Will AI Take Your Job?

Rick McCathron, President and CEO of Hippo, gives the honest answer to the question every one of his employees is quietly asking about AI, and explains why thirty three years in insurance has taught him this panic has happened before.

A Bakersfield kid who played left tackle at Oregon State until two ruptured discs ended it, Rick traces the path from underwriter trainee at Mercury, to running a Texas acquisition at twenty six after saying yes on the spot, to founding First Connect, to a meeting with Assaf Wand that was supposed to be business development and turned into the rest of his career.

Discover why he says expense ratios have barely moved in forty years despite orders of magnitude better technology, why Hippo's hackathons now involve sitting beside the person doing the work, and what a South Carolina board member meant when he said no matter how many times you weigh a pig, it doesn't get any fatter.

In this episode:

00:00 - Cold Open
00:26 - Welcome and what Hippo actually does now
03:55 - Bakersfield, a left tackle at Oregon State, and two ruptured discs
05:05 - An assistant sheriff father and an independent agent family
09:39 - If you have personality be a reinsurance broker, if not be an actuary
11:25 - Why EQ beats IQ and why he hates Zoom
16:32 - The Dallas conference room and twenty panicked new employees
19:03 - The ninety tens and when the downside outweighs the upside
20:26 - A poker game, a promotion he did not want, and Texas at twenty six
25:20 - The three things, and doing twenty visits when the goal was fifteen
32:00 - Washing the car twice by two o'clock on Monday
35:14 - Starting First Connect with lunch instead of a salary
37:33 - A Texas storm, a reinsurance problem, and a meeting with Assaf Wand
40:11 - Everyone said direct to consumer, he bet on independent agents
43:36 - No company's path to success is ever a straight line
45:49 - Is AI going to take my job
47:29 - Expense ratios have not moved in forty years
48:38 - Claude for every employee and seat rides with the people doing the work
49:25 - The verbs in a business
50:25 - Weighing a pig doesn't make it fatter
51:40 - Vision without execution is hallucination

Richard McCathron is the President & CEO of Hippo and has been a member of the Board of Directors since February 2017. Before Hippo, Rick held senior executive positions at various insurance companies, including First Connect Insurance as President & CEO, Superior Access Insurance as President & CEO, and Mercury Insurance Group as Regional Vice President. Rick is both a Chartered Property & Casualty Underwriter and a Certified Insurance Counselor and sits on the board of directors of Spinnaker Insurance Company, First Connect Insurance, The National Alliance of Insurance Education and Research, and Players Health. He is an advisor to several insurtech companies and holds a BS in finance from Oregon State University.