Some episodes wander into gold on accident—this is one of them. On a snowy Denver morning, Matt and Anne fall into a raw, surprising conversation about early-career scrappiness, ego in your 20s, asking “dumb” questions as a superpower, and why distilling chaos into a single clear droplet is the mark of a strong founder. They unpack how emotional maturity shapes work dynamics, why some leaders stop learning, and the difference between wartime vs. peacetime CEOs. It’s an unexpectedly deep dive ...