Conley is especially fit to foster a conversation about bringing an open-minded attitude to personal reinvention, and about the bridgeable gap between generations.
A lifelong meditator at 58, he exudes a calm but vibrant energy. He is possessed by a curious intellect, and, in conversation, jumps from heady academic studies to the poetry of Rumi to the soul-searching work of psychologist Viktor Frankl without taking a breath. He’s a longtime devotee of Burning Man, the countercultural gathering in the Nevada desert, and serves as a member of the event’s board of directors. A California native, today he splits his time among San Francisco, El Pescadero, Mexico, and Austin, Texas.
There’s a quote he likes, which he once heard from an executive recruiter and now seems to embody. Paraphrased: “If you are curious and passionately engaged, somehow your wrinkles evaporate.”
Long before Airbnb, Conley was a young Bay Area disruptor himself, founding Joie de Vivre in 1987, after receiving his bachelor’s degree and MBA from Stanford. Even though, at 26, he knew nothing about the hotel business, he bought a pay-by the-hour motel in San Francisco’s seedy Tenderloin district and transformed it into a rock ’n’ roll-themed destination, The Phoenix. David Bowie came to stay, as did Linda Ronstadt and Johnny Depp.
Conley then opened 51 more properties, each of them unique, quirky, and—unlike many other boutique hotels—affordable. Under Conley’s guidance, Joie de Vivre became the second-largest independent boutique hotel brand in the U.S.
The financial crisis of 2008, however, took an emotional and financial toll. He sold the company in 2010. He planned to move to El Pescadero, and to semiretire. He learned to surf. He started Fest300, an evolving guide to the top 300 festivals in the world, which has since been acquired by Everfest.
He felt adrift, though, until Airbnb CEO Brian Chesky and his two youthful co-founders came calling in 2013. Chesky had read Conley’s book, Peak: How Great Companies Get Their Mojo From Maslow. Airbnb was already a tech darling. But the founders wanted to expand into a full-service hospitality company. They needed an experienced hotelier’s help.
Conley was asked if he’d work 15 hours a week. That quickly became 15 hours a day, as the business grew and Conley and Chesky mentored each other. They spent weekends in Conley’s San Francisco backyard, sharing insights. Chesky taught Conley about the cultural trends driving younger generations, about the staggering pace at which unicorns grow, and about the needs of Silicon Valley investors. Conley counseled Chesky on managing people. Once, when Chesky had worked his executive team particularly hard, Conley suggested that the CEO send gifts to their spouses, to recognize the sacrifices they had made—thank-you notes for the families, along with a bottle of wine or flowers.
Both men were invigorated by the mutual mentorship and by their embrace of the “beginner’s mind,” a Zen Buddhist concept that, in short, encourages openness and the acceptance of new ideas, free of preconceptions. It’s similar in some ways to the growth mindset described by Stanford psychologist and motivation researcher Carol Dweck, whose work has been an inspiration to both Conley and Chesky.
“There are people who believe that your potential is unlimited, that who you are is not fixed, and that you can evolve and grow,” says Chesky, now 37. “These are people with growth mindsets. I think Chip and I just had that worldview, that we can constantly have a growth mindset at any age.”
Conley relates a story about the 27-year-old woman who was his direct report in the hospitality department at Airbnb. She once told him how he’d influenced the company. Much of Conley’s hotel knowledge—for example, how many rooms a maid can clean in an eight-hour shift—was useless. But because he understood people, he understood how to get things done, she told him. If the company needed to make a change, Conley could identify the three people at Airbnb who needed to know first. That kind of knowledge proved invaluable to the young company.
Jaja Jackson, 45, Airbnb’s director of global multifamily housing partnerships, says Conley was effective because he listened to his younger colleagues and valued their opinions. “Chip made it very clear that he was not interested in always being the smartest person in the room, so he was able to bring a certain amount of humility into any conversation,” Jackson says. “What he did was empower other people around him to ask questions and be teachers, when they might have otherwise yielded a bit to Chip’s reputation and robbed him of the chance to learn.”
Conley’s collaborative approach paid off. During the four years he worked full-time at the company (he’s now a part-time consultant), Conley developed Airbnb for Work, which more than 700,000 businesses use for travel. He created new quality standards that all Airbnb hosts had to honor, resulting in guest satisfaction reviews that surpassed those of the hotel industry. He also expanded the company’s Superhost program, for the company’s most experienced hosts, from 200 to nearly 500,000 hosts around the globe.
It was a transformative experience, one that Conley hopes to cultivate for others at his Modern Elder Academy.