Books From the Show
Three books, two hosts, one industry. The long-form arguments behind what we’ve been talking about on the podcast for seven years.
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: 179 episodes, 162 guests, roughly 1.3 million words of transcript, recorded in real time from July 2019 through June 2026.
The argument: the conversation was the leading indicator. The market was the lagging one. The operators who said, on the record in 2019 and 2020, that software does not repeal the laws of underwriting were proven right by the public markets in 2022 and by the incumbents in 2025.
Four parts: the genesis of InsurTech (2016 onward), the four eras (Disruption · Funding Peak · Hangover · Industrial Adoption), twelve big lessons that recurred across the catalog, and a forward look at the 2030 industry. With named guests on every page.
Be Your Own VC
10 Bootstrapping Principles to Generate Cash and Keep Control.
Published by Houndstooth Press in 2022: ten principles for building a company on its own cash instead of someone else’s. The story of bootstrapping JBKnowledge from a college dorm room in 2001, with a $5,000 investment from his father, to hundreds of employees across three countries and a multimillion-dollar exit, without ever taking a dollar of venture capital.
The thesis is straightforward: bootstrapping isn’t anti-VC, it’s a discipline: build what you have to so you can build what you want to. Half a million businesses start in the U.S. every year. Less than five percent will raise outside capital. Ninety-five percent of ideas have to bootstrap to survive. Be Your Own VC is the playbook for the ninety-five.
It also turns out to be a useful companion to Geek Out. The principles in this book are the principles the venture-funded insurtech wave largely ignored, and Geek Out is, in part, the field report on the experiment Be Your Own VC argued against.
The End of Insurance As We Know It
How Millennials, Insurtech, and Venture Capital Will Disrupt the Ecosystem.
An Amazon bestseller written by Rob Galbraith, co-host of the InsurTech Geek Podcast, longtime insurance executive, and one of the industry’s most quoted commentators on what comes next. Published in February 2019 by Insurance Nerds.
Written before the IPOs, before the SPAC wave, and before the funding peak collapsed, the book lays out the case for why the next generation of customers, a new class of insurtech challengers, and a wave of venture money would force the insurance industry to remake itself. Several of the calls Rob made in 2019 have aged remarkably well, particularly his read on the demographic and distribution pressures the legacy industry was already underestimating.
It is also one of the cleanest on-ramps to the conversation Rob and James have been having weekly on the show ever since.
“The world deserves great insurance. Go out and make it worthy.”
Three books. One conversation.
If you’ve been listening for any length of time, you already know our biases. Rob’s book called what was coming. Be Your Own VC argued against the way the industry funded it. Geek Out reports what actually happened. Read them in any order; they argue with each other in interesting ways.