Stop Fearing AI: Why Curious Leaders Will Win | Bart Caylor

Bart Caylor spent his early career marketing cell phones and televisions before realizing the work that actually moved him was helping colleges tell their story. In this conversation with Greg Aden, he talks about being a first generation college student, why he fired every client outside of higher education to get clear on his focus, and what he learned writing Chasing Mission Fit and Know What You Don't Know.

He also shares a story about a small school spending a million dollars a year on ads it did not understand, and how one school hands every graduate a servant's towel along with the diploma. Greg and Bart get into the mindset shift at the center of it all, moving from fear to curiosity, whether the subject is marketing, AI, or being a better parent. Nobody asks why anymore because they are afraid of looking like they do not already know.

Thanks to Interworks for sponsoring this episode.

Want to keep the conversation going? If something here landed with you, if you have a question about how I work with leaders and their teams, or if you just want to share your own experience, book a 15 minute conversation with me.

Chapters: 0:00 Intro and InteraWorks Sponsor 1:15 Meet Bart Caylor and His Work in Higher Education 4:01 How College Changed Bart’s Life 6:19 Why Bart Wrote Chasing Mission Fit 7:35 Why Clear Messaging Attracts the Right People 12:21 Finding Purpose and Mission in Higher Education 13:50 What Servant Leadership Really Means 17:12 Building a Legacy Through Trust and Service 19:14 The $3 Million Marketing Mistake 21:50 Why Great Leaders Stay Curious 24:12 How Bart Became an AI Early Adopter 25:54 Using AI as a Tool, Not a Threat 28:39 How AI Can Make You Better at What You Do 29:56 Greg’s Takeaways: Courage, Curiosity, and Service 30:43 InteraWorks Best Year Yet and Closing Thoughts