CyberWire Daily - Jon DiMaggio: Two roads diverged. [Strategy] [Career Notes]

Episode Date: May 1, 2022

Chief security strategist from Analyst1, Jon DiMaggio shares his story on how he grew to become apart of the cybersecurity world. He describes different jobs that paved the way to the knowledge he has one the industry right now, and he even shares about an experience that led him to path that split and which decision he would make, would be crucial in his career. He explains which way he ended up going and how a critical part of his career helped to determine that path. He say's "there's two paths when you have that happen, you can either let it defeat you, or you know, you come back swinging." We thank Jon for sharing his story. Learn more about your ad choices. Visit megaphone.fm/adchoices

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from a very young age. And I literally taught myself how to build computers and, you know, learned every aspect of it that I could. And I just got a passion for technology. I could. And I just got a passion for technology. I have a bachelor's degree today, but I have never been a big fan of school. I have a learning disability and it's just, it's always been a struggle for me. So I didn't go to college, but what I did do is, you know, the bubble had just popped, you know, the technology bubble. It was like 2001, 2002. And because a lot of companies are going out of business and I was able to buy routers and switches and servers for pennies on the dollar.

And I set up this, I had this one bedroom apartment and it looked like the Batcave when I was done with it. I had a rack with all these Cisco devices in it and I would spend every day at lunch, every night, my weekends, all I would do is study, read, and practice hands-on on these things. And I did that for about two years. And I went and passed the CCNA exam, the Cisco Certified Network Associate. And then a few weeks later after that, I got in a Microsoft System Administrator certification. And you'd think that that was where the story led to me getting a job,

but it wasn't. It still took me another two years because there were so many experienced people out of work. And eventually, I got hired at General Dynamics. I got hired at General Dynamics. You know, I did that sort of networking and system administrator role for a number of years. Fast forward to 2007, I had a program manager who left and he went to work for the U.S. Army's Information Command. And he was managing a group of signals intelligence analysts. And he was like, I know you've never done this, but, you know, we're creating sort of a new role. We need analysts who can do intelligence reporting

and have a technical background. And he's like, you know, I already know you're good with talking to customers. I think we can teach you the writing. And I think that we can teach you the intelligence part. So would you be interested? And, you know, I said, yeah, that sounds awesome. And so I went from, you know, engineering and doing administrative work to literally learning how to chase bad guys. And I can't talk about some of the exact things that I did there. But what I can say is that once I had that job, that is where I really fell in love with what I do for a living now. I stayed with government and I did that for many years. It wasn't until 2014 that I actually decided to get out. Now, the scary part, when you leave the government, you have all these really cool resources and tools on the government.

What I found, though, once you took those away, it forced me to be a better analyst. I tried to leave the government twice. So the first time I left the government, I went to a private sector organization, and it was a coveted team of analysts. And getting this job, I was so excited. And what I found was when I got there, I wasn't as fast and efficient as some of my peers were. as some of my peers were. And, you know, I really like doing things where I'm creating fake personas, you know, enumerating the infrastructure and figuring things out on my own in different creative ways. So I was not enjoying the way that they had me doing my job. And what ended up happening was, unfortunately, it ended up leading to me being let go and given severance and being shown the door. And I eventually then ended up at Symantec, where that really set my career on fire working with those guys.

And really, in my mind, I proved everything that I needed to prove based on that situation. But there's two paths when you have that happen. You can either let it defeat you or you come back swinging. And that's the route that I took. And that's the route that anybody who believes in themselves when they face a situation like that, you know, that's really what you have to do. I don't blame the company either. There's certain jobs that just aren't right for certain people.

And I'm very creative and I like to do things a certain way. And I need that freedom to do it. I love what I do. So, you know, I really wanted to continue this path. So looking at feeling that my self-worth wasn't there and that I wasn't as good as this job as I thought that I was, I realized, you know what, I can't sit here in self-pity. I really believe in myself and in my capability. And it was like fuel to fire. I mean, gas to fire. It just ignited something in me. And I wouldn't be where I am today if that hadn't happened. I mean, I came back twice as hard, you know, researching, reading, learning new skills on top of my job, you know, doing like blogs outside of work because I just lived and breathed this.

And I wanted to be the best analyst in the world. That's never going to happen where you're the best analyst in the world. But you know what? I'm a damn good one today. And I love that I can say that. And I love what I do. am good one today. And I love that I can say that. And I love what I do. While that was the worst day in my career, it was also the best day in my career because it set the path to where I am today. Self-inspiration and motivation can go just as far as having a degree in no experience,

meaning if you want something and you go after it and you have the discipline to teach yourself and read and learn new tools and resources and ways to do things, you can do things, especially with the resources today like LinkedIn, where you can create posts and you can submit to groups

and you can network without having to already be in a career field and just put yourself out there. Don't worry about if you get something wrong and you look like a fool. If you don't have money for college, if you can't go to college, if you don't have the experience or whatever,

don't let that stop you. Go find ways to put yourself out there, get involved, go to the different groups, post stuff, write things, talk to people, communicate, go to conferences, meet people, and you'll end up getting there. Thank you. I have to say, Delete.me is a game changer. Within days of signing up, they started removing my personal information from hundreds of data brokers. I finally have peace of mind knowing my data privacy is protected. Delete.me's team does all the work for you with detailed reports so you know exactly what's been done.

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