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.

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.

Navigating cyber risk in today's rapidly evolving tech landscape requires more than just "whiz-bang" gadgets; it demands a strategic, aerial view, and that's precisely what we dive into with our special guest, Domingo Guerra, a patented outdoorsman, cybersecurity company founder, and early-stage investor! In this episode, John Riley and Domingo peel back the layers of cyber threats and risk transference, exploring the differences between cybersecurity "trench warfare" and the bigger-picture strategic thinking required for executives. Domingo, with his unique blend of technical know-how, go-to-market expertise, and investor insights, shares his experiences from building and selling his mobile security company and his current focus on helping other founders in the space. We discuss the most significant cybersecurity threats facing companies today, including the AI revolution, quantum computing's potential impact, and how startups can prioritize security without breaking the bank, plus some great insights on his love of skiing (Black Diamonds included). If you're looking for actionable advice on reducing cyber risk and understanding the future of security, you won't want to miss this dynamic conversation!

Understanding and achieving CMMC (Cybersecurity Maturity Model Certification) is vital for businesses working with the Department of Defense, and it's not as simple as saying, "Trust me, we're secure." In this episode, John Riley sits down with the passionate and insightful Valerie Cobb, a CMMC expert with Omnistruct, to dissect the complexities and necessities of CMMC. Valerie doesn't hold back, addressing common misconceptions like "we're too small" or "Congress will change it," with a direct, no-nonsense approach that matches her zeal for protecting critical data. Together, they dive into why CMMC is crucial now more than ever, contrasting it with the limitations of FedRAMP and highlighting the shift from self-attestation to third-party and DOD audits. Valerie emphasizes that compliance is not just a cost, but an opportunity for businesses to stand out, encouraging proactive steps towards certification and leveraging it as a strategic advantage in securing government contracts. If you're looking to understand CMMC and how it can transform your business's security posture and growth potential, this episode is a must-listen!

The Trump administration’s deregulation effort is causing underlying risks for the cybersecurity space. With compliance rules getting blurry across states, how can you protect your data from hackers and keep them private? John Riley and Valerie Cobb discuss how businesses can deal with data breaches, information processing, and confidential data management as deregulation is being rolled out. They also emphasize why compliance should be seen not just as a goal to be accomplished but as a never-ending journey of keeping up with the rapid pace of technology.

In today’s digital landscape, organizations need to build a secure foundation to protect their data. Yasir Ali is the Founder and CEO of PolymerHQ DLP, a company that offers a unique approach to data loss prevention designed for SaaS applications. He brings valuable insights about protecting your organization’s data and his approach to data loss prevention. He also shares emerging trends impacting the future. Yasir also draws the curtain to show how PolymerHQ DLP started. Join us in this conversation about protecting your organization’s data.

Artificial intelligence is sweeping every aspect of the digital space right now, and it always finds its way into our personal lives in more ways than one. Despite its many benefits, concerns regarding data privacy arise. Caroline McCaffery of ClearOPS is here to discuss the state of data privacy laws and regulations as AI becomes more ubiquitous. Joining John Riley and George Usi, she discusses how to ensure data protection and prepare ample cybersecurity budgets amid the ever-evolving AI landscape. Caroline also explains the right way to handle a cyber crisis without having to delete all of your data.

Cybersecurity incidents usually stem from human-enabled actions. But to err is human; it is only by learning from those mistakes that we can improve. In this episode, John Riley and George Usi sit down with Wendy Epley, Principal Analyst and Information Security expert at the University of Arizona. As a seasoned professional with over 15 years of experience in regulatory trade compliance, Wendy discusses the critical importance of understanding cybersecurity contracts. She emphasizes the need for organizations to carefully review and negotiate terms, ensuring robust security clauses to protect against potential threats. Wendy shares insights into the evolving landscape of cyber risk management, shedding light on the emergence of NIST Special Publication 800-171 as a pivotal framework. Tune in to learn about Wendy's exciting project, "CyBoRG," an internal resource at the University fostering knowledge sharing and aligning security practices. Don't miss this episode full of practical advice for building a resilient cybersecurity posture.

Effective cybersecurity isn't just a checkbox – it's an ongoing investment in resilience. It starts from the top, where collaboration between IT and leadership paves the way for a secure digital future. In this episode, we have Seth Guntharp to shed light on the challenges and triumphs of achieving CMMC (Cybersecurity Maturity Model Certification). Seth spares no details— he discusses CMMC's evolution, the changing landscape of compliance regulations, the crucial roles of CEOs, and more. Tune in and learn how to be ready to tackle cybersecurity challenges head-on!

In this pilot episode, John Riley and George Usi discuss the recent cyberattacks on Las Vegas casino giants MGM Resorts International and Caesars Entertainment. Their conversation centers not so much on the technical aspect but more on the leadership side, discussing how business executives should swiftly act and appropriately react. John and George compare cyberattacks to arson, drawing effective response tactics from firefighting operations. They also discuss why executives must never let their emotions cloud their judgment when addressing these attacks and how to regain the trust of clients (and employees) after hackers blemish your well-guarded reputation.

As technologies become even more interconnected and deeply embedded in our lives, facing cyber risks has become more real than ever. Cyber security could be the only thing that keeps you and your business safe. In this episode, John Riley and George Usi sit down with the President of PingWind, Inc., Clarence Dingman, to discuss how executives and leaders can prevent cyber-attacks from happening and keep their businesses safe. What is the most significant cyber threat executives are facing right now? How should a CEO prioritize cyber risks and how can a CFO budget for that? What does a cyber disaster look like for executives? Bringing insights not only from his experience in the industry but also from his background as a former military, Clarence gives a fresh point-of-view on facing the dangers in today’s cyber world. Join him as he shares more about fortifying cybersecurity as leaders today!

There are a lot of parallels between web design and cybersecurity, and keeping your website secure may be the first step to making sure your business is safe from threats from bad actors. Mary Putnam, the CEO at DesignYourSite.net, straddles this intersection by providing comprehensive web services for businesses that include security audits and secure web design. Mary tells us how WordPress can be your superpower in making sure you’re putting checks in place and effectively shielding your business from what she calls “not-friendly actors”. Tune in to find out more about their services and Mary’s profound insight into the larger subject of cyber risk and cybersecurity.