All Episodes

September 22, 2025 41 mins

Why should you listen to us? Honestly—you shouldn’t. But if you do, know this: we’re not just two jokers talking theory.

In this episode of Legitimate Cybersecurity, Frank Downs and Dustin Brewer open up about their real beginnings—from accidental entry into US Intelligence after 9/11, to packet-hunting puzzles, Wi-Fi tinkering, and Linux dependency hell, to Dustin’s Coast Guard days that led him into DoD cyber operations and battlefield coding.

What you’ll hear:

Frank’s unexpected pivot from English major → Arabic → US Intelligence → Packet Hunters → ISACA → vCISO

Dustin’s childhood obsession with modems, Prodigy, and “Hackers” → DoD cyber ops → Iraq deployment software award → BlueVoyant leadership

Why Wireshark still matters more than ever in an encrypted world

The three inflection points that changed Frank’s career forever

Why frameworks (NIST, ISO, HITRUST) keep failing—and Dustin’s PhD research into the human factor of security

What we focus on today: AI, vCISO work, penetration testing, and the balance of family + cyber

🎯 If you’re looking for career inspiration, real stories, and unfiltered lessons from two practitioners who’ve done the work—this episode is for you.

Timestamps below.

📩 Questions? admin@legitimatecybersecurity.com

💬 Drop a comment—we reply fast.

🔔 Subscribe for more real-world cybersecurity with humor and honesty.

Chapter Breaks

00:00 Cold Open – “Why should you listen to us? You shouldn’t.”

00:19 Meet your hosts: Dustin & Frank

00:36 Why this episode: career steps & credibility check

01:23 Setting the stage: our backgrounds in cyber

02:06 Frank’s accidental entry into cybersecurity (post-9/11, US Intelligence)

03:26 The language grind: Arabic immersion & Spanish surprises

05:24 From Nordstrom suits to DoD analyst (wrong master’s degree first!)

07:15 Building real skills, Packet Hunters, and ISACA transition

07:40 Discovering Wireshark: packets as puzzles with real-world impact

09:02 Wi-Fi experiments, streaming flex, and home internet humility

09:48 Frank’s advice: explore cyber early—or you’ll be miserable

10:19 Dustin’s story begins: Palm Bay, Florida + engineering neighbors

11:14 Simpsons saxophone teacher → first coding mentor

12:32 AOL for DOS, Prodigy, CompuServe → modem obsession

13:26 Networking excitement & “Hackers” movie inspiration

14:23 Linux from scratch & dependency hell at age 15

15:17 School vs passion: community college frustrations → military track

16:25 Coast Guard IT school → voluntold to Fort Meade (DoD cyber ops)

18:03 Ground-up learning → teaching others by doing

19:13 Linux from scratch = trial by fire learning

19:51 Wireshark packet analysis as the foundation skill

21:02 Policy + frameworks: the cowboy days before NIST awareness

22:43 Frank’s 3 inflection points: contracting leap, Packet Hunters, discovering NIST

25:50 Dustin’s inflection points: first root login, Project Phalanx, Iraq software success

27:54 Building impactful systems → Army Achievement Medal for battlefield code

29:27 Perspective: cyber ops under fire → calm in the private sector

30:22 Frank now: family focus, vCISO variety, and AI’s cultural impacts

34:14 Tech culture & identity: from iPods to Meta glasses

34:53 Dustin now: pen testing, vuln mgmt, and a PhD on framework adoption

37:42 Why frameworks keep failing: the human layer

39:31 Rethinking cybersecurity like medicine, not just militaristic defense

40:15 How to reach us & engage with the show

41:04 Sign-off

#cybersecurity #careerstories #packets #wireshark #linux #dod #usintelligence #techcareers #careeradvice #pentesting #vCISO #humanfactors #ai #frameworks

Mark as Played

Advertise With Us

Popular Podcasts

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

The Joe Rogan Experience

The Joe Rogan Experience

The official podcast of comedian Joe Rogan.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.