How to Lead Your Insurance Agency with Heart and Heroism

What if the advice you've been following is exactly why you're stuck? Not bad advice — just advice for a different stage of your agency.

In this episode, Craig and Jason sit down with Jennifer Haring for a conversation that cuts right to what matters. No rehearsed talking points — just an experienced agent sharing what they've learned the hard way, including the mistakes that cost them the most money and time.

The Problem Nobody Talks About

The craziest thing that ever happened to me as an agent is we took over a very, very small book of business couple 100 policy because an agent was let's leaving the company and come to find out not only what they steal the money from every client that he had, which was a nightmare when we started, but he burned down his own house to collect insurance. So obviously an odd situation and not the.

That framing matters because it shifts the conversation from 'what do I do?' to 'what am I doing wrong?' — and those are very different questions with very different answers.

Jennifer Haring: "Oh, my gosh, so this person was not only stealing from every single did you purchase the book?."

That's the kind of thing you hear and immediately think about your own agency. It's uncomfortable because it's specific — and specific is where change starts.

What This Changes

For agents running a book between $800K and $2M, this is where things shift. You're past survival mode but haven't cracked the scalability code. The answer isn't more effort. It's different infrastructure — and this episode maps it out.

The agents who act on this don't wait for the perfect moment. They pick one thing, implement it imperfectly, measure the result, and adjust. That cycle — action, measurement, adjustment — is the real competitive advantage in this business.

This connects to what we've covered in [INTERNAL: insurance-dudes-podcast-guide] . Same fundamentals, different angle. Stack them and the compound effect is real.

Craig: "Oh my gosh, did they know that he was stealing from the clients when they put you in there?."

Your Move This Week

Here's where this stops being a podcast episode and starts being a business decision:

1. So obviously an odd situation and not the greatest way to start, but it was a very big learning experience for us. This isn't someday-maybe territory. Block the time this week and get it done. The agents who implement within 48 hours of hearing an idea outperform the ones who bookmark it by a factor you wouldn't believe.

2. It's not a building I would have been in but Okay, great. This isn't someday-maybe territory. Block the time this week and get it done. The agents who implement within 48 hours of hearing an idea outperform the ones who bookmark it by a factor you wouldn't believe.

Hear The Full Episode

There's a lot more where this came from. Craig and Jason go deep with Jennifer Haring in the full conversation — including war stories that didn't make it into this post and the specific frameworks that changed how Jennifer Haring runs their agency. Worth every minute of your commute.

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🎙️ Listen to the full episode: Jennifer Haring’s Happy Hearted Harbinger Of Heroism PART 1 Apple Podcasts | Spotify | YouTube

The Insurance Dudes — Separating the real from the BS in insurance sales since 2019.