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In this lively installment of “Phishing for Answers,” our host kicks things off with a quirky, AI-generated rap—then challenges guest Dean Sapp, SVP of Information Security at Filevine, to a game of “Stock or Not?” to test just how convincing AI images can get. But the conversation quickly turns serious as Dean reveals how scammers are weaponizing these same AI tools to spin up highly targeted—and eerily authentic—phishing emails and counterfeit websites.

Drawing on his years of experience building cybersecurity programs and guiding law firms, Dean walks us through a jaw-dropping story of an “unhackable” client who thought strong passwords alone would stop an open-enrollment benefits scam. Spoiler: it didn’t. Along the way, he pinpoints the big blind spots many companies miss, from unpatched software on the perimeter to that shady old printer on a forgotten VLAN. Whether you’re running a small legal practice or a high-traffic SaaS platform, Dean’s bottom line is the same: turn on multi-factor authentication, build empathy-driven awareness programs, and keep everything—from firmware to browsers—patched and hardened. Because in this age of AI-fueled cybertricks, your best defense is a well-prepared, forward-thinking human.

Joshua Crumbaugh is a world-renowned ethical hacker and a subject matter expert in social engineering and behavioral science. As the CEO and Founder of PhishFirewall, he brings a unique perspective on cybersecurity, leveraging his deep expertise to help organizations understand and combat human-centered vulnerabilities in their security posture. His work focuses on redefining security awareness through cutting-edge AI, behavioral insights, and innovative phishing simulations.

PhishFirewall is a cutting-edge cybersecurity company revolutionizing security awareness with AI-powered training and phishing simulations that eliminate the need for manual campaign management.

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