Exploring Life and Career with Kevin Jackson: From First Cars to Cybersecurity Success

I wish I was in the car with him , because he has a really cool car now . My guest is Kevin Jackson . He's the CEO of his own company here . We'll talk about that . When I've known Kevin for about eight years , we worked together for a number of those , but I really remember Kevin .

He's driven a minivan for about 20 years and he just upgraded to this really cool Mercedes . So we'll get to that . We'll get to that later on in the show , but he's a cybersecurity professional Just excited to catch up with him . It's been a few years . We've seen each other on and off , but really haven't spent much time together .

So welcome to the show , kevin .

A cybersecurity guy , an XIT guy , a consultant , definitely an entrepreneur , but really , at heart , just a family guy , someone who loves the Lord , someone who loves being able to connect with people , spend time with people , and someone who likes even though I'm all into technology who likes being able to be on the creative side of things too .

I'm a part-time musician , a part-time writer on the other side of the coin , when I'm not doing technology in IT . So that's really me in a nutshell .

And it was not the most sturdy , not the most I don't know well-engineered car , but I absolutely ran it into the ground . I can't even tell you how many miles I put on that In the years I drove it through high school and college . It was one of the favorites of all my friends at the time .

You know there's so many stories about , first of all , running that car to its extremes and fixing it . Often that's how I learned how to do a little bit of car repair . My dad was a car repair guy .

He was someone who I've seen many times with friends , you know , taking an engine out of a car and putting another one in in our driveway and he would do all of his own work on engines .

And I learned very little of that , I'm sad to say , but I learned enough to be dangerous with that Cavalier , you know , I learned how to fix and take off and put back on a starter , how to change the brakes , how to do the new full brake jobs and do all the changes and those things .

It was all you know , with my dad , which is honestly some of my best memories where I've keeping that car running , with my dad showing me what to do and what not to do and yelling at me when I did things wrong but encouraging me to do things right and just keeping it going until you know .

So literally the wheels probably fell off towards the end of its life . It was a great car and my friends still you know , 35 , whatever it is years later , my friends still talk about that Chevy Cavalier and how great it was .

So instead of repairing it , we just left it that way so that anyone who knew me could just take another key or even a screwdriver and turn the lock and get into my car . So there was no security back then for that and we kept it that way from years . It was . It was great for hauling things .

You could lay down the back seats flat and use the hatchback and you could almost fit a full sheet of drywall back there . And it was . You know it was . It was a great car .

Then I had my first job , then , out of college , and bought my own first car , which was a Nissan Sentra , a black Nissan Sentra . That I thought was , you know , just the most luxurious thing I'd ever seen . And I first bought it and it was actually pretty basic , but it had features in it . You know .

It actually had power windows and and back then had power seat belts , which I'll never forget , those sliding seat belts .

So there's no tourists , there's no tourist attractions , there's nothing except the houses and some golf courses and some small places to eat . Friends of ours turned us on to this place and we fell in love . The thing is it's nowhere near an easy airport and if you're going to stay a week , you got to take not only luggage but your beach gear .

It's not easy to transport all that down there , especially with five now grown kids . So we started back in I think it was maybe 2018 , 2019 , we started renting a giant sprinter van to drive down all seven of us and have room for all of our gear . That ended up being a real exciting part of every summer Also all piling into this .

You know 15 passenger , you know tall enough to stand up inside sprinter van and all getting together leaving the love of night .

I love the leaves in the dark because I didn't want to , didn't want to have to have half of the trip spent with everybody awake and wishing we were there and because in fact then we had younger kids they're older now so we would start going at you know one or two in the morning and we would just get on the road and I loved it and they would sleep and

we get up and have breakfast , stop a little bit along the way and it became a really exciting part of the vacation just enjoying the road trip component of it . This year we actually did an augmented version of that because for the first time , instead of just a regular sprinter van , we have rented this party bus . It's a really nice .

It's a really nice Mercedes sprinter . It's got televisions inside of it , it's got leather recliner captain's chairs instead of just the bench seating , it's got an upgraded sound system , all these things .

And we were kind of forced into this , even though I love it , because we used to rent from one place right here in Eindale and they no longer have them for rent . They totally canceled our reservation and said oh sorry , we can't rent to you anymore . We ran out of inventory .

So we went and found another place and it is fabulous , just this gorgeous luxury van . So the kids are excited , I'm excited , we're going to have a great time and it's always just a great time to bond .

We don't really ever spend time together , except for major holidays all seven of us but we get into that van and we're spending the whole week together and it starts off with that long trip in the car and we just have a great time Sharing music and chat . Everybody's always laughing , everybody's in good spirits . It's become a special thing .

The person who rented it just brought it back from a fishing trip . When they brought it back , the cooler in the back , full of fresh fish , had turned over and spilled fish water all over the inside carpet in the rear of the sprinter van . So they said we've been trying to clean it for the last 24 hours and it still smells like fish .

We don't know what we're going to do . We were faced with okay , are we going to take the fish van or are we going to just drive our own cards , which would ruin the whole vibe of being together . We didn't know what we're going to do and they said we have a new chemical , we're going to try . Just give us another two hours .

So we didn't know what we're going to do . We waited two hours and , sure enough , when we got to the van they opened it up . They said all right , just tell us honestly , do you smell any more fish water ? And about this time I called my wife and let the kids know and they were just beside themselves .

But we got to take the raw fish van to South Carolina and I'm like I don't know we're going to see what happens . And sure enough they got it out enough when we got in there and I couldn't smell a thing . So at the last minute we went ahead with the rental and drove down there .

But the whole week the kids referred to it as the fish van and it's become the nickname for that whole trip .

in the cars . When I got out of college and started having family , kids , I kind of let that go . I kind of let it , I kind of let that slide because , honestly , we didn't have enough money to buy nice cars . You know we were starting off or getting our family , so we had a bunch of kids and I just got to let that go .

And because we have five , we became minivan people and for most of the time we were . You know we started in Maryland with our first four kids . We had a fifth year in Ohio . You know I drove minivans and my wife and I had dueling minivans . You know , one red or blue and the other one silver , in our driveway , in our garage .

For you know easily it's 15 , 16 , maybe 17 straight years , because that's made sense right To get all of us in a car and drive anywhere . You needed space . I mean you need space for groceries and strollers . I really let go of the whole car thing for literally for decades and just kind of forgot about it .

I kind of let that part of me just kind of go fade away . Sure , just this past year and I realized my Bennyman's getting old and I really don't love it anymore . I never really loved it . It was functional , right , it got the job done .

I mean , I was literally thinking I would talk to my wife like you know , I'm not really sure what I like anymore in cars and it was a really kind of an interesting moment . I'm like I don't know what I like . I mean , I used to love cars , and now here I was going to go buy one .

My thoughts are newly went back , though , to a friend of mine who I was out in Maryland , maybe I don't know four or five years ago , and he had this Mercedes CLS 550 that he was driving , and it I've never felt a car move like that , unless except for maybe I've got a friend who has a Porsche and it's phenomenal , I mean , it's got all .

It's a little Boxster , just incredible . Sure , Love the thing , and I've never felt a car move like this , like this Mercedes did , and I realized , well , I didn't really did enjoy getting ride in that thing , Never got to drive it , and then , the more I looked around , I was seeing more of those on the road and I thought you know what ?

Maybe a used , nice car like that would be just the thing . It took me a while . I spent probably six months re-learning what I really wanted and , because I knew I wanted something , I wanted horsepower .

I didn't want a lot of cost either , but I realized especially recently you know , as the new car market was was how it's been post COVID I thought , well , maybe I can still get a deal on a used , low mileage , really nice little Mercedes . And really that CLS 550 was calling my name . It's got a lot of horsepower , it's just gorgeous .

And shockingly , I found exactly what I was looking for last fall . It's a 2015 CLS 550 , a formatic leather interior , all the bells and whistles , sunroof . I've never had a sunroof in my life . I'm so excited to have a sunroof . Here's the thing it only has 40,000 miles on it .

It is so incredibly fun to drive . So , unlike anything , I've ever had my wife and kids in the economy . They're like , yeah , he's looking for an excuse to go drive that car again .

It's just a beast , and so I'm really , really excited . It's gotten me back to that car love that I had when I was a teenager .

So really I found myself early in my career at a little bit of crossroads because I was an electrical engineer by degree . I started off my career doing hardcore engineering and antenna work and radar engineering , some satellite engineering work . But I got to a point where , you know , in the around the turn of the nineties and the year 2000, .

That you know , I had the option to either stay in hardcore engineering or move more towards IT and information systems work and compliance and security . Back then I remember I talked to a friend of mine who was older who gave me a piece of advice I'll never forget and he's like you know what you really want to move towards security .

That's going to be the future . And it was that point when I started leaning more into things about security architecture , enterprise architecture and compliance .

And I've never regretted that choice , kind of turning my back on , you know , being a hardcore electrical engineer and really becoming an InfoSec guy so and the opportunities kept coming because that field really has grown so much over the past 20-some years .

So when I came out here to Ohio I worked for Booz Allen up at White Pat Air Force Base in that compliance and IT , enterprise architecture and security architecture space and it just kept , you know , it just kept developing and it just kept getting more and more useful and I saw that , as all the threats expanded , that space just kept , you know , drawing me in

. And then we worked together and I was , you know , in a security person then , and that's when I realized it's time to lean into another part of my background that I had kind of ignored , which is my entrepreneurial side . Yeah , my dad never worked for anyone else that I knew and the whole time my dad was alive and he passed away back in 2020 .

He was his own businessman . He had started a company before I was born doing janitorial services in Central Maryland , cleaning office buildings mostly government and DOD contractor office buildings in the Annapolis and Baltimore areas in Maryland , and I'd never seen either of my parents work for someone else .

They both worked for that company , which is called Bay Janitorial Services I mean the Chesapeake Bay and I'd always kind of wanted to go that direction , but it never worked . I'd never been able to make it work . All of a sudden , I realized the timing was right .

It was , you know , early 2019 to go out on my own and to become a consultant in cybersecurity . It worked . It worked really well . So I started off as a cybersecurity advisory services provider in early 2019 . That company , waypoint Cybersecurity , is still up and running today .

But , more importantly , a year ago I started a second cybersecurity company , actually making a product and a software as a service product for cybersecurity decision makers that we're actually selling now .

We built a team , we've got 20 employees now and we've developed a software tool for those in cybersecurity to have , basically a tool to use to calculate the optimal approaches for cost benefit in their cybersecurity program . That's been just an incredible ride getting that up and running , and we're kind of off to the races with it now .

But now this is a different sort of a way to help cybersecurity be managed globally by producing a single tool that has a global reach and that we're gathering data from all over the world and we're analyzing cybersecurity strategy data to calculate and let users know if you really need to keep your organization secure .

But you've got limited dollars and you've got limited people . What are the things that have the best bang for the buck ? What actually are the highest value activities and approaches and tools that you can use for a company like yours and your industry and of your size ?

That's something that I always wanted when I've been working in cybersecurity and I realized we could create that tool , and so that's what we've done , and it's really exciting to be able to offer something that can really help and that's honestly revolutionary .

We patented our approach because there's no other tools out there that calculate the best strategies using real world data and that really take into account people costs and tool costs in doing so .

Yeah , it's all the above and it's industry agnostic because we have data from almost every industry under the sun , we can get close to almost every industry . There is a code for . So we're really kind of size and industry agnostic .

They're not in the company and I think they're pretty much determined to not be in the company . The older three are absolutely involved in helping us grow this and it's really exciting because it works . They work well together and we're working well with our overall team and it's been really great to get to see that .

I want to go to Israel and get to do that kind of tour . I've got lots of friends who have gone and done it . I know people who , in fact I have a friend of mine who's going again here in January's and telling me I need to go . I don't know when I'm gonna have the time to make that happen or where it's gonna work , but it's really been on .

You know , that's something that's been on my heart for a long time to get to go and do those those no foot tours , those walking tours through all those areas from biblical history and see it for myself . It may be a while till I get to do it , but it is really high on my list to get to do that something . It's much more , I don't know smaller scale .

That's on my bucket list . I've seen advertisements for these places where you can go and and rent or just buy time driving like a supercar . Sure he's amazing , these amazing Automobiles and gets a drive on one , a real track , and all that my same friend who has a Porsche . He sent me a couple of times some ads for one of them down near Atlanta .

I think it is where you can like drive a Lamborghini or a Ferrari and just put it through its paces . That's on my list . Got to make that happen .

Quieter , but still lets me , you know , go to town playing some rhythms . I love drumming , but I'm a better guitarist than I am a drummer , so I'll put it that way .

When I was in high school and college , I was part of a garage band . My friends and I would Would play pretty regularly you know self-taught and would just have fun playing covers of the songs we love , mostly classic rock and it's just . It's so much fun and I still love whenever I get a chance to play .

I write mostly young adult and middle grade fiction , fantasy fiction , my , my , my whole goal in life , honestly big picture , is to be able to , you know , go through the cyber security Security company development cycle and have that be successful and one day retire from cyber security and , as it , as an older retiree , get back to writing books , get back to

Creating stories that are going to relate and connect to kids , rather their teenager or even younger kids , what stories that have real meaning .

I was heavily influenced by CS Lewis , by the writings of Tolkien , fantasy stories that are really allegories to teach real-world messages to young people all over the world , and that's one of the things that's always is kind of , you know , burned inside me . Is there's not enough of these stories being told ?

I don't , I feel like , especially to younger kids , especially younger kids that are not necessarily growing up in the nice suburbs , younger kids who are growing up in , in harder conditions or they're anything , in their city .

They're , you know , they come from backgrounds where Stories that teach and connect with them deep inside can really change their outlook , can maybe help Change how they grow up and what choices that are made . Just always been a believer in that , so that's that's always in my mind , even while I'm , you know , deep , deep in the tech world .

Now , one day I'll also be able to put more time back into writing .

And we don't even have many pictures because , again , given where , where that was , my father was born in 1935 , yeah , both of his parents died before he reached age 20 . So I never , I never met them , never knew them , and I think we have maybe two pictures of them and all of our Picture collection that survived until now .

Honestly , that my answer to that is I would love to take a road trip with my grandmother and grandfather from my father's side of the family that I never got to meet , because I it . Honestly , he doesn't remember him very well back when we talked about it .

He would say now he remembers few stories here and there , but he didn't actually spend a lot of time with them growing up . A lot of his time growing up he was raised by his aunt and uncle down in South Carolina .

I would love to just get to find out who they were and Ask them what their stories were and you know what they liked and didn't like and I don't know Just kind of get to know them , because I knew my mom's parents really well . My , my granny Carol , my mom's side actually just died about 10 years ago on my father's side .

There's just a whole set of stories there that have already kind of been lost , that we don't really know what their stories were , and I would love put them in a car . I put them in my Mercedes , honestly , because I think they really like it .

Yeah go for a drive , you know , in the back country and and just find out what their lives were like and you know what their dreams were and who they were that would be so fun .

We were able to do that with Linda's dad . I did not get to do that with my parents .

I really just didn't think about it , always thought , oh , there'll be tomorrow , you know , there'll be the right and I just I encourage everybody find these stories because when people pass away You're left with hundreds of questions that you wish you had asked absolutely right , yes , and just recently I was out in Maryland visiting my mom again .

It's so true , so important and get to have that time and use it to capture all those memories .

Yeah , that's where you can find me anytime in . The same same names are out on Twitter , instagram , facebook , elsewhere , of course . Happy to be found as we are very much in a growth mode In our and our cyber security practice that we're we're building at level

six .