The Watchtower

AI Doesn't Give Us Judgment

Episode Summary

Is AI helping us make better decisions or just giving us more data to misinterpret?

Episode Notes

Is AI helping us make better decisions or just giving us more data to misinterpret?

In this episode of The Watchtower, Ash Hunt speaks with Tony Martin-Vegue, founder of NinetyFive Risk Advisory and author of From Heat Maps to Histograms, about cyber risk, decision-making, and the role of AI in risk analysis.

Tony explains why security teams often have more data than they realize, but still need the judgment to evaluate that data, understand its quality, and use it responsibly.

Highlights

• Why AI can supercharge risk analysis without replacing human judgment
• How LLM outputs should earn their way into a risk model
• Why red/yellow/green heat maps limit executive risk conversations
• How cyber risk quantification helps security leaders speak in business terms
• What cybersecurity can learn from meteorology, epidemiology, actuarial science, and financial risk management

Connect

Tony Martin-Vegue on LinkedIn

95 Risk Advisory

Chapters

0:00 The judgment problem AI can't solve

1:24 From IT janitor to risk analyst with Tony Martin-Vegue

5:19 Explaining risk in dollars vs colors

9:35 Not enough data is not an excuse

13:50 The DBIR, data quality, and the 500-report flood

16:46 Industry reports or Twitter polls

17:39 Decision engineering: operating under uncertainty

20:35 The CISO's real job isn't stopping attacks

21:31 The most influential cybersecurity book

28:41 AI launders bias

31:49 Decision engineering at scale: agentic context across the business

39:43 Cyber risk math was invented by 18th-century gamblers

41:20 What cybersecurity needs to steal from other fields

43:44 Toyota, Taylorism, and why your heat map has to die

45:53 Where to find Tony and the book