Ep17 - Kirby Winters — Scout Skills, Leadership Hacks, and Smart Security in the Age of AI

Joining us in the Sky Lounge today is Kirby Winters—tech entrepreneur, cybersecurity expert, and partner at TechCXO. Kirby takes us through his journey from telecom to launching (and selling) his own business before diving back into consulting. He also shares some serious Eagle Scout leadership insights, breaks down the world of cybersecurity, and how AI is changing the game. Chapters [00:00] Introduction to Kirby Winters and His Journey [03:04] Leadership Lessons from Scouting and Mentorship [06:10] Navigating Career Paths: Technical vs. Management Roles [09:03] The Entrepreneurial Leap: Starting a Business [11:56] The Exit Strategy: Selling a Business [14:59] The Importance of Cybersecurity in Business [17:57] Social Media and Personal Security Concerns [21:01] Scams and Vulnerabilities: Protecting Yourself [23:56] The Role of Cyber Insurance in Business [26:55] Understanding Cyber Breaches and Their Causes [29:45] The Changing Landscape of Cybersecurity [33:14] The Future of Data Centers and Cloud Services [35:51] Compliance and Cybersecurity Regulations [39:01] The Business Cycle and Cybersecurity Investments [42:00] The Importance of Proactive Cybersecurity Measures [44:57] Travel Stories and Personal Reflections [47:57] Conclusion and Contact Information ABOUT OUR GUEST Kirby J. Winters is a leader in the cybersecurity and technology-based communications industry with extensive experience across multiple sectors. Since 2016, he has led the Information Security Practice at TechCXO, working with healthcare, banking, and Department of Defense clients. His leadership has delivered innovative solutions, including advanced Electronic Medical Record systems, AI-driven practice management, and wireless health monitoring tools. Kirby has held executive positions across numerous industries. Kirby founded Winter Media in 2011, offering custom application development and information security services to clients like the US Navy, Department of Defense, and various healthcare organizations. Socials/Web TechCXO Profile X/Twitter and Instagram—@kirbywinters LinkedIn What is THE SKYLOUNGE? Tales from the SkyLounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. ABOUT OUR HOST Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO. Subscribe and turn on notifications to listen to new episodes as they launch! YouTube Spotify Apple Amazon Follow Tales From The SkyLounge on Social Media X/Twitter Instagram Learn more about TechCXO