What does it look like to take a chance on yourself—and keep climbing?

In this episode of Taking Chances – Why Not You?, I sit down with Matt Ostrom, a Quad Cities entrepreneur whose journey is built on grit, vision, and saying yes to opportunity.

Matt takes us back to his roots growing up in Iowa, his days playing college baseball at Iowa State, and the moment he realized chasing pro ball might not be the path forward—after even heading to Canada to give it a shot. From there, his story takes an unexpected turn: a part-time job at Active Endeavors in Coralville making just $5 an hour, where he learned the ropes in sales, inventory, and customer service.

Fast forward nearly three decades, and Matt is now the owner of Active Endeavors, having grown it into a thriving specialty retail business—including a brand-new brick-and-mortar store in the Quad Cities. He shares how the business evolved from a mountaineering and gear shop into a modern footwear and apparel destination, and what it takes to stay relevant over 28 years.

But Matt’s journey isn’t just about business.

In one of the most incredible chapters of his life, The North Face invited him on a trek to Mt. Everest. With the support of expert training—and help from mutual friend Kyle Dietz—Matt pushed himself to new limits, climbing to over 21,000 feet at Everest Base Camp.

This is a story about endurance, reinvention, and saying “yes” when life presents an opportunity.

Whether you're chasing a dream, building a business, or standing at the base of your own mountain—this conversation will inspire you to take that next step.

Why not you?