How Do You Build a Thriving Agency Without Losing Your Marriage—or Your Mind?

How Do You Build a Thriving Agency Without Losing Your Marriage—or Your Mind?

Author: Heath Shearon June 19, 2025 Duration: 31:22

In this epsisode of Insurance Town the mayor sits down with two of his favorite people Jessica Holder and Keenan Rice on a previously recorded episode of the VIP Podcast. I am so impressed with these two, their marriage, parenting, agency, etc  this forward-thinking power couple are continuing to rise above and face various challenges head on. Jessica and Keenan have such an amazing balance at home and at the office. They have a great balance of community involvement and innovative technology at their fingertips, and lastly, they have a great balance of work and fun in their agency. 

We talk about:

The delicate balance of marriage and co-ownership of a growing agency
How human touch and community involvement is possible with the right technology in your agency
How the emphases on educating their community on the intricacies of insurance is so valuable to their growth
Their powerful message of staying true to yourself and not sacrificing authenticity 
Get ready to be inspired and educated by this episode. It's a good thing there is a rewind button, this one is full of impactful moments.

A special shout out to Vertafore for letting me reuse this episode : vertafore.com 

 A Special Thanks to Our Sponsors:

🛠️ Smart ChoiceYour partner for market access without the headaches. Whether you're a new agency or a seasoned vet, Smart Choice helps you stay independent while expanding your carrier options.

🔐 Canopy ConnectThe one-click solution for collecting insurance data. Save time, improve your close rate, and give your clients a seamless experience—because the quoting process shouldn’t feel like pulling teeth.

📬 Olde School MarketingDirect mail that actually works. Handwritten postcards, real human touch, and just the right dose of nostalgia to stand out in a digital world.


Heath Shearon has spent years navigating every corner of the insurance industry, and in Insurance Town, he acts as your guide through its often complex landscape. Think of each episode as a casual, informative conversation held on the front porch of a town built entirely on insurance knowledge. Heath, who jokingly refers to himself as the Mayor, doesn’t just lecture; he brings in the many friends and colleagues he’s met over his career for genuine discussions that break down real-world scenarios. You’ll hear practical advice, behind-the-scenes insights, and straightforward explanations designed for both industry newcomers and seasoned professionals. This isn't about dry theory-it's about the tangible how-to and the why behind common business and personal coverage questions. The tone is welcoming and grounded in experience, set to a bluesy soundtrack courtesy of Daddy Long Legs. Tune into this podcast for a unique blend of business education and relatable storytelling that makes the intricacies of insurance feel approachable and even engaging.
Author: Language: English Episodes: 100

Insurance Town
Podcast Episodes
Why blindly trusting technology can lead to significant risks... [not-audio_url] [/not-audio_url]

Duration: 36:34
In this engaging conversation, Heath Shearon and Alex Rodov explore the vibrant culture of Toronto, the evolution of technology and quality assurance, and the critical role of testing in the insurance industry. Alex shar…
No such thing as a bad lead... here's why... [not-audio_url] [/not-audio_url]

Duration: 53:22
This week in Insurance Town I sat down with my friend Evan Smith of Mav. We had an incredible conversation about growing your sales with leads and building an inside sales team . We discussed the importance of recognizin…
AI in Insurance: Beyond the Buzzword [not-audio_url] [/not-audio_url]

Duration: 46:41
In this episode of the Insurance Town Podcast, Heath Shearon hosts Christopher Frankland to discuss the intersection of technology and insurance, focusing on AI's impact on the industry. They explore the concept of the '…
Who would you invite to your block party? [not-audio_url] [/not-audio_url]

Duration: 24:06
This is an episode recorded at the PIA VADC conference in Virginia Beach with my man Byron Roberts. It is a fast, on-the-ground conversation about how Openly built for independent agents, why speed still matters, and how…
Grit, Growth and Gumption , Revisted [not-audio_url] [/not-audio_url]

Duration: 54:59
In this weeks episode, the mayor sits down with his good friend Tinsley English to discuss her latest book titled Grit, Growth & Gumption. But this episode is way beyond that we discuss being a leader in this service ind…
Hard to Place, Easy to Profit: The Art of Captives [not-audio_url] [/not-audio_url]

Duration: 1:02:07
In this episode, the Mayor sits down with industry veteran Jeff Kleid a 30-year insurance innovator, MGA, and carrier leader to talk about the business of hard-to-place risks, the truth about captives, and how brokers ca…
The best tech make great service feel effortless (re-visit) [not-audio_url] [/not-audio_url]

Duration: 52:09
In this weeks episode of Insurance Town, The Mayor welcomes good buddy Patrick McBride to the show. Patrick, a seasoned insurance professional, shares his journey, experiences, and insights on the industry's evolving lan…
What are the biggest data challenges in Insurance right now? [not-audio_url] [/not-audio_url]

Duration: 47:59
In this episode of Insurance Town, the Mayor, Heath Shearon welcomes Jamie Peers really just to catch up and have a chat, but this lead to hitting the record button, and discussing the evolving landscape of the insurance…