Insurance technology, from the inside.
I've spent twenty-five years building software that runs inside insurance carriers, MGAs, and TPAs — and the last seven holding a microphone in front of the people building the rest of the industry.
Bootstrapped JBK since 2001.
166 guests, 7 years on record.
ITC Vegas, RISKWORLD, NetDiligence, WCI.
Geek Out (2026) · Be Your Own VC (2022).
Geek Out
Ten Years of InsurTech, Told by the People Who Built It.
A first-person account of the decade insurtech went from word to category to public-market crater to industrial absorption — told through the catalog of the InsurTech Geek Podcast: 182 episodes, 166 guests, roughly 1.3 million words of transcript, recorded in real time from July 2019 through July 2026.
The argument: the conversation was the leading indicator. The market was the lagging one. Four eras, twelve big lessons, a look ahead to 2030. Named guests on every page.
In final manuscript · Publishing 2026.
Where I've been on stage
Four keynote topics
Tailored for carrier, broker, venture, and association audiences.
The Decade of InsurTech
Seven years and 182 podcast episodes inside the InsurTech movement — what worked, what failed publicly, and what every carrier, founder, and investor should be doing in 2026 and 2027. Drawn from Geek Out.
The Agentic Revolution
How AI agents are about to reshape financial services from quoting to claims to underwriting to customer service — and what the next three years of carrier IT roadmaps need to look like to keep up.
From Pilot to Production
The 2025–2026 carrier playbook for moving GenAI from lab projects into millions-of-records-a-day production workloads, with the data, governance, and human-in-the-loop architecture to make it safe.
Bootstrapping & Operator Discipline
The cash-disciplined operator mindset, drawn from twenty-five years of bootstrapping JBK and the Houndstooth Press bestseller Be Your Own VC. For founders, boards, and innovation leaders.
The InsurTech Geek Podcast
Co-hosted with Rob Galbraith — seven years of conversations with the operators actually building this industry.
Who's on
Carrier CIOs and chief underwriters, founders at every funding stage, venture investors, reinsurance modelers, regulators, TPA executives. 166 guests across 182 episodes.
What we cover
AI in underwriting and claims, embedded distribution, parametric and climate risk, the MGA wave, the public-market repricing, the carrier-side innovation work that doesn't make headlines.
Where it's going
Still publishing bi-weekly. Friends-of-the-show program returning the most important repeat guests in 2026 and 2027 as the industrial-adoption era plays out.
Let's talk.
Speaking inquiries, podcast guest pitches, book press, or just want to compare notes on what's happening inside the insurance industry — I read everything that comes in.
Contact James