Hard to Place, Easy to Profit: The Art of Captives

Hard to Place, Easy to Profit: The Art of Captives

Author: Heath Shearon October 9, 2025 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 can turn complex accounts into profitable opportunities.

From selling insurance on the internet in the ‘90s to building niche programs for cannabis, film, and trucking, Jeff shares real-world lessons about taking chances, trusting data, and transforming the way independent agents think about risk.

In this episode, we discuss:

  • The evolution from retail broker to MGA and carrier
  • Why most agents misunderstand captives (and how to use them right)
  • Building programs for high-risk industries like towing and hemp
  • How to niche down without boxing yourself in
  • The role of AI in underwriting and program innovation

Key Takeaways:

  • Don’t fear the hard-to-place — that’s where opportunity lives.
  • Captives aren’t restrictive; they empower growth and control.
  • Niche success is built on relationships and risk awareness.
  • AI is a tool, not a replacement — human insight still wins the day.

Connect with Jeff Kleid:


Special Thanks to Our Sponsors:
🧡 Smart Choice – The fastest-growing agency network helping independent agents write more business and earn more income.
🔗 Canopy Connect – The easiest way to collect your client’s insurance information in seconds.



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
Lazy River Files Part 3 [not-audio_url] [/not-audio_url]

Duration: 22:41
In this weeks episode we release more from the Lazy River, Casey Nelson's idea that has been such an amazing addition to the show. I appreciate all of the feedback I have gotten from these, so I will leak a few more out…
How do I know if I am burned out or just stressed out? [not-audio_url] [/not-audio_url]

Duration: 59:56
This Week In Insurance Town, we uncover practical insights and inspiring stories with Chelsea Bell Carpenter as she shares her journey through the insurance industry, mental health strategies, and the importance of inten…
What Are the Secrets to Long-Term Success in Insurance? [not-audio_url] [/not-audio_url]

Duration: 54:18
In this episode, Jason Peacock shares invaluable insights from his nearly three-decade career in insurance, emphasizing the importance of relationships, niching, and strategic follow-up. Whether you're just starting out…
Choose Africa - Re-Visit [not-audio_url] [/not-audio_url]

Duration: 54:51
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 sh…
Are You Truly Connecting with Your Clients or Just Talking at Them? [not-audio_url] [/not-audio_url]

Duration: 42:07
You know that room in grandmas house that was that room that you didn’t sit in the furniture, you didnt touch anything? It was just pretty and you gotten threatened every time you went into that room?In this weeks episod…
More from the Lazy River Files [not-audio_url] [/not-audio_url]

Duration: 36:20
It's another episiode of Insurance town from the Lazy river!! With Ben Morrow, Brenden Corr, Marques Ogden, Jessica, Casey Nelson, Caleb Cramer, etc. Its FunSponsorsCanopy Connect MAVGoli= Go.Goli.com/Mayor
How to stop being overlooked! (warning this one is High Octane) [not-audio_url] [/not-audio_url]

Duration: 46:17
In this episode of Insurance Town, the Mayor sits down with his good friend, Emily Merola. Emily Merola is an executive presence expert, speaker, and founder of The Blazer Society who helps leaders go from overlooked to…