June 19, 2026

Episode 592 - Smart People, Silly Systems: With Debra Kilsheimer

Episode 592 - Smart People, Silly Systems: With Debra Kilsheimer
Episode 592 - Smart People, Silly Systems: With Debra Kilsheimer
The Soul of Enterprise: Business in the Transformation Economy
Episode 592 - Smart People, Silly Systems: With Debra Kilsheimer
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Debra Kilsheimer joins Ron and Ed for a lively discussion about leadership, culture, AI, persuasion, human nature, and the curious ability of professionals to simultaneously complain about a problem and defend the system causing it.

We'll also explore what wisdom comes with experience, why logic is a surprisingly ineffective tool for changing minds, and whether the accounting profession is finally approaching an inflection point—or just finding new ways to avoid one.

And yes, at some point we'll probably talk about the Pink Cadillac.

Debra's Bio

Debra Kilsheimer is what happens when you combine a CPA, a stand-up comic, a leadership coach, a technology enthusiast, and enough energy to power a small city. A longtime champion of helping accountants become better leaders, communicators, and human beings, Debra has spent years challenging firms to stop doing things simply because "that's the way we've always done it."

She's a speaker, consultant, podcaster, AI enthusiast, former Mary Kay superstar, and one of the few people who can simultaneously make you laugh, think, and question your entire business model. She's a friend of the show, and recently returned from Scaling New Heights, where she was recognized for her work in AI innovation.