You know the place, even if you haven't been there.
From the outside, it has a spare, severe look. But inside, past the flower stall and barbershop, the vibe is serene and hushed. Long tables and worn leather chairs invite people to cluster; the scent of locally roasted coffee mixes with the sound of the nearby photo booth, whirring in the background. There are vintage records on the shelves and slinky indie pop on the speakers, and the late afternoon sunlight makes puddles on the century-old wood floor. The feeling is both of the moment and timeless.
To a remarkable extent, this place, the Ace Hotel, is the brainchild of a single man, a lean, mop-haired native of the Pacific Northwest named Alexander Calderwood. A kind of hipster polymath, he was able to look around the corners of culture and see what was coming years, if not decades, before everyone else.
In his 20-year career, Calderwood cofounded a barbershop, a nightclub,a record label, and an experiential marketing agency in addition to the Ace, but what his projects all shared was a particular vision of what "cool" could be. At once deceptively simple and meticulously curated, they catered to subcultures that were both trendy and upwardly mobile; as a result, his influence far exceeded even his considerable financial success. By his late forties, though reserved and aw-shucks quiet, Calderwood was one of the most sought-after creatives of his generation.
"When I think about him at night, I think of him half-watching TV, half-reading the newspaper, and having three books around him, all of them open," says Calderwood's best friend, Caterina deCarlo, who shared an apartment with him for many years. "He definitely worked a lot, but I don't want to peg him as this dysfunctional workaholic. We all worked like that. I mean, we found each other for that reason." Says Seattle arts journalist Tricia Romano, "He basically refused to brag. You could talk to him all night and not know who he was. At the same time, he was up at 6 a.m., and still up at 2 the next morning. He was the kind of person who didn't stop working or playing—who literally just cannot sleep because they're so motivated."
Though it did not define his life, Calderwood was also an addict. Pills, booze, and powders were all a part of his world, as they were a part of the rock-and-roll lifestyle his businesses embraced. Whether he turned to them as an escape, as a recreation, to calm his relentless energy, or for reasons only he could understand, we will never know: Last November, Calderwood was found slumped over the foot of the bed in one of his hotels, dead from a lethal combination of alcohol and cocaine. He was 47 years old.
What we are left with is a portrait not only of extraordinary creativity and energy but also of their reverse—lapses and relapses and darkness. Speaking late last year, a friend voiced an idea common among the members of Calderwood's inner circle, who knew him to have an almost superhuman ability to do more, to keep going. "He was built a different way from the rest of us," the friend said.
It certainly seemed that way, until he was gone.
Seattle in 2014 is a sleek, modern boomtown. Facebook and Google both keep large offices here, and in the South Lake Union neighborhood, where Amazon recently received approval to build three interlocking biospheres—the core of its new international headquarters—a glass-and-steel luxury high-rise seems to spring up every other week.
In the early '90s, Seattle was much scruffier, a hotbed of nonconformist art and music, and home, as one local remembers, to a small army of "freaks and geeks, gays old and young, activists, broke students, and way-left liberal weirdos." Rent was dirt cheap; grunge music, with its savagely distorted angst, was ascendant. In the evenings, dive bars, art galleries, and underground music clubs rumbled with energy. This was the Seattle to which twentysomething Alex Calderwood arrived.
"To us, Seattle was a new frontier," says Jared Lovejoy, one of Calderwood's closest colleagues. "I'd been to design school in New York, and out there, you were fighting over scraps. It felt not very friendly or collaborative. But in Seattle, we were all trying to pay it forward, to keep all that energy circulating, to keep each other alive."
Calderwood had grown up in Bellevue, a working-class city nestled between Lake Washington and Lake Sammamish, near the foot of the Cascade Mountains and within sight of Greater Seattle. His father was a contractor and his mother a columnist for a local newspaper, but they divorced when he was young, and his father remarried a woman with whom Calderwood had trouble getting along. He was one of four children, but he thought of himself as a bit of a loner, happiest living in his own head. Classmates at his Catholic high school remember a calmly charismatic kid, confident and happy, able to move seamlessly among various cliques—the jocks, the geeks, and the punks.
Sometime after high school (there's disagreement among his friends as to exactly when), he found a job in merchandising at International News, a clothing store in Seattle's low-slung Belltown neighborhood, and took a small apartment above the shop. He had "a nerdy, spazzy energy," recalls someone who knew him at the time, and a thousand interests—film, books, fashion—all of which he pursued with abandon.
Almost immediately, Calderwood's talent for design was obvious. Amit Shah, the proprietor of International News, has said, "He saw what you could do with material that nobody else wanted." He made trips to the Boeing Surplus Store and crafted desks and light fixtures for the shop out of scraps of metal; on the side, he helped source vintage denim for local boutique Jack Hammer, which had found an eager audience in Japan.
In 1992, then-26-year-old Calderwood, along with Wade Weigel, opened a barbershop called Rudy's, near the top of Capitol Hill. At the time, Weigel, a former boyfriend of Calderwood's, was running a series of illegal parties in a condemned hotel in the Warehouse District and waiting tables on the side. Both men believed there was an opportunity for a barbershop that would cater to the kind of people they socialized with—the artists, the record-label guys, the club kids. To amp up the appeal, they offered tattoos on the side. "When we started, I remember our receptionist was smoking and reading tarot cards at the counter," says David Peterson, an early employee who later joined as a partner. "It was raw. But that's what our clients were coming for. They wanted raw." Within a few months of opening, the wait time for a walk-in at Rudy's was an hour and a half.
Soon, a second Rudy's went up in Fremont, a hyperliberal, rapidly gentrifying enclave in the north of the city, and a third in Belltown, on the waterfront; Phinney Ridge and Ballard locations followed close behind. By the mid-'90s, Rudy's was printing money, and Calderwood, the "spazzy" kid barely into his thirties, was officially a successful entrepreneur.
In those early days, booze and drugs were everywhere—intrinsic components of the nightlife circles in which Calderwood traveled. And yet if Calderwood partook, he was rarely obvious about it. In the 1990s, he was a reserved presence, friendly and warm but more likely to be sitting at the back of the club, bobbing his head under a knit beanie, than swinging off the chandeliers.
A close friend speculates that drinking and drugging was initially a release valve of sorts—"a manual shutoff. I think for Alex it was just kind of a way to power down. And let's face it: Sometimes, the harder you're working, the harder it is to turn off your brain." The drinking may also have been a form of social lubrication; by all reports, including his own, Calderwood could be shy and had a tendency to withdraw.
By the mid-'90s, with his barbershop venture solidly established, Calderwood had turned his eye to party promotion and club nights, working first by himself, and later with Jared Lovejoy and several other friends, under the mantle of a production company dubbed Tasty Shows. Calderwood was soon presiding over what Lovejoy calls a "little baby empire," encompassing Tasty Shows, a record label called Sweet Mother, and in 1998, a full-scale club called ARO.Space, in the clamorous Capitol Hill corridor. "You'd have drag queens and the bridge-and-tunnel crowd. Seattle was siloed, but we brought them all into one room," says Nasir Rasheed, a cofounder of Sweet Mother who deejayed frequently at ARO.Space.
Calderwood initially discounted his talents for curation and connecting disparate tribes. "Alex appreciated people who could paint or draw, and for a long time, he didn't think of what he did as really creative," Lovejoy says. "But in his late twenties, he relaxed. He got comfortable with his role as a cultural editor. He talked about that a lot: how creating an experience is also an art form."
But putting on events at someone else's club turned out to be a lot easier than fighting to fill their own, and in 2000, Calderwood, along with Lovejoy, Rasheed, and Caroline Davenport—another member of the Tasty Shows crew and a co-owner of the venue—shuttered ARO.Space. Together with Rasheed, they shifted their attention to Neverstop, the marketing agency they'd started four years earlier, which specialized in the then-avant-garde art of interactive branding. Corporate bigs such as Nike and Microsoft would hire Neverstop to create interactive experiences: pop-up shops, scavenger hunts, backstage gifting suites at major music festivals, and mobile projection vans that beamed logos across city streets.
The multiple businesses Calderwood was juggling in the late 1990s and early aughts created a knot of interlocking and overlapping ambitions, and to describe them now is to wonder how the man managed to keep it all straight. According to Linda Derschang, a longtime Seattle power broker and restaurant owner, the boyish Calderwood "made everything he did seem fun and easy."
Around 2004, Calderwood's substance problems grew more visible. Out at clubs, he'd snort coke, pop pills, knock back booze. "It was crazy, because for many years he was the relatively sober one among all our crew," one person close to Calderwood says. "I just figured he finally had accomplished enough to relax and party."
Still, he was a master at compartmentalizing. The same friend who calls drugs a "manual shutoff" for Calderwood stresses that the partying didn't interfere with his work. "He was never, like, missing meetings or fucking shit up," the friend says. "Never, never, ever."
The idea for a hotel seems to have first occurred to Calderwood in the mid-'90s. He envisioned a variation on the Rudy's theme—affordable but hip, deliberately shaggy, a refined edition of a rock star's crash pad. The kind of place, he explained, where the "people we knew—DJs, artists, magazine creators, graphic designers, musicians—would want to stay."
After a couple of years and some false starts, Calderwood and Weigel toured a derelict flophouse in Belltown, initially in the hopes of finding a location for a Rudy's branch in that neighborhood. Calderwood had a different suggestion: Why not make it into a combination barbershop and hotel, with a small number of rooms on the second and third floors and the salon downstairs, on street level? A third friend, Doug Herrick, joined as partner. "We jumped in very naively, just jumped in with both feet. I think our naiveté actually was a benefit, in a way, because we just approached it the way we would approach it," Calderwood would say of that first hotel. "We didn't think about what's conventional or unconventional."
When the Ace finally threw open its doors, in 1999, it felt like a victory. Just as he had curated every part of the Tasty shows, Calderwood had his hand in every part of the new property—he recruited street-artist friends to decorate the rooms; obsessed over the wallpaper prints; reviewed every light fixture. "When 99 things are right, nobody notices or comments," he later said of the Ace design process. "It's that one thing that's wrong that people notice. It's on a very subconscious level, and people feel when something is off."
Calderwood said he took the name for his hotel from the playing card, which is both the high and low point of the deck. ("Ace" was also Calderwood's childhood nickname.) It was a good fit: From its inception, Ace carefully balanced designer touches and a Euro-style hostel feel. There was a common buffet dining area, and there were rooms with bunk beds for under 60 bucks a night, but for a little more cash, guests could upgrade to "deluxe" chambers with Shepard Fairey prints hanging over the bed and water views.
The hotel earned a fair amount of press, and with it, the recognition of industry veterans, who suddenly found themselves forced to contend with the incursion of a bunch of outsiders.
Hotels are high-margin businesses, but getting them off the ground requires a good deal of orchestration and the management of a byzantine array of funding streams. Each is, in effect, a baby empire.
Partially for this reason—and partially because Calderwood at the time had been so consumed with Neverstop, and Weigel with Rudy's, and Herrick with the day-to-day operations of the Seattle Ace—the Ace group had shied away from opening another hotel. That changed in 2006 when the partners met Jack Barron, an architect who had contacted them blindly through the Ace website. Barron restored some of the team's momentum, Weigel recalls. Originally, Barron had argued for a European Ace, but when space opened up in the elegant old Clyde Hotel, in downtown Portland, Oregon, they readjusted course. "All of a sudden," Weigel says, "we were really in the hotel business."
As Ace grew, so did the scale of the company's ambition. The original Ace had 28 rooms. The Ace Portland had 79. The Ace Palm Springs, opened in 2009 in California, had 179. Although the Ace had a formula, it was largely defined by Calderwood's ability to adapt each new property to its surroundings—to "make you feel like you're a guest in the neighborhood," as a business collaborator, Wieden+Kennedy creative director John Jay, puts it—which heightened the complexity of each new hotel. The Portland Ace had coffee from local roaster Stumptown; cozy blankets from Pendleton, which first started making woolens in Oregon in 1909; and handmade steel bikes available for loan. Meanwhile, the Palm Springs Ace, with its swim club and spa and shaded grottoes, felt like the lair of a luxury-minded desert hermit. In describing his properties, Calderwood spoke of "intangible psychogeographical criteria."
It was the kind of language that left the Ace chain open to charges that it was too precious by half, and reviews of some of the later properties mentioned "poorly trained" but well-dressed employees and "a shabby-chic style" that lost its appeal as prices edged into the $500-a-night range. (In a biting sketch from the second season of Portlandia, Fred Armisen and Carrie Brownstein play smug, hipster clerks at the "Deuce" hotel, where they distribute typewriters to guests.) Still, Calderwood was increasingly viewed as a kind of master prognosticator, with the ability to innovate much faster than his competitors. As one analyst has noted, even today, "a lot of hoteliers are still playing catch-up."
In 2009, the Ace group purchased the historic Breslin Hotel, a down-and-out single-room-occupancy establishment in Manhattan's Garment District. For the Ace team, the project represented the opportunity to do what they did best: revitalize an aging property and open up the surrounding area to new business, this time in one of the world's largest, most visible tourist economies.
They called upon a mix of local and out-of-town kindred spirits: Stephen Alesch and Robin Standefer, of the celebrated New York design firm Roman and Williams, handled the interiors. Carol Lim and Humberto Leon, whose eclectic and well-edited Opening Ceremony downtown boutique is similarly culturally fluent, opened a travel-themed branch in the Ace lobby. Because New York at the time was a good-coffee wasteland, a Stumptown was installed on the ground floor, and Ken Friedman and April Bloomfield, the duo behind the gastropub sensation the Spotted Pig, opened up two restaurants in the hotel, the Breslin and John Dory Oyster Bar.
The New York project wasn't Seattle, Portland, or Palm Springs—it was an enormous multimillion-dollar undertaking in the middle of the biggest city in the United States. Calderwood was thrilled, friends say, but the pressure to pull it off was intense. The Ace team ran into problems clearing the 268-room property of its preexisting tenants, who were loath to give up their stake in such a plum piece of real estate. Local blogs chronicled every noisy accusation that the Ace people, far from showing any concern for the neighborhood, were just out to enrich themselves.
In the run-up to the New York launch, Calderwood and Barron had a falling out. Barron said he had no interest in "big business," as he put it, or in building relationships with the types of deep-pocketed developers necessary to get a hotel the size of the New York Ace off the ground. He called the city a "ruthless, demanding, fairly inhuman place," and added that Calderwood's drinking did little to make the situation more tolerable.
Calderwood at the time was open about his addiction, and said publicly that he'd recently completed a stint in rehab and was five months sober. "Just so you know, I'm very proud of my sobriety," he told The New York Times in 2010. Calderwood may have been playing down his problems to placate the incredible number of people now relying on him, but he could also be streaky when it came to self-betterment. According to Weigel, though, Calderwood "always had good intentions."
Within a year of its opening, the Ace property in New York was being lauded as a cultural landmark—a hub for tech entrepreneurs, who huddled in the lobby to down caffeine and take advantage of the free Wi-Fi, and the kind of place where you could bump into celebrities such as Olivia Munn and Kirsten Dunst.
But Calderwood had already moved on.
A pattern soon emerged: scout out a location, secure funding, oversee renovations, preside over opening, repeat. There was little time for rest, but Calderwood may have preferred it that way. He was always in the air, rarely home, always moving. He smoked a lot, as much as a pack a day, and struggled to eat healthy. He'd never had any trouble attracting boyfriends, but given his schedule, maintaining a relationship was a different matter. He complained of ending up with the "wrong" men.
In 2011, the Ace group started work on perhaps its most ambitious project to date, a grand 182-room hotel in downtown Los Angeles located on the site of the old United Artists Theatre. Calderwood and his partners made the decision to keep intact the 1,600-seat performance space and much of the original touches of the 1927 building, a property that Calderwood envisioned mixing the glamour of Old Hollywood with the punk-rock ethos of the '80s—"both great, wild moments of revolutionary creativity, not to mention some experimentation and dangerous excess," he said. At the same time, Calderwood was commuting regularly to Panama City, where his Ace offshoot, Atelier Ace, was building a luxury property to be opened under the name American Trade Hotel.
But as Ace was entering its next growth phase, Calderwood had begun divesting himself of responsibilities, much as he'd done with his previous endeavors. By the early aughts, Calderwood had become essentially a silent partner at Rudy's, removed from quotidian business matters. Meanwhile, he'd off-loaded control of Neverstop to Rasheed, who later bought Calderwood and the rest of the partners out of the operation entirely.
Calderwood still planned on remaining involved with the Ace on a macro level, but his restlessness was always driving him toward new projects. In 2012 and 2013, Calderwood was busy collaborating with John Jay on a youth hostel, the Grove, to be built in Seattle's Chinatown neighborhood. He was also helping his friend and sometime roommate Caterina deCarlo conceptualize a rock-and-roll dive bar in L.A., expanding the size and scope of the Ace Atelier group, and overseeing the hunt for new hotel locations. In addition, he had purchased a cabin on Orcas Island, in the verdant San Juan chain, where Jared Lovejoy had opened a cocktail lounge called the Barnacle.
Though he had the freedom to pursue his interests and appeared to be flush with success, friends say that he was occasionally chewed up by anxiety. The number of funding sources behind his various projects was increasing, as was the amount of money involved. Speaking to British design blog Cool Hunting last October, Calderwood seemed to reference tension between bottom-line-oriented investors and the creative-minded Ace team. "As we grow and things we're doing are more complex, there's a group of people who are like, 'Process, process, process,' " he said. "And process is important, but we also have to go with the flow—the process has to be flexible to allow us to achieve what we want to achieve. It's a balance." This was a far cry from the Calderwood who'd told Interview magazine back in 1994, "I'm just a barber and a tattoo pimp."
For a decade, Calderwood had been mulling the possibility of a European Ace—he had looked at various points in France and the Netherlands— and by late last year, he was close to realizing his dream with a new property recently launched in the East London district of Shoreditch. Early reviews were ecstatic: Writing in the Financial Times, architecture critic Edwin Heathcote had pronounced the place "pulsating with life."
Shortly after the opening, Calderwood and Kelly Sawdon, Ace's managing director, arrived in London to spend a few days putting finishing touches on the hotel. On Friday, November 8, they had an early morning meeting, and later that day Calderwood traveled to the nearby countryside, where he planned to spend the weekend relaxing and reading.
There has since been a good deal of disagreement about Calderwood's mental state at the time. Some friends have argued that he was overworked and overstressed, and worried about the L.A. and Panama City projects, both of which were slightly (if manageably) behind schedule. Others described him as predictably cheery and upbeat. For her part, Sawdon says that Calderwood returned from the weekend trip energized. "I'm so proud of what we've built," he wrote to her in a text message that Monday.
But when he stopped answering his phone, Sawdon grew concerned, and on Thursday, November 14, she used a master key to enter his room. The space was "tidy," investigators later noted, "but there were bottles littering the floor," including one that had been converted into a makeshift crack pipe. She found Calderwood lying on the foot of the bed, facing the door. He wasn't breathing.
In the weeks and months after Calderwood's death, a handful of newspaper reports attempted to draw a direct line between the stress of opening the London hotel and Calderwood's drug use. Speaking to The Guardian, Lovejoy said that Calderwood used booze and drugs to find "stillness." And in an off-the-record conversation, another close friend did express a fear that Calderwood was spreading himself too thin.
But the current Ace partners—including CEO Brad Wilson, real estate man Michael Bisordi, and Sawdon herself—have pushed back hard against this interpretation. They say that Calderwood, far from being consumed by stress, remarked that the London opening was the "easiest" he could remember. "The truth is that [Calderwood] was the victim of addiction," Wilson says. "And you can try to write things that fit your own plot, but it's just a tragedy. There were times when [Calderwood] fought it, and there were times when he didn't. People like to think it's a cause-and-effect thing. That's not what addiction is about."
In early March, four months after Calderwood's death, the Ace group confirmed it had finalized plans to purchase a 55,000-square-foot Salvation Army shelter up for sale in New York's East Village neighborhood and convert it into a 180-room hotel. That property, plus another one currently under construction in Pittsburgh and set to open next year, would bring the Ace chain to nine properties, including Panama City, and more than 800 employees. Total revenue for the year 2014 is expected to reach $110 million.
A few days after the New York announcement, Bisordi, Sawdon, and Wilson were in Pittsburgh touring their under-construction hotel, in an abandoned YMCA on the outskirts of town. The Ace group had done its due diligence, in a manner that Calderwood once described as "intuition mixed with market intelligence." The neighborhood, East Liberty, had gone through a period of blight during the '60s and '70s, but was now slowly filling back in. There were bars and boutique eateries, and Google had bought up space down the block, with plans to double its Pittsburgh staff.
Upstairs, contractors were dividing the warehouse-size second and third floors into chambers of various dimensions—as at other properties, there would be both smaller, more attainable rooms, and larger luxury suites. Downstairs, in the tiled chamber that once housed the lap pool, Bisordi perched himself on the sill of an east-facing window and peered out at the snow-crusted spires of the Presbyterian church across the street. He recalled an earlier visit with Calderwood to the site, before renovation had started. Calderwood was wide-eyed and excited, inspired by the possibilities. "Alex put together a whole collective," Bisordi says, "and we're going to move forward as a collective too."
He stood up, and the team wandered into a large, open ballroom. Shivering a little in the cold, Sawdon spoke of how common spaces like this one would help tie the Pittsburgh property together—how musicians might take the stage at that end of the room, or newly married couples might dance across the floor once it had been refurbished.
A few weeks earlier, at a meeting in New York, Sawdon and her partners had spoken mournfully of Calderwood, alternating tears with half-lit smiles. The sadness was still there, but so was a sense of purpose; in addition to Pittsburgh and the second New York location, there was still some tinkering to be done with the L.A., Panama City, and Shoreditch properties, all three of which were now accepting reservations. As Sawdon said of Ace openings, "You don't just hand over the keys and it's done."
The ballroom smelled of must and ice; ghostly cyclones of dust swirled toward the ceiling. Blur your eyes and you could imagine Calderwood kicking at the piles of debris, examining the cracks in the aging plaster walls. Sawdon's favorite part of the process, she'd said, is when the furniture and the art start to arrive. "You're actually able to be in the space and feel the space, and feel the layers and the textures," she'd said then.
For Calderwood, the reward was always in whatever came next.
A version of this article appeared in the July/August 2014 issue of Fast Company magazine.
Slideshow Credits: 01 / Photos by Daniel Shea;