Rob Oden joins us on Security Confidential for a two part series. This is part 1 and he discusses his personal journey from humble beginnings to a great cybersecurity architect. He shares his story and the many challenges he faced and the qualities of people wanting to create success for themselves in the field of cybersecurity.

The topics discussed in this episode are

00:00 Introduction

02:12 Journey from humble beginnings to cybersecurity architect

05:30 First exposure to cybersecurity

09:30 Taking responsibility and owning it

14:13 The crab effect

23:42 Is a traditional computer science path necessary for cybersecurity?

30:23 The transition from Military to Civilian life

39:43 The soft skills for a great career

46:30 Check in with yourself-have a true North

49:35 Be comfortable with being uncomfortable

Rob can be found on linkedin

Manoj Tandon can be found linkedin…

To learn more about Dark Rhino Security visit

The link to the podcast can be found…


Video Transpcript

– Hello, everyone, welcome to another episode of “Dark Rhino Security’s Security Confidential”. Today, we are honored to have Rob Oden join us. Rob is an Air Force veteran and a cybersecurity architect with over 16 years of experience, evaluating, defining, advocating, and driving adoption of policies, programs, strategies, and technologies that advance cybersecurity. He has multiple talents. His expertise includes cybersecurity, information protection and information rights management, insider threat risk management, certification and accreditation, enterprise architecture, risk management frameworks and compliance, and some things we can’t talk about, because of his background. But we’re honored to have him for two episodes. And the first part of this, today, what we’re gonna talk about is Rob’s background and his journey into cybersecurity. ‘Cause as talented as he is, I think his journey is a unique one, and it’s an inspiring one. And it would be great for everyone out there that is thinking about transitioning to cybersecurity or wants to make a career out of it to take a listen to some of his guidance and his roadmap and share his thoughts and insights. Welcome to the show, Rob, thank you.

– Thank you for having me.

– I appreciate it. So Rob, we know you have a great background as a security architect. But what people may not know is a couple interesting facts. You were on “House Hunters”.

– Yep.

– Right? That’s a side note, but anybody who wants to search for Rob there… You were on “House Hunters”. You grew up in Alabama.

– Yep, South Alabama, or as we know it as LA, Lower Alabama.

– And you spent… Your first stint was with the Air Force. So describe a little bit of this journey. How does someone with a humble beginning get to the place that you are?

– Well, so it’s interesting. When I started my senior year of high school, I had an expectation, like, I wanted to be a pilot. This is what I wanted to do. I had applied for the Air Force Academy, and some Rossi programs, because I was like, “I just wanna fly.” And as what happened, a friend of mine and I had a relationship and a little girl came about that. And so life just changed, right, in my senior year. And unfortunately, it is a very common story in South Alabama. But I knew that for the life that I wanted to provide for my child, I needed to do something a little bit more. And college and the academy was no longer a viable option. And talking to my family, I joined the Air Force, kind of provide it. This is probably a comment. You know, I had the traditional South Alabama experience. For a long part of my childhood, I did grow up in a trailer park. So much so that I knew the different qualities of trailer parks from the ones that the cops get caught onto, and to the ones that, you know, are a subdivision in of itself, right? Has lawns.

– Really?

– And so I knew that I wanted to provide for this new child that was coming in. I wanted to give more. And so I joined the Air Force. And when I first joined the Air Force, I know anything about computers. Barely, the internet was a thing that rich people had. We didn’t have a computer in the house. I spent some time-

– There was no WiFi, or anything-

– No. You know, I had to go to my aunt’s house to have dial-up internet.

– So this was in that era.

– Yeah, that era. This was ’90s, or early 2000s. So when I graduated, was in early 2000s, DSL, those types of things were coming to like Northeast. But really for Alabama, you had doubt, and only for those who can afford the computer. So when I joined the Air Force, they asked me, it’s like, “What do you want to do?” And I made the joke. I’m like, “Well, I wanna make money.” So what can I do to make money? And they’re like, “What do you think about computers?” I’m like, “Let’s do it.” And that got my kind of introduction from this redneck from the sticks to kind of a crash course. Think of it like every week, you’re doing a midterm, and learning all things about computers. In the Air Force, it was just like, “If you have a willingness, you have a desire, we’ll give you the skills.” And not only did this give me my start for information technology and become a technologist. But there was the final class that you take, it’s about a six to seven-month program. And the final class is they give you a room full of containers, two rooms, you get split into two teams. And this was my first taste and desire into cybersecurity, is they said, “Okay, you have to set up a network. Here’s your pipe, your connection.” This one’s Langley, one’s Hickam. So Hawaii, Virginia to kind of replicate a couple known Air Force bases. And you have to build everything. You have, I think it was either four six hours to build up the entire network, set up routers which is the entire infrastructure. And the team who finished first and completely checked off, got extra points, got about 10 extra points for 100. And so we did that, we connect everything. First thing we did, we plugged in the cable to the line, started setting everything up, and the other team-

– This is from ground zero then, there was nothing.

– Nothing, but then that was the expectation is that we would go get deployed and set up an entire infrastructure, is your bare minimum, or tap into whatever was locally available. So we tie, we connect it right into the line to connect us to the other sites, started getting things set up. And one of the other team members from the other side completely deleted our profiles, was able to log in. We still had admin, admin. They logged into and just started deleting stuff. And we threw our hands up, it was like, “What’s going on?” And the instructor was just like, “If you do that in real-world, and somebody did that to you, which they would, you’re gonna blame yourself. You did that to yourself.” And I think of that almost 20 years later after that test. And I look at solar winds, right? That just had the… Well, one of our interns shared, or very generic, very known password. And that lesson that started as a technologist and the information technology specialist and laying the foundation for what I would built for security was really prevalent is that I can’t be mad at the other guy for attacking me if I myself, I’m starting off with open vulnerabilities or my configuration is not putting… Let me first shut my door and lock it before I build, you know, put valuables in there. And that got me started, I was very lucky. I got to work with some amazing people. I primarily worked with aircraft such as intelligence, surveillance, reconnaissance. So the YouTube, the Global Hawk, the Predator got really big into UABs, you know, go to Korea, Iraq. And just having an experience where you’re dealing with all, you know, information sharing for different levels of sensitivity, needing to be protected in some of the most crazy climates in the world, and in having multiple missions of why you need that information and sharing. And so that really started my foundation, information technology and in all throughout that, cybersecurity was a component of my job from a certification, right? You know, the Rainbow Series and the District 63 for those government heads. And then transitioning to what we know as the NIST 800 series and ISO 27,001, and some of your PCI and those kinds of compliance requirements, all those things were starting to get built into and getting more thought of, instead of just a, you know, system check mark QA, but more of an enterprise look at how do we do this at scale? And not so much for, “I got hit, so let me, you know, block it,” but take a step back and go a little bit longer.

– See, Rob, what you’re describing, one thing that is occurring to me is that you took a great deal of responsibility, both personally and professionally for the situation, and made the best of a situation that many others might find very difficult to navigate. Did you have, I mean, do you attribute that really to… Is it just mindset that got you out of that trailer park in Alabama? Or is it something more? Is it taking that responsibility and having such a positive outlook and doing it, or is there more to it?

– So I’ve had this conversations. My daughter is now 17-years-old. We’ve been able to have some really conversations. And you know, of course, I’ve talked to her about her own opportunities, her own challenges that she has in life. And there has been, you know, some really deep conversations about “Do you regret that?” You know, these… And I’m like, “Look, yes, it was a harder, it was a struggle, and it made me grow up quicker.” But yet it being in that situation, being in a situation where I saw my peers and other classmates have so much more, and me wanting to do that and wanting to do more. And then my parents who, you know, again, we started working, I wanna clarify it right, in the trailer park, going from that but both my parents worked, worked, worked. And then, by the time that I was graduating, was able to buy their first home, and continue to build their life. And so I saw really great examples of just hardworking men and women in kind of tanking, you know, carve out with the American dream. And I also saw my own parents of saying, “Look, this is your responsibility. This isn’t something you can shirk, you know.” My father said there’s one qualification to be a man. And that is owning your responsibility. Nothing else, know how you dress, know how you act. All that is what really makes a man a man,

– Great advice.

– Is taking your responsibility and owning it. And I think that drove me to want to do better for myself, for my daughter. I am married now and have two other additional children. So I’m very lucky to have three beautiful children.

– Fantastic.

– But that drive really did come from that. So there’s a concept of the crucible, right? And then there was the story during the Puritan age of taking an experience at high pressure, high heat, high stress, and taking those impurities inside of you and rising it to the top. And that’s usually the only way that we can really find who we are as individuals and people is by putting us in those high-pressure situations, putting us in situations that, you know, really make us work, but it takes those impurities out of us, and then make us a more better version of ourself. And I believe that experience did that for me. It made me more focused, more dedicated, and take more ownership of both myself and my career, my development.

– I think… See, that’s a wonderful story that the ideation that tests in life are not meant to destroy us, they are very much meant to… They’re opportunities to evolve, both as people to a much higher level. And that power rests within. I think a lot of that, certainly in the school system has never… I don’t think it’s taught that way. I don’t think that kind of responsibility is, it’s not taught. And I think sometimes then kids who are in those disadvantaged situations, they have all the talent and the skillset, but they don’t have the guidance on “How do I make it?” You had great parents that set a fantastic example, and showed you how responsibility works. We do a lot of work with disadvantaged school systems. We try, and cybersecurity is… Right now, we have a flip demand-supply curve. So it’s a great way for a young person starting out to look at it as an opportunity to get out of that situation that they find themselves in right now. But they oftentimes don’t have that mindset, and that-

– So I think there’s some interesting… There’s one, how we come. Do we talk to people about what is possible, right? So in the trailer park and in the south, there was this crab effect, right? There’s this whole thing, like my momma’s family, she’s from Nagaland. And when I was a really young child, we used to go on the value and good preps, and he takes the meat, pull them up and you put them in a bucket, and-

– That’s gotta taste fantastic, by the way.

– Yeah, my mom was cooking great. But the crowds would pull each other down and keep them all in the bucket. And I actually had a conversation when I first joined the Air Force, I was stationed and Langley Air Force Base in Hampton, Virginia. And I did Big Brother Big Sister. And there was some children that I was working with in Section 8 Housing. And there was a conversation like, “Well, how can you really relate to me? Like we have such different backgrounds. You know, you, South Alabama. I’m here from Virginia.” You know, there was discussions about race, discussion of background, all of these things. And you all think, look, it’s like the mentality, the struggles, I think absolutely, there are struggles that you have that I’ve never had. And that I can’t relate to as well, but I can share how the struggles and the relations of the challenge is. And if I’m not an example, kind of, here’s how I did it. Take it as just a one, it’s one voice. And if what I did, that doesn’t work for you, look for something else, but know that there are pathways to better yourself, to better your situation. I have been very grateful and lucky. I’ve had a lot of people come out and say, “Hey, I see something in you. I’m gonna spend a little time, I’m gonna share some guidance. I’m gonna share some words of wisdom.” Gave me a chance, and there’ve been many opportunities that I had failed, and I had fallen down. But I think throughout my life, I’ve been very grateful to have a lot of people come and say, you know, “I see something in you, I think there’s potential.” And I think for kids to say, “Hey, someone sees that in me.” Instead of just being like, “Oh, you’re the trailer park trash,” go get a… You know, you’re gonna just do this manual job. You’re in this bucket. And I think for kids being able to see that like, “Hey, if you let someone else tell the story, you’re supporting character in your own novel,” right? So you have to be able to take kinda that more on yourself. But I think if people don’t know that they can do that, or feel like it’s so daunting, it’s steps, it’s minor steps. But you know, again, I’ve been very grateful and very lucky for kinda the opportunities I’ve had, and I’ve tried to maximize them. Sometimes I did, sometimes I didn’t, but it’s continuous of being… Something else is, and I have conversations with young men, primarily for, you know, mentoring, I can share my experiences of saying life is not a race, it’s a marathon, right? It’s not a sprint, you’re not going. And it’s not the distance, it’s the competition. A marathon runner is not competing, unless you’re like the top three, like you’re the Bezos-

– Yeah, if you’re running a consistent four-minute mile for 26 miles, well-

– Yeah, but you’re not. For most people who do a marathon, isn’t trying to rank with other people.

– I agree.

– Their biggest competition is themselves. All of these people who are running, but the person that they’re competing against is not a guy or a woman beside them, but themselves. And I think changing that mentality. I do think there’s a… You know I don’t wanna be generalize them, right? But like, “Oh, kids, two days.” But I do think with social media, I do think this idea of, “Oh, my life isn’t as good as this person on Facebook or Instagram,” or what have you, instead of focusing on like, someone else’s life is their life. And you’re not always gonna see what their life is, and the values of somebody and what they think is, has it, you know, that’s like trying to wear your dad’s suit. It’s not really gonna fit for you. But taking your own life and in running that marathon of being, what do you want out of your life? How are you trying to build and grow from there? I think is really important. And I think a lot of times we talk about doing comparison, keeping up the Joneses, but like, what’s going to make you happy. Is it more time with your wife and kids? Is it in a life of adventure? Is it having an impressive title? And none of those are better than the other. It’s just, what is it, you as an individual? What is your primary goal and driver? And in understanding that, and then pursuing that. And I think that for me, having that hunger is a constant reminder, is I am not better than anyone in this world, but I am better than the man I was yesterday, or at least I attempt to be. And I think that drive is internal.

– It is, and the only thing I would say is that maybe you have to have a little bit of an environment that can catalyze that thought process, right? If you grow up in a household where the child is abused, or they’re constantly exposed to drug use, they may never have the chance. They just may never have the chance, because what you described that journey from. So in the roles of life, one role that a lot of people love to play as the victim. ‘Cause it’s the easiest role in the cast, right? You’re not responsible for anything, whatever happened, happened to you. You had no control over it, and always me, right? That kinda becomes their mantra. It’s the way it is. But to become your own hero, you have to take responsibility. And then, you have to realize exactly that you are your own person, and you have an extraordinary skillset that other people may not, and you have to discover what that is and then go for it. The titles don’t matter. You know, the job won’t matter, if you can do, if you are passionate about it, I think you will be successful. I’ve never seen a case where someone’s been really passionate about something that they engage in, and they don’t reap some rewards for that extraordinary effort resulting from their passion that was put forward.

– And you know, I would agree with that to a point, right? One, everybody has different journeys, right? Everybody has different struggles. And to compare myself to even someone who seem economic situations, but as you mentioned, you know, didn’t have supportive parents or there was the drug issues, or having racial inequalities that get added on to it, right? Or even women in IT, right? From the opportunities that are opened up for me, right? There were struggles that I had. And then there was a lot of opportunities that I had. And you know, the exception doesn’t make the rule, right? Just because I’ve been successful from my background doesn’t mean that everyone’s gonna be successful. But I think to your point is, okay, but that’s just this generic version of successful. I think everybody can take on some level, if it’s a title or something like that, there’s gonna be struggles, and you might have to work harder than this other person right beside you, even though you came, you have a similar background. But I do think that you can be your own hero. You’re gonna have struggles. Everybody has, and some people are gonna have a lot more struggles than I’ve ever faced. There’s people who have, there’s Dr. Kim, who, you know, I think of, who was the Navy SEAL, the doctor, and is now an astronaut, right? Who’s just been like phenomenal. If I try to compare any of my successes to him, you know, he went to Harvard-

– Any of us, yeah.

– You know-

– Mere mortals.

– Yeah, and I think sometimes we get into that, right? We look at that, and we look at our struggles, and then compare with your peers. I love having conversations with my peers and kind of checking in, like, “Hey, how are you doing?” And their successes. There’s a couple of guys I work with that are CISOs of, you know, small and medium-sized organizations, and even large ones, and have had phenomenal careers. And I look at that, I’m like, “That’s awesome.” And it motivates me to do what I wanna do. But my success in my career path is all gonna be on what I put into it. And I don’t ever want someone else to look at their career path and be like, “Well, it’s not as good as Rob, either at this time or what have you,” but I’m just a reference. I am not your judge, I’m not your… Or no one like me. And so I think having that internal, like, what do you want? What are you going for? And you might have more struggles than me or the next person, but just, it doesn’t matter. He’s gotta keep churning through it. And I think if you have that mentality, some version of success, as you defined it, you will find.

– Let me change direction just a little bit here then, and ask you, do you think that to be very successful in the field of cybersecurity, you have to follow a traditional path of education, high school, college, master’s, become computer scientist?

– Absolutely not, with a caveat. So I got out of the Air Force and I didn’t have a bachelor’s degree, right? I was very successful, I had training, I had certificates, and I had a clearance. So there was a job that I was able to take that somebody who had a master’s of science was there. But that was as for group, my pay scale and kind of the job title I could do without having at least a bachelor’s. So I went to school full-time, but it was doing about 18 credit hours a semester while working full-time to finish my bachelor’s. And then, I went straight into my master’s at UVA. And then even now, I’m now finishing MBA at University of Florida, because I wanna be an executive in cybersecurity, to speak where I think for the C-level, has to be speaking as peers. I want it to be able to understand the business, the financial impact, the strategic, all of that. Now, that’s the direction that I wanted to be in my career. Those things that, maybe the formal education process might not be a requirement, some organizations it is, but I felt it would better serve me for that. But if you’re somebody who wants to be in incident response or you know, reverse malware, or one of our best guys on my team doesn’t have his bachelor’s degree, but he is wicked smart. He knows, he has OSCP, OSCE, like he has the certificate. He is just a phenomenally big-headed brain guy who understands incident response, can just crawl a network. And when he talks, I shut up and everyone else does as well. So my education doesn’t mean anything from the diplomas or whatever I have. When this guy speaks about a problem, I wanna understand it, because he understands it. So depending on where, how you wanna take cybersecurity, there is a lot of different avenues for cybersecurity. If you wanna be more of the offensive or kinda pentesting or you know, incident response, you can have a lot more leadway on your education and you know, getting in your hands. If you want to be DevSecOps, where you’re creating better code or helping people create better code, having more of an experience, actually having code that you can develop is more beneficial, but depending on where you wanna take your career, depending on the industries that you wanna join, there may or may not be more check mark type requirements for. It gets you past the recruiter. But I do think myself and my peers, we have, as we become in more leadership positions, and we talked about hiring, there has been an honest conversation about what actually does a degree bring to you? Some places, yes, absolutely, the degree is important for certain positions, titles, what have you. But a lot of times it’s having a willingness to show that you have a passion for this. You can show you have a familiarity with either how code is combined, IT infrastructure, the tools such as if we want an analyst position, you know how to do that. And I think that’s growing more and more, but again, there is a caveat that certain industries, or even certain companies might have that just because they’re in that mentality. So having the degrees aren’t gonna hurt you. And they might give you something to differentiate you, yourselves, but I wouldn’t say like, if you don’t have a degree, you’d be like, “Oh, I can’t do cybersecurity.” That might be a hurdle that you either have to have additional years of experience, or maybe that company is just, that’s gonna be their hangup. And then you had to go from a different company, unless you have that.

– Sure, but I think, you know, shattering that myth is really important, because we’ve seen it. I mean, some of our best engineers don’t have a college degree, and they’re brilliant. They know the topic inside out, and I would put them up against any one of their peers in the industry. The experience that they’ve had.

– I follow a lot of people on Twitter and some of these men and women are just, I’m just like, feel like I’m drooling over myself. I’m like, “Okay, what are you talking about? Securing Kubernetes?” They’re like… And they don’t, and they just go like, “Oh, I don’t have a degree, I taught myself how to do this.” And you’re like, “I’m not smarter than that person.” You’re like, “I just have a degree, doesn’t make me better.” I do think that is a mentality that’s having to change. But just with the understanding that I don’t think you need a degree to get into the field, but just because I personally don’t think you need it, that doesn’t mean that, that can’t be a hang-up. Especially if there’s a specific company you wanna work for-

– sure, there’s gonna be certain companies, like, if you’re going for the big four consulting firms, you might have a problem, right? Or if you’re going into management consulting, you might have some issues there.

– And again, if you wanna have like management of cybersecurity, right? The personnel, people, the resources, there’s gonna be an expectation if you have a college education-

– That’s right

– Do you have a higher level college? You know, you have some type of master’s, not required, but you know, there’s more and more expectation, especially as the CISO becomes more of a C-level peer. And some of that pedigree might be expected for that position. But Twitter, Netflix, all right? Some of these organizations that are doing phenomenal. I’m sure that they’re not like, “Yeah, this is the person we want, because they’re the most qualified, not because they went to this MBA program.”

– That’s right, that’s been a personal mission of mine, get people educated, quote, unquote, no pun intended there on this topic, that if you have the desire, the passion, and the talent, don’t let that lack of a degree stop you from pursuing it. Let me ask you this as well. Being an Air Force veteran, we work with an organization called the Seven Eagles Group. ‘Cause we have a lot of veterans inside of our company, and we try and do our best to support the veterans and their transitions from military to civilian life. What we have heard is that it is not easy for veterans to find jobs in the civilian world. Was that your experience or not?

– So I was very fortunate, in the Air Force out of all the branches, their job descriptions, how do they describe is more of a civilian equivalent, especially if you have an IT background. First and foremost, getting out of the military is the scariest thing you’ll ever do. I’ve been shot at, I’ve had bombs blow up around me. Getting out of the Air Force was scarier than any of that.

– Really?

– Yeah, because it’s like the safety blanket, right, you’re in it. Yeah, you’re gonna go through the sack. There’s times when you just like, “Ah, I don’t really like this,” but you have your pay. You’re not gonna get fired, right? Unless your gross negligence. There was a stability on expectation of how you get, like all the things laid out. You’re not allowed to put in Brian, next duty assignment. I’m not giving a resume and getting shot down, right? For multiple companies. You don’t deal with that. And so when you’re transitioning, first and foremost, if you have something that isn’t a one for one, it’s hard to show like, “Hey, I got some really valuable insight experience,” what have you. And there is almost like a a different language between vets and civilians, right? How we describe, so we get into acronyms, and there’s almost a lexicon for all these different things. And when that transition, it’s how do I get, I have to change my mindset that I’m no longer in the military. The military doesn’t matter. You know, I had those experiences. Now I need to convert them to what the civilian sector is looking for. And so much, so that’s not even just the sector, it’s the industry that you’re at. And so first and foremost, I think there has been a concentrated effort, and one that needs to grow about working with vets and saying, what is it you want to do? What have you done? Let’s use a translation service and putting it to where you’re not getting automatically filtered out by HR systems or HR personnel, because we didn’t use the right word. So we didn’t use right phrasing. That’s expected for this particular industry. Also, there’s other-

– And that’s a key point though. I do wanna say, there’s a lot of automated systems, and we’ve seen it like when we’ve taken on vets and then built up their resumes, and a year later, they move on, they move on to some extraordinary organizations that wouldn’t pay them the time of day. And a lot of it was what you’re just describing that they’re not using the right language. The translation is missing. I would like to believe that a little bit of experience helped too, but-

– You know, so if I’m trying to go in financial industry, right? If I try to go into hospitality, I have a very strong DOD, Intelligence Community, US government, and aerospace and defense. Those I can talk the term, the expectation, the pain points, all of those I can go in detail. If I wanted to transition into manufacturing, online retail, FinTech, there is going to be an exposure. And I had to change how I look at the problem sets and how it changed my language. And sometimes as military members, we have to break our mind out of that, that this is the military. It’s the way we have to communicate how that particular industry communicates to that. So even though, if you were doing something similar in the military, you’re in a new industry, so you have to change, you have to define and how you describe what you did, taking the same lessons. Like the military does a really good job of “Tell me the thing you did. You know, what was the impact? Or what was the result? And what was the impact of that?” But putting that in terms and figures that that particular industry cares about, I think is something we don’t serve or transitioning members very well with. And that’s something just getting into that mentality. There’s also, I’m hoping it’s changing, but there was some concept of PTSD and potentially military members being too rigorous and not being able to conform and transition to a civilian workforce or for that area, which is funny because most of us got moved into all these different groups, where you have to go and relearn. You have to be moldable. The military is like, “I want you to do X, Y, and Z.” And then, next week, they be like, “You’re doing something completely different.” So there is already a-

– But they’re providing you a detailed playbook on how to do it, right? Often in the civilian world, you don’t have that.

– Sometimes, yes, absolutely. Sometimes you have technical orders or you know, processes, procedures. So the military was all AFIs, Air Force instructions. Even how you dressed yourself. But there’s a difference between, I would say, like I used to make a joke that the difference between a consultant and a contractor is you pay a contractor to provide you answers, you pay a consultant to provide you questions. And as the transition, right? Like, “Okay, here’s what we supposed to do.” But if I’m a mid or senior enlisted personnel, right? Yes, the order came and do this. How that gets implemented, why that gets implemented in a certain way. Is there any changes that need to be done? These are strengths that military members can bring to the table, yes, we are used to standard, structure, and trying to bring that standard and structure. But if you go into a battlefield, if you go to Iraq. Not anymore, but you know, form that mentality is like, yeah, and that has to break because, you know, the plan meeting first contact with the enemy, right? Not surviving is a thing. And so having that flexibility of thought. Now there is some things about, well, this is what the TO says, and this is what the procedures say. And it is, gets a safety blanket, but you take that away, the benefits that kind of the military culture can bring to it. And a service member who’s transitioning, you can just understand that and understand that from the view of not, “Oh, this is what I did, but this is what they need. And how do I communicate what I’m good at or what I’ve learned,” to be able to apply from that. And I think if we can do better for our service members for that, the numbers would be better. Obviously, there’s issues with, if you were infantry, I’m trying to be in cybersecurity, right? There’s the technical skills shortage, but man, there’s Cybrary, there is members like myself, anyone who’s seen this, who have questions about this, please reach out, that can say, “Hey, go do these online trainings. Go do these awareness.” If you like, there are truckers that I follow that when they stop at rest stops, they’re practicing code and they’re learning Java and all of this, I’m like, “Man, it’s…” Daniel Hawthorne who wrote The Scarlet Letter, was very famous for quoting, “Any man can educate himself. Most just lack the discipline to do so.” Those technical skills, we can build, we can share. And those things that made you great in the military are easily transferable. If they know how to communicate, how that can be transferable, and/or willing to have the constructive criticism on, “Hey, communication is gotta change.” The expectations are gonna be changed, but-

– And you know, also, one of our-

– Sorry-

– No, no, no, no, no, no, I’m interrupting you actually. I probably shouldn’t. But one of the founders of Dark Rhino Security, a gentleman by the name of Tyler Smith, he spent a lot of time in Afghanistan in the infantry. And what you were describing there, you know, that from infantry man to founder of a cybersecurity company. It was a interesting journey-

– Understands threat, understands risks, and how to prioritize, how to lead people. Again, there is a lot of skillsets. It’s just, usually, we get hung up on the technical. Either you didn’t change, check this box or what have you, but that can be learned if you show willingness.

– You’re right, I mean, oftentimes, as an employer, when we’re looking for people, and I’m gonna pick on sales, because that’s been my background, okay? So I’m just gonna pick on that for a second. I don’t want to… I can teach someone how to sell, but I can’t teach someone how to be personable, right? So it’s a personality. If you have that, I’m looking for an outlook in life, in your approach, in dealing with people, your ability to empathize with people, to understand people, to listen, all those soft skills, your ability to write. I would say one of the great, if you want a great job, know the English language amazingly well. That would be requirement number one, can you write and complete sentences that make sense? If you can be articulate, and you have that mindset, then I can teach you the rest. I can teach you the technology, I can tell you what we sell. I can tell you where it matters, where it doesn’t matter. All those things can be taught. But I can’t teach you the human element of it.

– So that’s interesting, ’cause I actually do follow a number of sales personas online. I’m a guy who usually gets hit up like 30 to 50 emails a day. I get at least five to 10 cold calls a day. But I follow this because there’s a partnership. Technologists can survive without sales, and sales can’t survive without technologists. We need each other because, that your product might be able to augment myself or my team to meet either be more effective or efficient from a problem set, or address the complete green field. But that’s never a decision, I would be like, “You know what? I just had, you know, this random scripted email that you sent to me, yes, this is the thing.” It’s building the relationship. It’s, you know, not being salesy. All right, great, it’s, you know, just like all relationships, if you force it, it’s not gonna go. But I do agree, I think there are some salespeople that I’ve had really beneficial, to get to know either on LinkedIn from a virtual, or just in personal. And just kind of the understanding of being like it’s not about a quarter, it’s not about like, “Hey, downloaded all this information, and you should know.” But it’s a partnership for, “Hey, here’s a difficult decision, and can I help you and lead this?” And I honestly believe that my product or whatever is best. I’ve never been in a sales job. You know, other than skids, like, I hear stories of Mitt Romney, and talking about how he’s been a Mormon, and going to door-to-door and hearing the rejection, and being kind of having that personal connection of how that helped him be a better businessman better salesman, ’cause it’s kind of understanding what you are offering. Understanding rejection is kind of part of it, and building that personality can reach out, things like just you have that. And as you worry, you know, it’s funny. I think cybersecurity is the same way, is that I can give you the skills, but if you’re not curious, if you’re not wanting to make stuff better, if you wanna do status quo, this is not a status quo industry.

– That’s right, not at all. And I think sale’s the same way. I feel that this industry is like, you jump into a river that’s going downstream. If you don’t keep swimming, you just have to keep swimming just to stay where you are. And you have to put in a significant amount of effort to go upstream. And if you’re not willing to put in that effort, you’re not willing to constantly be learning, constantly have the humility that you could be wrong. There is no quote-unquote wise man on the hill in cybersecurity, because the domain keeps changing. And the technology.

– Second by second, yeah.

– Absolutely, so if you don’t want to do that, which there were some industries you don’t have to have that, right? Then don’t get in it, because you’re gonna get burned out really quickly, and you’re gonna get pushed out. I get mad, again, I hear the same thing from sales, having that same thing, like, “Look, it is just a constant grind.” But I feel like cybersecurity is rewarding is that if you have the drive, you have the curiosity, there is something about just getting it right. That it’s the most rewarding I’ve ever had in my field. I love my job, I love what I do. You know, I do work some crazy hours sometimes. I do have some challenging problems, where I’m just like, “Man, I just need to recharge.” But I love what I do, ’cause I feel like I’m providing value. There’s a mission I can support. I have a team of people that I work with, that I learned from, and I grow from. My peers also in the industry as well are so much smarter than me. And so it’s always kinda passing information back and forth. And even though there’s that constant challenges, constant growth, but you having that is the most rewarding thing I could ever do. Even if I was like a Wall Street broker and just making, you know, 10 times the amount of money I was making right now, I don’t think I’d be as satisfied as working what I’m doing right now for the challenge. And just the personal success that I feel that I have in this.

– Oh, keeps the sense of wonder alive.

– Absolutely, you know, it’s a whole, stored in a stone where Merlin goes and says the only thing that you can look forward to in life is that there’s always something for you to learn. And I think that’s a very relevant and it’s driven me in my own career. I could be perfectly honest, 10 years ago, I didn’t think this what I was gonna be doing. Five years ago, you know, I didn’t know this industry. And as I grow, as I learn, as I take advantage of opportunities as they come to me, and if I can pass on any words of wisdom, it’s, I believe I’ve had the success or the whatever success that I’ve had in my career and what I’ve been able to do, is because I never let my past expectations shackle me to a path. Sometimes we start off and says, “I have to do X, Y, and Z. And if I don’t do that, then either I’m a failure, or that’s not the right path.” Having a North Star, having a goal, having a desire is fantastic. But if you want to progress, if you want to grow, if you want to be fulfilled, you as an individual, is gonna change throughout your life, whether you’re 20-years-old or 40-years-old. The things that are important to you changes. They might stay the same. But being able to check in with yourself, with your peers, with your family and having the flexibility of saying, “Well, you know what, maybe this isn’t exactly what I thought I wanted to do, but I’m gonna try it. I’m gonna have the courage to step out and grow.” ‘Cause growth is never a linear path, right? It’s messy, it’s all these things. But if you can have that, I feel that your personal satisfaction with where you are isn’t gonna be artificial. It isn’t gonna be about the Joneses. It’s gonna be about like you as an individual, what makes yourself… Obviously, you know keep your true North Star. I look at my career, and as of right now, where I wanna progress is I eventually want to be a CISO of a large international organization, having a seat at the table, having the ownership of that mission space, because it is something, and that is my true north, but I look at my-

– And we have no doubt that you’re gonna be there sooner than later. And then you’re gonna have to come back, and I wanna know, did you want this? Is it as good as you thought it was gonna be?

– You know, I’ve had people ask me like, “Why?” But I’ve had some really great my own boss, Michael Higgins, who I work for now at L3Harris. This is over the last eight to nine years. It’s been a wealth of knowledge for me. And there’s been opportunities to take on things that I didn’t think I really wanted to do, but I’ve done that for working on the Presidential Task Force that I had the opportunity to work on, to taking an opportunity, coming down to Florida to work for an aerospace defense contractor. To, you know, taking the green doors, I mean. Like any of what is being is don’t let your path block you into a box, and it’s real easy. And just having kind of that humility and flexibility is like if you have a great opportunity, go for it. And the other thing is never wait for the opportunity to prepare for the opportunity. If you wait to say, “Okay, I’m gonna do this. And then I’m gonna change jobs in three to five years.” And then you wait till like the four years, you know, to just prepare for that opportunity. If you do that, it might be too late. Because when an opportunity comes, it comes. And if you’re constantly waiting for the opportunity to come before you prepare, then it’s already too late. And I see that for kids for the curiosity and where you wanna grow is… Because if you’re saying, “Hey, I’ve done this.” Maybe you’re not quite ready, ready, but you doing that preparing, sets you up that you can learn on your feet. Whereas if you just wait, opportunity comes, and you’re trying to do a learning curve and prepare for that as well as do the job, then either you’re not gonna feel confident to take it, or you’re gonna be setting yourself up for success. I mean, setting yourself up for failure.

– And on that note, one, we’re actually coming up right on the hour here. So we wanna be cautious of that. This has been a wonderful discussion, but what you just stated that you might not take the job. I’ve seen a lot of people do that. They shouldn’t, I think you know what? Don’t be afraid. Take the job that you might be least comfortable with. If that is the direction which your compass is taking you, don’t wait for it. If that opportunity comes, go for it, and-

– I actually had, oh, sorry.

– Go ahead, go ahead, yeah, you, go ahead.

– I actually had one of my mentors speak to me. You know, it was about kind of growth area and comfort levels. And I joked and so I was like, “No, no, no, I wanna do X, Y, and Z,” and he’s like, “Why would you say no before?” I’m Like, “You don’t know if this is, you know, like it’s not guaranteed to you, so why would you shut it down before you even have the conversation? Why don’t you shut down to even fail?” And so and I joked, I was like, “Man, you know, I usually tell other people that same advice, and then I’ve gotten burned by it myself. And even for this opportunity here.” I was like, “How would I feel? I feel this is like, I’m truly what they need for this position.” It’s really exciting. You know, I think it’s what I wanna do, but I can see all the areas where I’m lacking, or I’m not, you know, the imposter syndrome. We can’t go and talk on a cybersecurity without talking about imposter syndrome. Comes into place, and it says, you know, “No, no, no, you’re not ready yet, be prepared. And if you fail, you fail,” right? But if someone’s talking to you and showing interest in you, then you have at least something that they think is worth enough that the other things they can get through. You’re going to fail in your career, but don’t allow yourself to shut down your own success before you even attempt it. And I think I completely agree with that. I think it’s very prevalent, especially for a younger side of us. Actually younger and then the older, because then we started getting into a comfort level, and I know people who started their career in cybersecurity in their 40s and are phenomenal now. So just take that chance, worst case you fail. But you can learn from that, and you constantly move forward. Fail forward, just keep moving. And you’ll be just blown out of the way, based off my own experience of what you can achieve when you just keep moving forward.

– That is a great note to end this segment on. And when we come back for part two, everyone who’s listening, stay tuned ’cause we’re gonna get into some really interesting cybersecurity topics. But Rob, thank you so much for providing these insights. And I hope to everyone that’s listening, there is some inspiration, and you can find the passion in yourself to pursue what you really want. Thank you.

– Thanks, the water is warm, jump on it.

– Yeah, that’s exactly right. Thank you, Rob.

– Thank you.

– Thank you.

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