What 50 years in insurance teaches about relationships, change, and why the basics still matter.

In Episode 1 of The Long Game, Mitch Long sits down with Wes Connor to talk about how he got into insurance, what kept him in it, and what 50 years in the business has taught him.

They get into family business, remote selling, hiring challenges, commercial and personal lines, and why life insurance still stands apart from products people are required to buy. It’s a grounded look at what still matters in the business, what has changed, and why the basics still win.

WHAT WE TALK ABOUT

How Wes Connor got into insurance in 1975
From kitchen table sales to DocuSign and video calls
Why relationships still matter in a more digital business
Working with family across generations
Hiring challenges in today’s insurance market
Commercial versus personal lines in a changing market
Why life insurance feels different from mandatory coverage
Disability, long-term care, and planning before it’s too late

CHAPTERS

00:20 – Mitch welcomes Wes Connor
00:41 – How Wes got into the insurance business
03:15 – Starting out and falling in love with the work
05:21 – How selling insurance has changed over the years
08:00 – Podcasts, technology, and the next generation in the business
11:00 – Working with family and building an agency over time
12:00 – Hiring challenges and the shortage of new agents
16:23 – Disability insurance, income protection, and planning gaps
16:52 – Wes breaks down his agency’s commercial and personal lines mix
19:19 – Why selling life insurance is more satisfying
21:00 – Real examples of how life insurance changes outcomes for families
23:29 – Long-term care, aging, and staying healthy

Connect with Mitch Long: LinkedIn | KazInsurance | Read: Pagers & Payphones
Connect with Wes Connor: LinkedIn | Website | Instagram

More from the KazSource Network

The Real ROI of Podcasting — KazCM
What Happened to CFB Bowl Games — SportsEpreneur
Remote Work in Today’s Financial Advisory Industry —Entrepreneur Perspectives

About This Podcast and Series

The Long Game is a series under Entrepreneur Perspectives. Produced by QuietLoud Studios — a modern media network and a KazSource brand.

Get in touch with Eric Kasimov:
X | LinkedIn

Credits:
Music by Jess & Ricky — SoundCloud