Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)

Overview

This episode features Chip Conley, a hospitality entrepreneur turned tech mentor, who shares his journey from founding Joie de Vivre hotels to becoming Airbnb's Modern Elder and later establishing the Modern Elder Academy (MEA). The conversation explores intergenerational collaboration, thriving in midlife, and the intersection of wisdom and technology.

Notable Quotes

- People won't notice your wrinkles as much as they'll notice your energy. – Chip Conley, on staying relevant in the workplace.

- Midlife is not crisis; midlife is the chrysalis. – Chip Conley, reframing the narrative around aging.

- Despair equals suffering minus meaning. – Chip Conley, on finding purpose during challenging times.

🛠️ Joining Airbnb in His 50s: Lessons in Adaptation

- Chip joined Airbnb at 52, reporting to CEO Brian Chesky, who was 21 years younger. He described the experience as being both a mentor and an intern.

- He struggled with tech lingo and had to learn humility, often feeling like the dumbest person in the room.

- His outsider perspective helped Airbnb redefine its product focus, emphasizing hosts and experiences over just technology.

- Chip highlighted the challenges of working under a founder in founder mode, including unrealistic goals and relentless work expectations.

🧠 The Value of Intergenerational Collaboration

- Chip emphasized the synergy between younger employees' fluid intelligence (speed and focus) and older employees' crystallized intelligence (holistic thinking and pattern recognition).

- He advocated for mutual mentorships, where older and younger colleagues learn from each other.

- At Airbnb, Chip championed the inclusion of older hosts and employees, creating a more diverse and empathetic workplace.

🌟 Thriving in Midlife and Beyond

- Chip reframed midlife as a chrysalis for transformation rather than a crisis.

- He shared research showing that happiness often increases after 50, as people shed societal expectations and embrace freedom.

- His Modern Elder Academy helps individuals navigate transitions, redefine purpose, and build transitional intelligence.

📈 Wisdom in the Workplace: Tactics for Older Professionals

- Chip advised older workers to stay curious, maintain high energy, and embrace a mentor and intern mindset.

- He suggested focusing on generalist skills, which are increasingly valuable in the AI era.

- For hiring managers, he recommended leveraging older employees' emotional intelligence and institutional knowledge to foster team success.

📊 Frameworks for Navigating Anxiety and Meaning

- Chip shared practical emotional equations:

- Despair = Suffering - Meaning: Increase meaning to reduce despair.

- Anxiety = Uncertainty x Powerlessness: Reduce anxiety by clarifying what you know and what you can control.

- He encouraged using these frameworks to tackle challenges with clarity and purpose.

🏡 The Modern Elder Academy (MEA)

- MEA is the world's first midlife wisdom school, offering workshops to help individuals navigate transitions and reimagine their purpose.

- Located in Baja and Santa Fe, MEA combines hospitality, wellness, and education, with a focus on fostering a positive mindset toward aging.

- Chip described it as The Four Seasons meets Blue Zones meets the Esalen Institute.