Silas Wray calls cyber insurance a bet you place with a company whose entire commercial model is not paying. Daniel agrees with almost all of it — and then argues that insurers did more to improve small-business security in five years than the entire security profession managed in twenty, by attaching a price to the answer.
They split hard on ransom payment, and Silas lands the hit: it is easy to have principles about funding criminals when it is not your payroll on Thursday.
In this episode
- Why most claim denials are self-inflicted at the application, not invented by the insurer
- “Don’t lie” is the wrong advice — the real problem is rounding up
- The exclusions worth reading with a lawyer, and the three most people miss
- The first forty-eight hours of a claim, and why you call the policy before your lawyer
- The losses no policy covers — and why the bill arrives twice
- Insurers have stopped believing the questionnaire and started scanning you instead
About the show
All Eyes takes one question the industry is arguing about, puts two people who genuinely disagree in a room, and does not let either off easy. Hosted by Vivian Calloway, with Daniel Ramos and Silas Wray, who argues the other side for a living. New episodes most Tuesdays.
🔊 This podcast uses AI-generated voices. Every voice you hear is AI-generated, including the host. Daniel Ramos's voice is his own, cloned with his written consent. We disclose this at the start and end of every episode. Read exactly how we use AI →