Episode 0x10: Breaking In Without Breaking Down

In this episode of Hack Dissection, Mike Lisi sits down with Spencer Alessi, senior penetration tester at SecureIT360 and host of the Cyber Threat Perspective podcast, to talk through the world of internal penetration testing, assume-breach assessments, and what it really takes to break into — and secure — modern networks. Spencer shares how his background as a systems administrator shaped the way he approaches offensive security, why help desk and IT experience can be so valuable for aspiring pen testers, and how real-world environments often expose assumptions that organizations do not realize they are making. From passwords sitting in file shares to misconfigured Active Directory permissions, Spencer explains why testing an environment is often the only way to understand what can actually go wrong. The conversation also explores practical training paths, certifications like PNPT and CRTO, the importance of knowing your tools, and how intuition develops through hands-on experience. Mike and Spencer dig into the role of AI in penetration testing, the value of open-source security tools, lessons from real engagements, and Spencer’s DEF CON Red Team Village lab built around kiosk breakouts and Active Directory attack paths. Along the way, they also discuss burnout, responsible research, the importance of community, and why offensive security is about much more than running tools — it is about curiosity, troubleshooting, and understanding how systems fail in the real world.

In this episode of Hack Dissection, Mike Lisi sits down with Donna Grindle, CEO and founder of Kardon and host of the long-running Help Me With HIPAA podcast, to unpack the complex world of healthcare cybersecurity, HIPAA, privacy, and patient data protection. Donna breaks down what HIPAA actually covers, why compliance alone is not enough, and how the real financial and operational risks often come from ransomware, business disruption, failed mergers, insurance requirements, and poor preparation — not just regulatory fines. The conversation also explores why healthcare data should never be thought of as just “records,” but as real people whose care, privacy, and safety can be impacted when systems fail. From real-world privacy violations to ransomware events affecting patient treatment, Donna shares why security in healthcare is deeply personal. Mike and Donna also discuss the future of healthcare technology, including AI, bias in large language models, telehealth, electronic medical records, volunteer work through the Health Sector Coordinating Council, and why organizations need practical, reasonable, and appropriate security programs before the next wave of HIPAA changes arrives.

What actually happens at the world’s biggest hacker conference—and why are thousands of cybersecurity professionals volunteering their time to break things? In this special bonus episode of Hack Dissection, Maltek Solutions’ Mike Lisi is joined by Click Stream Studios Founder Matt Masur, who traveled with Mike to Las Vegas for DEF CON 2026. Together, they look back on their experience documenting the conference and explore what makes DEF CON unlike almost any other technology event. Mike and Matt take listeners inside the unique world of DEF CON villages, Capture the Flag competitions, electronic badges, Red Team vs. Blue Team security, AI, and the massive volunteer community that makes the event possible. Along the way, they revisit conversations with hackers working on everything from Active Directory and pinball machines to cars, boats, aviation, cloud security, and critical infrastructure. More importantly, they tackle the idea at the heart of this year’s coverage: Hacking for Good. Because learning how technology can be attacked, manipulated, or exploited is often the first step toward making it safer. Whether you work in cybersecurity, are thinking about entering the industry, or have simply wondered what really happens at DEF CON, this bonus episode offers an inside look at the people, technology, creativity, and community behind DEF CON 2026.

In this episode of Hack Dissection, Mike Lisi sits down with Tony Martino, a longtime digital forensics expert whose work has crossed law enforcement, the Secret Service, corporate investigations, incident response, and even true crime documentaries. Tony shares how a homicide investigation in Utica helped launch his path into computer crime, what early digital forensics looked like before the tools became more automated, and why understanding the fundamentals still matters. From floppy disks and hex editors to cloud data, mobile devices, BYOD policies, cyber insurance, and the overwhelming amount of telemetry companies now collect, Tony breaks down how digital forensics and incident response continue to evolve. The conversation also explores the future of DFIR, the growing role of internal investigations, the challenges of privacy and encryption, and why cybersecurity needs to become more proactive before incidents happen.

In this episode of Hack Dissection, Mike Lisi sits down with Wayne Koback from NRECA to talk about the cybersecurity challenges facing electric cooperatives and rural utilities across the country. Wayne shares what makes the co-op utility space so unique, from massive organizations with nuclear assets to small-town teams where one person may be handling IT, utility operations, and town management all at once. Mike and Wayne dig into the realities of protecting critical infrastructure with limited resources, the importance of practical cyber goals, and why collaboration across co-ops matters when facing threats to the grid. They also explore how data center growth is impacting rural utilities, why vendor security needs more accountability, and how SCADA knowledge can open doors for cybersecurity professionals in industries far beyond electric power. For anyone interested in cybersecurity, critical infrastructure, rural utilities, or building a stable and meaningful career in tech, this episode offers a grounded look at where cyber work has real-world consequences.