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Tyler Ramsbey
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Aug 31, 2026
I Left My $100K Job to Hack Independently (Here's What Happened)
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7:54DakotaHOST
you know, it sounds like, like what made you decide to take kind of pivot from the easy, you know, just doing part of, you know, the pen test to handling, you know, everything and starting your own company.

Tyler RamsbeyGUEST
I have a degree in cybersecurity and I have a master's degree in divinity, which means I spent three years academically studying like theology and philosophy and history, things that most people are bored by, but I'm fascinated by them.

Tyler RamsbeyGUEST
So I've always had an interest in entrepreneurship, business ownership, even going back to high school.

Tyler RamsbeyGUEST
Like I used to, this microphone that I have here, way back when I was super broke, I had a bunch of side gigs.
19 MINS LATER
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27:18DakotaHOST
What are some of the first tools that you unfold on the corporate network to start, you know, getting your foothold into things? Yeah.
#72 He Quit His Cybersecurity Job to Start a Pentesting Company ft. Tyler Ramsbey
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Tyler RamsbeyGUEST
So if you would have asked me when I was first getting in-- Well, I've been in IT for a long time.

Tyler RamsbeyGUEST
So I've been in IT in some form or capacity for, like, 10 years, but it was always kind of a side gig in order to pay bills.

Tyler RamsbeyGUEST
But when I went to really doing it full time when I was done with ministry, I even told my wife, like, my long-term plan is I want to start my own company in some shape or form, 'cause I've always been entrepreneurial, even back, like, in high school.

Tyler RamsbeyGUEST
I was basically self-employed, didn't have really bosses or supervisors above me.
