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Watch > Episode > Chip Conley - A Maverick Entrepreneur's Journey of Wisdom and Innovation

Chip Conley - A Maverick Entrepreneur's Journey of Wisdom and Innovation


The Making of a Modern Elder

Chip Conley, an entrepreneur, author, and hospitality visionary, has left an indelible mark on the business world with his innovative approach to leadership and his transformative contributions to the hospitality industry. In this exclusive London Real interview, Chip discusses his ventures, insights on leadership, and the wisdom he has shared through his bestselling books.

Born in 1960, Chip Conley’s journey into entrepreneurship began with a spirit of curiosity and a thirst for knowledge. While studying at Stanford University, Conley founded Joie de Vivre Hospitality in 1987, an innovative boutique hotel company that would redefine the landscape of hospitality in the years to come. This marked the beginning of Conley’s entrepreneurial voyage and his commitment to creating unique and memorable guest experiences.

Under Conley’s leadership, Joie de Vivre Hospitality became synonymous with distinctive, personality-driven hotels that reflected the culture and spirit of their surroundings. Conley’s innovative approach to hospitality challenged industry norms, introducing themed boutique hotels that catered to diverse tastes and preferences. From the artsy and avant-garde to the luxurious and sophisticated, Conley’s portfolio of hotels celebrated individuality and set a new standard for the guest experience.

In the early 2000s, Chip Conley faced a unique challenge when he found himself in a leadership role working with a team significantly younger than him. This experience inspired him to explore the concept of “Wisdom@Work” and write a bestselling book by the same name. The book, published in 2018, delves into the value of intergenerational collaboration, highlighting the unique strengths that each age group brings to the workplace. Conley’s insights challenge conventional notions of leadership, emphasising the importance of wisdom gained through experience.

In a surprising turn of events, Chip Conley found himself in the tech industry when he joined Airbnb in 2013 as Head of Global Hospitality and Strategy. As a mentor to Airbnb’s young leadership team, Conley brought his decades of hospitality experience to a company disrupting the travel industry. His role at Airbnb reinforced his commitment to the principles of Wisdom@Work, fostering an environment where diverse perspectives and experiences could thrive.

Building on the themes explored in “Wisdom@Work,” Chip Conley co-founded the Modern Elder Academy (MEA) in 2018. Situated in Baja California, Mexico, MEA offers a transformative experience for individuals in the midlife and beyond, providing a space for reflection, learning, and personal growth. The academy embraces the concept of the “modern elder,” recognising the value of individuals who bring a blend of experience and curiosity to the table.

Chip Conley’s impact extends beyond the business world. His unique blend of entrepreneurship, mentorship, and a commitment to lifelong learning has made him a sought-after speaker and advisor. Conley’s legacy is evident in the lives he has touched, the innovative businesses he has built, and the wisdom he continues to share with leaders and aspiring entrepreneurs around the globe.

Chip Conley’s journey from boutique hotel entrepreneur to a champion of intergenerational collaboration and wisdom in the workplace reflects a remarkable evolution. His ability to embrace change, challenge norms, and cultivate environments where individuals can thrive has redefined the concepts of leadership and success. As a maverick entrepreneur, bestselling author, and advocate for the modern elder, Chip Conley continues to inspire individuals to lead with wisdom, curiosity, and a commitment to making a positive impact on the world.


00:00 | Trailer
02:25 | Brian’s thoughts on the episode
03:32 | Brian’s introduction
04:16 | Why Chip loves London05:43 How dying taught him how to live
09:07 | What he saw on the other side each time he died
11:04 | Request to become a mentor for Airbnb leads to the realisation that led to his book Wisdom at Work
20:05 | How a modern elder in the company can be really helpful in a company of younger people
22:19 | Companies need to have mutual mentorship across generations
25:24 | Being interested not interesting
29:29 | Mentorship can be a beneficial mutual relationship
41:25 | The mid-life edit opportunity
1:01:05 | Looking towards a time when people live to 120 or 150 years
1:02:55 | The purpose for creating the Modern Elder Academy
1:09:08 | Burning Man, what it is
1:13:33 | Chip’s daily practice
1:15:42 | What it was like to learn he had prostate cancer
1:23:15 | Why Chip moved from San Francisco to Austin, Texas
1:27:44 | What is Chip’s superpower
1:29:44 | The worst and best days of his life
1:36:45 | What scares Chip
1:46:44 | What we would be surprised to learn about him
1:50:48 | What keeps him awake at night
1:51:49 | Success secrets
1:53:18 | Brian’s summing up.


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