#243 | The Courage To Be Called "Crazy"

#243 | The Courage To Be Called "Crazy"

From Win Today by Ryan A. Cass

March 9, 2026 · 23 min · Season 6

About this episode

This episode explores how bold goals are often labeled 'crazy' before they achieve success, highlighting examples from notable figures.

Send us Fan Mail What if the word “crazy” is just how people describe commitment they don’t yet understand? In this episode, we explore why bold goals—whether building a business, pursuing elite performance, or chasing an unconventional dream—often look irrational before they look successful. From the persistence of Walt Disney to the entrepreneurial leap of Sara Blakely and the fan-first innovation of Jesse Cole, the pattern is clear: meaningful work gets labeled “crazy” before it gets respe...

People in this episode

Host: Ryan A. Cass

Topics covered

  • commitment
  • bold goals
  • entrepreneurship
  • innovation
  • persistence
  • unconventional dreams

Keywords

  • crazy
  • commitment
  • entrepreneurship
  • Walt Disney
  • Sara Blakely
  • Jesse Cole
  • innovation

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