Cyber risk is no longer just about firewalls and passwords—it’s about reputation, trust, and preparation in a world where AI can amplify threats. Awais Farooq, Head of Digital Claim Solutions, Catastrophe, & Contractor Connection in Canada for Crawford & Company, joins John Riley to unpack the evolving cyber risk landscape, from phishing scams and “Shadow AI” to the growing role of cyber insurance. He explains why reputational damage can outweigh financial loss, how organizations should prepare for cyber disasters, and why proving preparedness matters more than promises.

Cybersecurity and cyber risk are evolving faster than most organizations can keep up with, and understanding the difference is critical for leaders today. John Riley speaks with Leopold “Lee” Lueddemann about how companies can analyze risk through the lens of threats and vulnerabilities, prioritize limited resources, and prepare for the “collision course” between privacy laws and artificial intelligence. Lee explains why CEOs must focus on compliance and liability reduction, shares emerging trends from AI-powered phishing to global IP concerns, and stresses the importance of advanced incident response planning. He also reflects on his career in privacy and IP law, his global travel adventures, and his latest project helping a museum protect its digital assets.

The risk of experiencing a cyber disaster these days is steadily increasing as technology evolves. Therefore, you must get ready for anything and do not let yourself be caught off guard. John Riley chats with Peter Busam, founder and CEO of Equilibrium Consulting, about the importance of crafting and designing your own disaster recovery plan to mitigate cyber risks and handle threats accordingly. He shares how his training as a Navy veteran allows him to nurture a well-disciplined culture of security in his own team. Peter also talks about using AI for better market data analysis and taking note of every bit of customer feedback to constantly improve cybersecurity measures.

Many people are becoming numb when it comes to data breaches. If your business has been a victim of cybersecurity attacks, they simply move on to another business. But in today’s interconnected world, this is not the best mindset to have. Matthew Koenig, vice president of Channel Sales at Nodeware, joins John Riley to discuss how businesses must approach cybersecurity and navigate this kind of public perception. He explains why humans cause the biggest threat to cybersecurity today and the right way to mitigate it. Matthew also emphasizes why CEOs should never set aside foundational cybersecurity measures despite their efforts to catch up with today’s rapid technological progress.

By fully educating your team on the most efficient ways to reduce cyber risk, you can save everyone from numerous headaches in today’s highly digital environment. John Riley sits down with Sten Svendsen, vice president of the ASF Liquid Logistics Division, to discuss the importance of building and nurturing a culture of cybersecurity in your organization. Drawing from his first-hand experiences dealing with cyber disasters, Sten explains why training your team about cybersecurity from the get-to is essential in combating the rising threat of data breaches and attacks. He also shares what it takes to handle the use of AI for fraudulent means and how to maintain your integrity as you pursue all of your business goals.

What’s the real cost of ignoring your internal cyber risk? In this episode, entrepreneur and NoteAffect CEO Jay Tokosch reveals how insider threats—often unintentional—pose one of the biggest dangers to company data. He shares eye-opening stories about information leakage, explains why AI is both a cybersecurity threat and solution, and offers practical advice for CEOs navigating risk in high-growth environments. From mobile security innovation to the value of content protection, this conversation breaks down the strategic and technical moves leaders should make now.

Cyber risk isn’t just a technical issue—it’s a leadership priority. In this insightful conversation, Joe Lazzarotti, cybersecurity and privacy attorney at Jackson Lewis, unpacks the evolving landscape of cyber risk, from data breaches and insider threats to AI governance and executive accountability. He and host John Riley explore the biggest misconceptions leaders hold, the impact of supply chain vulnerabilities, and why proactive planning—not panic—is the key to business resilience in today’s threat environment.

Conquering cyber risk isn't just about technology; it's about understanding the human element and anticipating the adversary. Join us as Perry Boyle, CEO of MITS Capital and a seasoned adventurer who has skied in Antarctica and bicycled 148 miles in a day, shares his profound insights on navigating the complex world of cyber threats. Discover the unique challenges of operating in a war zone, the ever-present human vulnerabilities within cybersecurity, and the looming impact of cutting-edge technologies like AI and quantum computing on our digital defenses. Perry also delves into the often-misunderstood realm of cyber insurance and highlights the critical need for a proactive, owner-like mindset in managing cyber risks.

AI is rapidly changing the nature of cyber risk, and most executives aren't ready for the fallout. In this episode, cybersecurity strategist Christophe Foulon joins John Riley to unpack how generative AI is not only fueling smarter attacks but also exposing critical gaps in governance, incident response, and data protection. From deepfake threats and shadow AI use to the limits of cloud reliance and the realities of zero trust frameworks, this conversation lays out what business leaders need to know now. Drawing from experience at Capital One and Microsoft, Christophe offers clear strategies for improving visibility, setting enforceable policies, and preparing for the next generation of cyber threats.

Self-attestation may be convenient and a huge time-saver, but it may have some loopholes that could put your data in jeopardy if not executed properly. John Riley talks all about it with Valerie Cobb, Chief Revenue Officer of Omnistruct. Together, they discuss the legal actions one has to face after falsely self-attesting compliance and audit. They also explore the growing challenges of distinguishing reality from AI-generated content, the pitfalls of the “trust me” model, and the increasing shared responsibility for data protection.