He transformed S.F. hotels and helped Airbnb go public. Now he wants to redefine our ‘midlife’

But while Baja and New Mexico are a long way from the first hotel he bought at age 26 in the Tenderloin, Conley remains connected to San Francisco, where he owns five hotels, Kabuki Springs & Spa and a home in Potrero Hill.

Today, Chip Conley is a regular of the TED Talk circuit and has appeared on shows like “Good Morning America.” He is tall and bald and lives with his dog in Baja and Santa Fe, with frequent visits to San Francisco and Houston — where Conley, who is gay, has two sons whose mothers are a lesbian couple he’s been friends with for years.

But back in 1986, Conley was a recent Stanford Business School graduate working on converting the Masonic Temple on Van Ness Avenue into an office building. Hospitality wasn’t on his mind until he met famed concert promoter Bill Graham, who was interested in collaborating on a South Bay music venue. While those talks didn’t bear fruit, Graham suggested Conley open a hotel catering to touring rock groups.

“It was Bill Graham who said to me, when I was 25 years old, ‘Chip, you’ve got to create a rock ’n’ roll hotel in San Francisco,’ ” Conley said. “I started looking around.”

After securing a $1.1 million loan, Conley was able to buy the 44-room, by-the-hour Caravan Motor Lodge on Eddy Street, renovate it, and open for business as the Phoenix. The project took less than three months. Meanwhile, he cultivated relationships with tour managers and bookers at music venues like the Warfield, the Fillmore, Great American Music Hall and others.

“There were a lot of hotels in town that didn’t necessarily want the rock bands,” Conley said. “They were like, ‘Why don’t you go to the Phoenix?’ ”

The $49 room rate was appealing, but tour managers were also attracted to the free parking for tour buses. That, and the fact that any manager who booked at least 12 nights was given free massages. Stars like David Bowie, Linda Ronstadt, Johnny Depp and Kurt Cobain all became regulars.

“To have Pearl Jam and the Red Hot Chili Peppers and Nirvana taking over the hotels at the same time and having them jam in the courtyard with no audience other than their roadies and groupies was very cool,” Conley said.

At the time, the boutique hotel movement was just taking off, with pioneers Ian Schrager and Bill Kimpton opening the first in New York and San Francisco. These iterations, much smaller than the typical big-city downtown hotels, were focused on design and fitting into their urban neighborhoods, rather than trying to impose something grandiose. 

After opening the Phoenix, Conley and the staff at Joie de Vivre opened 22 more San Francisco hotels, often taking over rundown motels or second-rate inns and infusing them with personality. They eventually expanded across California, and had hotels in Washington, D.C., Chicago, Arizona and elsewhere.

The idea was to “create joy for the traveler at every opportunity,” said Visit Oakland CEO Peter Gamez, who spent 26 years at Joie de Vivre as a vice president of sales and marketing.

“We took our philosophy on the road,” Gamez said. “Our philosophy was always very simple: You start with the community and stay true to the identity of that community.”

The company developed the Vitale Hotel on the Embarcadero and had five hotels on Geary Street within a few blocks of Union Square. 

“The Rex Hotel had a literary theme. The Maxwell, two blocks away, celebrated San Francisco’s theater movement. The Nob Hill Lambourne was about health and wellness, yoga and meditation,” Gamez said. “None of them felt like a chain.”

After the dot-com economy crashed in 2000, the company was able to swoop in and pick up real estate on the cheap, growing to 52 properties. Conley was seemingly everywhere. He was on the board of Glide Memorial Church and Burning Man. He tutored at the Boys and Girls Club, not far from the Phoenix at the crossroads of Hayes Valley, Civic Center and the Western Addition. He bought Kabuki Springs and Spa in Japantown. 

But by the time the Great Recession started in 2008, Conley was burned out and looking to do something different. In 2010 he sold most of the properties to an investment group led by Hyatt Hotel heir John Pritzker.

After spending a year traveling to festivals around the world, he received a call from Chesky, the Airbnb CEO, who explained the concept of his startup, which would allow people to host their rooms or entire homes to travelers for short or extended periods.

“I thought it was a terrible Idea,” Conley said. “I said, ‘This will never work, Brian.’ He told me, ‘Hey, it’s growing fast and millennials love it. I said, ‘Well, I’m a boomer and I don’t get it, but I want to understand it more.’ ”

It was Chesky who suggested that Conley’s role be that of “a modern elder.” After much reluctance, Conley embraced the role, and the company. 

“I was an idiot,” he said. “At 52 I joined the tech company and didn’t understand any of the lingo. I had to be curious because I was the dumbest person in the room. But I was also the wisest person in the room because I was the oldest.”

He traveled the world meeting with Airbnb “super hosts” and tried to instill in the culture best practices from the hospitality industry.

“I treated the hosts like entrepreneurs — how do we make you a successful entrepreneur so you can deliver great service, because if you do you are going to get great reviews,” he said. “Accuracy was important. Checking in with guests before the stay so you know what they need. So much of it was hospitality driven.”

San Francisco Chamber of Commerce President Rodney Fong said that the evolution of travel, from classic big hotels to boutique inns to Airbnbs, was all part of the same trajectory, which Conley understood.

“People wanted to experience San Francisco as if they were residents, and Chip understood that,” Fong said. “The Joie De Vivre hotels were smaller, more creative and homier. The evolution to Airbnb was an extension of that, of how people travel now, that pattern of ‘I want to blend into a neighborhood.’ ”

Lateefah Simon, a BART board member who is running for U.S. Congress, met Conley when she was in middle school. He tutored at the Boys and Girls Club, where he became a foster dad to one of her friends, Damien, who, like other kids in the crack-ravaged Fillmore and Tenderloin neighborhoods of the early ’90s, was couch surfing and riding the 22-Fillmore all night when they had no place to sleep. 

Conley had bought the Abigail Hotel, where he gave rooms to some Tenderloin residents who had nowhere to sleep.

“I was one of those kids who cut school. I was not in a good place,” Simon said. “My best friends were deeply involved in the juvenile justice system. We were kids from the Tenderloin and Fillmore. Chip was a young, well-to-do hotel owner. We didn’t know what he was doing, but he made sure Damien and his friends were off the street every night.”

Later, Simon and her whole group of friends would go to Conley’s house in Potrero Hill, where she tried organic produce for the first time, as well as fancy dark chocolate and lamb chops. They were not allowed to drink soda, only juice, she said, recalling afternoons when “15 kids from the projects would be sitting on his balcony eating food from Rainbow Grocery.”

“He has been a mentor to me ever since. He pushed me to go to college. He took me to dinner and pushed me to go to graduate school during COVID. He has stayed on me throughout my life,” she said. “Chip is a business CEO, but he is also a super hippie, into healing and justice and opportunities for young people to center themselves.”

Looking back at his hotel CEO days, Conley says he suffered from being an “admiration addict,” adding that “social comparison is the recipe for misery.”  

These days it’s not just young people Conley is helping find themselves. 

Through his TED Talks, podcasts and seven books — his latest is “Learning to Love Midlife: 12 Reasons Why Life Gets Better” — Conley has become more of a philosopher and self-help guru than business person. He has taken up Spanish and surfing and yoga and likes to ask middle-age people at cocktail parties what they are “a beginner at.”

But while Conley is mostly focused on his modern elder academies, he has struggled over the last four years to get a handle on the crime and encampments outside of his first hotel, the Phoenix, which he still owns.

He said the street conditions at Eddy and Larkin streets have been so dire that even some of the punk and metal bands that typically stay at the Phoenix have taken a pass, threatening the hotel’s future.

“If a rock ’n’ roll band is not going to stay there because it’s too dodgy, what about the family from Iowa?” he said.

Conley said none of his San Francisco hotels are doing well, which is a common story in the city, but they carry little debt so they're not in danger of foreclosure.

Still, running struggling businesses would be enough to push some people into a midlife crisis. But not Conley. He’d rather focus on helping other people avoid that fate.

Reach J.K. Dineen: jdineen@sfchronicle.com