Insurance Town

In this episode of Insurance Town, Heath Shearon sits down with Kimiko Donahue, an insurance pro who has done it all—captive agent, independent agency owner, carrier rep, and now a coach helping business owners find their path.

What You'll Learn in This Episode:
🚀 Kimiko’s Journey – From selling car washes to running a successful independent agency.
💡 Lessons from Captive to Independent – Why her training in the captive world helped shape her sales approach.
🤝 Building Strong Carrier Relationships – How understanding the carrier side can make you a better agent.
🔥 Coaching & Mentorship – Why finding the right mentors and mastermind groups can make all the difference.
💪 Turning Adversity into Strength – How overcoming personal struggles has fueled her success.
🎶 The Power of Music – How music can be a game-changer in business and life.

Key Takeaways:
✔️ The importance of selling on value instead of price.
✔️ Hard markets affect everyone, but mindset and strategy make the difference.
✔️ Why turning away the wrong business can actually help you grow.
✔️ The power of mentorship, coaching, and masterminds to break through limitations.

Kimiko’s story is inspiring, insightful, and packed with wisdom for agents at every stage.

Sponsors:
A big thank you to our sponsors for making this episode possible!

Smart Choice – Looking for a great partner to help grow your agency? Check out Smart Choice for all your agency needs.

Canopy Connect – Want to simplify the way you collect client information? Visit  to see how Canopy Connect can help streamline your agency’s processes.

Olde School Marketing – For all your marketing and promotional needs, Olde School Marketing has you covered. Reach out today to level up your marketing game!

🎧 Listen Now and get inspired!

In this captivating episode of the Insurance Town Podcast, Mayor Heath Shearon welcomes the tech-savvy and insightful Mike Todasco. Known for his rich background in innovation and technology, Mike shares his journey from working at PayPal to becoming an expert in generative AI.

Together, they dive deep into how AI is transforming industries, including insurance. Mike explains the disruptive journey of PayPal, the evolution of mobile payments, and the strategic pivots that kept the company at the forefront of digital transactions. The conversation then shifts to the power of AI and its incredible potential to revolutionize the way agencies operate.

From comparing insurance policies to streamlining daily tasks, Mike and Heath explore innovative AI use cases that can simplify processes and enhance customer experiences. Whether you’re an AI skeptic or already experimenting with ChatGPT, this episode is packed with practical ideas and inspiration to take your agency to the next level.

Key Takeaways:

• AI's Role in Business Evolution: How PayPal leveraged AI and technology to transform digital payments.
• Generative AI in Insurance: Practical use cases for streamlining policy comparisons and enhancing customer communication.
• Embracing Technology: Why insurance agencies should overcome tech hesitancy to stay competitive.
• Personalized AI Applications: How to tailor AI tools to fit your agency's unique needs and voice.

Sponsors:
A big thank you to our sponsors for making this episode possible!

• Smart Choice: Looking for a great partner to help grow your agency? Check out Smart Choice for all your agency needs.
• Canopy Connect: Want to simplify the way you collect client information? Visit UseCanopy.com/heath to see how Canopy Connect can help streamline your agency’s processes.
• Olde School Marketing: For all your marketing and promotional needs, Olde School Marketing has you covered. Reach out today to level up your marketing game!

Tune in now to discover how AI can transform your agency and learn from one of the industry's brightest minds!

In this episode I just want to say thank you and to make an announcement or two !! Please take a few minutes to subscribe and download this little episode for future listen if ya want but make sure you do. We have some big things coming up here in Insurance town! Love you all! thank you all !! See you soon ! 

Sponsors:

A big thank you to our sponsors for making this episode possible!

Smart Choice – Looking for a great partner to help grow your agency? Check out Smart Choice for all your agency needs.

Canopy Connect – Want to simplify the way you collect client information? Visit UseCanopy.com/heath to see how Canopy Connect can help streamline your agency’s processes.

Olde School Marketing – For all your marketing and promotional needs, Olde School Marketing has you covered. Reach out today to level up your marketing game!

🎧 Listen, Subscribe & Leave a Review!
If you enjoyed this episode, please subscribe and leave us a review on your favorite podcast platform. Stay tuned for more great conversations in Insurance Town! 🚀

In this episode of Insurance Town, host Heath Shearon sits down with Brenden Corr to catch up on life, career changes, and the powerful work he's doing with Project 55—a mental health initiative focused on supporting employees in the insurance industry.

Brenden shares insights into his transition from Lost Run Pro, the importance of prioritizing family, and his passion for mental health advocacy in the workplace. The conversation takes a deep dive into how mental health affects insurance professionals, especially during challenging market conditions.

Key Takeaways:

• Life Updates from Brenden Corr – Moving from Lost Run Pro and what’s next.
• The Reality of Small-Town Montana – Why locals have mixed feelings about Yellowstone.
• Understanding Project 55 – A movement aimed at providing free mental health resources to insurance professionals.
• Workplace Mental Health Awareness – Why leaders need training to support their teams effectively.
• The Hard Market’s Mental Toll – How insurance agents, CSRs, and account managers can manage stress.
• Breaking the Stigma – Heath and Brenden discuss generational shifts in mental health conversations.

About Project 55

Project 55 is designed to bridge the gap between mental health struggles and access to help, offering:

• Free resources for mental health education.
• A community forum for peer support.
• A first responder training program for agency leaders to better support employees.

Check it out: Project55.org

Final Thoughts

Mental health isn’t a weakness, and you’re not alone. Whether you're struggling with tough client conversations, workplace stress, or personal challenges, help is available.

📢 Don’t forget to share this episode with your colleagues—mental health awareness starts with a conversation!

Sponsors:

A big thank you to our sponsors for making this episode possible!

Smart Choice – Looking for a great partner to help grow your agency? Check out Smart Choice for all your agency needs.

Canopy Connect – Want to simplify the way you collect client information? Visit UseCanopy.com/heath to see how Canopy Connect can help streamline your agency’s processes.

Olde School Marketing – For all your marketing and promotional needs, Olde School Marketing has you covered. Reach out today to level up your marketing game!

In this episode of Insurance Town, host Heath Shearon sits down with Kyle Kuest, a dynamic sales professional at Vertafore, to talk about his unique journey from ministry work to the world of insurance technology sales. Kyle shares how his background in the church, his passion for history, and his experience in teaching shaped his approach to sales, customer service, and leadership.

Kyle and Heath discuss:
✔️ Lessons from Ministry & Teaching – How active listening, empathy, and organization play a vital role in sales.
✔️ Sales Strategies in a Hard Market – Why agencies should focus on organization, proactive communication, and leveraging technology.
✔️ The Power of Workflow & CRM – How AgencyZoom and Vertafore’s management systems help agencies streamline their processes.
✔️ Overcoming Challenges – Advice for insurance professionals navigating the current market.
✔️ The Importance of Community & Collaboration – Why independent agencies should work together rather than compete in isolation.

Kyle also shares his winning strategies that helped him earn awards in his first year at Vertafore and provides practical tips for insurance professionals looking to level up their sales game.

Connect with Kyle Kuest:

📌 LinkedIn: Kyle Kuest
📌 Vertafore: www.vertafore.com

Sponsors:

A big thank you to our sponsors for making this episode possible!

🟠 Smart Choice – Looking for a great partner to help grow your agency? Check out Smart Choice for all your agency needs.

🟠 Canopy Connect – Want to simplify the way you collect client information? Visit UseCanopy.com/heath to see how Canopy Connect can help streamline your agency’s processes.

🟠 Olde School Marketing – For all your marketing and promotional needs, Olde School Marketing has you covered. Reach out today to level up your marketing game!

🎧 Listen, Subscribe & Leave a Review!
If you enjoyed this episode, please subscribe and leave us a review on your favorite podcast platform. Stay tuned for more great conversations in Insurance Town! 🚀

#InsuranceSales #HardMarket #InsuranceTechnology #Vertafore #AgencySuccess

In this episode of Insurance Town, Mayor Heath Shearon sits down with his good friend and insurance powerhouse, Ariel Rivera, the newly appointed President of PIA National. Ariel shares his journey, the responsibilities of his new role, and how he’s embracing the challenges of leadership in the independent insurance world.

Episode Highlights:
✅ Ariel’s Journey to Leadership – From starting in the industry to becoming the youngest-ever PIA National President, Ariel reflects on his path and what drives his passion for the independent agency space.

✅ What PIA Does for Agents – Ariel breaks down the advocacy, education, and networking opportunities PIA provides, and why agents need to be engaged to reap the full benefits.

✅ Hard Market Realities – Ariel and Heath discuss the ongoing hard market, its impact on independent agents, and what agents can do to navigate these challenging times.

✅ Advocacy Matters – Hear Ariel’s firsthand experience testifying before Congress about flood insurance reform, and why agents need to be aware of legislative issues affecting the industry.

✅ Cyber Insurance & RGS – Ariel shares his work with RGS, helping agencies provide cyber coverage solutions in a rapidly evolving digital landscape.

✅ Stronger Together – The importance of unity and collaboration in the insurance space, and how the PIA is growing stronger through collective action and support.

Heath and Ariel bring the energy, passion, and love for the industry in this episode—one you don’t want to miss!

Sponsors:
A big thank you to our sponsors for making this episode possible!

🔹 Smart Choice – Looking for a great partner to help grow your agency? Check out Smart Choice for all your agency needs.

🔹 Canopy Connect – Want to simplify the way you collect client information? Visit UseCanopy.com/heath to see how Canopy Connect can help streamline your agency’s processes.

🔹 Olde School Marketing – For all your marketing and promotional needs, Olde School Marketing has you covered. Reach out today to level up your marketing game!

🎧 Tune in now and let’s talk insurance! 🚀

In this episode the Mayor, interviews his new friend Caleb Burkey, and experiences a light bulb moment!  We really hope you do as well. This one is a game changer on so many levels. If you want to actually understand Parametric Insurance AND get to eaves drop on a great conversation, press play now. This one is a good one.

Sponsors:

Smart Choice Insurance 
Canopy Connect
Olde School Marketing

Replay Episode !!

This week In Insurance Town the Mayor sits down with his good friend Becky Monfre, VP of Digital Accounts at Coterie Insurance. Becky Monfre, joins us in Insurance via the Vertafore Insurance Podcast. to talk about how Coterie is making small commercial Insurance easier. She has been in the industry her entire career and understands the value of speed and efficiency for commercial insurance.  As the head of digital distribution, she loves helping agents to embed small commercial insurance capabilities on their website. Becky and the Mayor talk about everything from Raising Kids to Growing small commercial insurance and even get into some Hot takes along the way... 

Sponsors:
Smart Choice
Canopy Connect 
Olde School Marketing 

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 industry. We discuss the challenges, the customer service, reps face, the challenges that managers face.

We also discuss accepting God’s calling in your life no matter how difficult that might be, or scary that might be. This episode is a really really good one. 

I couldn’t do this show without my amazing sponsors 

Smart Choice – the fastest growing agency network hands-down. With over 10,000 agencies across the country, trusting them and over 11 billion written premium

Canopy connect – you’re one click solution to getting the deck pages you need to quote your prospects

Olde school marketing -the new school approach to an old-school way of marketing

In this episode of The Insurance Town Podcast, host Heath Shearon sits down with Teresa Kitchens, a dynamic agency owner and podcaster, to explore her remarkable journey of resilience, leadership, and transformation both personally and professionally.

Key Highlights:

• Facing and Overcoming Adversity: Teresa shares deeply personal experiences, including her children's mental health struggles and navigating divorce, while balancing business challenges. These life-altering events shaped her leadership philosophy and the structure of her agency.
• Virtual Agency Model: As a pioneer of virtual operations, Teresa discusses the motivations behind creating a remote-friendly business and the positive impact it’s had on her team and culture.
• Leadership and Team Development: Insights into fostering a collaborative and accountable team culture, where members are supported through challenges and empowered to lead.
• Personal Growth and Mindset Shifts: How self-reflection, books like John Acuff's Start, and introspection allowed Teresa to transform her fears into stepping stones for growth.
• Blended Family Dynamics: A candid look into the ups and downs of second marriages and blended families, with lessons on communication, compromise, and perseverance.
• Building Strong Client Relationships: Teresa emphasizes the importance of humanizing client interactions, understanding their struggles, and aligning business operations with empathy.

Memorable Quotes:

• “Our fears were creating everything we didn’t want, but acknowledging them allowed us to grow beyond them.”
• “As a leader, you must give your team space to heal and grow. Honor their journey—it strengthens the entire organization.”

I love interiewing other podcasters its so fun, Listen to her podcast, Power Women in Insurance, where she uplifts voices and stories of women in the insurance industry.

Sponsors: A big thank you to our sponsors for making this episode possible!

• Smart Choice: Looking for a great partner to help grow your agency? Check out Smart Choice for all your agency needs.
• Canopy Connect: Want to simplify the way you collect client information? Visit UseCanopy.com/heath to see how Canopy Connect can help streamline your agency’s processes.
• Olde School Marketing: For all your marketing and promotional needs, Olde School Marketing has you covered. Reach out today to level up your marketing game!