How He Built a Billion-Dollar Cyber Empire

Repost: Defending the Underdogs — Cybersecurity Lessons from Kyle Hanslovan (Huntress) This is a repost of an earlier episode of the Jess Larsen Show on Innovation & Leadership. In this episode, Jess Larsen sits down with Kyle Hanslovan, cybersecurity expert and CEO of Huntress, to unpack what it really takes to protect small and mid-sized businesses from modern cyber threats. Long before Huntress became a trusted name in defensive security, Kyle’s journey began in the U.S. Air Force, continued through the intelligence community, and ultimately led him into the front lines of cybersecurity entrepreneurship. Kyle shares how thinking like an adversary—rather than just reacting to threats—became foundational to his approach, and why strong communication skills are just as critical as technical expertise in the security world. He also tells the origin story of Huntress: a real-world challenge, a bold proof-of-concept, and a clear realization that smaller organizations were dangerously underserved when it came to cyber defense. Even years later, this conversation remains strikingly relevant—offering timeless insights on leadership, problem-solving, and building mission-driven companies that protect the people most often overlooked. If you’re interested in cybersecurity, entrepreneurship, or leadership forged under pressure, this episode is well worth revisiting. Learn more about your ad choices. Visit megaphone.fm/adchoices