Insurance Town

This week  Heath Shearon, the Mayor of Insurance Town,  sits down with his good friend Craig Bender, the visionary behind InsureU2. In this episode, Craig shares his journey from a  big player in the paintball community as a young "kid" to a leader in the insurance industry. Discover how his unique approach to marketing and community building is reshaping the way insurance is perceived and practiced. Craig discusses the importance of authenticity in content creation, the power of community in driving industry change, and his vision for the future of insurance. He also opens up about his personal experiences, from his family's influence on his career to his innovative strategies for marketing and growth. Whether you're an industry veteran or new to the field, Craig's insights offer valuable lessons on leadership, resilience, and the art of building a lasting brand.

Chapters:

0:00 - 5:00- Introduction to Craig Bender

-Heath introduces Craig Bender and his accomplishments.
-Discussion on Craig's bi-coastal lifestyle and recent award.
 5:01 - 15:00Early Beginnings and Family Influence
-Craig's introduction to the insurance industry through his family.
-The impact of his mother's career and his early experiences.
15:01 - 30:00- Marketing Innovation and Insure U2
-Craig's pivot to marketing and the creation of InsureU2.
-The philosophy behind the brand and its community focus.
30:01 - 45:00 Content Creation and Industry Impact
-Craig's approach to content creation and its influence on the industry.
-The importance of authenticity and consistency in marketing.
45:01 - 60:00 Future Vision and Community Building
-Craig's vision for the future of Insure U2 and the insurance industry. 
-The role of community and collaboration in driving change.

Quotes:

"Unity is everything... it shows that we're all together and on the same page." - Craig Bender

 "If I want something, I need money for it. How do you get money? You work." - Craig Bender 

"The content is what's going to live forever... it's the message that I'm saying." - Craig Bender 

"It's not about speed to market when you're building a longevity company." - Craig Bender 

"I love insurance, but I also love seeing other people win." - Craig Bender

Tune in to hear more about Craig's inspiring journey and his plans for the future of the insurance industry. Don't miss out on the insights and strategies that can help you grow your own brand. Subscribe now for more episodes!

Sponsors:
Smart Choice Agents Program
Canopy Connect
Olde School Marketing

Episode Summary: Join us for an insightful conversation with Draye Redfern, a marketing expert with a rich background in insurance and a knack for innovative strategies. Draye shares his journey from working in his family's insurance agency to founding Redfern Media, a marketing agency that has helped numerous businesses thrive. Discover the power of direct mail, the importance of knowing your numbers, and the value of building personal connections in business.

00:02:00 Introduction to Draye Redfern and his background in insurance 
00:10:30 The power of direct mail in modern marketing. 
00:22:15 Draye discusses the ANKR framework for business growth.
00:35:45 The importance of personal branding and social media presence.
00:48:00 Understanding business metrics and their impact on success. 
1:05:00 Closing thoughts and Draye's upcoming projects.

Memorable Quotes:

"Good marketing is really, really impactful." – Draye Redfern 
"The riches are in the niches." – Draye Redfern
 "It's five times to 25 times more expensive to go get a new customer than it is to simply retain an existing one." – Draye Redfern
 "The sweetest sound of someone's ears is the sound of their own name." – Draye Redfern

Guest Information: Draye Redfern is the founder of Redfern Media and a seasoned marketing consultant. Connect with him on social media @DrayeRedfern or visit fractionalcmo.com for more insights.

Explore Draye's book, "The Recession Survival Guide," available on Amazon and Audible, and stay tuned for his upcoming release on the ANKR framework.

Sponsors:
Smart Choice
Canopy Connect
Olde School Marketing

In this Episode of Insurance Town, The Mayor Himself sits down and shares his experiences from IB FutureFest 2025, He shares his exhilarating experience at Future Fest, an innovative insurance festival held on the Santa Monica Pier. Discover the unique atmosphere, engaging activities, and insightful sessions that set this event apart from traditional conferences.

Festival Vibes: Future Fest's outdoor setting on the Santa Monica Pier created a vibrant, festival-like atmosphere with activities like yoga, putt-putt, and live music. Attendees enjoyed a unique blend of professional development and leisure. Engaging Sessions: The event featured diverse sessions on AI, cybersecurity, and leadership, with industry experts like Christopher Franklin sharing their insights. The sessions catered to both agencies and carriers, offering valuable content for all attendees. Networking Opportunities: Future Fest fostered meaningful connections, allowing attendees to engage in deep conversations and build lasting relationships. The atmosphere encouraged networking in a relaxed and enjoyable setting. Sponsors & Support: A special thanks to sponsors Smart Choice, Canopy Connect, and Old School Marketing for their continued support, enabling such enriching experiences.

Key Quotes:

"If you do what you love, you never have to work another day in your life."

 "Future Fest was like adult summer camp, with new friendships and meaningful conversations."

"The atmosphere was phenomenal, the backdrop was phenomenal, the speakers were phenomenal."

Shout Out: A big thank you to Insurance Business and Key Media for organizing such a groundbreaking event. Their dedication to creating a unique and engaging experience truly set Future Fest apart

Call to Action: Don't miss out on next year's Future Fest! Visit insurance.myfuturefest.com to join the waitlist for 2026.

Sponsors:
Smart Choice
Olde School marketing
Canopy Connect 

 Join us as we dive into an insightful conversation with Peter Flynn, who leads the personal lines vertical in the Americas for Exceedance. Discover his journey from an underwriting trainee at Chubb to his current role, and learn about the innovative ways Exceedance is transforming the insurance industry.

Peter's career path and experiences in the insurance industry The role of Exceedance in operationalizing insurance companies Insights on AI's impact on personal lines and customer service The evolving landscape of the E&S and MGA markets The importance of partnerships in the insurance ecosystem

Key quotes 

"Exceedance does everything an insurance company does except for take risk and distribute products."

"We tend to overestimate the impact of technology in the near term and underestimate it in the long term."

"If I were to invest my capital in taking risks right now, I'd want to do it on an E&S basis."

"I don't want to be called a vendor, I want to be a partner."

Sponsors:

Smart Choice
Canopy Connect
Olde School Markting

n this week’s visit to Insurance Town, I had the pleasure of sitting down with Spencer Witcher, a second-generation insurance pro who’s doing big things with Smart Choice. We had a real talk about the challenges agents face in hard-to-place markets — and how finding the right partners can make all the difference.

We peeled back the curtain on:

• What Smart Choice is doing to help agents thrive in California and other tough states
• How to write the business others shy away from — without jumping through hoops
• Why MGAs and non-traditional carriers might just be your new best friends
• The critical importance of relationships — not just for quoting, but for long-term success
• Building your book with depth, not just volume

Whether you're a seasoned agency owner or a producer looking to grow smarter, Spencer delivers actionable insights that’ll challenge the way you think about growth

 A big THANK YOU to the amazing folks who keep the lights on in Insurance Town:

  Smart Choice – Helping agents grow their book without adding overhead
  Canopy Connect – Making gathering client info as easy as pie
  Olde School Marketing – Bringing you hand-written, high-touch prospecting that works

 Make sure to like, subscribe, and leave a review!
New episodes drop weekly — straight from the heart of Insurance Town.

Think ChatGPT is just for writing emails? Think again. In this episode, Chris Green drops real-world prompts and jaw-dropping use cases that will make you rethink how you engage every prospect and client.

Is AI just another shiny object… or the secret weapon your agency has been missing?

In this high-energy episode of Insurance Town, the Flood Guru himself, Chris Green, steps into the Mayor’s office and throws down example after example of how he's using ChatGPT right now to:

✅ Personalize client interactions
✅ improve your team's experience
✅ build your own in house They ask you answer intranet
 ✅ Simplify complex insurance language
 ✅ Improve response times
 ✅ Drive more leads
 ✅ And yes… actually close more business

If you’ve ever said, “I don’t have time to figure out this AI stuff,” this is the episode you can’t afford to skip. Chris lays out a playbook so practical, you’ll be tempted to pause and try it mid-episode.

🔥 Brought to You By:

💥 Smart Choice – The fastest-growing agency network in the game. More markets, less headaches.
💥 Canopy Connect – The one-click solution for collecting insurance data without all the back and forth.
💥 Olde School Marketing – Direct mail that actually works. Get noticed, get leads, get growing.

🎧 Listen Now and Learn:

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 Choice – Your 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 Connect – The 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 Marketing – Direct mail that actually works. Handwritten postcards, real human touch, and just the right dose of nostalgia to stand out in a digital world.

In this episode of Insurance Town, host and Mayor, Heath engages with Allen Hudson at the PIA Virginia DC Conference. They discuss the critical importance of information sharing in the insurance industry, especially for independent agents. The conversation highlights the role of technology, particularly AI, in enhancing efficiency and specialization within agencies. Allen shares insights on the resurgence of independent agents and the necessity of niche specialization to compete in a changing market. The episode concludes with advice for both new and seasoned agents on how to adapt and thrive in the evolving insurance landscape.

takeaways

• Information sharing is essential for independent agencies.
• AI can streamline processes and improve efficiency.
• Niche specialization helps agencies stand out in the market.
• Independent agents are seeing a resurgence in demand.
• Proactive communication with carriers fosters better partnerships.
• Understanding carrier appetites is crucial for success.
• Technology can significantly enhance agency operations.
• Specialization allows for better training and support for staff.
• The insurance market is evolving, requiring adaptability.
• Building relationships with carriers can lead to better opportunities.

Chapters

00:00
Welcome to Insurance Town
02:12
3 people you would invite to your block party dead or alive?
03:53
what peice of tech could you not live without?

4:45
The Importance of Information Sharing
5:00

Embracing Technology in Insurance

05:14
Niche Specialization in Insurance

12:25
The Resurgence of Independent Agents

14:26
Advice for New and Existing Agents

20:25
Leveraging Technology for Efficiency

In this weeks episode the mayor sits down with his good friend and 2nd tine guest in Insurance Town. Only this time These two are live in The Home of Elvis Presley!

The mayor simply asked Marcus what have you learned about the insurance industry of the last year and some of the answers he gave to us blew my mind. 

Cause he’s working and Consulting with insurance agencies and said he talks about:

Insurance agencies don’t treat themselves like professionals and how they can do that better

The importance of AI, data, and automation is for your business

This man is so inspirational so much fun you gotta check this one out. It’s short sweet.

“The enemy of great is not bad it’s good.” 

Sponsors 

Smart Choice Agents 

Canopy Connect

This episode was recorded live from Memphis Tennessee at Graceland, Home of Elvis Presley, the King of Rock and Roll. From the PIA of Arkansas annual convention, the Mayor got to sit down with long time friend Courtney Fenske to talk about her life from Account Manager to successful Territory Manager at Accuity. She is such a value add to not only her agents but also this industry earning her multiple awards over the past few years and the respect of so many. Check out this amazing conversation and hear more from her journeys in Arkansas.

Sponsored by :

Smart Choice Agents -

Canopy Connect -

Olde Schoool Marketing

And watch it on Youtube as well.