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)

From Boutique Hotels to a Movement: Joining a Startup in Your 50s

Chip Conley’s career reads like a masterclass in reinvention: a successful boutique hotel founder, an executive at Airbnb in his fifties, a near-death experience that recalibrated purpose, and the creator of the Modern Elder Academy, a midlife wisdom school. In a wide-ranging conversation, Conley explains how age can be an asset in fast-moving tech companies, why culture matters more than ever for distributed teams, and how midlife can be reframed as a chrysalis rather than a crisis.

What It Really Felt Like To Join Airbnb Later In Life

At 52, Conley walked into a company whose average age was 26. He quickly learned the language of product, navigated founder intensity, and discovered the practical value of being the voice for hosts and customers often overlooked by younger product teams. He emphasizes humility, curiosity, and the tactical approach of building credibility by getting close to customers—going on a world tour to visit hosts—so that experience and authority earn respect in rooms dominated by faster technical expertise.

Practical Lessons For Working With Founders And Founder Mode

• Start meetings with clarity: state the intention and define success at the top to keep founder-driven meetings grounded.
• Limit reliance on rigid slide decks: founders can take conversations off-script; keep materials lean and principle-driven.
• Build credibility: bring customer insights and qualitative evidence to support recommendations.

Age, Brain Diversity, And The Future Of Work

Conley reframes older professionals as carriers of crystallized intelligence—pattern recognition, systems thinking, empathy and emotional intelligence—that pairs powerfully with younger colleagues’ fluid intelligence and technical speed. He argues that distributed, remote, and AI-augmented workplaces increase the value of generalists and wisdom-based roles while making culture and “invisible productivity” — elevating others’ output — more important than ever.

Midlife As Chrysalis: The Modern Elder Academy And A Pro-Aging Mindset

Out of his experience at Airbnb, and after a life-altering near-death event, Conley launched the Modern Elder Academy (MEA): an immersive midlife wisdom school that helps people reframe transitions and repurpose their careers and lives. MEA’s curriculum mixes hospitality, retreat-style intensive learning, and academic partnerships to teach people how to manage transitions, build transitional intelligence, and take meaningful action toward a second act.

Concrete Tools For Older Professionals And Hiring Managers

• Resumes should showcase one thorny problem, the skills used, and the outcome rather than enumerating roles.
• Older candidates can negotiate flexible time or reduced salaries to create value while staying on the team.
• Companies should hire generalists, set up mutual mentorships, and create employee groups that give voice to older workers.

Data-Backed Reasons To Rethink Aging

Conley references research showing a U-curve of life satisfaction—where many people’s happiness rebounds after midlife—and studies that link positive beliefs about aging to longer life. His practical approach to aging emphasizes curiosity, energy, and the discipline of asking what you will regret not learning in ten years as a catalyst for action.

Across stories of hospitality, product meetings, boardrooms, and personal transformation, Chip Conley insists that midlife is not an ending but a resource. Whether you’re a hiring manager, a founder, or an experienced professional contemplating a pivot, the conversation offers pragmatic tactics—align meetings up front, gather customer evidence, craft resumes around problems solved, and cultivate curiosity—that make age an asset in modern organizations. The throughline is clear: wisdom managed and shared can transform careers, cultures, and companies.