Exit Buddy: Veteran Stories to Guide You
Exit Buddy: Veteran Stories to Guide You shines a light on the real struggles and triumphs of veterans navigating life after military service. Each episode dives into the heart of military transition—sharing tales of resilience, setbacks, humor, and growth as veterans move from boots to business or rediscover purpose in civilian life. If you’re seeking inspiration, practical advice on military transition, or just a reminder that you’re not walking this path alone, Exit Buddy is here to help you find your way forward and thrive beyond the uniform.
Exit Buddy: Veteran Stories to Guide You
Producer Pick: Buckle Down & Break Through to Cyber Success
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This is a producer pick from Exit Buddy: Veteran Stories to Guide You — one we still recommend every time someone asks for a strong transition story.
Marine veteran Tom Eston went from infantry to cybersecurity leader, podcaster, and mentor. In this episode, he shares how curiosity and self-discipline fueled his career shift, why mentorship doesn’t have to be formal to be powerful, and how the skills he built in the Corps still set him apart in the corporate world. He also talks about launching a podcast and the risks that paid off along the way.
It's worth another listen if you haven’t heard it (or even if you have).
Original show notes and transcript: https://www.buzzsprout.com/2535619/episodes/18159486-buckle-down-break-through-from-devil-dog-to-cyber-champion
Follow along for more veteran stories, and send this one to a service member who’s mapping out their next chapter.
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.
Hello everybody, this is Ashley with Exit Buddy, and I've got another producer pick for you today. One of those episodes that seems to hit every time I listen back. We've got Marine veteran Tom Easton queued up. He's gonna take us from his infantry journey to a cybersecurity trailblazer, sharing how curiosity, self-discipline, and a willingness to take risks shaped his path. He's gonna talk about finding mentorship in unexpected places, turning those military skills into corporate strengths, and even a little backstory on how he got into podcasting himself. So let's hear some practical, honest, good advice from our friend Tom Easton.
SPEAKER_03I'm Kathleen, and I am joined by the one, the only, the incomparable, Rachel. How are you doing today, Rachel?
SPEAKER_02With 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.
SPEAKER_03So I know we're all excited, but I am especially excited to welcome Tom Easton, a Marine Corps veteran who now thrives as a cybersecurity just god. You know, 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.
SPEAKER_00What an intro. I don't even know. I I can't even follow that. But uh yeah, thank thank you so much for having me on the show. Um, yeah, we get to flip the script a little bit because I'm usually interviewing you. Uh Kathleen, you've been on my podcast uh several times in the past. So uh yeah, I'm excited. Yeah, excited for the show.
SPEAKER_02Well, 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?
SPEAKER_00Yes. Great question. Uh I would say that um 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 we'll just say that, right? Um 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 I miss being in uniform. I miss the, you know, sometimes I 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, you know, just I did a lot of great things. I got to travel the world. It was, I made amazing friendships and all those things. But uh, I don't think I'd want to do it again at this phase of my life, if that makes sense.
SPEAKER_03I 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. Uh, 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?
SPEAKER_00Yeah, great question. I I think I've always been involved in some type of technology or electronics, you know, even from an early age. Um, you know, I grew up uh a child of the 80s, and so, you know, video games, I was the first uh, you know, kid on my street to have an Atari 2600 and then uh Nintendo NES. And, you know, I've always been into, you know, kind of tinkering around with electronics, and I was very curious about all of these things. And even I'd say early, early hacker culture, you know, started to emerge a little bit of, you know, there were situations you see online or discussing with people connecting to your bulletin board system of like, you know, hey, you know, these people are pirating software and they're, you know, you know, trying to uh crack codes and games so you can get them for free and things like that. And and you start seeing this other side of things, and that really kind of built a curiosity in myself of like, oh wow, these things can be broken, things can be hacked. And, you know, 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, you know, I think a couple guys had some had old, you know, 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 like explore more of that because I 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, you know, this is 1997, we're getting into the dot-com era, and there was just an explosion of jobs at the time of you know, break fix type of jobs, help desks. This was there was just a great opportunity of like if I wanted to get into technology, I found myself, you know, gravitating towards that and then doing kind of my own networking and just you know finding the right people to talk to. I found people that gave me that opportunity to kind of get my foot in the door. Um, 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, you know, for school. Like the the military is helping you pay for your school. And to me, that helped me get a two-year degree in uh it was a network communications technology, and then eventually a bachelor's. And that paid for most of my schooling um when I got out of the military. So I think combined with the military experience and just, you know, figuring things out, and then this the going to college using the GI Bill really helped me find the right role for me when I got out.
SPEAKER_03So, 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. I mean, how did you navigate that leap of faith? And were there any mentors you were able to lean on?
SPEAKER_00Yeah, that's a good question. I 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 uh previous uh 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. Um, you know, I built this team, helped build this team, and I and the reason I got into pen testing and hacking was because I had to hire our first pen test. I had to hire a third-party company to come in and do a full pen test of the whole company. And so we hired this 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 on the network. And I'm just like, who is this? This guy 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'd 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 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, you know, taking my career to more towards the pen testing realm.
SPEAKER_02Very cool. So it sounds like you had some great guidance, some great mentorship.
SPEAKER_00I I I did, and I I'd also say that it was a lot of just um, 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 gonna do whatever it takes, whether that's going to school, get a degree, get certifications, um, talk to other people in the industry, um, find mentors, all of those things really helped, but it was a lot of just self-discipline at the beginning to like, you just gotta 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.
SPEAKER_02That'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, you know, 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 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?
SPEAKER_00I I would definitely say um there's so many great programs and opportunities now. So I would tell veterans, I tell people that are just getting trying, you know, 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, you know, getting your resume and and putting together a profile for yourself that you can get on LinkedIn and you can start kind of showcasing who you are, what what skills you bring to the table, because it isn't always about, you know, 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 you know, 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, you know, don't be afraid of like sharing your knowledge. That's one of the biggest things I get a lot from a lot of vets is like, well, you know, I didn't have those experiences in the military. Like, people are gonna think I'm, you know, crazy come trying to learn. And like, no, like that's 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 of 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, you know, 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. But take those little things and what you've learned, and uh, 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 um you know I think are just so valuable, and companies see that. Um, 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. Um, I've had lots of opportunities just come my way that, you know, 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.
SPEAKER_03It's really interesting that you talk about sort of going to these conferences and stuff. And I just want to put a plug that you know, security B sides definitely welcomes veterans. The uh Black Hat actually has a Black Hat Veterans program, which I'm very uh 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?
SPEAKER_00Definitely 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. Um, that's something I learned very early on in the military because there were situations I was in where, you know, things are life and death situations in the military, right? Um, and you're thinking about the lives of your fellow Marines and you're thinking about, you know, civilians and crossfire and all these things. And so I've learned kind of throughout the military and then into my civilian uh careers, it's been about like addressing situations, especially around employee performance or about, you know, uh 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, you know, whether it's, you know, an employee situation, your your significant other, your kids, like these things all transcend to each, you know, different parts of your life. Um, so I think that's one big thing that I I look back and and I'm grateful that I had those experiences. It really does start with a lot with some self-reflection. And that's something that um 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, you know, 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, you know, 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.
SPEAKER_02So, what inspired you to start this crazy thing talking into a microphone, um, putting your voice out there? And, you know, how has it impacted you both personally and professionally?
SPEAKER_00Yeah, it's um, you know, we've been doing this podcast for since 2009. You know, 16 years later, we're now doing the podcast, still doing the podcast over 400 episodes. And um, 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. Um, I think it's important that we put our put our own perspective on that. Um, 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, you know, 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, you know, 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 um, you know, podcasting and speaking and all those things just it helps 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 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 B-sides and 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 you know, we're right now in the golden age of like education. I mean, we really are. Um, 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?
SPEAKER_03What 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?
SPEAKER_00Yeah, that's the the million-dollar question. Yeah, that's that's it's a tough one. And it's different, I think, for everybody, um, based on your own personal, you know, situation or based on who you are and how you perceive, I think, kind of the rest of the world. But the one advice I would give um 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 um, you know, network and to be your kind of your buddy, right? Your exit buddy, you know, no pun intended, but um, but seriously, like um 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 you know, it's okay to reach out for help. It really is, like, and 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 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, you know, 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 like people that you maybe maybe you 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 gonna 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 you know, being motivated and doing things like that, but all of us had help at some point. There was always somebody there that was gonna help guide us and 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. And they don't have to be like, 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 it doesn't always have to be like that. And I've had mentors that have just given me, you know, some just really sound advice, and I don't talk to them for a year after that, right? Like it that's what we mean by mentorships, is like at the right time and the right place in your life right now, um, are sometimes the best conversations of some of the people that you can meet.
SPEAKER_02Absolutely. Fantastic advice. It sounds like you've got a lot of advice, but we're gonna throw a little twist in here, Tom, because sometimes it's hard to give ourselves advice. So I'm gonna ask you to go back. If you remember, I know you talked uh earlier in our conversation about how our identities change when we're in the military, when we leave, and we become different persons. Um, 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 risk 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?
SPEAKER_00Yeah, it's a it's a good question. I I think, you know, I I've always been a little bit of a risk taker. Um, I think I was more, I think I'm more risk-adverse now in my older age than I was back then. And maybe that's just something of Yeah, it is. Honestly, it's like physically and mentally, you know, I you're just a different person in your 20s. And, you know, I'm thinking back to my relationships, and you know, I didn't have kids yet, and you know, I was still somewhat dating my wife at the time and getting engaged, and there's this very like different times of of how you live your life. And I would to to my younger self, I would tell him to maybe like not uh you know not go crazy like I did in the 20s. Like, you know, partying and like, I mean, that was all part of my military experience too. It's like I had a great time. I traveled around the world. I met tons of people and you know we may have gotten into some trouble the overseas, you know, doing things like that that I right. I mean I just would not do again. Like I'm not saying I regret anything, but you know, I would probably tell my younger self to be like, you know, uh you know enjoy your time, but um you know don't do anything stupid. Right. And uh I you know honestly I honestly 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 look back 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 wouldn't drank that much and my hacking career and all of that. So you know 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 um regardless right still made me who I am today you know 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 you know the opportunities I have today and for the people in my life that have really helped um 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 the where do we want to go with our our 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 you know all I know Kathleen you have too and every everybody right so don't be afraid to ask for help um think about the experiences you've had and how they can help you today um and just remember that you know getting old isn't isn't horrible right it's like you can still relive your glory days but take that wisdom right it's so important.
SPEAKER_03We still have glory days coming of course we do yeah we're just in different stages yeah Tom thank you so much for joining us um I just want to say happy birthday devil dog and this is thank you uh 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 your background and your journey to the the veteran community so thank you thank you it's been an absolute pleasure being on the show and uh thank you for all that you do you both do for veterans uh it's super super important 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 you know 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.
SPEAKER_02Rachel what did you like about our conversation with Tom Absolutely I love the conversation around the importance of using your network building a network having those mentors but I also really liked his ref his reflections on self-discipline that he was able to really get from the military and that self-resilience and it's about you know 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 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 toward your future see you next time bye bye
