Information Security Leadership

Strategic oversight of organizational cybersecurity and compliance programs, including the role of Chief Information Security Officers (CISOs) in protecting digital assets.

4 episodes

Parallel Entrepreneurism: Shipping Startups Side by Side | Kirby Winters, Ep 50

Parallel Entrepreneurism: Shipping Startups Side by Side | Kirby Winters, Ep 50

Kirby Winters discusses launching multiple ventures simultaneously using AI-powered development, including Cyber Savi (a compliance automation platform), a vodka brand, and Unshucked (an oyster tracking app). He explains how agentic AI enables building production-ready software in weeks instead of years, the shift from consulting to outcome-based services, and strategies for selling cybersecurity compliance tools through MSP channel partners.

Business Model First, Product Second: Thirty Years of Building Smarter | Steve Subar, Ep 40

Business Model First, Product Second: Thirty Years of Building Smarter | Steve Subar, Ep 40

Steve Subar, serial entrepreneur and inventor of MatFresher, discusses his business-model-first approach to building companies. After 30+ years founding and exiting ventures including Open Kernel Labs (acquired by General Dynamics), Subar explains how he validated product-market fit for MatFresher—an automated yoga mat cleaning machine—by manually cleaning mats at studios before building the product. He emphasizes innovating business models alongside technology, the importance of experience over information, and why wisdom beats rapid iteration.

Phishing, AI Scams, and the Ever-Intensifying Cybersecurity War | Antonio Pagano, Ep 23

Phishing, AI Scams, and the Ever-Intensifying Cybersecurity War | Antonio Pagano, Ep 23

Antonio Pagano, CTO and co-founder of Symbol Security and founder of Wano, discusses the evolution of cybersecurity threats—particularly AI-enhanced phishing attacks—and the human vulnerabilities that remain the weakest link in security. He shares insights from running two companies across continents, bootstrapping Symbol Security for six years, and building Wano's 45-person development team in Colombia while maintaining work-life balance and continuous learning.

Scout Skills, Leadership Hacks, and Smart Security in the Age of AI | Kirby Winters, Ep 17

Scout Skills, Leadership Hacks, and Smart Security in the Age of AI | Kirby Winters, Ep 17

Kirby Winters, fractional CISO at TechCXO, discusses his journey from telecom to cybersecurity consulting, emphasizing leadership lessons from Eagle Scouts and entrepreneurship. He covers the evolving threat landscape—from social engineering to AI-enhanced phishing—and explains how fractional security leadership helps SMBs navigate SOC 2, HIPAA, and CMMC compliance without full-time hires. The conversation explores VPN evolution, cyber insurance realities, and the critical need for proactive security planning before customer mandates or breaches force action.

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