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. Kirby breaks down the world of cybersecurity, from social engineering scams to compliance audits, and how AI is changing the game. Along the way, he shares stories of leadership—both good and bad—that have shaped his approach to balancing innovation and risk.

[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, with a focus on Technology Product Management, Information Security Certifications, Web and Mobile Product Development, and interim CISO/CTO/CIO roles. He served as interim CISO for a $20b bank, implementing significant improvements in security governance and compliance, and still serves on the bank’s Cyber Security Advisory Board.

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. Previously, he co-founded Solar Velocity, LLC, where he directed IT initiatives and consulted for clients such as AT&T Wireless, AFLAC, LegalZoom, and Morehouse School of Medicine.

Socials/Web
https://www.techcxo.com/team_members/kirby-winters/
X/Twitter and Instagram—@kirbywinters
https://www.linkedin.com/in/kirbywinters/

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. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

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.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

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Production/Design: James Liebman
Music: Soundstripe/Cody Martin-Sunrise