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.

SHOW NOTES

Segment one

Debra just returned from Scaling New Heights where she was a main stage speaker https://www.woodard.com/speaker-listing-scaling-new-heights-2026
On resistance to change in the accounting industry: “What’s the WORST thing that can happen if you make a mistake as an accountant? You pay a fine.” —Debra Kilsheimer
As a CPA, Debra did the tax returns for a Mary Kay salesperson. Thinking about leaving the accounting industry, Debra made the transition to Mary Kay early in her career. And yes, a pink Cadillac was involved.
Today I learned, on the basis of sales commissions, Mary Kay claims to have created more female millionaires than any other organization in the United States

Segment two

Why did Mary Kay choose pink? In the 1960s, most American bathrooms were white. So pink was chosen for the Company's packaging to give women beauty products they could keep conveniently on their bathroom counters.
Interesting conversational theme from Scaling New Heights this year: It mostly focused on AI and the reticence or fear around adoption. In other words, many accounting professionals are excited but do not know where to begin.
On magic vs logic work (with a hat tip to Tim Williams): “How are we creating additional value for those that we serve, and how can we use AI to do that?” —Ed Kless

Segment three

Ron: “We spend hardly any time discontinuing obsolete practices. Why do you think that is?”
Debra: “Well, they’re easy. I’m used to doing it like that. Making a change is hard.”
Did you see new tech at Scaling New Heights that excited you? “People are getting really excited about the AI GLs that are coming out.” —Debra Kilsheimer
Rise2040: Co-creating our profession’s future https://www.aicpa-cima.com/advocacy/landing/rise2040
How do we recruit new accountants with a message on a wrapped car? “If you want to make someone’s dreams come true, follow me!” —Debra Kilsheimer

Segment four

GetBlazr is a new venture from Debra Kilsheimer. Check it out here: https://getblazr.ai/
“I love being an accountant. I love it. I do think we change lives. So, I just want to make it more fun for the people on the side, the customers.” —Debra Kilsheimer
A big THANK YOU to Debra Kilsheimer for joining us today. You can find her on LinkedIn at this link https://www.linkedin.com/in/debliberate

Bonus Content is Available As Well

Did you know that each week after our live show, Ron and Ed take to the microphone for a bonus show? Typically, this bonus show is an extension of the live show topic (sometimes even with the same guest) and a few other pieces of news, current events, or things that have caught our attention.

Click the “FANATIC” image to learn more about pricing and member benefits.