Getting Weird in Detroit With the Help of Airbnb Experiences


“No shit? You’re Kid Rock’s guitarist?”

Kenny Olson smiles at the two 20-something male tourists from Pittsburgh, both of whom seem genuinely starstruck.

“Used to be,” Olson says in a raspy baritone. “I’m doing other stuff now. Got a gig tonight.” He gestures toward a poster on the wall behind him, which features a picture of Olson himself wailing on a guitar and making a pained “I am rocking so hard” expression.

The tourists lean in for a closer look. “Kenny Olson and Friends,” one of them reads aloud from the poster. They turn to look at me and my small assortment of new friends hovering near Olson. The majority of us are dressed in black leather, all of it way too tight for healthy circulation. Also, one of us is wearing a lizard mask.

“These your friends?” the tourists ask Olson.

“Fuck yeah,” Blind Bob shouts back. Blind Bob—his nickname isn’t hyperbole; he’s actually blind—is the one in a lizard mask, which makes his declaration especially ominous.

“You guys in a band?” they ask.

We laugh, but nobody answers. Because technically, no, we’re not. We’re just Olson’s entourage, or at least we are today. What’s more, we paid for those bragging rights. We’ve signed up for Motor City Rocks, a new Airbnb “Experience” that offers a different kind of vacation. For $375 a head, we get to drive around Detroit in a limo, get day-drunk and listen to a guy who used to tour with Kid Rock tell stories about midgets, rock excess and that time Florence Henderson grabbed his ass backstage.

Olson has had an impressive music career for a relatively unknown axman. He was Kid Rock’s lead guitarist for 11 years, providing riffs and blistering solos for such hits as “Bawitdaba,” “Cowboy” and “Only God Knows Why.” He quit recording and touring with Rock in the mid-2000s—“The reasons are complicated,” Olson says—but he hasn’t been hurting for opportunities. He’s played with the likes of Metallica, Sheryl Crow and Snoop Dogg. Keith Richards once called him “one of the best rock guitarists on the scene right now.” Keith Richards! That’s like the Pope saying, “That guy over there is the best Catholic I’ve ever seen.”

We’re outside Third Man Records, the vinyl shop and recording studio of Detroit native Jack White. Olson doesn’t know White personally, but “the store is pretty badass,” he assures us. It’s the latest stop on a citywide tour that has been meandering at best. So far, we’ve seen the Motown museum, Saint Andrew’s Hall (where Eminem got his first break) and the Majestic club. Olson has played at every venue except Motown, but his ex–father-in-law was one of the Temptations.

Skip Franklin, Olson’s manager, inserts himself between us and the Pittsburgh admirers, ushering us back toward the limo. “Come on, guys, let’s keep it moving!” he barks at us. “We’re on a schedule here.” This is not entirely true. Other than driving around looking for music landmarks, we don’t really have anyplace to be until sound check at seven p.m. But we happily play along with the ruse, because there’s something thrilling about having a big, burly rock manager, with a face that looks like it’s not unaccustomed to receiving punches, treat you like somebody too important to talk to civilians.

Back in the limo, Olson unfurls another rock tale—something about debating the many variations on the peanut-butter-and-jelly sandwich with Michael Jackson. Olson is easy to like. He’s scraggy and disheveled, with a paunch and a big grin that peeks out of a gray goatee. He zigzags between topics randomly, following no apparent logic. One minute he’s explaining why that Journey song “Don’t Stop Believin’ ” sucks because there’s no such thing as “south Detroit.” Then, apropos of nothing, he’s telling us about the time Joe C, Kid Rock’s three-foot-nine sidekick, tried to beat up Gary Coleman during the video shoot for “Cowboy.”

This is his first full-fledged Motor City Rocks outing for Airbnb. The first few were just “test runs,” he says. “They were mostly friends coming in from out of town. We’d just drive around and laugh.” Which isn’t all that different from what we’re doing now. But the customer base has definitely expanded. Our group includes Blind Bob, a New Yorker by way of South Carolina who lost his eyesight in an “explosion” (the details are sketchy) and rebuilds car engines for a living (the details of how he does that without the gift of sight are also sketchy) but whose real passion is drumming. His eyes are as white as a Michigan winter, and he carries around a pair of drumsticks and a seeing eye dog named Buddy, a Maltese with a spike studded collar and a weirdly calm demeanor despite all the noise. Blind Bob—he hands everyone a business card that reads “Blind Bob the Lizzard Man”—met Olson during a recent rock-and-roll fantasy camp in Hollywood and decided he needed to make the pilgrimage to Detroit.

There’s also Frank Faisst, a German corporate exec who deejays and shoots music videos on the side, barely speaks English and is dressed as though he’s heading to an S&M dungeon. He’s here with Dacia Bridges, a Michigan native who has spent the past two decades in Germany, working on her dance and electronica singing career. Rounding out our traveling party is Bella Bond, a small-framed brunette with enormous fake breasts—she shared this info with me moments after we met—that are barely contained by a skimpy leather halter top. She traveled here from West Palm Beach, Florida, where she works as a model (mostly for biker conventions) and has a doctorate in pharmacy. Oh, and she has minor brain damage.

“I got hit by two trucks, in the head,” she tells me. “I was driving, and they smooshed my car. The front was fine, but the trunk was pushed up into the passenger’s seat. Whatever cut my head was in my trunk. I don’t remember. I had amnesia.”

“Wow,” I respond, not sure what else to say. “I’m glad you’re okay.”

“The doctor said I’m not at full mental capacity,” she tells me. “So, if I forget your name, I’m sorry. I’m not all there.”

It might be the drugs talking—when somebody pulled out a joint, I didn’t say no—but this is hands-down the most entertaining vacation I’ve taken in years. And I say that as somebody who never much cared for Kid Rock, or white-boy rap-rock in general. I’m not even all that impressed with the Detroit music scene. I love Iggy Pop and Motown, but not enough to fill my phone with photos of the empty stages where they once performed. There’s nothing about this tour that’s nearly as exclusive or “underground” as promised. Get yourself a flask and a GPS and you could easily re-create it. But you’d be missing the point. Like that old saying goes, it’s not about the destination; it’s about taking the journey with a blind drummer, a German in tight leather and a guy who used to perform in front of thousands with a little person.

We pull up to the Fox Theatre, where Olson has arranged for an all-access backstage tour. We’re joined by a few others, most of them musicians performing tonight with Olson. Tino Gross, a local bluesman who looks like a character from a Tom Waits song—he’s a skinny white guy in a fedora and black sunglasses with a voice that sounds like he smoked a pack of cigarettes before breakfast—tells me he performed in this very theater with Bob Dylan.

“I was in the lobby before the show,” he explains, “and Bob’s manager, Mitch, runs up to me and says, ‘Bob wants you to play tonight.’ He took me backstage and pointed to a Marshall amp. He told me, ‘When Bob looks at you, take a solo. And then when he looks at you again, stop.’ That was the only thing I knew going in.”

We all nod in quiet reverence, sitting in the dark and staring at the stage that has seen so much history. Even Olson is at a loss for words. But then Blind Bob breaks the silence. “Are we done here?” he shouts, scooping his dog Buddy off the ground. “It’s drink-30. Let’s do some fucking shots!”

We all laugh. Classic Bob move!


Last November, Airbnb co-founder and CEO Brian Chesky unveiled the company’s new Experiences program to an audience at L.A.’s Orpheum Theatre. In his speech, he recalled pleading with his parents as a child to take a family trip to “the most magical place on earth, the North Pole.” Their vacations rarely got more ambitious than an Anheuser-Busch factory tour, and his lingering disappointment helped inspire Experiences, which Chesky promised would make vacations “magical” again. How do you do that? By using the “hero’s journey” narrative structure coined by mythologist Joseph Campbell.

“A character starts in their ordinary world,” Chesky explained. “They cross the threshold—think Wizard of Oz—to this new magical world, where they meet people.… They have a moment of transformation, and they return to the ordinary world.”

You couldn’t ask for a better summation of Airbnb Experiences—created by a guy who’s still pissed off that his parents never took him to Santa’s Village and founded on the same creative philosophy that helped George Lucas come up with Star Wars.

Airbnb currently offers about 800 Experiences in 20 international cities, with plans to expand to more than 50 by the end of this year. An Airbnb spokesperson says that roughly 34,000 people have started the process of creating an Experience.

Many of the existing excursions cover well-trodden territory, like drinking and eating. But since the program’s launch, the Experiences have gotten uniquely weird. You can pay to ride around London in a penny farthing bicycle, or do yoga with a Barcelona model, or make plastic food in Tokyo, or visit Nelson Mandela’s prison with his former prison guard (included: “a meal in prison”). For $619 you can spend the night with an actual wolf pack, which includes a long hike into the mountains of Los Angeles, sleeping under the stars next to creatures that could ostensibly eat you, and s’mores. Some of the Experiences sound like they were created with Mad Libs. Come feed homeless people in Capetown . . . with a local DJ. Learn how to make your own lamp . . . while drinking margaritas. Take a walking tour of historic London sites . . . while learning how to play the ukulele.

“They’re creating an industry that doesn’t exist,” says Brad Stone, author of The Upstarts: How Uber, Airbnb and the Killer Companies of the New Silicon Valley Are Changing the World, “which is harder than it looks. But they’re trying to cater to a millennial mind-set, which is ‘Don’t sell me some cookie-cutter thing. Give me something I haven’t seen before.’ But that’s hugely challenging, because you’re trying to sell people things that maybe they don’t even know they want.”

The common denominator for all Experiences, the thing they all offer without explicitly stating it, is temporary friendship. A Paris Experience, billed as an “Urban soccer challenge,” is a pickup soccer game, followed by a drink at a bar with your new friends—all for just $35. You can eat tapas in Barcelona with “foodies” (i.e. people who like food), or go vinyl-record shopping with a guy in Osaka, or “meet cool people” at a party in Paris, or have a picnic with a stranger in San Francisco. For $95, Amanda in Los Angeles will drive around the city with you and eat tacos. You pay for your own tacos, but she’ll show you where she likes to eat tacos, and then the two of you can eat tacos together.

Courtney Nichols, a self-described “purveyor of kitsch,” sells an Experience that’s essentially drinking with her and her friends for an evening. On her Airbnb ad she promises to take you to “bizarro landmarks” and hang out with her “martini-guzzling…outlandish entourage” at “invite-only dance marathons.” Nichols tells us that her $299 Experience is about “meeting my social circle. I surround myself with a group of bohemian eccentrics. A lot of drag queens are in my social circle. A lot of artists. A lot of people who are just quirky.”

Customer reviews tell a different story. Airbnb users who tried the Nichols Experience have been less than satisfied, with one complaining on the website that “she took us to her friends’ apartment, where we sat around for another hour waiting for them to get booze.” Another claims they “expected to go out to a few L.A. bars and dance, instead we spent most of the night at her home and a friend’s apartment,” and they “left the experience feeling confused.”

It’s possible some of the Experience hosts have loneliness issues of their own. For $25, a young couple will take you up to the Hollywood sign and explain their complicated reasons for moving to L.A. There’s an $84 tour of the Louvre in Paris that’s advertised as “Meet the funniest guy in the museum,” which is nothing if not a cry for help. If you’re in Florence and your idea of a good time is “walking at night in silence,” there’s an Airbnb host willing to charge you $79 for the opportunity. (Don’t worry; the host provides a “small flashlight,” so it won’t be weird or anything.) A web designer and video editor in L.A. is offering an “intimate, exclusive comedy experience” in his living room. For $20, you can come to his house and he’ll make you dinner and then perform stand-up just for you. And then murder you and bury your body in his backyard? Hopefully not, but that’s definitely what it feels like.

Chris Wren, a software engineer for Airbnb, is both an Experience host and an enthusiastic Experience customer. For him, the platform has never been about feeling less alone. “You can meet new friends, but it’s not really about that,” he says. “I think the best kind of travel is when you become a new person, when you take it beyond the shallow touristy thing and embrace the fantasy of it.”

How far could that fantasy be taken? It’s not that big a leap from “Let’s play soccer” to “Let’s have a masked orgy.” I asked the Airbnb reps if they would accept Experience proposals that were sexual in nature—maybe not so far as soliciting prostitution but at least involving nudity and adult behavior—and they directed us to the “quality standards” web page for prospective Experience hosts. It doesn’t mention sexual content. The company’s main concern is that hosts craft a compelling three-act fantasy. “Consider the beginning, middle and end,” the Airbnb site advises. “How will you greet guests when they arrive? What is the main activity they’ll do with you? How will you draw the experience to a close?”

Kerri Aultman, a fetish model in Miami, hopes to be one of the first to take the Experiences in a bold new direction. She’s currently overhauling a loft space for maximum kink possibilities. There will be a stripper pole and a mirror ball and a “costume room” full of wigs, slutty costumes and fetish gear for experienced and newbie clients alike. Her Experience, she says, is designed to be only for women who want to spend a day and a night exploring their kinky sides.

“I live in a fantasy world all the time,” she says of her day job. “I want to create an Experience where people can try that for themselves. They can put on some wigs and fishnets, find a new sexual identity, see what it feels like. We’ll go out on the town in costumes and then come back and have a slumber party.”

So basically what Chesky and Joseph Campbell had in mind, but this hero’s journey ends with pillow fights and a stripper pole.


Now we’re at a fancy restaurant–music venue in suburban Detroit. It’s just like the rock clubs on 8 Mile Road but with more white people and a menu that includes duck cotechino. Olson and friends are performing here tonight, and the backstage lounge is packed with a dozen or so musicians, friends and pay-to-play “friends.” Actually, the backstage is just a small room off the restaurant’s kitchen, with a few couches that smell like sweaty leather, pizza slices balanced on every available surface and a big tub of canned beers on ice.

A stern-looking woman bursts into the room from the kitchen. “Guys, please,” she says. “There is absolutely no smoking weed in here!”

Nobody says a word. We just pretend we have no idea what she’s talking about. Because obviously, none of us were smoking weed. What gave her that idea? That thick cloud of blue smoke hanging in the air must’ve come from someone else.

I return to my conversation with Joe Sax, the lead singer and bassist of Olson’s new trio, the Scorpio Brothers. Sax is dressed all in black, with long black hair and black sunglasses that never leave his face. He could just as easily be a cat burglar.

“I told Kenny, ‘I’ve listened to your stuff, and a lot of it is “Oh, I’m fucking high on cocaine, I’m drinking too much, I want some pussy,” all this shit,’ ” he tells me. “I’ve already done that. If we’re going to do this, you have to let me sing about shit that matters to me. The working title for one of our songs is ‘Changing Minds.’ The chorus is ‘Changing the world is changing minds, this is the world we leave behind.’ Because you gotta care about what we’re leaving behind, right?”

As it’s happening, it feels like the greatest conversation I’ve ever had with another human being. But I know it’s all about context. Change a few circumstances, and I’d probably want to kill myself. But sitting backstage before a show, where the beer and pizza are free, people keep handing me joints and Olson’s manager keeps checking on me—You need anything? A plate of mussels, a bourbon cocktail, a foot rub, a new pair of pants?—I feel special.

I’ve learned a lot about Detroit today. Maybe not a version that most tourists get, but a more intimate one. I’ve learned there’s a catwalk above the Fox Theatre that nobody is allowed to use, but Olson and Dweezil Zappa snuck up there once. I learned that the club where Jack White punched a guy in the face has a great deal on mid-afternoon shots. I learned that the mansion of Motown founder Berry Gordy is for sale, for a mere $1.6 million, and Olson is thinking about buying it. (We drove by to check it out and take a bunch of selfies in front of it while making rock horns, which really confused the gardeners.) I learned that Hot Tamales is the only strip club in Detroit that doesn’t charge a cover. I learned quite a few things about strippers, in fact.

Franklin interrupts a scintillating conversation about the strippers of Flint to let us know it’s time for sound check. Olson and the band head to the stage, and I take this opportunity to talk to my other Experience cohorts. Why exactly are they here?

“Some places have dinner packages with the stars, where you can meet them before or after the show and have a drink, but this is different,” says Dacia Bridges. “It’s more authentic. You don’t feel like a fan getting a meet-and-greet. You’re just hanging out.”

Nobody in our group is under the illusion that this might be their ticket to a music career. They don’t expect to be discovered or given a record contract if they just impress Olson enough. “I don’t have any musical talent,” Bella Bond tells me. “I just like being around these guys, feeling like I belong here.” Most of them are happy with their non–rock star lives. Blind Bob has created his own weird universe. He tells me he’s heading down to Myrtle Beach, South Carolina tomorrow to be a judge at a beauty contest at a biker bar called Suck Bang Blow.

“Do I want to ask how you do that?” I say.

Blind Bob chortles sinisterly while petting Buddy, who hasn’t left his side all day. “You want my vote, your boobs better be covered in braille.”

The show starts late. At least 300 people squeeze into the small space, and they’re ready to bob their heads enthusiastically while drinking craft beers. The Scorpio Brothers get started around 11, and it’s an aural blitzkrieg. Olson delivers slushy guitar riffs at a volume that makes my genitals vibrate like a speaker’s woofer. Bridges jumps onstage to join them for a cover of Hendrix’s “Little Wing,” belting out the tune with the soul of a seasoned R&B performer. The crowd hollers in approval, and so does the Olson Experience gang, but we do it more meaningfully because we’ve been partying with her for the past 30 hours. We have a connection that none of these civilians would understand.

When it’s over, we stick around as Olson and his bandmates pack up their instruments and pound more drinks and sneak away for joints in the alley and talk about what an awesome gig it was. There’s a lot of exchanging of e-mail addresses and phone numbers, and promises that this is the beginning of something, though nobody says what that “something” might be.

“You’re stuck with me, Bob,” Olson says, giving Blind Bob a lingering hug. “For the long haul. You and me.”

“I love you, brother,” Bob says, still wearing his lizard mask. “Don’t let anybody know, though.”

I wake up with ringing ears and a pounding head and clothes that smell like bad decisions. I have no idea how I made it back to my hotel room. My phone is yelling at me, and I see I’ve gotten a text from Olson. “Thank you for all your support my soul brother,” it reads, followed by several rock horn emojis.

I stare at my phone for a long time, not sure what to think. Are we pals now? Can I legitimately say, “Me and Kid Rock’s guitarist are soul brothers?” I guess that’s cool, but I was hoping for something a little more profound. Chesky had promised a hero’s journey. Where was my “moment of transformation”? Had I learned about myself through this experience?

Well, I guess I learned I can smoke rock-star weed and still have coherent conversations. I learned that my rock-and-roll dreams from childhood haven’t gone away, as just standing behind the velvet rope at the side of the stage during a concert gave me goose bumps. I came to this Experience with a sneering adult cynicism, but by the end of the night I was flashing rock horns unironically. I was a kid again, pretending to be an adult, or at least my kid fantasy of what being an adult would be like.

I’m like the guy who visits a Caribbean island and decides he’s going to move here and open a rum drink stand on the beach and he’s totally serious, just you wait and see! Nobody actually follows through with that insane idea. We just enjoy the fantasy. We like the fleeting belief that this might be what our lives are now. It fades eventually, like all fantasies. We sober up and the vacations end and we get back to the real world. But while it lasted, it was beautiful.

I crawl out of bed to look for my pants. They are nowhere to be found. For a split second, I think about texting Franklin. He’ll know what to do.

[This story originally appeared, in a slightly different form, in the July/August issue of Playboy magazine.]