Playbook Success Profiles

Interview Profiles

Eleven founders and executives answer the same six questions: their biggest mistake, the skills that mattered, advice to their high school self, how they keep learning, the problem in front of them now, and how they handle risk.

Maritime · February 5, 2026

Former Tidewater Chairman: I Didn't Start My Own Company Until 55, Then Sold It For Half A Billion

Larry Rigdon

Telecommunications and Investing · March 16, 2026

Former Windstream CEO: Map Every Plan By Probability And Raise The Money Before You Need It!

Tony Thomas

Banking Software · March 16, 2026

Banking Software CEO: I Doubted I Could Lead Engineers. Now I Turn Down Every Investor!

Elizabeth Glasbrenner

Agribusiness · March 4, 2026

Former Windstream CFO: The Task You Won't Delegate Is The One Slowing Your Company Down

Brent Whittington

Manufacturing · December 24, 2025

Bad Boy Mowers President: I Turned Down A CEO Job Because Of Bad Advice. Trust Your Gut!

David Brogdon

Education Technology · January 29, 2026

Apptegy Founder: Stop Rushing Success. Work For Someone Else First!

Jeston George

Environmental Services and Healthcare · February 4, 2026

Serial Founder: Never Bet More Than 5% Of Your Cash On One Idea!

Cory Davis

Business Consulting · April 28, 2026

Former USA Truck Executive: I Micromanaged Everything Until I Learned To Trust My Team

Werner Hugo

Commercial Landscaping · May 4, 2026

Landscaping CEO Who Grew From $1M To $35M: Finding Workers Is The Hardest Part Of This Business!

Bobby Jon Head

Offshore Oilfield Services · May 13, 2026

Founder Who Sold To Expro: I Waited Too Long To Fire The Wrong Hire!

Patrick Placer

Convenience Retail · May 18, 2026

Former E-Z Mart CEO: My Father Died In A Plane Crash And I Followed His Plan For Too Long

Sonja Hubbard