In this episode, host David McClelland sits down with John McClure, Chief Information Security Officer and Senior Vice President of Enterprise Infrastructure and Cloud at Sinclair Broadcast Group, to explore the evolving intersection of media, cybersecurity, and innovation. As the media industry undergoes massive disruption—from shifting viewer habits to the rise of NextGen TV—John shares how Sinclair is rethinking its legacy infrastructure to deliver new kinds of digital services. They discuss the strategic advantages of ATSC 3.0, including one-to-many data transmission, and the potential for over-the-air updates to vehicles, digital signage, and emergency systems. John also unpacks the cybersecurity implications of Sinclair's broad digital transformation, detailing how the organization is managing an increasingly complex threat landscape across IT, cloud, and operational technology. From third-party risk to legacy tech challenges, he explains how Sinclair is building a secure, resilient foundation for the future. Beyond the tech, John reflects on his leadership philosophy, the impact of military experience on staying calm under pressure, and why mentoring has been a cornerstone of his success. As media companies face rapid technological and cultural shifts, how can CISOs lead with both strategy and empathy? And what does it take to safeguard the future of critical infrastructure in a digital-first world? Steve also shares career lessons, unconventional leadership insights, and a thought-provoking question for future guests. As AI reshapes cybersecurity, how can CISOs and CIOs stay ahead? And what’s the cost of falling behind?