Into the Great Wide Open

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by Alex May

Chip Conley is in motion. He’s owned an award-winning hotel company, penned four books, garnered the first Head of Global Hospitality title at Airbnb, and started a burgeoning travel website, Fest300. So far, he’s been to 30 festivals in 22 countries, with the numbers ever climbing. He’s pared down his speaking engagements, including a TED talk, from a staggering 160 last year to a manageable, or so he says, 40 to 50.

His calendar is perpetually filled, but the 52-year-old shows no signs of slowing down. He’s been this way for quite some time. Conley grew up in Long Beach, attending the famed Long Beach Poly High School, where something sparked in the lanky Caucasian. He became curious of his surroundings and the various colors, shapes, and sizes that surrounded him. His family didn’t travel extensively, but it was enough to get his legs moving. Conley went on to Stanford University, where he left with a bachelor’s degree and an MBA and started the Joie de Vivre hotel company at just 25 years old. That endeavor lasted almost 30 years. He sold a majority interest in 2010 and set off to pursue other projects.

Thus came Fest300, a place he calls a living museum of the most influential festivals across the globe. The concept spawned on a book tour when someone asked why he loves Bali so much, a country he’s visited 11 times. He went off the script and tapped into what he says was happening in his subconscious. “Wouldn’t it be nice,” he asked the Manhattan crowd, “if there was a place you could go to look at the 300 best festivals in the world and figure out which one’s right for you?”

He’d been toying with the idea for some time, but when approached with it point-blank, he realized this was his next undertaking, as a conduit for the other inquisitive souls in the universe seeking the transformative.

He believes the evolution of the human experience relies on the constant flow of cultural information. He pledged to find a way for everyone to feel the power cross-cultural education provides. “Curiosity is an opening up to possibilities,” he says, “and there’s a certain humility that comes with curiosity, which means you don’t know it all.” That persistent voice pushing us to discover what once was unknown, he believes, is the true fountain of youth.

The three-month-old site has aspirations of grandeur. He’s using social media to connect with the like-minded millions scratching the itch to get away and see life on the road less traveled. The first 50 or so Facebook responders were invited to his house on Dia de los Muertos (Day of the Dead), a Mexican holiday widely revered by San Francisco’s substantial Latino population. In keeping with the Fest300 vision of cultural education through human-to-human connection, he opened his home to perfect strangers.

“Yeah, why not?” he says, shrugging across the phone line.

I ask him if he has any downtime and he lets off a good laugh. “Frankly, no,” he says. But he understands this is part of the process. This is the energy it takes to make certain his passion is passed on.

His place in this big picture is established, and it’s a result of hard work, a few strokes of providence, and the dynamic, intangible elements ingrained in his DNA. He politely needs a reminder where this conversation would eventually end up, and I tell him. A subtle nod to how busy he is. The conversation ends, and the man whose wheels are constantly spinning looks forward to a few quiet hours alone. But tomorrow, he knows, is a new day, and Chip Conley will be ready and willing to see what he can do to make it better.

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