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

Summary

CyberWire Daily: Jon DiMaggio – "Two roads diverged"

Host: N2K Networks
Episode: Career Notes
Date: December 7, 2025

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Episode Overview

In this episode, Jon DiMaggio—Chief Security Strategist at Analyst One—shares his unconventional career path, the pivotal moments that shaped his journey, and the importance of resilience within the cybersecurity industry. Through authentic storytelling, Jon delves into early interests, obstacles overcome, and his philosophy for career growth, offering practical and motivational guidance for listeners navigating their own professional journeys.

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Key Discussion Points & Insights

Early Aspirations: Law and Acting

• Childhood Ambitions:
  • Jon reflects on his youthful aspirations of becoming an actor or a lawyer.
  • Quote (01:44):

    "I was dead set. I was either gonna be an actor or a lawyer. Very different paths. But that was what I had decided I wanted to do from a very young age."

  • Realized the demands of law school weren't a fit and acting never materialized.

Discovering Technology & Self-Driven Learning

• Curiosity Sparks Passion:
  • Early interest in computers—Jon teaches himself hardware assembly and IT basics.
  • Quote (02:10):

    "I literally taught myself how to build computers and learned every aspect of it that I could and I just got a passion for technology."

• Learning Disability:
  • School posed challenges, so rather than pursue a traditional college route, Jon leverages hands-on experience and self-study.
  • Utilizes technology hardware from post-dot-com-bubble sales to create a home "bat cave" lab.
• Certifications over Degrees:
  • Earns CCNA and Microsoft System Administrator certifications, yet breaking into the industry is difficult due to market competition (post-bubble layoffs).

Breaking Into the Field & Early Career

• Persistence Pays Off:
  • Eventually lands a role at General Dynamics after significant effort.
  • Performs network and systems administration for years.

Career Pivots: From Tech to Intelligence Analysis

• Opportunity in Intelligence:
  • A former manager recruits Jon to the US Army's Information Command as a signals intelligence analyst, combining tech skills and analytical writing.
  • Quote (03:50):

    "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."

• Falling in Love with Cybersecurity:
  • Finds true professional passion for threat analysis and intelligence work.

Facing Setbacks: Government to Private Sector

• Transition Challenges:
  • In 2014, Jon leaves government work—acknowledges difficulty adjusting without government resources.
  • First attempt at private sector ends with being let go from "a coveted team of analysts," feeling outpaced by peers.
  • Memorable Reflection (05:41):

    "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."

• Rebounding at Symantec:
  • Lands a role at Symantec, which becomes a career-defining moment; rededicates himself to his craft.

Growth Through Adversity

• Resilience & Self-Respect:
  • Describes being fired as both the best and worst day of his career, turning adversity into motivation.
  • Quote (06:51):

    "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."

• Continuous Self-Improvement:
  • Commits to non-stop learning, blogging, and pursuing expertise outside formal work hours.

Advice for Aspiring Cybersecurity Professionals

• Self-Motivation Over Formal Education:
  • Encourages listeners to pursue their passions regardless of educational background.
  • Quote (07:56):

    "Self inspiration and motivation can go just as far as having a degree and no experience."

• Actionable Networking Tips:
  • Leveraging LinkedIn, writing, meeting people, attending conferences, and engaging with communities.
  • Emphasis on putting oneself out there despite fear of mistakes or lack of experience.

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Memorable Quotes & Moments

• On Early Interests:
  • "A movie star or a great argumentative lawyer." (01:44)
• On Overcoming Setbacks:
  • "You can either let it defeat you or you come back swinging. And that's the route that I took." (05:41)
• On Personal Growth:
  • "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." (06:51)
• On Accessible Career Paths:
  • "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." (07:56)

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Important Timestamps

• 01:44: Jon discusses childhood career dreams.
• 02:10: Spark of curiosity for technology and self-learning.
• 03:50: Transition from IT to intelligence analysis.
• 05:41: First private sector setback and lessons in resilience.
• 06:51: Growth from adversity and renewed motivation.
• 07:56: Advice to aspiring professionals—networking, learning, and the value of self-motivation.

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Summary Takeaways

Jon DiMaggio’s story is a testament to resilience and passion in cybersecurity. Despite nontraditional beginnings and setbacks, Jon's drive for self-improvement and his knack for adaptation led him to leadership. His episode is rich with advice: formal degrees are helpful, but self-motivation, perseverance, and community engagement are just as vital. Those entering or advancing within cybersecurity will find his journey both instructive and inspiring.

Transcript

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[A]

Hi, I'm john dimaggio and I am the chief security strategist at analyst one.

I was dead set. I was either gonna be an actor or a lawyer. Very different paths. But that was what I had decided I wanted to do from a very young age. I changed over the years when I saw how much school it would take to be a lawyer. And you know, acting just never was something I did pursuing. But I thought for sure I was going to be one of those two things. A movie star or a great argumentative lawyer.

I was so curious about computers and technology from a very young age and I literally taught myself how to build computers and learned every aspect of it that 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, you know, pennies on the dollar. And I set up this, you know, I had this one bedroom apartment and it looked like the bat cave. When I was done with it, I had a rack with all these Cisco devices in it. And I would, and 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. There were so many experienced people out of work. And eventually 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 US 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, from 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. 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. And I really like doing things where I'm creating fake Personas, 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, you know, 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 you know, 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. I don't blame the company either. Like 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 at 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. 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 and no experience. Meaning if you want something and you go after it and, 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, you know, don't worry about if you get something wrong, 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.

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