Lighting a fire — with Diana Miller

By Paul Wilson & Lily Peterson
Podcast
October 21, 2026 at 03:53 PM
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In this episode, we sit down with Diana Miller, benefits advisor at Conner Insurance and a 2025 Advisor of the Year finalist!

We discuss her experience growing up in Colombia during a turbulent political era and her journey to the U.S. for college, where she had to navigate the complex and costly immigration system before she became a U.S. citizen. Diana discusses her surprise $40K hospital bill that helped open her eyes to health care markups and motivated her toward to seek career in health benefits and patient advocacy. She also shares how these experiences influenced her perspective and empathy.

We touch on her career arc, going from banking to a traditional benefits agency to her meeting Ben Conner, CEO of Conner Insurance, a connection that moved her into the world of non-traditional, cost-effective benefit strategies.

We also chat about Diana's advocacy for direct primary care in Iowa through her personal experiences with rushed pediatric visits and surprise charges under traditional fee-for-service models, as well as the challenge of balancing industry critiques with optimism.

Finally, we close out the conversation by getting to know Diana on a personal level. We talk books, hikes (both in Colombia and Dubuque, Iowa) and how Diana chooses to relax and refresh!

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