What happens when you build a successful business—then lose it all? In this raw and honest conversation, Kelly Olcott shares the hard lessons behind his journey from Marine to millionaire contractor, to bankrupt entrepreneur, and finally to building again with more purpose than ever before. It’s not just about money—it’s about legacy, leadership, and learning the difference between chasing success and building something that lasts. If you’ve ever hit a wall in business or life, this episode is for you.