Dec. 18, 2025

043: Ego, Early Careers & Wartime Leadership

043: Ego, Early Careers & Wartime Leadership

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 into confidence, humility, and how to grow without losing your edge. 

🚨 Stuff You’ll Want to Remember

  • “If you can distill the ocean into a single droplet, you can lead anything.” — Matt
  • “Asking the ‘dumb’ question is how you give everyone permission to learn.” — Anne
  • “When times are tough, crack the whip. When times are easy, be deeply empathetic.” — Matt
  • “Your emotional age shows up at work more than your resume ever will.” — Anne

📡 Where to Find Us