Sept. 25, 2025

021: The Planner vs. The Improviser - Travel, Poker, and Startup Pressure

021: The Planner vs. The Improviser - Travel, Poker, and Startup Pressure

Anne and Matt compare two founder mindsets: Anne thrives on preparation and systems, while Matt embraces last-minute decisions and unpredictability. From hunting flight deals to playing high-stakes poker, they unpack how different approaches to stress and planning reveal much deeper truths about entrepreneurship.

This isn’t just about travel—it’s about the psychology of pressure, the art of controlling what you can, and learning when to let go.

🚨 Stuff You’ll Want to Remember:

  • “Having a go-bag and pre-packed toiletries makes travel feel effortless.” — Anne
  •  “I’d rather book last minute and keep the mental clutter out of my head.” — Matt
  •  “Food routines matter on the road—bringing your own keeps you at peak performance.” — Anne
  •  “Poker is the best example of how people react under pressure.” — Matt
  •  “I love the anticipation of a trip—it’s a positive stress for me.” — Anne
  •  “For me, there’s no such thing as positive stress—if it’s stress, it’s bad.” — Matt
  •  “Both preparation and improvisation get you to the same destination—it just depends on your style.” — Anne

📡 Where to Find Us