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476: How Coastline Academy Modernized a Fragmented Industry and Became the #1 Driving School in America

July 29, 2026

This week's Misfit Entrepreneur is Nigel Tunnacliffe. Nigel is the Co-Founder and CEO of Coastline Academy — the nation's largest driving school and, according to Inc., the 6th fastest-growing education company in America. Now, when most entrepreneurs are chasing the hot, crowded spaces, Nigel did something genuinely misfit: he looked at the fragmented, fading, mom-and-pop world of driving schools and saw a massive opportunity hiding in plain sight. By acquiring and modernizing local schools,...

475: From Fighter Pilot to Transformation Leader: Will Steel on Escaping the Prison of Your Own Mind

July 15, 2026

This week's Misfit Entrepreneur is Will Steel. Will is one of the world's most highly regarded transformational leaders — but his path there is anything but typical. He graduated from the Royal Air Force College Cranwell with the Leadership Trophy, flew as a military pilot for 10 years in high-stakes operations around the globe, then flew commercially before making a radical career pivot into personal and professional development. He went on to spend 21 years leading one of the world's top tr...

474: The Greatest Startup in History, Independence Day Lessons for Misfit Entrepreneurs

July 04, 2026

Happy Independence Day, Misfit Nation. In this solo episode, I'm stepping back from the usual playbook to reflect on something bigger — the "5,000-Year Leap." For nearly all of human history, ordinary life barely changed. Then, 250 years ago, in one young nation, everything exploded. That leap wasn't luck or geography — it was a set of principles. And they're the same principles that build a great company, a great career, and a great life. I walk through four of them — personal responsibility...