Episode Details

The moment everything starts falling apart might be the moment your life finally comes together.

In this episode, Chip Conley sits down with entrepreneur and author of Grow or Fold, Matt Ross, to explore a powerful story of midlife reinvention. From a high-pressure career in radio to building purpose-driven businesses, Matt shares how personal crisis, burnout, and uncertainty became the catalyst for real change.

Here’s what you’ll take away:

• Why feeling “stuck” at 50 is often the start of something better
• The simple mindset shift that turns breakdown into breakthrough
• How to treat your life like a business—and actually redesign it
• What it really means to “find your magic” (and how to do it)
• Why growth, not comfort, is the key to a fulfilling second half of life

If you’re at a crossroads, questioning what’s next, or just know there’s more out there for you—this conversation will hit home.

Watch now and take the first step toward your next chapter.

Timestamps:

(00:00) Intro

(05:00) Breaking into CBS and early career growth

(08:24) Turning around a failing radio station

(11:16) Music strategy and audience targeting

(13:57) Leaving radio and industry decline

(15:35) Joining School of Rock as CEO

(18:15) Launching One River School at 50

(22:18) Writing Grow or Fold and personal crisis

(26:06) Treating life like a business

(29:52) Personal struggles and rebuilding

(30:15) Vision planning and long-term goals

(33:15) Lessons from age 50 to 65

(37:42) Grow vs fold mindset

(41:46) Midlife purpose and transformation

(45:54) Entrepreneurship and self-awareness

(47:54) Final life lesson and philosophy

Learn more about MEA at ⁠https://www.meawisdom.com/

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