ZeroSum is a new cybersecurity podcast that aims to talk honestly about the state of the cybersecurity industry. The show rejects standard "threat of the week" news breakdowns and instead focuses on the reality of the market. Viewing the industry through the lens of game theory, the podcast explores how the current cyber market is no longer a rising tide that lifts all boats; for massive VC gambles to win, the burnt-out practitioners on the ground are often the ones losing. The show features guests from all perspectives, including vendors, investors, workers, and CISOs.
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/ (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
6 Oct 2026
AI Attacks That Take Six Months, Not Six Minutes - with Jackson Reed
Jackson Reed built the red team at the US Army Corps of Engineers and took it through certification, then spent four years rebuilding and leading Target's. He isn't worried about swarms of agents overwhelming your SOC — defenders are good at bursty and anomalous. What concerns him is the operator with ten thousand actions a day of compute budget who spends ten of them, in each of a thousand environments, for a year.
We get into what a six-month timeline does to log retention and correlation windows, the two opposite ways red teams fail, why the frontier labs stopped measuring what matters in their system cards, and the Bronze Age analogy that explains most of the AI tooling being built right now.
TIMESTAMPS
0:00 Cold Open
1:14 Meet Jackson Reed
6:29 Are You Hopeful or Upset?
12:33 Patience Beats Zero-Days
21:21 Agents Criminals Don't Have to Trust
24:01 Red Teaming in a Hall of Mirrors
29:46 Can AI Clone a World-Class Red Team?
33:35 What's Actually Scalable with AI
38:05 One Frontier Model, or Ten Thousand Custom?
40:58 AI Overkill: When Less Is More
44:58 YOLO Security
46:08 Chinese Models and Who Has Your Data
52:05 Barding: Can You Handle an Intrusion?
53:32 What System Cards Stopped Measuring
1:02:35 AI's Bronze Age
1:07:34 Holding an Industry Hostage
1:10:44 Where to Find Jackson
ABOUT JACKSON
Jackson Reed studied international affairs before moving into computer science through the CyberCorps Scholarship for Service. He did think tank and SOC analyst work, then threat attribution and intelligence analysis at CrowdStrike, built and led the red team at the US Army Corps of Engineers through certification, and rebuilt and led Target's. He launched Barding Defense in March and works with BT6 on assessments and jailbreaking for frontier labs.
Blog: twelvetables.blog
Barding Defense: bardingdefense.com
#cybersecurity #redteam #aisecurity #threatintel #infosec #aiagents
5 Oct 2026
AI Hacks That Takes Six Months, Not Six Minutes - with Jackson Reed
Jackson Reed spent four years running the red team at the US Army Corps of Engineers and four more rebuilding Target's. He is not worried about swarms of agents overwhelming your SOC. He's worried about the attacker who has ten thousand actions a day of compute budget and spends ten of them, on each of a thousand different environments, for a year.
We get into why bursty behavior is the easy problem, what a six-month intrusion does to your log retention and your correlation window, why red teams fail in two opposite directions, and the Bronze Age analogy that explains every AI harness shipping right now.
TIMESTAMPS
0:00 Cold Open
1:22 Meet Jackson Reed
6:37 Are You Hopeful or Upset?
12:36 Patience Beats Zero-Days
21:24 Agents Criminals Don't Have to Trust
24:05 Red Teaming in a Hall of Mirrors
29:49 Can AI Clone a World-Class Red Team?
33:38 What's Actually Scalable with AI
38:08 One Frontier Model, or Ten Thousand Custom?
45:22 YOLO Security
46:34 Chinese Models and Who Has Your Data
52:30 Barding: Can You Handle an Intrusion?
53:57 What System Cards Stopped Measuring
1:03:00 AI's Bronze Age
1:07:59 Holding an Industry Hostage
1:11:09 Where to Find Jackson
ABOUT JACKSON
Jackson Reed studied international affairs before moving into computer science through the CyberCorps Scholarship for Service. He did think tank and SOC analyst work, then threat attribution and intelligence analysis at CrowdStrike, built and led the red team at the US Army Corps of Engineers through certification, and rebuilt and led Target's red team. He launched Barding Defense this March and works with BT6 on assessments and jailbreaking for frontier labs.
Blog: twelvetables.blog (http://twelvetables.blog)
Barding Defense: bardingdefense.com (http://bardingdefense.com)
#cybersecurity #redteam #aisecurity #threatintel #ransomware #infosec
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