The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half

The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half

Chip Conley is a hospitality maverick, founder of Modern Elder Academy, and the entrepreneurial sage who helped transform Airbnb from a startup to a global phenomenon. This conversation explores midlife as a chrysalis rather than a crisis—a transformative journey from ego to soul. Chip illuminates the path from horizontal achievement to vertical growth, addressing life's longest yet least understood phase. We discuss his near-death experience, the nature of wisdom, and why friendship becomes essential to wellness as we age. In the process, Chip creates space for me to reflect honestly on my own lifelong pursuit of achievement. Chip is a treasure. This exchange is for anyone seeking to avail themselves of midlife's deeper possibilities. Enjoy! Note: Chip and I invite you to experience these insights in person in Los Angeles on June 5th for a special gathering with the MEA faculty. Register at meawisdom.com/richroll. Show notes + MORE Watch on YouTube Newsletter Sign-Up

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Rich On Rock Bottom, Resolutions & Reframing Family Dynamics

Rich On Rock Bottom, Resolutions & Reframing Family Dynamics

Roll On returns! Just in time for the holiday gauntlet. Adam Skolnick and I unpack three questions the season demands: how to navigate family gatherings when the same dynamics play out like clockwork...

4 Dec 20251h 25min

Todd Marinovich: The Superstar Quarterback Who Lost Himself In Drugs & Found Himself In Love

Todd Marinovich: The Superstar Quarterback Who Lost Himself In Drugs & Found Himself In Love

Todd Marinovich is a former NFL quarterback, USC Rose Bowl champion, and the subject of the ESPN 30 for 30 documentary "The Marinovich Project." This conversation explores the duality of engineered p...

1 Dec 20251h 55min

The Productivity Myth: Oliver Burkeman On Our Broken Relationship With Time, Embracing Our Limitations & Why More Isn’t Always Better

The Productivity Myth: Oliver Burkeman On Our Broken Relationship With Time, Embracing Our Limitations & Why More Isn’t Always Better

Oliver Burkeman is a bestselling author, journalist, and the mind behind “Four Thousand Weeks: Time Management for Mortals” and “Meditations for Mortals.” We explore our broken relationship with time...

24 Nov 20251h 59min

Fasting Compilation: Leading Experts On Water-Only Fasts, Fasting Mimicking Diets & The Optimal Fasting Window For Longevity

Fasting Compilation: Leading Experts On Water-Only Fasts, Fasting Mimicking Diets & The Optimal Fasting Window For Longevity

This Fasting Compilation features Dr. Alan Goldhamer, Dr. Valter Longo, and Dr. Michael Greger to discuss the science of strategic deprivation. We explore why visceral fat behaves like a tumor secret...

20 Nov 20251h 8min

Interview With An Icon: Katie Couric On The State of Media, Institutional Distrust, Cancer Advocacy & What Actually Creates Happiness

Interview With An Icon: Katie Couric On The State of Media, Institutional Distrust, Cancer Advocacy & What Actually Creates Happiness

Katie Couric is a journalist and the first woman to solo-anchor a major network evening newscast.  We explore the disintermediation of news media, institutional distrust, and the fragmentation of sha...

17 Nov 20251h 57min

Tig Notaro Is Treading Water

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Tig Notaro is a comedian, actor, screenwriter, producer, and co-host of the podcast Handsome. This conversation explores Tig's legendary 2012 set—delivered days after her cancer diagnosis—and how los...

10 Nov 20252h 41min

Modern Manhood: A Compilation On Redefining Masculinity, True Strength & Igniting Purpose, Community & Vulnerability In Men

Modern Manhood: A Compilation On Redefining Masculinity, True Strength & Igniting Purpose, Community & Vulnerability In Men

This Modern Masculinity Compilation features Scott Galloway (ep. 826), Terry Crews (ep. 676), Jonathan Haidt (ep. 827), Arnold Schwarzenegger (ep. 784), John W. Price (ep. 939), John Pearson (ep. 739)...

6 Nov 20251h 19min

It Begins With You: Jillian Turecki On Why Dating Is Broken, Self-Awareness Is Everything, & What Actually Makes Love Last

It Begins With You: Jillian Turecki On Why Dating Is Broken, Self-Awareness Is Everything, & What Actually Makes Love Last

Jillian Turecki is a relationship expert, New York Times bestselling author of It Begins With You, and host of the podcast Jillian on Love. This conversation explores why intimacy reveals our charact...

3 Nov 20252h 7min

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