Erin Diehl: The Fail-fluencer Behind The Business of Joy—Laughing Through Limbo — Part One

Part One.

Today’s guest is Erin Diehl, founder and CEO of Improve It, a company that uses improv to help teams grow and thrive. Like me, she’s also a top podcast host!

From a young age, Erin dreamed of becoming a talk show host. Why did she choose that path? And how did her journey lead her to combine improv and business?

I told Erin, “You’re in the business of joy.”

But beyond joy, we also talked about failure. Erin calls herself a “failfluencer”—a blend of failure and influence. This two-part series dives into her unique approach to joy, failure, growth, and learning.

Key Highlights of Our Interview:

Improv Meets the Corporate World

“I didn’t plan to merge improv and business. But during my nine-to-five at a recruiting firm, my nights were dedicated to stages at Second City and ImprovOlympic. Suddenly, I saw how listening, empathy, and quick thinking from improv transformed my work life. The dots connected.”

United We Innovate

“Pitching an improv workshop to United Airlines was a gamble, but it paid off—literally. What started as a passion experiment became a calling when United became my first paying client. Improv wasn’t just for the stage anymore.”

The Teacher’s High

“That feeling of guiding someone toward growth is intoxicating. It’s a high I kept chasing, and the more I taught, the more I wanted to do it. Seeing others find joy became my own source of joy.”

From ROI to ROO: The Objective Shift

“We don’t measure ROI; we measure ROO—Return on Objective. Every engagement starts with a consult call to pinpoint your specific challenges and objectives, ensuring everything aligns with the participants’ needs.”

Connect with us:
Host: Vince Chan | Guest: Erin Diehl

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