The InsurTech Geek Podcast.
Co-hosted with Rob Galbraith. Seven years of practitioner-to-practitioner conversations with the operators actually building the insurance industry.
An operator's microphone.
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.
166 guests, including:
- Ken Bunn — Vice President of Claims, Builders Mutual Insurance Company
- Freddie Scarratt — Global Deputy Head of InsurTech, Gallagher Re
- Rick Wong — Head of Insurance, Parametrix Insurance
- Paul Andrews & Mark Elliott — PoloWorks
- Danilo Raponi — Group Head of Innovation, Generali
- Dr. Thomas Kuhnt — CIO & COO, HDI Global SE
- Caribou Honig — Co-founder, InsureTech Connect
- Bill Cassidy — CIO, New York Life
- Charlotte Creech — Innovation, USAA
- Chris Griffith — Operations, American Coastal
- Sasha Sanyal — Insurance Lead, Microsoft
- Frank Schmid — Chief Data Officer, Gen Re
- Steve Kappel — CIO, Safety National
- David Bell — CEO, ALPS
- Preetha Sekharan — Enterprise AI, Unum
- Holly O'Dell — CEO, Montana State Fund
- Amir Kabir — Founder, Overlook Ventures
- Kobi Bendelak — CEO, InsurTech Israel
- Skip Brechtel — the very first guest
- and 146 others.
James as a guest.
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 →
For 2026 and 2027 episodes.
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.