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"You Think That's Your Problem. It's Not." episode artwork

EPISODE · Sep 20, 2026 · 39 MIN

"You Think That's Your Problem. It's Not."

from Risk Raiders · host Brent Borgstedte/Jeff Shropshire

Every business owner thinks they know what's wrong with their business. Most of them are wrong. That's the message Carey Wallace and Lindsay Sexton — the mother-daughter team behind Agency Focus — deliver over and over again to owners who invite them in to "look at one thing" and end up staring at five bigger things they never saw coming. This week, they sit down with two insurance gurus (that'd be us) to share what they actually see inside hundreds of family businesses: perpetuation, valuation, the messy family stuff nobody wants to talk about, and what happens when AI starts telling everyone exactly what they want to hear. Also covered: • The consultant who told Jeff he had a 5% chance of surviving as a third-generation owner (jury's still out) • Why "buy low, sell high" falls apart when it's YOUR business • The Texas dad who wished he'd been kinder to his own father • The $50 million real estate deal ChatGPT killed • Why you probably shouldn't write your own will • The one number about to matter more than EBITDA • Advisors, not processors — the AI shift every agency is missing Whether you run an insurance agency, a family business, or any company with employees and something worth protecting — grab a coffee. This one gets real. GUESTS Carey Wallace & Lindsay Sexton — Agency Focus Business Refocus Podcast → https://agencyfocus.net or on Youtube- https://www.youtube.com/@agencyfocus CHAPTERS 00:00 A moment for 9/11 00:35 Meet Carey & Lindsay 02:06 "5% chance you make it" 02:40 The mother-daughter origin story 07:30 Everybody has a story worth hearing 08:24 "You think that's your problem. It's not." 13:04 When the business IS the brand 14:10 The daughter who takes notes at mom's speeches 16:22 "I wasn't kind to my dad" 18:00 The identity crisis nobody warns you about 19:07 The mastermind for owners letting go 21:52 Start planning 5 years out. Maybe 10. 26:46 Buy low, sell high (except with your own business) 28:40 The AI question every agent is afraid to ask 31:27 Advisors, not processors 34:06 The $50 million ChatGPT mistake 35:21 Don't write your own will 37:44 Know your numbers. Build your community. 39:02 Where to find Carey & Lindsay ABOUT RISK RAIDERS Two guys. Too many opinions about risk. Occasional wisdom. New episodes every Sunday. ⚠️ Disclaimer: Risk Raiders is an independent podcast and is not affiliated with, endorsed by, or sponsored by Texas Tech University. All products, services, brands, or businesses mentioned on the show are for entertainment and conversational purposes only. A mention does not imply endorsement, recommendation, or sponsorship — by us of them, or by them of us. Paid sponsorships and partnerships will always be clearly disclosed. Finally, this show is entertainment and industry perspective only, nothing on this show should be considered insurance, legal, financial, or professional advice. Always consult a licensed professional for guidance on your specific situation. © 2026 Risk Raiders LLC. You’re welcome to share this episode by linking to or embedding the original video. Downloading, re‑uploading, or editing this content without written permission is prohibited. #RiskRaiders #FamilyBusiness #AIinBusiness #Perpetuation #InsuranceAgency #SuccessionPlanning #BusinessPodcast #SmallBusiness #ChatGPT #FractionalCFO

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