Why I Launched My Own Business: The Genesis of White Oak Security
The Catalyst of Entrepreneurship: Reflecting on "Why"
Every so often, I'm asked why I decided to dive into the risky waters of entrepreneurship and start my own business.
Ok, nobody actually says it like that. That would be weird. But, I do get asked why I started White Oak Security… just with more normal words.
The initial reasons that spurred the creation of White Oak Security differed from why we decided to expand and, eventually, to exit. But, like any good Marvel movie that takes you back to a character's origins, let's start at the beginning.
Transition from Contributer to Leader: A Crossroads
Back in the day, when I was still knee-deep in vulnerabilities as a penetration tester, I landed a long-term gig at Best Buy via Symantec, a solid name in cybersecurity. Interestingly, I think I only visited the Symantec office once, just to refresh my laptop! Over time, Best Buy realized it made more fiscal sense to in-source their penetration testing team. Why keep paying the middleman when you have all these techno wizards at your disposal?When Best Buy proposed I switch from contractor to team leader, it was tempting. Since getting into cybersecurity, I had one goal, to climb the corporate ladder and eventually become a Chief Information Security Officer (CISO), the top of the food chain in my eyes. This opportunity with Best Buy was another step in that direction, however, it came with a caveat: moving away from the hands-on work I loved.
Maintaining Technical Expertise: The Core of Effective Leadership
Reflecting back over my career, I realized the leaders I admired most weren't just figureheads. They were the ones who understood their teams' day-to-day tasks. It struck me that if you lose touch with the nitty-gritty of the work, you can't effectively clear the obstacles your team faces. This empathy gap was something I was desperate to avoid.
If I moved away from Nmap, Burp Suite and Metasploit and towards Outlook, Excel and PowerPoint, it wouldn’t be long before I lost my technical edge. The answer seemed to be maintaining a dual focus: leading and doing, going the Dr. Jekyll and Mr. Hyde route.
I needed to keep my hands on the keyboard, hacking away as I had always done, mapping, scanning, manipulating payloads, to truly understand and advocate for my team.
Side Hustle to Main Hustle: The Beginning of White Oak Security
Nervously excited, I approached my mentor at Best Buy. I proposed starting a side hustle, back before they were a staple of every LinkedIn profile. To my surprise, they agreed, with one rule: I couldn't sell back to my day job. Fair enough! I hadn't even figured out my first client yet!
This approval kick-started the foundation of what would become White Oak Security. It allowed me to not only lead but also continue developing my technical skills, ensuring I didn't become one of those leaders who couldn't remember the last time they'd done the work themselves.
Reflections and Looking Ahead
Starting White Oak was about more than just maintaining my skills; it was about crafting a space where I could lead effectively and empathize deeply. It was about ensuring that as we grew, I didn’t just ascend to the realm of abstract strategy but stayed grounded in the real challenges faced by my team.
As I look forward to the next chapters of this entrepreneurial journey, remember: the best leaders are those who stay connected to their roots. And in cybersecurity, where the landscape shifts as quickly as the scenes in a Marvel flick, staying true to your technical roots isn't just helpful, it's essential.
This approach to leadership, keeping one foot firmly planted in the technical trenches while the other strides forward in strategic leadership, was a founding principle of White Oak Security. It's a journey of balancing growth with staying grounded, ensuring that as we scaled, we never lost sight of what made us successful in the first place.
