What if the most valuable thing you build isn’t your company—but your character and the relationships that outlast it? In this conversation, Matt Middleton (Founder & CEO, Future Proof) shares how a COVID pause became the moment to redesign events around human connection, intentional matchmaking, and joy. He talks candidly about growing up with financial stress, conforming early in his career, and choosing to create something different—even when it meant risk, doubt, and starting from scratch. 

For leaders navigating money and meaning, Matt makes a simple, profound case: bet on yourself, iterate relentlessly, and remember that real wealth shows up at home. The metric that matters most isn’t attendance or AUM—it’s the kind of dad, partner, and human your family remembers.