Co-hosted with Rob Galbraith. Seven years of practitioner-to-practitioner conversations with the operators actually building the insurance industry.
In July 2019, four years into the insurtech movement, with the conference circuit packed and venture money flowing, James sat down with a microphone and started asking the people building this industry what they actually did, what they actually believed, and whether it was actually working.
The trade press was covering insurtech as news — each round, each launch, each down round a separate headline. The podcast had the same people, on the record, across the entire arc. We can set what a founder told us at their Series A next to what the public market told them at their delisting. We can set a carrier CIO's 2023 prediction next to her 2025 results.
The conversation turned out to be a leading indicator. The market was the lagging one. That's the spine of Geek Out — the seven-year field report on what the microphone caught first.
When James isn't hosting, he takes the other chair — talking technology adoption, bootstrapping, and what's actually shipping inside the industry.
More guest appearances in the press & media archive →
Best pitches: a specific operator with a specific build, a contrarian read on a consensus-bullish topic, or a long-tenured executive with a sharp take on what's coming. Send a one-paragraph description and one-line summary of why they'd be worth an hour.
