The Midlife Chrysalis

Feeling Stuck at 50: How to Find Your Magic and Start Again | Matt Ross

4 snips
May 11, 2026
Matt Ross, entrepreneur and author of Grow or Fold who built School of Rock and founded One River School, shares his midlife reinvention journey. He recounts leaving radio, the crisis that sparked starting One River at 50, treating life like a business, and how to pivot, find your magic, and plan the next decade.
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ANECDOTE

Scaling School Of Rock Through Live Performance

  • Matt rescued School of Rock when it was nearly burning cash, growing it from five to 55 schools in 3.5 years.
  • He used performance-based music education shows at real venues to prove value and attract families.
ANECDOTE

Turning Crisis Into One River School

  • Matt Ross hit rock bottom at 50: health issues, multiple family crises, job loss, and his son with severe autism being institutionalized.
  • That year triggered him to open One River School with no art experience and invest in art education training at NYU first.
ADVICE

Treat Your Life Like A Business

  • Treat your life like a business: create a vision, strategy, goals, and run inventories on what's broken.
  • Matt used a therapist's perspective and built a Vision Plan (MVP 10) of 10 goals for 10 years to reorient his life.
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