Season 1. Episode 7. Unscripted with Rajiv Dattani

Rajiv Dattani helped run METR, the organization that evaluated whether OpenAI's and Anthropic's frontier models were too dangerous to release, before leaving to build something stranger: insurance for AI, underwritten through Lloyd's of London.

In this conversation, he tells Jeff how METR measured model risk in human hours, meaning how long it would take a person to complete the most complex task an AI model can now do, and why that number matters for tracking how close AI gets to automating its own research and development. He walks through the historical playbook insurers have used to get ahead of new technology risk before regulation catches up, from Benjamin Franklin's fire insurance audits to Progressive's early seatbelt and airbag discounts, and explains why AI insurance can, for the first time, be priced using simulated red-team evaluations instead of waiting years for real loss data to accumulate.

He pushes back on the panic around the viral stat that 95% of AI pilots fail, arguing that's a healthy sign of experimentation rather than a warning, and says most failed pilots are management failures, not model failures, because leaders often don't understand their own processes well enough to know where AI should even go. The conversation closes on what worries him most: not one catastrophic AI failure, but the lack of infrastructure to catch small, compounding errors before they cascade into systemic economic risk once AI is embedded across banking and payments infrastructure.

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Episoder(19)

Season 1. Episode 19. Unscripted with Matthew Guggemos

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8 Aug 52min

Season 1. Episode 18. Unscripted with Camberley Bates

Camberley Bates has spent 30-plus years as one of enterprise technology's most respected independent analysts, paid to cut through vendor hype and tell executives what's real. On this episode of Unscr...

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Season 1. Episode 17. Unscripted with Russ Wilcox

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27 Jul 52min

Season 1. Ep[isode 16. Unscripted with Keith Pijanowski

Every impressive AI demo sits on an enormous, expensive, and very unglamorous foundation of data. Keith Pijanowski is one of the people who built it. After a decade-plus at Microsoft (where he helped ...

22 Jul 45min

Season 1. Episode 15. Unscripted with Klas Nilsson

Everyone is promising humanoid robots in every home and factory. Klas Nilsson has spent 40 years on the part that turns out to be hard. The Cognibotics founder, who built one of the first digital robo...

20 Jul 45min

Season 1. Episode 14. Unscripted with Lena Smart

Lena Smart has spent 30 years securing the systems we genuinely cannot afford to have fail — the power grid, financial markets, and as longtime CISO at MongoDB, one of the most widely used databases o...

12 Jul 33min

Season 1. Episode 13. Unscripted with Sarah Chardonnens

Dr. Sarah Chardonnens is a professor at the University of Freiburg with a PhD in the science of learning, and in this conversation with Jeff Pedowitz she takes on the question everyone has an opinion ...

10 Jul 36min

Season 1. Episode 12. Unscripted with Juergen Weichenberger

Juergen Weichenberger has been building AI since the 1990s, well before it became a mainstream conversation, in domains where the cost of being wrong isn't a typo, it's a shutdown: factories, energy g...

10 Jul 34min