In this episode of Exit Buddy: Veteran Stories to Guide You, Kathleen and Rachel sit down with Army veteran and West Point grad Bryson Bort, who went from feeling “complete ignorance and sheer terror” in terms of military transition, to successfully building multiple cybersecurity companies and a nonprofit. From a global commodity manager who didn’t know what an RFP was, to an IT asset manager, to the creator of a global CMDB that actually worked, to offensive cyber in the intelligence community, Bryson shows how curiosity and tying your work to dollar value can open doors you never knew existed. He also delivers some tough‑love truths: why you need to stop sacrificing yourself for the mission in profit‑driven environments, what risk in entrepreneurship really looks like, and how networking and reputation can turn even your missteps into momentum.

Chapters

• 02:09 – Meet Bryson: Choosing West Point Over MIT
• 04:50 – Medically Discharged & First Civilian Interviews
• 06:30 – “What’s an RFP?” Alone, Unqualified, and Learning Fast
• 09:06 – Back to Tech as IT Asset Manager & CMDB Builder
• 10:30 – Cracking the Corporate Code with the CFO
• 11:57 – State, DIA, Special Forces & Googling “What’s a CTO?”
• 13:40 – Building an Offensive Cyber Unit at the Tip of the Spear
• 14:55 – Tough-Love Truth: Stop Sacrificing Yourself for the Mission
• 15:31 – From Napkin Sketch to Launching GRIMM
• 17:59 – Rethinking Risk & Failure in Entrepreneurship
• 20:57 – Co‑Founding ICS Village & Giving Back to the Community
• 22:08 – Network, Ask Questions & Fix Your Resume

Key Takeaways

• Tie Your Work to Dollars: In corporate environments, showing financial impact keeps projects alive through leadership changes and budget cuts. Bryson’s global CMDB didn’t simply survive because it was technically elegant; it survived because he could show hard dollar savings to the CFO.
• Stop Sacrificing Yourself for the Mission: Bryson’s wake-up call to veterans in the civilian, profit‑driven world is, if you’re yoked to the mission at the expense of your health and family, someone else is profiting from your sacrifice. You are allowed to set boundaries.
• Entrepreneurial Risk Is Often Lower Than You Think: For professionals with strong reputations, starting a consultancy is usually a measured risk. Worst case? You build a bigger network, deepen your expertise, and become more valuable when you step back into a traditional role.
• Network Your Way into Clarity: If you don’t know what civilian job fits your MOS—or if you even want that path—conversations are your intel‑gathering. Each coffee chat narrows the options, sharpens your resume, and reveals opportunities that never get posted.
• You Already Know How to Figure Things Out: From West Point to Signal Corps to offensive cyber, Bryson kept succeeding in jobs he didn’t initially understand by doing what veterans do best: figuring it out under pressure, seeking guidance, and taking ownership.

Follow us for more real veteran stories to guide your transition, and share this episode with someone who feels afraid of what lies ahead. They may just need a new mission and permission to bet on themselves.

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