Why Humility Decides Whether AI Actually Gets Adopted | David McFarland, Coterie Insurance

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.

00:00 - Cold Open

00:31 - Welcome and what Coterie actually does

01:37 - Four hours of work for a two hundred dollar commission

03:18 - Hollywood, Florida, a jet engine dealer, and an opera singer

06:16 - Fight school and why fighting felt like math

09:49 - The formal logic class that created an actuary

11:47 - Setting a record for credit hours to graduate on time

14:35 - Poor people aren't stupid and the IQ swing of scarcity

19:12 - Only one company called back

21:11 - Baptism by fire at a boutique consulting firm

23:58 - Why join a crappy little personal auto startup

28:24 - 3:30 AM oatmeal and almost twenty four hour coverage

30:11 - Refusing to be the guy who was too scared to try

32:46 - The investor who said just sell other people's products

35:17 - A term sheet and a baby born the next morning

36:38 - Eight years in, still on the original vision

39:02 - Thirty four million of OpEx, then and now

41:30 - A Ferrari on a cow path

45:59 - Integrity, intelligence, passion, and humility

49:01 - Nobody is building a real working lightsaber

50:53 - Selling vitamins instead of pain pills

52:49 - First order negative, second order positive

55:24 - Fifty books a year and the one he recommends most

57:37 - Six kids and staying humble

58:33 - How 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.

Mentioned in this episode:

Coterie Insurance - https://coterieinsurance.com

Connect with David McFarland on LinkedIn - https://www.linkedin.com/in/davidmcfarland23

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