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.

Aside from saving lives, one of the most important priorities of the healthcare industry is safeguarding patients’ most confidential information about their medical conditions. Without the right cybersecurity measures in place, their records will always be at risk from potential cyberattacks. Board-certified psychiatrist Muhamad Aly Rifai is here to discuss how hospitals and clinics should navigate cybersecurity to keep their electronic record systems away from data breach and leakages. He also discusses how scammers and cyber terrorists trick people into doing something they do not want by playing around with their personality types and using AI tools in the most cunning ways possible.

Navigating the wild west of Artificial Intelligence and how data privacy plays into the game is a hot topic for all, from solopreneurs to large enterprises. In this episode, John Riley and Valerie Cobb dive deep into the world of AI policies and data security, exploring the nuances of modern AI usage, its risks, and its exciting potentials. They discuss everything from ChatGPT's data retention to how your company's information might be unwittingly shared, plus hilarious AI jokes and the importance of cybersecurity policies. Join us as they unpack practical steps for protecting your data, especially as the tech landscape rapidly evolves, and get ready for some Gen X perspective on the digital age! Valerie and John also touch on the fascinating intersection of AI and cybersecurity, including the concept of "hiring hackers," making this a must-listen for anyone keen on staying ahead of the curve in tech, business, and yes, even corny jokes.

In today's rapidly evolving digital landscape, understanding the difference between cybersecurity and cyber risk is crucial for executives aiming to protect their organizations. Join host John Riley in this insightful episode as he dives deep into this critical distinction with special guest Ashwin Rangan, CEO of DoubleCheck. Ashwin, a published author and seasoned expert with decades of experience in internet technology and cloud infrastructure, shares his unique perspectives on prioritizing cyber threats in the age of AI, navigating the financial implications of security investments with CFOs, and emerging trends that will profoundly impact cybersecurity in the near future. This episode is packed with actionable advice, real-world examples, and even some humorous anecdotes, providing listeners with a comprehensive understanding of cyber risk management and how to stay ahead of evolving threats. Tune in for expert insights and practical tips to safeguard your business and personal data.