This week’s conversation is with Chip Conley, a boutique hotel entrepreneur who helped Airbnb's founders turn their fast-growing tech start-up into a global hospitality brand.

After selling Joie de Vivre Hospitality, the company he started as a rebel entrepreneur at age 26, Chip wasn't sure what was next.

He could have retired at age 52 but the young founders of Airbnb came calling.

Chip served as Airbnb’s Head of Global Hospitality & Strategy for four years — while also being CEO Brian Chesky’s mentor — and continues today as a Strategic Advisor to the company’s leadership.

Chip wrote about that experience in Wisdom@Work: The Making of a Modern Elder where he shares his unexpected journey at midlife — from CEO to intern.

While writing Wisdom@Work, Chip was inspired to build the world's first "midlife wisdom school," the Modern Elder Academy, with a 3-acre oceanfront campus in Baja California Sur, Mexico.

So why does Chip care so much about this idea of a “modern elder?”

It’s because there were a few key points in Chip’s life where something was eating at him… he knew he wasn’t on the right path but it could have been easy to stay the course.

Chip made the difficult but necessary decision in those moments to make a change and that’s at the heart of this conversation.

This is about authenticity, it’s about being in touch with your core principles, and ultimately, it’s about wisdom.

Chip’s seen it from every angle – entrepreneur, founder, mentor, and continues to make an impact on the next generation.

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