New Podcast Episode: Taking the Monopoly Iteration Story Off the Page

A while back I broke down what Monopoly and Hugh Grant can teach us about iteration. The article sparked a lot of good conversations about how products evolve, why they stall, and why even the classics need reinvention.

Now I’m taking that story to the podcast.

In this episode, we dig deeper into the idea that iteration is never a straight line. Monopoly’s endless versions, Hugh Grant’s scene-stealing villain energy, and the strange lifecycle of legacy products all point to the same truth: standing still is the fastest way to lose relevance.

You’ll hear more about:

• Why iconic products survive only through constant reinvention
• How teams misread signals during iteration cycles
• The traps legacy products fall into when they stop listening
• Why segmentation sits at the center of Monopoly’s long run
• What modern product teams can steal from nearly a century of board game pivots

🎧 Listen to the full episode: https://open.spotify.com/episode/1uPavdDMiJzOWpLXUMWFRI?si=YIn-a-twQoCLEJvubmmejQ