Why Humility Decides Whether AI Actually Gets Adopted

David McFarland, Founder and CEO of Coterie Insurance, explains how his MGA grew from thirty four million to nearly three hundred million in premium without adding a dollar of operating expense, and why most of the industry is driving a brand new Ferrari down a cow path.

A Hollywood, Florida kid who found an outlet in math and fight school, David traces the path from a history major who stumbled into a formal logic class, to a record twenty six credit semester on the actuarial track, to NCCI, Madison Consulting, and Jewelers Mutual, to living in Kyle's Chicago loft as Clearcover's second employee, to an investor call at a going away party that nearly ended Coterie before it started.

Discover why he says AI only pays off when your systems actually talk to each other, why humility is the core value that makes a company willing to destroy what it built, why agents turned out to be the pain pill when platforms were the vitamin, and what it means to do things that are first order negative and second order positive.

In this episode:

1. 00:00Cold Open
2. 00:31Welcome and what Coterie actually does
3. 01:37Four hours of work for a two hundred dollar commission
4. 03:18Hollywood, Florida, a jet engine dealer, and an opera singer
5. 06:16Fight school and why fighting felt like math
6. 09:49The formal logic class that created an actuary
7. 11:47Setting a record for credit hours to graduate on time
8. 14:35Poor people aren't stupid and the IQ swing of scarcity
9. 19:12Only one company called back
10. 21:11Baptism by fire at a boutique consulting firm
11. 23:58Why join a crappy little personal auto startup
12. 28:243:30 AM oatmeal and almost twenty four hour coverage
13. 30:11Refusing to be the guy who was too scared to try
14. 32:46The investor who said just sell other people's products
15. 35:17A term sheet and a baby born the next morning
16. 36:38Eight years in, still on the original vision
17. 39:02Thirty four million of OpEx, then and now
18. 41:30A Ferrari on a cow path
19. 45:59Integrity, intelligence, passion, and humility
20. 49:01Nobody is building a real working lightsaber
21. 50:53Selling vitamins instead of pain pills
22. 52:49First order negative, second order positive
23. 55:24Fifty books a year and the one he recommends most
24. 57:37Six kids and staying humble
25. 58:33How many sides does a circle have

David McFarland is the Founder and CEO of Coterie Insurance, a managing general agent (MGA) specializing in tech-enabled, streamlined property and casualty coverage for small businesses. An actuary by training and a Fellow of the Casualty Actuarial Society, he brings a rigorous, data-centric approach to underwriting discipline, risk management, and insurance program design. Under his leadership, Coterie Insurance merges data, advanced technology, and modern distribution channels to scale profitable growth, optimize loss ratios, and forge strategic carrier partnerships. Driven by a commitment to operational excellence, David leverages automation and artificial intelligence to build a lean, high-efficiency operating model. He currently resides in Wisconsin with his wife and their six children.

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