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!