Connected Conversations in Insurance | Episode 8 ft. Michael Overstreet
What do lawn care and insurance have in common? According to one of our guests on Connected Conversations in Insurance, more than you’d think. I had the chance to sit down with Michael Overstreet, Chief Marketing Officer at Heritage in Arizona—the same Michael you might know online as The Gardening Nerd. What started as a conversation about marketing quickly turned into a broader reflection on passion, content, and how blending the personal and professional can build real connections.
How Michael Found Insurance—and His Voice
Like a lot of us in the industry, Michael didn’t grow up dreaming of insurance. He got pulled in by family ties, his dad worked in life insurance, and started his career at Allstate. Fast forward almost 20 years, and he’s helped co-create Heritage through a series of mergers and partnerships with other agents. Michael found his niche when it came to marketing. “Jeremy and Caleb said, ‘Hey, we don’t like marketing. You’re good at video content. You be our CMO,’” he told me. And that’s exactly what happened. He leaned into what he was good at, and it started to click.
The Gardening Nerd Is Born
Now here’s where it gets fun. Michael didn’t stop at insurance content. He took his love for gardening—specifically Arizona-style lawn care—and started posting videos and tips online. It turns out, people loved it. “People like content that I make about insurance—and insurance is boring,” he joked. But the gardening content? That took off. His YouTube channel and newsletter now reach thousands of people who know and trust him, not just as an insurance pro, but as someone who helps them with their yard.
“As long as you have personality and you give people the answers to their questions, they don’t really care about production quality.”
Michael Overstreet, Chief Marketing Officer at Heritage
In other words, it’s not about having a polished studio setup. It’s about showing up and being helpful.
Turning Passion Into Pipeline
You might be wondering: how does gardening lead to insurance leads? Michael broke it down perfectly. He runs a Facebook group called Perfect Lawns of Arizona, filled with homeowners who care enough to spend time on their yards. And guess what? Those folks are often great insurance clients. “Anybody that takes time to take care of their lawn...they're a preferred insurance client,” he said. They’re usually homeowners, they’re detail-oriented, and they’re engaged. That group has become a powerful (and organic) pipeline.
The Power of Just Hitting Record
Michael’s advice for agents trying to get into content: keep it simple.
“Get out your cell phone, shoot a video, show your passion. People are gonna come to you.”
Michael Overstreet, Chief Marketing Officer at Heritage
And he’s living proof. We talked about how sometimes the best-performing content isn’t the slickest. It’s the selfie video, the unfiltered take, the one where you’re just being yourself. When Michael shows his face on camera, he says, engagement doubles. And he’s right. In a world full of ads, it’s the authenticity that cuts through. It’s the emotion. It’s the story behind the post. That’s where the magic is.
Blending Life and Work (Without Forcing It)
Michael’s approach is refreshing. He doesn’t force a connection between gardening and insurance. It happens naturally because he’s genuinely interested in both. And that shows. “Now people know me as a personality,” he said. “Then whatever service I’m gonna offer them, whether it’s insurance or yard care consulting, they already know, like, and trust me.” If there’s one big takeaway from our conversation, it’s this: lean into what lights you up. Whether that’s lawn care, baking, travel, or dogs, whatever you genuinely enjoy, share it. You never know who’s watching or how it might open doors in your business.
Listen to the full episode of Connected Conversations in Insurance wherever you get your podcasts. And if you want to follow Michael’s journey, check him out on Facebook as Michael Overstreet and on Instagram at @the_garden_nerd.