Some CISOs "can't handle the fire that's coming." Advisory CISO Gina Yacone on why the leaders who came up guarding the firewall are running out of road, and what the job looks like now.

Gina joins Aaron to trace how security leadership changed: from castle-and-moat network defense, to cloud and identity, to AI agents working inside the walls. They get into why compliance isn't governance, why budgets buy visibility but never remediation, how shadow AI turned employees into insiders, why board metrics only describe a sliver of the environment, and what resiliency means beyond backups. Plus Gina's advice for anyone who wants to lead security in the next era.

TIMESTAMPS

0:00 Cold Open

1:09 Welcome, Gina Yacone

2:44 From castle-and-moat to cloud to AI

8:28 Compliance isn't governance

10:42 Visibility budgets, no remediation

12:30 Why would AI security be free?

13:55 Gina's AI advice for CISOs

18:18 Shadow AI and data loss

21:26 Developers were incentivized wrong

23:48 Mythos and exposure management

27:24 The short-tenure CISO problem

32:38 Why security metrics are flawed

36:32 Tokens as a metric

40:42 AI layoffs or bad bets?

44:16 How much trouble are we in?

49:48 Never waste a good crisis

51:43 Personal resiliency and cyber careers

58:08 Where to find Gina

ABOUT GINA

Gina Yacone is an advisory CISO at Trace3, Vice President of ISSA Denver, a Rotarian, and a frequent keynote speaker. Follow her on LinkedIn: https://www.linkedin.com/in/ginayacone/

ABOUT ZEROSUM

ZeroSum is a cybersecurity podcast for practitioners and leaders navigating AI, breaches, and the business of security, hosted by Aaron Mog.

#cybersecurity #CISO #AIsecurity #securityleadership #shadowAI #infosec #ZeroSum