From Oregon Trail to Offensive AI Research with Richie Vinson

What does it take to go from hacking your way to more time on Oregon Trail in third grade to doing offensive AI research for a living?
Richie Vinson, an offensive AI security researcher at Cobalt, took the long way into cybersecurity, going from a rugby career and a help desk job to security work on the nuclear side, and now research into how AI is changing penetration testing.
Richie shares how his advice for breaking into offensive security has changed in just the past year, why building your own model from scratch can teach you things a certification never will, and what hardware you actually need to start running local LLMs at home. He also gives his honest answer on whether AI will replace pen testers, why so many companies are quietly hiring back the people they cut, and why he thinks local models are about to become a much bigger deal for organizations watching their token costs.
Richie also opens up about why volunteering and community helped him find his footing as an introvert, and gives a first look at Hack Myrtle, his new small-format cybersecurity conference on December 5, with an AI training from Royce Davis the day before. Whether you’re working toward the OSCP, experimenting with local AI models or trying to get better at networking, this episode is packed with practical advice from someone who started at the bottom. Stick around to hear about Netrunner, the upcoming documentary about his journey.
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Connect with Richie Vinson:
LinkedIn: https://www.linkedin.com/in/r2600/
Hack Myrtle website: https://hackmyrtle.com/
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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie