bozeman as they welcome Tom Eston, a Marine turned cybersecurity trailblazer, podcaster, and mentor, for an inspiring dive into his journey. From his infantry days to carving out a security career, Tom shares how curiosity, self-discipline, and determination fueled his rise. Tom emphasizes the importance of mentorship, continuous learning, and leveraging military-learned skills in the corporate world. His story is a testament to the potential within every veteran to reinvent themselves and excel in new fields.

Chapters

• 01:44 - Tom’s Marine Corps Infantry Days
• 03:07 - The Spark of a Tech Career
• 06:56 - Leaping into Security with a Real Estate Gig
• 09:58 - Advice on Seeking Mentorship
• 13:03 - Military Skills in the Corporate World
• 15:48 - The Birth of a Podcasting Passion
• 17:47 - Overcoming Nerves to Take Risks
• 20:38 - Advice to His Younger Self

Key Takeaways

• Self-Discipline Drives Success: Continuous learning and personal motivation are critical for career transformation. Your ability to set goals, stay focused, and push through challenges determines your professional growth.
• Mentorship Comes in Many Forms: You don’t need a formal mentorship program to seek guidance. A single conversation or brief connection can provide pivotal insights for your career journey.
• Skills Can Be Learned, Character Cannot: Technical skills can be taught, but the leadership, adaptability, and problem-solving skills gained in military service are irreplaceable and set you apart.
• Network and Share Your Knowledge: Attend conferences, start a blog, and put yourself out there so people can learn who you are. As Tom learned, sharing your knowledge can help educate you in return.

Follow us for more veteran stories to guide your transition journey, and text this episode to a fellow service member who’s navigating their exit. Catch you next time!

Visit us at https://exitbuddy.buzzsprout.com to learn more about the show.

Have feedback or questions for us? Email us at ashleyjones.creative@gmail.com.

Transcript

Kathleen Smith  00:24  

Hello everyone, and welcome back to another episode of Exit Buddy: Veteran Stories to Guide You. I'm Kathleen, and I am joined by the one, the only, the incomparable Rachel. How are you doing today, Rachel?

Rachel Bozeman  00:38  

With an introduction like that, I better be doing pretty stinking amazing. And I am so excited to be here, excited to hear some more stories, and excited to hear who's on the show today, Kathleen.

Kathleen Smith  00:53  

So I know we're all excited, but I am especially excited to welcome Tom Eston, a Marine Corps veteran who now thrives as a cybersecurity expert. He's a podcaster, he's a leader, he's an instructor. He may know one or two things about podcasting and teaching people, but I love having him on the other side of the microphone today and hearing about his experience. So welcome to the show, Tom.

Tom Eston  01:22  

What an intro. I don't even know. I can't even follow that, but yeah, thank you so much for having me on the show. We get to flip the script a little bit because I'm usually interviewing you, Kathleen. You've been on my podcast several times in the past, so yeah, I'm excited for the show.

Rachel Bozeman  01:44  

Well, perfect. Now let's get down to business. Now that we know how incredible you are, let's share your incredibleness with our audience here. So you joined the Marine Corps right out of high school. So first and foremost, thank you for your service there, but now we want you to take us back in time to when you were there in those four years that you served in the infantry. Does anything particular come to mind when you think of those good old days?

Tom Eston  02:08  

Yes, great question. I would say that. I would say that it's the best thing that I've ever done in my life that I never want to do again. We'll just say that, right? Definitely one of the best experiences I've ever had in my life, the camaraderie that you have amongst other people you served with. I mean, you'll never, I'll never get that back, right? There's times I miss being in uniform. I miss sometimes life was so simple back then. But then I also have to look at like, well, I was in my 20s, and I'm like, I was such a different person in my 20s. So yeah, I think that's when I look back. I think of just I did a lot of great things. I got to travel the world. It was amazing friendships and all those things, but I don't think I'd want to do it again at this phase of my life, if that makes sense.

Kathleen Smith  03:07  

I think not many of us would really want to go back. We don't want our joints and our muscles to hurt as much as they do now, but that uncomfortableness, I think I'll be willing to pay for the wisdom for the price of the creaky back. So what I find absolutely fascinating is that you carved a cybersecurity career for yourself, but when you transitioned out, cybersecurity technically didn't. It did exist, but we were calling it something else, and it wasn't this big industry that it is now. So what initially drew you to tech? I mean, was there some hobby, something that you did in the military, something that sort of sparked you into this tech come cybersecurity career?

Tom Eston  03:54  

Yeah, great question. I think I've always been involved in some type of technology or electronics, even from an early age. I grew up a child of the 80s, and so video games. I was the first kid on my street to have an Atari 2600 and then Nintendo NES. And I've always been into tinkering around electronics. And I was very curious about all of these things. And even, I'd say early, early hacker culture started to emerge a little bit. There were situations you see online or discussing with people connecting to your bulletin board system, of like, hey, these people are pirating software, and they're trying to crack codes and games so you can get them for free, and things like that. And that really kind of built a curiosity in myself of like, oh wow. These things can be broken. Things can be hacked. And I was always the mindset of, like, if I could take a technology or computer or something like that, and maybe I can make this do something it wasn't designed to do, that was always kind of something I was really interested in. And I think when I was in the military, I didn't touch electronics at all, except for I think a couple guys had some, had old laptop computers that we were like playing games on and things like that. But I found that when I got out, I really wanted to explore more of that, because I always felt that I wanted to do something in technology. And I think I came in at the right time, because it was right around, this is 1997 we're getting into the.com era, and there was just an explosion of jobs at the time of break, fix, type of jobs, help desk. This was there was just a great opportunity. Of, like, if I wanted to get into technology, I found myself gravitating towards that and then doing kind of my own networking and just finding the right people to talk to. I found people that gave me that opportunity to kind of get my foot in the door. But I'd say it also had to do with education too, because one of the big things I got out of the military was my GI Bill, and that's something I always tell veterans of like, take advantage of that, because that is essentially your ticket to school, like the military is helping you pay for your school. And to me, that helped me get a two-year degree in it was a network communications technology and then eventually a bachelor's, and that paid for most of my schooling when I got out of the military. So I think combined with the military experience and just figuring things out, and then going to college, using the GI Bill, really helped me find the right role for me when I got out.

Kathleen Smith  06:56  

So speaking about when you got out, you mentioned in our pre-call that falling into a security career came from because a real estate company you worked for needed a security department. And how did you navigate that leap of faith, and were there any mentors you were able to lean on?

Tom Eston  07:16  

Yeah, that's a good question. I think it was an opportunity presented to me, because at the company I worked for at the time, I was the person that was patching all the systems. I was, I mean, there wasn't really a security role yet, but I was doing the functions of somebody that would be in security, right? So they hired a previous former auditor to kind of build this new security department, and I found that that was something that really interested me, because I didn't really have that no one really had that kind of experience where we had to build this team from the ground up. But it really was just trial by fire in a lot of cases. I built this team, helped build this team, and the reason I got into pen testing and hacking was because I had to hire our first pen test. I'd hire a third-party company to come in and do a full pen test of the whole company. And so we hired this small company, this guy came in, and I was just enamored with this guy. Like, I was just like, he is, like, took him all, like, a whole five minutes, and he had access to everything the network. And I'm just like, who is this? This guy's some magician. Like, what's happening here? And I sat next to him, and I was just like a sponge. I was just like, asking him questions. I was like, how did you do this? What tools are you using? Like, how'd you gain access to this? And I was just taking all that in, and that's what really like. I always look back to that guy as, like, not like an official mentor, but he kind of gave me that push that I needed to how do I get into pen testing? How do I do more security type of work, like, how can I get more technical and really figure these things out. And so that kind of gave me that motivation of taking my career more towards the pen testing realm.

Rachel Bozeman  09:10  

Very cool. So it sounds like you had some great guidance, some great mentorship.

Tom Eston  09:15  

I did. And I'd also say that it was a lot of just and something that the military taught me a lot of was just that self-discipline to just buckle down and figure things out right. So I was always had that mindset of, I'm going to do whatever it takes, whether that's going to school, get a degree, get certifications, talk to other people in the industry, find mentors. All of those things really helped, but it was a lot of just self-discipline at the beginning to like, you just got to do this, right? If you want to do something great with your life? Well, you're in control, so you need to just do it.

Rachel Bozeman  09:58  

That's it. You're in the pilot seat. Get her done. Get her done. Well, awesome. Well, kind of speaking in that mentorship lane, sometimes it is difficult, especially people that are transitioning out have kind of got that mindset of, I can do this, I can do this, and aren't necessarily willing to reach out and maybe tap somebody on the shoulder or dig into their network or ask for that mentor to give them that advice. So is there advice that you would give to folks that are transitioning on, that are maybe a little hesitant in asking for that help or that advice as they're transitioning out?

Tom Eston  10:29  

I would definitely say, there's so many great programs and opportunities now. So I would tell veterans, I tell people that are just getting, trying, they're about to get out. I would say, look for those opportunities where there's organizations that can help you, and they can help you with your networking, same thing with like getting your resume and putting together a profile for yourself that you can get on LinkedIn, and you can start kind of showcasing who you are, what skills you bring to the table. Because it isn't always about, well, you got to have these previous experiences. Like, I've talked to a lot of veterans that want to get into cybersecurity, and they didn't do cybersecurity in the military, or they didn't even do intelligence, or other types of similar roles. And they're like, well, how do I get into pen testing? And it's like, well, first of all, find a mentor, right? Find someone like myself, or I can recommend other people that you know, go to a conference, start networking, get yourself out there so people kind of know who you are, start a blog, start these little things to start, just even if you don't be afraid of like sharing your knowledge. That's one of the biggest things I get from a lot of vets is like, well, I didn't have those experiences in the military. Like, people are gonna think I'm crazy coming trying to learn. I'm like, no. Like, that's what we want. We want to see people that are willing to learn, and in fact, in an entry-level type of role, I'm willing to give people more of a chance, because they're showing me motivation. They're showing me that they can learn. They're showing me all these skills that they learned in the military. These are hugely valuable skills, even more so in a lot of ways, than the technical skills. Technical skills can always be taught. But I always look at, and I've talked a lot of vets about, I mean, look at the experiences you've had and the things you've had to deal with, take those little things and what you've learned and you can apply them to the civilian world quite easily, especially the corporate world, because that's one thing that I think military veterans have above their civilian counterparts, is they've had these life experiences that I think are just so valuable, and companies see that. That's why a lot of companies will see like, oh, you were a veteran, and you should always check that box. Like, when you apply to a job, that you're a veteran. I've had lots of opportunities just come my way that just through applying, and they want to talk to me, because they know I've had these experiences, these life experiences that are so super important.

Kathleen Smith  13:03  

It's really interesting that you talk about sort of going to these conferences and stuff. And I just want to put a plug that Security BSides definitely welcomes veterans. The Black Hat actually has a Black Hat Veterans Program, which I'm very appreciative of, because it takes a small group of veterans and takes them through Black Hat. So one thing that I love looking at your background is that your civilian career is not what your military career was. And I know that this is a big challenge that a lot of veterans have, that they believe they just need to change their uniform rather than change their entire career. So can you just sort of share briefly, some of the military skills that you believe helped you in your corporate career?

Tom Eston  13:52  

Definitely, a bunch of things come to mind. I would say one of them, in particular, especially now I've been in a leadership role. I would say, how to have difficult conversations. That's something I learned very early on in the military, because there was situations I was in where things are life and death situations in the military, right? And you're thinking about the lives of your fellow Marines, and you're thinking about civilians and crossfire and all these things. And so I've learned kind of throughout the military and then into my civilian careers, it's been about addressing situations, especially around employee performance, or about decisions that need to be made, maybe from a strategic level, and like making those decisions and having the hard conversations early and then being transparent about situations, those are all things that I learned in the military and still prove. I mean, I use them all the time, right? Because I think we all struggle a lot with those difficult conversations. Whether it's an employee situation, your significant other, your kids, like these things all transcend to each different part of your life. So I think that's one big thing that I look back and I'm grateful that I had those experiences. It really does start with some self-reflection, and that's something that I'm able to do a lot more now. I think when you're in your 20s, it's like self-reflection is like, yeah, whatever you're young, why would I reflect on any of this stuff? But as I've gotten older, I do do a lot more of that retrospect, where I want to understand, okay, who I am today is because of the things and the experiences that I had when I was younger, and a lot of that was the military experience.

Rachel Bozeman  15:48  

So what inspired you to start this crazy thing, talking into a microphone, putting your voice out there, and how has it impacted you, both personally and professionally?

Tom Eston  15:59  

Yeah, it's been something we've been doing this podcast for since 2009. Sixteen years later, we're now doing the podcast, still doing the podcast over 400 episodes, and I think it's been one of those things that I keep doing because, number one, I think it's important that we continue to share insights into what's going on in the industry with everybody. I think it's important that we put our perspective on that. It's one of the big reasons I love having guests on the show, because I want to hear their opinions. I'd like to hear their thoughts. And I think it's a way of just getting out there. And I don't think I would be where I am today without the things I've done with podcasting, with public speaking, with just paying it forward wherever I can, because so many people early in my career gave me these opportunities. So I've had a lot of those experiences, and I felt that podcasting and speaking and all those things just help educate me too. Because I think the best way that you can become a teacher is actually by getting yourself out there and learning yourself. And I think today, there's just so many opportunities to learn than we had in the 90s. It's just like there's so many programs, there's YouTube videos, there's look at all the great conferences, like BSides, and all these, all these opportunities that are just out there waiting for people to just take advantage of. And I think we forget that. We're right now in the golden age of education. I mean, we really are. It doesn't get any better than this. And so the opportunities are there. It's just you got to be that person that has the self-discipline to go after it, right?

Kathleen Smith  17:47  

What is your one piece of advice to go out and sort of say, hey, this is a place for you to be, be it online, be it in person. But how do you take that risk? How do you get beyond being nervous and putting yourself out there?

Tom Eston  18:06  

Yeah, that's the million-dollar question. It's a tough one, and it's different, I think, for everybody, based on your own personal situation, or based on who you are and how you perceive the rest of the world. But the one advice I would give if you are kind of more on the side of being a little more shy, a little more reserved, is to find somebody that can kind of help you network and to be your buddy, right, your exit buddy. No pun intended, but seriously, like, there's so many things in life that we need others to help us with, and I think it takes a lot of just self-understanding ourselves that it's okay to reach out for help. It really is like, especially with your career, and so that's why I always encourage people just like, even if you find someone that, like, I remember, like, first time I met like, HD Moore, like, who was like, a demigod in security, right? Like, I'm like, I can't talk to this guy. Like he's gonna think I'm an idiot. Like, I'm afraid to go up to him. And like, I remember a friend of mine introduced me to him, and like, this guy's the nicest guy in the world. Like, he's actually wanted to have a conversation with me. And I'm like, don't be afraid of people that you maybe look up to in the industry, and you would be surprised, like, just coming up to them at a conference, and they're more than happy to talk to you. And like, there's so many good people in our industry that want to help, that want to pay it forward. And just look for those opportunities to find someone that's going to kind of help guide you, and maybe even make those introductions for you, because you can't do all these things by yourself. I mean, I know I talked about self-discipline and being motivated and doing things like that, but all of us had help at some point. There was always somebody there that was going to help guide us and give us that advice to find the career and find the job, and so that's what I'd encourage people to do, is just try to find those connections. They don't have to be like a lot of people think mentorship is like this, some big, official thing, right? Where there's a program you have to go through and all these things, and doesn't always have to be like that. I've had mentors that have just given me really sound advice, and I don't talk to them for a year after that, right? Like, that's what we mean by mentorships, is like, at the right time, in the right place in your life right now, are sometimes the best conversations, and some of the people that you can meet.

Rachel Bozeman  20:38  

Absolutely fantastic advice. It sounds like you've got a lot of advice. We're going to throw a little twist in here, Tom, because sometimes it's hard to give ourselves advice. So I'm going to ask you to go back. If you remember, I know you talked earlier in our conversation about how our identities change when we're in the military, when we leave and we become different persons. But if you go back and you had to think back to those four glorious years, are there things or advice you would give yourself, maybe risks that you could have taken, or things that you would have done differently, or things that you could share now that would help those that are in this journey?

Tom Eston  21:13  

Yeah, it's a good question. I think I've always been a little bit of a risk taker. I think I was more, I think I'm more risk averse now in my older age than I was back then. And maybe that's just something, it is, honestly, it's like, physically and mentally, you're just a different person in your 20s. And I'm thinking back to my relationships, and I didn't have kids yet, and somewhat dating my wife at the time and getting engaged, and there's very different times of how you live your life. And I would to my younger self, I would tell to maybe like, not go crazy like I did in the 20s, like partying and like, I mean, that was all part of my military experience too. Is like, I had a great time. I traveled around the world and met tons of people. And we may have gotten into some trouble overseas doing things like that that I right. I mean, I just would not do again. Like, I'm not saying I regret anything, but I would probably tell my younger self to be like, enjoy your time, but don't do anything stupid, right? And I, honestly, I look it back. And one of the other things I talk a lot more about publicly is like, I'm sober now. So I've been sober for almost two years. Actually, this end of this month will be two years. And I also like how much thank you. And I look back of how much like alcohol like influenced my military career, and I'll be honest, like, I probably ended my hacking career much, and my hacking career and all of that. So for me, it's been like the last two years. I look back of like, yeah, probably shouldn't have partied that much in the military, but regardless, right, still made me who I am today. I look back as not a negative experience at all, but it also allowed me to reflect on my own sobriety now and how grateful I am for the opportunities I have today and for the people in my life that have really helped helped me get to where I'm at. I couldn't have done it alone. I've always had just great people in my life that I've either sought out or just happened to show up, right? And there is some luck maybe to some of this, but I do think that we all have to just be as proactive as we can to like, really think about, what are the goals? What are where do we want to go with our career and our life, and then who can help me get there? Because it's very, very difficult to do any of this on your own. I had help. We've all had help. I know Kathleen, you have to, and everybody, right? So don't be afraid to ask for help. Think about the experiences you've had and how they can help you today, and just remember that getting old isn't horrible, right? It's like, still relive your glory days, but take that wisdom, right? It's so important we still have glory days coming. Of course, we do. We're just in different stages.

Kathleen Smith  24:30  

Yeah. Tom, thank you so much for joining us. I just want to say Happy Birthday Devil Dog, and this is thank you, honorary exit buddy. I really appreciate you sharing your tips and your stories, and I am just so thrilled I was able to bring your background and your journey to the veteran community. So thank you.

Tom Eston  24:57  

Thank you. It's been an absolute pleasure being on the show, and thank you for all that you do. You both do for veterans. It's super, super important.

Kathleen Smith  25:07  

So Tom is such a great friend of the community, the veteran community, the cybersecurity hacking community. I'm so thrilled that we got to have him on the show. I loved his thoughts on finding a mentor, being able to say that get over your scaredy-catness and just walk up and talk to somebody. And mentorship isn't this big program. It is someone may give you a piece of advice, and then you might not hear from them for a year or so. So having that network of people you can tap on and ask them a question is just the really best way to have a mentor. Rachel, what did you like about our conversation with Tom?

Rachel Bozeman  25:51  

I love the conversation around the importance of using your network, building a network, having those mentors. But I also really liked his reflections on self-discipline that he was able to really get from the military, and that self-resilience, and it's about overcoming those things that might be a challenge to yourself, whatever aspect that is, and just how he's been able to share those through his platform and make sure that people are informed and really paying it forward. I thought was just such a good, good thing to kind of focus on, and just such a great time to learn together with Tom. So that's all for now, our friends, our exit buddies, toss this episode into a chat with your fellow service members. Hit follow for more stories and keep charging towards your future. See you next time, bye.