In this episode of the Bolder Business Podcast, Paul sits down with Ryan DeJoy to talk about the unexpected path that led from helping one struggling student to building Windham Woods School — a mission-driven organization that has grown through trust, community, and purpose.

Ryan reflects on nearly two decades in education, the decision to step into uncertainty, and how one conversation opened the door to something far larger than he ever imagined. Together, they explore what it means to recognize opportunity when it doesn’t look like a traditional business plan, why focusing on strengths changes outcomes, and how real growth is built through people, not systems.

The conversation also touches on fundraising, leadership, and the realities of building something meaningful without losing sight of why you started. It’s an honest look at entrepreneurship, education, and life — and a reminder that progress often begins by listening to the signal telling you it’s time for something different.