Jesse Davis: From Sleeping in His Car to Rebuilding Cybersecurity Careers — AI-Era Job Readiness, Certifications & Resilience | Be Yourself Podcast
Be Yourself Podcast

JesseDavis

Cybersecurity Professional, Educator & Founder of Cyber RST and Ambition Atlas — on Becoming Job-Ready in Cybersecurity, Why Certifications Alone Don't Get You Hired, the Rise of AI-Powered Hacking, and Rebuilding a Career From Rock Bottom

26 minutes
Cybersecurity · Career Transitions · AI & Cyber Threats · Resilience · Veteran Workforce · Cyber RST
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About This Episode

How to Become Job-Ready in Cybersecurity: Jesse Davis on Why Certifications Aren't Enough, the Rise of AI-Powered Hacking, and Rebuilding a Career After Sleeping in His Car

Jesse Davis didn't take a straight road into cybersecurity — he took one through real setbacks, including a stretch of his life spent sleeping in his car. That low point became the foundation for everything he does now as a cybersecurity professional, educator, and the founder of Cyber RST and Ambition Atlas, organizations built to turn people's potential into real, job-ready cybersecurity careers.

In this episode of the Be Yourself Podcast, Jesse makes the case that cybersecurity itself is, at its core, surprisingly simple — but the cost of ignoring it is anything but small. He breaks down what hiring managers and educators consistently get wrong about preparing people for cyber careers, why a stack of certifications and degrees often isn't enough without real hands-on experience, and what it actually takes to get hired in an industry being reshaped by AI.

He also goes deep on the rise of AI-powered hacking and what it means for defenders, and closes with a candid conversation about resilience, empathy, and unity — the human qualities he believes the next generation of the cyber workforce will need most, regardless of how fast the tools around them keep changing.

01
Why cybersecurity is simple in principle — and incredibly costly when ignored
Jesse opens with the core paradox of his field: the fundamentals of cybersecurity aren't complicated, but the price organizations and individuals pay for overlooking them can be massive.
02
Jesse's background and what's shaping the new generation of the cyber workforce
How Jesse found his way into cybersecurity, and what he's seeing in the people now entering the field — and what they need that previous generations didn't.
03
Sleeping in his car — the low points that shaped Jesse's mission
A candid look at Jesse's hardest moments, including a period of sleeping in his car, and how that experience became the starting point for everything he builds today.
04
From rock bottom to founder — building Cyber RST and Ambition Atlas
How persistence after setbacks led Jesse to start his own ventures, and what's still missing in how the industry develops its cybersecurity workforce.
05
Do certifications actually get you hired? The truth about degrees, certs, and hands-on work
Jesse breaks down why certifications and degrees alone often fall short, and what employers are really looking for when they hire into cybersecurity roles.
06
Getting hired in the AI era, the rise of AI-powered hacking, and why resilience, empathy & unity matter
What it takes to land a cybersecurity job as AI reshapes hiring and attacks alike, and the human qualities — resilience, empathy, and unity — Jesse believes will matter most going forward.

About the Guest

Jesse Davis — Cybersecurity Professional, Educator & Founder of Cyber RST and Ambition Atlas

Jesse Davis is a cybersecurity professional and educator whose path into the industry was anything but smooth. He's been candid about hitting real low points along the way — including a stretch of sleeping in his car — before turning persistence and hands-on learning into a career built around helping others avoid the same struggle.

He is the founder of Cyber RST, a training and career-transition program focused on turning certifications and classroom knowledge into real, job-ready cybersecurity skills, and Ambition Atlas, where he continues his work as an educator and advocate for people rebuilding their careers from the ground up.

Jesse is known for his straight-talk take on what's broken in cyber workforce development — from hiring practices to education — and for helping people prepare for a job market being reshaped in real time by AI, on both the defensive and offensive sides of cybersecurity.

His Path
From real setbacks — including sleeping in his car — to becoming a cybersecurity professional, educator, and founder of Cyber RST and Ambition Atlas.
What He Does Now
Runs Cyber RST and Ambition Atlas, helping people become genuinely job-ready in cybersecurity through hands-on training and honest, practical career guidance.
On Certifications & Hiring
Jesse's core message: certifications and degrees matter, but they're not enough on their own — real hands-on experience is what actually gets people hired.
On AI & Cybersecurity
Speaks openly about the rise of AI-powered hacking and what it takes to get hired and stay resilient in a cybersecurity industry being reshaped by AI.

Key Quotes

“

I have failed multiple times in my life. I've slept in my car more than once in my life. I've had failed relationships. I've been fired successfully from jobs. I've been laid off. It took me 1,400 tries to get the current job I have now — 1,400 tries just on LinkedIn.

Jesse Davis
“

Nobody wants to give me seed funding and I'm still trying to find it. Hey, 100 nos and one yes is still yes.

Jesse Davis
“

You either grab life by the horns, or it's going to grab you by the horns, and it's not going to be pretty. It's just how I view it.

Jesse Davis

Episode Chapters

0:00 Teaser & Intro 1:43 Importance of Cybersecurity 3:15 Jesse's Background 3:56 New Generation of Cyber Workforce 5:41 Low Points in Life 6:59 Entrepreneurial Start 10:32 What's Missing in Cyber Workforce Development 12:26 Do Certifications Actually Get You Hired? 14:50 Getting Hired in the AI Era 18:51 The Rise of AI-Powered Hacking 20:27 Resilience, Empathy & Unity 24:13 Final Words

Full Transcript

BTW: This episode of the Be Yourself Podcast is produced by Beverly Media. Also on the show:
Richard Moore — From 80-Hour Burnout to a Million-Dollar Coaching Business →
0:00 Teaser & Intro
Sergey When did you decide to become an entrepreneur, to work for yourself?
Jesse I have failed multiple times in my life. I've slept in my car more than once in my life. I've had failed relationships. I've been fired successfully from jobs. I've been laid off. It took me 1,400 tries to get the current job I have now doing it. Let me repeat that one more time. 1,400 tries just on LinkedIn.
Sergey So, what do you think is overlooked, or a missing piece, as far as creating the workforce that can and will change the world for the better?
Jesse I got one thing that could really change the workforce.
Sergey Hello everyone. Welcome to the Be Yourself podcast, the podcast on expressing our true selves. Today I'm joined by Jesse Davis, who's a cybersecurity professional and educator, and owner of two companies, Cyber RST and Ambition Atlas. He's helping students grow and develop their career in the mentioned field. So Jesse, welcome to the show.
Jesse Thank you.
Sergey How's life back there in Florida, in sunny Florida?
Jesse No, it's not bad. You know, weather's nice today, so good — 65, 70 degrees. I can deal with that.
Sergey Okay, cool.
Jesse Not too cold, not too hot.
Sergey Sweet. Well, we have a snowy, snowy January here in Ukraine. So, quite, quite opposite.
Jesse Yeah.
Sergey So Jesse, for my viewers who are not conversant with the term cybersecurity, can you brief us a little bit about the importance of cybersecurity and your involvement in the area?
1:43 Importance of Cybersecurity
Jesse So cybersecurity is used in everything now. You don't live without it, and you just don't realize it's there, right? The basics of keeping your information, your personal information, are vital, right? But think about this — it's so vital that people are willing and allowing mistakes to be made. Companies are allowing mistakes to be made that are costing millions, if not billions of dollars, every single day. Cybersecurity is so complex, but yet so basic, right? And if people would think about it like that, it's the very basic things you need to do. Change your password every once in a while. Don't leave things laying around, you know, like personal information. Just very simple things that people don't think about. Don't put too much of yourself out on the internet, but people still do anyways, right?
Sergey It's not hard to become somebody.
Jesse No, it's really not. Technically speaking, you can become somebody on the internet. Those are just about like a flick of a finger, right? So, cybersecurity is protecting oneself, or protecting a business, to keep things moving. And people are always wanting an easy buck. You don't have to throw on some pantyhose or leather hosen to rob a bank. All you got to do is flick a keyboard, right? That's how quick and easy it is. It doesn't take much.
3:15 Jesse's Background
Sergey And you decided to devote your entire life to this field. Is that a fair statement?
Jesse Yeah, as of late I have. I really want to fix the workforce development piece of it. I got into cybersecurity at a later age. I've got a very diverse background, should we say. I've worked construction. I've worked McDonald's, delivered pizzas.
Sergey Yeah.
Jesse Starbucks on the weekends right now to pay for my dream job, right? For my business, which is my dream, you know. I teach college as well, and then I'm still part-time military. I'm about to retire from that next year. But it's been 20 years in the military. Done a different array of jobs there as well.
3:56 New Generation of Cyber Workforce
Sergey So, how do you help — to create, as you say on LinkedIn — a new generation of cyber workforce? How do you do that?
Jesse Well, it's just like any other traditional career route, shall we say, back in the day. I'll say back in the day, in the 1500s, 1600s, 1700s, if you wanted a job, a career, what did you do? You went to a stonemason, you learned what a stonemason did, or a blacksmith, right? It was a trade. You learned right there from that person, who they would call a master blacksmith, right? You were learning what they were doing. So many industries — the medical field, being a mechanic, being a welder, pick something — they have a mentorship program. Somebody's going through school, yes, and they're learning the theoretical, but they're also learning a hands-on piece, and they have a mentor guiding them. Somebody that already knows the craft. They're teaching them how to do it. So, what I'm trying to do is bring in a mentorship program with a residency program. So, yes, they're going to be learning the theoretical from a book, but I want them to learn hands-on from my company, as well as a residency program at a company that we will partner with, where they're learning the theoretical aspect with us, the hands-on piece from us, but they're also going to a company and they're going to get a mentor, and they're going to learn what that company's about and what you need to do for cybersecurity, particularly for that company. That's how I'm trying to change it.
Sergey Cool. And you answered some of my questions that I sent you prior to this conversation, and it strikes me that, not once but a few times in your life, you had really, really low points. Is that fair to say?
5:41 Low Points in Life
Jesse Yeah. Yeah, that's — yeah, that's very fair.
Sergey Yeah.
Jesse I have failed multiple times in my life. I've slept in my car more than once in my life. I've had to stay with family at points, you know. I've had failed relationships. I've been fired successfully from jobs, very successfully, right? I've been laid off, right? I got fired, right? And I deserved those firings. And yeah, I've had some very low points in my life.
Sergey That's — I mean, if you're going to try anything, you're going to fail at some point. Failure is a part of the game.
Jesse Right now, this is one of the toughest things I've done in a certain aspect. I mean, I'm not giving up my home. I'm not into a bunch of debt for this business, but I've been told no multiple, multiple times already. They say, "Yeah, you got a great idea, but it's just not worth it." Or, "Ah, it's not going to work." Nobody wants to give me seed funding and I'm still trying to find it. Hey, 100 nos and one yes is still yes.
6:59 Entrepreneurial Start
Sergey So, when did you decide to become an entrepreneur, to work for yourself? At what point, and what triggered this decision?
Jesse I was going to say after — I spent, I lost my government job in April of last year, and with everything that's going on within the government, the cutbacks and everything else, I was like, man, I should be able to hopefully find another job. But it was hard to even get a job within cybersecurity. And it took me 1,400 tries to get the current job I have now doing it.
Sergey And that's not cyber, right?
Jesse 1,400 tries to get that job. But I didn't give up. Let me repeat that one more time — 1,400 tries just on LinkedIn. That doesn't include ZipRecruiter, Glassdoor.
Sergey Did you reach out to decision makers? What do you qualify as an attempt here — to get to the business?
Jesse Oh, a business — so you tried 1,400 times for different businesses to get my current job. My business came and stemmed from — I was tired of seeing people without a job, right? I'm tired of seeing people without a job. They've done exactly what the industry's asked them to do. Get a degree, get a certification, you'll have a job, right? They got their cybersecurity certifications. I've seen people with 5, 10, 15 certifications still not able to get a job. So, what stemmed from that — at first I was going to do a certification business, and I saw how flooded the market is with that. People are charging two, three, four, $5,000 for a simple certification, right?
Sergey Mhm.
Jesse Not really simple, but simplistic, in the sense you're just teaching from a book. You're having them study for a test. They take that test, and then they get the certification. The problem with the American educational system is they're pumping out degrees still. It has not changed, and you're not able to get a job. You're not able to get a career, right? And it pissed me off, straight up. I was done with it. So I said, you know what is lacking? And I started doing my research, and I was looking at all the jobs I'd applied for. And every single one of them were literally saying, right in front of my face, one to three years of experience for an entry-level job. Human resources do not know what the hell they're talking about. They're just pumping out what they think the company wants. It's not necessarily human resources' fault, but they're part of the problem. You want a CISSP, which is Certified Information Systems Security Professional — you have to have between five and ten years of experience, and you have to have someone sponsor you for that certification. It's not an easy one to get. There's only thousands of people that hold it out of the, what, 7 billion people on the planet. It's not a very high number, right? It's not even 1% of the world's population, right? And I just had enough. I kind of snapped, and I said, you know what? It's time to create something new. So, I'm trying to bring three problems that are out there together to make a solution. Those three problems are a degree, a certification, and no hands-on. So, I said, they need hands-on. Let's get the degree — it's already there. And the certification is already there. But those three have to be brought together. Got to make an equilateral triangle — for those of us that didn't pass math, right, that means three equal sides. That's what makes an equilateral triangle. If you have one that's off, that's an isosceles, right? And I'm not an algebra expert — I failed algebra and took it multiple times. I just remember that because I had a really good teacher stuck in my head, and I wanted to make that equal-out triangle. I want to make the perfect triangle. What is going to make this fixed?
Sergey Cool. So, what do you think is an overlooked or missing piece, as far as creating the workforce that can and will change the world for the better?
10:32 What's Missing in Cyber Workforce Development
Jesse I feel one thing that could really change workforce development is that colleges and universities need to be held to a higher standard in the United States. They're not — they're degree notes. And I was $88,000 in student loan debt that I paid off, and I didn't have somebody else pay it off for me. I paid it off out of my own pocket, right? So when people say that it can't be done, it can be done. Is it hard? Yes. I scraped and scratched and I paid that off, right? But again, part of it was my own fault. A big chunk of it was actually my own fault — I didn't take school seriously. My dad warned me multiple times: get good grades, son, make sure you get a good ACT score, these things will help, these are things that will help you so you won't have to get into student loan debt. What did I do? I was a typical teenage male. Didn't take school seriously. My grades were low, and I bombed the ACT, which is your college entry exam. And I got $88,000 in student loan debt. I got a bachelor's in history that was useless. Went back to school for my MBA — that didn't do anything. I started it, and I found out at the time I hated the business theoretical side of it. And I feel that the American educational system — university system, the whole system — needs to have, if they want money, it needs to be tied to them actually producing something, and there should be careers, not just "hey, here's a piece of paper, good luck, you partied the last four years," right. There needs to be something more tied to it that really tests.
Sergey So with the certifications that you issue, or that you help people obtain — can people, with high probability, actually get a job?
12:26 Do Certifications Actually Get You Hired?
Jesse Yes, that is the plan, because the certifications are already in place. But again, the piece they're lacking — you can still get those certifications, these are already industry certifications. All I'm doing is partnering with the companies that have these, and getting them trained for the certification, but also bringing on what's used on a day-to-day basis for cybersecurity — cyber softwares that are out there. Not just the simple "hey, I want to try HackMe or Hack The Box." No, the free stuff isn't — it's not working. You know what made Ford so productive, right? He had cheap cars and mass production, right? He took an idea that hadn't been done, and he didn't really invent the automobile — people always think he invented the automobile, he didn't. He created factories as we know them today, right? He had a crazy idea, and everyone's like, "That's not going to work." And it worked. So, I'm taking what's there, but I'm adding to it — something that is lacking. Again, not just a controlled environment — what I'm going to do with the students, it's going to be tough. What I mean by that is they're not going to encounter the same thing every day. When you're in cybersecurity, it's just like a paramedic — you're not always going to see the same thing every day as a paramedic. You're going to see some crazy off-the-wall things, like they show on those TV shows. I thought about being a paramedic at one point in my life. So, on the calls you go to, you're not expecting to see somebody on a roof in their underwear, right, because they're high as a kite — but you're going to see things, right? Things are always going to change in cybersecurity. You don't know what your enemy is doing, right? Their end goal is either to ruin your company or steal your money. Those are the two things, right? It's not complicated what they want, but what needs to take place is they've got to have that hands-on, which is what we're providing. And we're going to give them real-life expectations and real-life scenarios that they're going to have — it's going to change every single day, they're not going to know what to do. And that's the best part. How do you react in a tough situation? Do you know resiliency? And that's what I want to teach.
Sergey You mentioned, and I see it on your profile, that you have over 10 years of experience in talent acquisition, so you know how people recruit other people. What do you think, in the age of AI, should recent graduates — or anyone who wants to land a job offer — do to increase their chances, because obviously we are seeing all these layoffs and everything. So what do you think young people should do?
14:50 Getting Hired in the AI Era
Jesse I understand where they're coming from, because they've been there — I've been there more than once, unfortunately. Take the 2008 financial crisis, for example, right — 2007, 2008, the financial crisis was horrible. Roughly — every 1% is, give or take, however many millions of jobs in the United States, okay? So how many millions of people got laid off because of bad, dumb decisions? People that honestly should be in prison, right, for what they did — it was plain stupidity. If they don't go to prison, they need to at least be put in a straitjacket in a padded room, right? They literally ruined the American housing market, right? But what happened to my generation, as I was graduating college because of those decisions? We didn't give up. I had to find a job, and I had to adjust. Technology obviously was changing. Things were always changing, right? New political atmosphere was going out, a new one was coming in — that was when Bush was leaving office, Obama took over. You had a mess. I couldn't find a job to save my life, right? The baby boomers were laid off, and they were the ones taking the jobs at Lowe's and any other entry-level job I could get. So, what do you do in a situation where something that's very simple can be mass-produced? How do you keep up? What happened whenever the horse and buggy went away in New York? Literally overnight — overnight, the automobile took over. The city was tired of the smell of horse manure. When a horse died, they had to wait for the horse to decompose to be able to take it out, right? Then the automobile comes in — it was literally overnight. That's how fast the automobile took over. So if you want to live in this AI age, you have to adjust fire — as we'd say in the military, you have to adjust fire. You have to be prepared. Your enemy is not going to just sit still — they're going to move, right? And in this case, your enemy is the job market. You have to learn AI. How do you incorporate it into your everyday life, right? AI is becoming a part of cybersecurity. China has taken on AI. What's the difference between an AI and a person? An AI will not quit. As long as there's power, it's going to keep going — it's a program, that's all it is. They've created a computer program to continuously hack. AI doesn't give up — its whole program is to hack nation-states like the United States, Canada, wherever, right? Anywhere there's NATO technology, United States technology, that they're trying to take from the American government — they have an AI to do that. So, you have to take the cybersecurity professional, and they have to know AI, and I've incorporated that into the program that I've made. I've got all four of the major AI programs that are out there, and I'm looking to add more. What I'm doing is I'm going out and finding industry experts — people that have been doing the career 5, 10, 15 years, who want to change the industry, want to change the market. That's what I've been doing — I've been networking non-stop to find people that know what they're doing, whether it's AI, whether it's firewalls, networking, whatever it may be. That's what I'm doing right now — I'm trying to bring all that and incorporate it into my course curriculum.
18:51 The Rise of AI-Powered Hacking
Sergey Are there going to be, at some point, AI hackers that would pretty much try to steal your data using AI?
Jesse For the most part, AI is already there — it's already doing it. Like I said, it's already stealing your data. We're going to have to start — my plan is I'm trying to work with the JROTC, on something called Cyber Ranger. So JROTC is Junior Reserve Officer Training Corps. These are kids that are looking to go into the military — that's a good first step. There's 3,000 clubs worldwide, and they want to change cybersecurity for their generation, right? They're getting ready to take the torch from me — I retire next year. It has to start the freshman — between their eighth and ninth grade year, really, the freshman year of high school. Like, hey kid, what are you thinking about doing with your life, right? Nobody did that for me — just go to college, that's the whole thought process, you'll make money if you go to college, right? AI is there. Again, it's going to hack. You have to train people to know what to look for — the patterns, and how to deal with AI. Again, resiliency — how are you going to bounce back from a hard situation when the pressure is on? AI is going to be continually hacking, because they've made programs to do it.
Sergey So, how many years have you served in the military?
Jesse 19.
Sergey Oh, wow.
20:27 Resilience, Empathy & Unity
Sergey I think we want to finish our conversation strong. I'm going to ask you: what are the top three lessons you learned in the military that can be applied to everyday life, especially today?
Jesse I think society lacks a couple of things, and one of those is resiliency. Like I've talked about, I've mentioned it more than once — right now I'm facing a very hard time in my life, with the business and a couple other personal things, and I could have given up. I could have just rolled over. I could quit right now, right? What are you going to do? And that's one thing the military really taught me — and I come from a very poor background. What will you do when the time gets tough? Are you going to give up, or are you going to push through it? Another thing I think society is lacking, that I really learned from the military, is empathy. Not sympathy — empathy is when you feel sorry for someone. Empathy, you try to understand where they're coming from, right? Just as a world society — but let's back it up, let's go with the United States. We have every single culture across the face of the planet, and I've served with people from all over the world, different religious backgrounds, political backgrounds, from poor to rich and in between, people from what we'd call third world countries, right? And I try to empathize with them. I'm like, "Hey man, I've been poor." They're like, "No, you haven't been poor, dude — that's not poor." They're like, "Did you have food stamps?" I'm like, "Yeah, a couple times." And they're like, "You weren't poor — you had a chance to eat. There's days I had to go and dig in the garbage to eat." I was like, that's fair — that's, my friend, that's when you learn empathy, right? And I put in about 300 people in the military while I was in, maybe a little more, I don't know, I kind of lost count — because I was a recruiter for the Army. Put in a lot of different people, a lot of different cultural backgrounds, religious backgrounds, and again socioeconomic backgrounds. And at the end of the day, the one thing I learned is that we're all green. That's the third thing the military taught me, which sounds weird, right — we're all green. What I mean by that is, at the end of the day, they're an American serving with me. I don't care if they're from Laos, Cambodia, Nigeria, Russia, Ukraine, whatever it may be, right, Canada even — people from Australia were serving in the United States military, proud to serve and wear that uniform, and now there's six branches of the military, right. That's something that, at the end of the day, they're green — they are a brother and sister in arms, and they're trying to protect, at the bottom line, they're trying to protect this nation, whatever your political view is going to be, or religious view, however you view the world. Those three things, I feel like I live by. I can't judge anyone when I've made mistakes — it's like calling the kettle black. I'm not one to judge, because I try to keep those three things in the back of my mind, right? And I know I'm going to fail. I know that out of failure comes success. I'm not saying it's easy, because there's mornings I'd want to give up. But guess what — you're still going to have to put your pants on, you're going to have to get up, and you're going to have to move. If you don't, life's going to — you either grab life by the horns, or it's going to grab you by the horns, and it's not going to be pretty. It's just how I view it.
Sergey Yeah. Well, it's a great way to, I think, end our conversation.
24:13 Final Words
Sergey Keep it up. Keep pushing. Thank you for your time, Jesse.
Jesse Yeah, thank you. We have an Indiegogo we set up — we're trying to get this kicked off the ground. And I know, you know, I don't want any business — any business that starts off in debt is usually not a good thing, it leads to a business failing, and I'm not a greedy individual. I'm doing this for the love of cybersecurity. I want to make the next generation — even fix the current generation's problems. And those problems are very simple to fix, it just has to come from a culmination of things. Government has to change their mindset, that city, county, state, even federal — people have to change the lackadaisical attitude toward cyber. They have to understand it's a real thing, it's a serious threat. Look up the story of the 15-year-old that hacked MGM Grand. By the time everything is said and done, with the payouts and the insurance, there's about a billion dollars in damage for the MGM Grand casinos in Las Vegas. He was 15 years old — the kid turned himself in last year, he's now facing big-boy prison. So, a 15-year-old kid, right? Somebody that should have been doing their job should have been like, "You sound awfully young, you don't really sound like you work here" — but they gave him full access to the IT systems for the MGM Grand Casino. A 15-year-old kid, right? And we've got an Indiegogo going — I would implore and ask anyone out there, please jump in with us, I want to see this dream come true. And I'll just say, thank you for having me on. It means a lot. This company means a lot, and my team means a lot — they've been working diligently, we're working pro on it right now. But thank you.
Sergey You're welcome.