What if the fastest way to break into cybersecurity isn’t another cert, but a soldering iron, a home lab, and the courage to say “I don’t know”? We sit down with Rob “Bowtie Security Guy” Whetstine—prop builder, mentor, and former Disney security leader—who built his career from other people’s discarded tech and turned a bow tie into a personal brand that helped him conquer social anxiety and stand out in rooms that matter.

Rob takes us from dumpster diving to Fortune 500 leadership and lays out a practical roadmap for anyone trying to enter or advance in cyber. We talk about why tinkering beats test prep, how to build troubleshooting instincts, and what it really takes to succeed in high-pressure interviews at places like Disney, Google, and Amazon. Rob makes a compelling case for servant leadership: define success clearly, protect vacations, build redundancy, and bring calm to incident chaos with a simple check—“Is anyone dying?” The result is strong, sustainable teams that deliver consistently without burning out.

We also tackle the uncomfortable truth behind the “cyber talent shortage.” Many of those roles are unfunded headcount, which is why entry-level postings get thousands of applications and interviews flow through referrals. Rob shares how he social-engineered LinkedIn, sent targeted video intros, and turned weak ties into opportunities. If you’re neurodivergent, you’ll hear concrete ways companies can interview better—advance questions, work samples, real accommodations—and why honesty about gaps earns trust. The through line is simple: passion and proof beat pedigree when paired with clear communication and relentless curiosity.

Join us for a candid, practical, and human conversation that will sharpen your job hunt, reshape your leadership, and remind you why solving real problems matters more than sounding smart. If this resonated, subscribe, share with a friend, and leave a quick review to help more listeners find the show.

Send us a text

Support the show

https://www.vigilantviolet.com/
www.linkedin.com/in/jessvachon1

Reinvention isn’t a neat pivot. It’s a grind, a choice you make on hard mornings, and a mindset you carry when no one’s clapping. We sit down with Saeger Fischer of Omada Technologies—former educator, mom of three, and 17‑time marathoner—who rebuilt her career in cybersecurity by treating learning like training and partnerships like team sports. Together we trace the real skills that translate from the classroom to the SOC: structure, self‑teaching, differentiated learning, and the patience to process before speaking. If you’ve ever felt behind, this story shows how consistent effort compounds into momentum.

We also zoom out to the big picture leaders are wrestling with. Is the AI bubble nearing a correction as tools overpromise and underdeliver on simple workflows? Where do agentic SOC models fit, and how do we balance machine speed with human judgment? We break down why you can’t buy your way out of risk, how to separate signal from vendor noise, and why relationship‑driven selling outperforms quarter‑end pressure tactics. Then we dig into category shifts reshaping architecture: the rise of enterprise browsers like Island, collapsing brittle stacks, enabling zero trust without heavy VPNs or VDI, and speeding secure onboarding in minutes, not months.

Finally, we confront timelines most teams prefer to defer: post‑quantum cryptography. Ten‑year roadmaps are already stale, and “harvest now, decrypt later” is not a thought experiment. We outline pragmatic steps to inventory crypto dependencies, prioritize migrations, and budget in phases. We also talk about public‑sector headwinds and where practitioners can still find trusted signal—peer communities, credible advisories, and leaders who share what actually works. If you’re eyeing a move into cyber, or you’re in the trenches and need a reset, this conversation blends grit, guidance, and grounded predictions you can act on today.

If this resonated, subscribe, share with a friend who needs it, and drop your bold 2026 security prediction in a review—we’ll feature our favorites in a future episode.

Send us a text

Support the show

https://www.vigilantviolet.com/
www.linkedin.com/in/jessvachon1

If you’ve ever felt like the odd one out in tech, this conversation will feel like oxygen. Akira Brand joins us to share how a shy kid, bullied for being different, found sanctuary in two unlikely rooms—the choir room and the computer lab—and turned that mix of voice and logic into a career leading application security. We map the path from opera training to DevRel to AppSec leadership, and dig into the moments that change everything: the first terminal command that touched the internet, the DEF CON night when community said “you belong,” and the leadership shift from heroic bursts to steady, compounding wins.

We get tactical without losing the human thread. Akira explains why AppSec works best as enablement, not enforcement, and how a good leader “tailors” security into the SDLC instead of tearing it apart. Threat modeling becomes the star—recast from checkbox to business engine. We talk metrics that matter, risk you intentionally accept, and where compensating controls deliver the most value. You’ll hear pragmatic guidance on keeping velocity without sacrificing security, building credibility with developers, and designing programs teams actually use.

We also explore AI’s double edge. For seasoned engineers, AI can boost secure development and documentation at speed. For beginners, it can hide missing fundamentals and import flawed patterns. Akira shares how to keep human review in the loop, vet model provenance, and use agentic AI to ship real tools faster—without skipping security basics. The episode closes with a message for outsiders: keep your integrity, find your people, and let your craft be both voice and shield.

Subscribe, share with a friend who needs a lift, and tell us: what’s one security habit you’d “tailor” into your team’s workflow today? Your reviews help this show reach more builders, breakers, and brave weirdos—thanks for being part of the Voice of the Vigilant community.

Send us a text

Support the show

https://www.vigilantviolet.com/
www.linkedin.com/in/jessvachon1