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 min read

Connected Conversations in Insurance: James Jenkins

Published on
March 4, 2025
Contributors
Nick Berry
Demand Generation Marketing Manager

Nick is the Demand Generation Marketing Manager at Canopy Connect, where he brings 20 years of sales and marketing experience, including the last 6 years focused on broker tech companies. When he's not managing marketing campaigns, he's likely sipping on a dirty chai latte (hot) or building side projects to keep his skills sharp. Nick is a proud USAF veteran and a family man with 4 kids.

Hey everyone, Nick Berry here, Demand Gen Manager at Canopy Connect, and I’m excited to kick off the new season of Connected Conversations in Insurance! In our first episode, I had the pleasure of sitting down with my friend James Jenkins, the founder of RiskWell Insurance and host of the Agency Freedom Podcast. We dove into the evolution of podcasting in the insurance industry, the power of hyperlocal content, and why meaningful conversations matter more than chasing influence.


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How James Got into Podcasting

I had to ask James—why start a podcast? Turns out, he never planned on it. He got nudged (or maybe pushed) by industry peers who saw his knack for engaging conversations. What started as a resource for insurance professionals navigating the shift from captive to independent agencies has now become a platform for exploring freedom—freedom in operations, tech, branding, and growth.

Does a Podcast Actually Help Your Business?

Does having a podcast actually bring in business? James was pretty clear: his Agency Freedom audience isn’t full of prospective clients for RiskWell, but that’s not the point. The real win is thought leadership, networking, and credibility. He warned against the trap of trying to be "insurance famous"—instead, he focuses on delivering real value.

Why Hyperlocal Podcasts Are a Game Changer

Now, this is something I’m really passionate about. We talked about how hyperlocal podcasts can be a goldmine for insurance agents. James’ McKinney Podcast has helped him build deep connections in his community without ever directly marketing his insurance business. Just by having real conversations with local leaders, business owners, and city officials, he’s built trust—and, eventually, business opportunities.

Thinking of Starting a Hyperlocal Podcast? Here’s James’ Advice:

If you’re an insurance agent considering a podcast, James had three big takeaways:

  1. Plan Your First 50 Guests – This sets you up for success and ensures you’re not scrambling for content.
  2. Build Efficient Systems – Automate scheduling, guest intake, and production so you can focus on the conversations.
  3. Stay Committed – A lot of podcasts don’t make it past 20 episodes. Consistency is the key to growth.

Why Authenticity Matters

James and I both agree—success in podcasting isn’t about self-promotion, it’s about having real, valuable conversations. Whether you’re focusing on industry insights or hyperlocal content, authenticity is what resonates with listeners.

If you haven’t checked out the episode yet, give it a listen on your favorite podcast platform by searching Connected Conversations in Insurance. More great conversations coming your way this season—stay tuned!