The Hitstreak
The Hitstreak
Nick Hiter
Episode 257: Why Do Premiums Keep Rising? Inside the Agent Turned AI Founder w/ Caleb Herndon
1 hour 8 minutes Posted Oct 13, 2026 at 5:00 am.
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This week we are joined by entrepreneur, benefits consultant and founder of QuoteMap AI, Caleb Herndon! Let us know in the comments what YOU want to hear about next! Episode in a Glance: In this episode of The Hitstreak, I sit down with Caleb Herndon, a partner at Benefits Blueprint and the founder of QuoteMap AI. Caleb never planned on insurance. He started in financial planning, wanted to serve the W-2 employee instead of the high net worth crowd, and realized the only scalable way to do ...