Cyber Sip

Do you have a plan for when—not if—someone tries to steal your identity? Do you know the essential steps to take in the first 24 hours, first few days, and beyond? What can you do to protect yourself, your family, and your finances before it happens? Listen in to this fast-paced episode as Kevin Szczepanski breaks down crucial steps to take to protect yourself and respond. Learn about password management, credit monitoring, and effective response strategies to mitigate the potential negative results. You won’t want to miss this important episode.

Are you risking your legal case by chatting with open AI platforms like ChatGPT or Claude? You're not alone, and this episode reveals critical insights that could save your case—whether you're a lawyer, a client, or someone handling sensitive info. In this eye-opening discussion, Kevin Szczepanski dissects two landmark cases—US v. Heppner and Warner v. Gilbarco—that show how courts are scrutinizing AI communications in both criminal and civil contexts. Learn why, in the Heppner case, prompting AI without your lawyer's guidance led to the betrayal of attorney-client privilege, and why, in Warner, a pro se litigant’s use of AI didn’t waive work product protections. These rulings might seem straightforward, but they hold powerful lessons for anyone using AI to handle sensitive legal, financial, or personal information. Listen in for Kevin’s analysis and stay tuned for updates on this increasingly relevant and complex topic.

In this episode, Kevin Szczepanski walks through the details of United States v. Heppner. In this landmark case, a federal judge ruled that a client’s use of Claude, an open AI platform, is not protected. As Kevin explains, the court determined that using the AI to “do his own research” exposed the client and waived protections so that neither the attorney-client privilege nor the work product doctrine applied. Hear about why communications with open AI platforms like Claude, Gemini, and ChatGPT aren’t confidential; how courts analyze whether a client is seeking legal advice via AI; and practical steps for attorneys and clients in the era of generative AI. This episode is essential listening for lawyers, compliance officers, and legal tech adopters who want to avoid costly mistakes and leverage AI responsibly. If you rely on AI to assist your legal work—or plan to—listen in.

Kevin Szczepanski is back with a brief solo episode that explores a recent landmark case in New York State that addresses the serious consequences for attorneys and the legal profession of citing fabricated cases and misrepresenting legal sources. The courts, attorneys, and firms large and small must recognize and educate themselves about how AI can both help and hinder courtroom integrity. Join Kevin as he dives into the importance of fact-checking and the implications for legal professionals.

Kevin Szczepanski is back with the debut of Season 5, just in time for international Data Privacy Day and Data Privacy Week. In this first episode of the season, Kevin discusses critical aspects of data privacy and vendor agreements. He outlines five key negotiating points that organizations should consider when entering into vendor agreements, including data-use terms, data-security requirements, auto renewals and termination, indemnification, and insurance. This solo episode emphasizes the importance of clear agreements to mitigate risks associated with vendor relationships.

Kevin Szczepanski welcomes Adam Segal, the Ira A. Lipman Chair in Emerging Technologies and National Security and director of the Digital and Cyberspace Policy Program with the Council on Foreign Relations. They discuss the global AI race, particularly focusing on the launch of DeepSeek’s AI model R1. Kevin and Adam dig into how DeepSeek's advancements surprised many as its open-source model raised questions about AI leadership, export controls, and the development models driving AI progress. The conversation also touches on the implications of AI in foreign policy; the regulatory approaches of the US, EU, and China; and the potential impact of AI on various sectors, including military and economic domains. The discussion concludes with insights on the importance of understanding AI liabilities and the need for businesses to adapt to the rapid advancements in AI technology.

Host Kevin Szczepanski welcomes Damion Walker, managing director of the technology practice for insurance giant Gallagher, to discuss the intricacies of cyber insurance and the newer product, known as tech errors & omissions (E&O) coverage. They explore the evolution of these insurance products, the importance of understanding the differences between them, and how businesses can leverage insurance as a financial tool. Their conversation emphasizes the need for businesses to be proactive in their insurance needs, the significance of choosing the right broker, and the underwriting process. Damion and Kevin also address the challenges faced in the cyber insurance market, providing insights on handling claims and the importance of maintaining communication with brokers regarding changes in business operations. Listen in for the whole story.

Kevin Szczepanski welcomes Gregg Davis, managing principal and technical advisory solutions leader at EPIC Insurance Brokers & Consultants. Kevin and Gregg start by discussing the increasing risks of insider threats to cybersecurity and the sophistication of threat actors along with the need for organizations to create a culture of verification and for real-world training. Diving into strategies to mitigate insider threats, they emphasize awareness and proactive measures. Kevin and Gregg touch on business email compromise, insurance policies, the evolving role of the CISO, and much more. Tune in for the whole episode.

Kevin Szczepanski and guest Nick Reese, co-founder and COO of Frontier Foundry, discuss strategic applications of AI on this episode. Nick’s career evolution includes positions in the US Navy and within the US intelligence community, including a stint as director for emerging technology policy for the US Department of Homeland Security. His company is working on privacy-preserving AI. Kevin and Nick discuss the distinction between generative AI and artificial general intelligence and the need for small to medium-sized businesses to adopt AI strategically. The conversation emphasizes the significance of understanding data security, the role of human oversight, and the establishment of AI governance to ensure ethical and effective implementation of AI solutions.

Kevin Szczepanski and Michael Kurzer, a partner in the law firm Vinson & Elkins who leads the Technology Transactions & Intellectual Property Group, explore the burgeoning field of AI-ready data centers. Kevin and Michael discuss these data centers’ significance, the complexities involved in their construction and operation, and the legal challenges they face. In addition, Michael shares insights on the evolving landscape of data centers, the impact of AI on infrastructure, and the importance of robust legal frameworks to navigate the associated risks. Listen in for the full conversation.