Insurance Town

In this weeks episode of Insurance Town, The Mayor Heath Shearon, sits down with Valerie Bowden, founder of Crdle, to discuss the evolving landscape of outsourcing and the unique opportunities Africa presents. Valerie shares her journey from backpacking across Africa to establishing a successful outsourcing company that champions fair wages and ethical practices. Discover how Crdle is changing the game by connecting businesses with talented professionals from the continent.

 Introduction

Host introduction and episode overview Shoutout to sponsors: Smart Choice and Canopy Connect
[03:15] Valerie's Journey

Valerie shares her adventurous backpacking trip across Africa How her experiences led to the founding of Cradle

[10:45] The Cradle Mission

Discussion on ethical outsourcing and creating sustainable jobs The importance of fair wages and supporting African talent

[18:30] Bridging the Gap

How Cradle connects African professionals with global businesses Success stories and client experiences

[25:00] The Role of AI

Valerie's insights on AI's impact on virtual assistants How AI tools enhance the capabilities of offshore teams

[32:15] Tips for Hiring Offshore Talent
Valerie's advice for businesses looking to hire from Africa Best practices for onboarding and training virtual assistants

[40:00] Closing Thoughts

Valerie's vision for the future of outsourcing Final words and how to connect with Valerie and Cradle

Sponsors:

Smart Choice: The fastest growing agency network, offering a wide range of services to help agencies thrive. Visit smartchoiceagents.com for more information.
Canopy Connect: Revolutionizing the way agencies handle client data with their innovative intake form platform. Learn more at usecanopy.com.

Want to work with Crdle ?
want to contact Valerie Bowden

In this episode, Mayor Heath Shearon, sits down with Thomas Mann to explore the intersection of technology and operations in the insurance industry. Discover how Thomas's journey from a multi-generational insurance background to a tech-focused role has shaped his approach to agency success. They discuss the importance of integrating technology with operations, avoiding common pitfalls, and the value of involving your team in tech decisions.

"Nothing is fully launched until it's embedded in a process."

"You should design your processes and your tech stack around the customer journey."

"The greatest piece of tech that ever existed is just going to be a drain on the P&L if your people don't use it."

Key Topics:

The evolution from agency to tech operations 
Importance of aligning technology with agency processes
Avoiding shiny object syndrome in tech adoption
The role of team involvement in tech decisions
Insights on building a cohesive tech ecosystem

Connect with Thomas Mann on LinkedIn or visit agency-focus.com to book a call and explore how to enhance your agency's tech and operations.

Link in first comment.

In this weeks episode, you are simply eavesdropping in on a fun conversation with me and two of my faves, Lindsay Wallace & Caleb Cramer . It is part goofy, and part serious but it’s all heart and it’s all fun trying out a new format here on this one and I’d love to hear your thoughts.

I am so incredibly lucky I get to do this show every week. It makes me completely happy and it couldn’t be done without you. Thank you for listening. Thank you for subscribing. Thank you for helping me achieve my dreams.

Thank you to my sponsors
Smart Choice® fastest, growing agency network, hands-down.
Canopy Connect - the one click solution to getting dec pages,loss runs, but now they have a new intake platform you’ve got to check out

In this Episode Our Mayor, Heath Shearon as he sits down with Hari Srinivasan to explore the fascinating world of life insurance. From cricket to Cardinals, and from tech to insurance, Hari shares his journey and insights into making life insurance accessible and meaningful. Discover how iCover is revolutionizing the industry with its innovative platform and community-focused approach. Hari shows us the importance of personal passion in entrepreneurship. We also hear about iCover's unique approach to life insurance The role of community insurers

Thank You to Our Sponsors:

Smart Choice: Your partner in insurance solutions.
Canopy Connect: Simplifying insurance verification
Olde School Marketing: Bringing traditional marketing into the digital age.

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

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New episodes drop weekly — straight from the heart of Insurance Town.