Chip Conley, NYT Best-Selling Author, Multiple TED Speaker

Today, my guest is Chip Conley, a three-time TED speaker and one of the world’s leading experts at the intersection of business innovation, psychology and spirituality. As one of the creators of the boutique hotel movement and the “modern elder” to the young Airbnb founders, Chip’s been a disruptor and expert on entrepreneurship and business leadership.

But what sets Chip apart as a speaker is the fact that he’s written 7 popular books and is a globally-recognized thought leader on the future of work, the value of corporate culture, and the competitive advantage of a multi-generational workplace. Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, Chip founded Modern Elder Academy (MEA), the world’s first “midlife wisdom school.”

In this candid conversation, Chip shared the real stories behind his unique role as a “social alchemist,” his time mentoring the founders of Airbnb, and his ultimate mission to reimagine aging through the creation of midlife wisdom schools.

1. The Social Alchemist. Chip describes himself as a “social alchemist” or a “mixologist of people,” a realization he came to after repeatedly asking himself what unique mastery or gift he had to offer the world. Viewing his work as being the “crossing guard at the intersection of psychology and business,” he realized early on—while successfully growing his own massive boutique hotel company—that understanding human psychology is often the most neglected, yet critical, aspect of effective business leadership.

2. The Pregnant Writer. Despite desperately wanting to be a writer as a teenager, Chip abandoned the idea because his father told him it was completely impractical and wouldn’t pay the bills. It wasn’t until his late 30s, when a literary agent approached him after a speech, that he finally wrote his first book, which went on to feature a foreword by Richard Branson. Today, he writes daily and prefers to work between 4:30 and 7:30 a.m., noting that his raw, creative “writer wakes up before my editor”. He jokingly compares his ideation process to getting pregnant, explaining that it usually takes a nine-to-twelve-month mental gestation period to properly give birth to a fully formed book concept.

3. The Guide on the Side. After running his boutique hotel company for 24 years, Chip received a call from Airbnb co-founder Brian Chesky, asking him to help the young tech startup “democratize hospitality”. Serving as their head of global hospitality and in-house mentor for over seven years, Chip had to actively right-size his own ego. He transitioned from being the CEO and the “sage on the stage” to becoming the “guide on the side,” ultimately embracing his new identity as the company’s “modern Elder” who was twice the age of the average employee.

4. A Midlife Gap Year. Inspired by his mentoring time at Airbnb and a profound epiphany he had on a beach in Baja, Mexico, Chip founded the Modern Elder Academy (MEA), the world’s first midlife wisdom school. Dedicated to helping people in midlife safely reimagine and repurpose themselves, the academy is currently expanding from Mexico to new campuses and regenerative residential communities in Santa Fe, New Mexico. Looking toward the future, Chip’s ultimate dream is to take over a failing liberal arts college in the United States and transform it into a “midlife gap year academy” where older adults can spend an entire year refueling themselves for their next chapter.

Hsu Untied Interview with Chip Conley