How Seattle Built Cool — and Lost It

The Ace Hotel started in a Belltown halfway house in 1999. It bottled Seattle's cool and sold it to the world. Twenty-six years later, the founder is dead, the brand belongs to a Japanese conglomerate, and the cool that made it the Ace is gone.

Seattle built what it needed because no one was bringing it here. The city sits in the upper-left corner of the map, three thousand miles from the cultural capitals, two hundred miles north of anywhere else that mattered. So Seattle built its own.

It built the airplane. It built the cellular phone. It built the coffee chain that crossed every border, the department store that crossed every state, and the online marketplace that absorbed retail. It built the cloud. It built the software that ran the computers and the cargo network that delivered the boxes. Boeing. Microsoft. Amazon. Starbucks. Nordstrom. Costco. REI. Expedia. T-Mobile. UPS. McCaw Cellular.

Outside of New York, Los Angeles, and the Bay Area, no American city has produced more globally recognized brands. The isolation made it happen. The habit of building everything yourself produced a cultural confidence no other American city has matched.

By the late 1990s, Seattle had built something harder to name. It had built a new kind of cool. Irreverent, post-industrial, anti-pretension — drawn from grunge and the queer club scenes and the warehouse aesthetic of a working port city that had just discovered it could set the global tone. Belltown and Capitol Hill in those years were as cool as anywhere on the planet. Berlin would have its moment a decade later. Seattle was having it then.

In 1999, three Seattle natives in their early thirties built the object that carried the cool into hospitality. They built a hotel. The boutique hotel as a category — the thing every Soho House and Hoxton and cool urban hotel of the next two decades would descend from — was invented in Seattle.

They were a generation of Seattle people who took the city's cool and exported it. Sub Pop did it with music — Bruce Pavitt and Jonathan Poneman packaged the Seattle sound and sold it to the world, and the world bought it. Three Seattle natives did it with hospitality. They took the same sensibility — the warehouse aesthetic, the queer club confidence, the anti-corporate posture, the way Seattle put things together — and built a hotel around it. Then they scaled it. Portland, New York, Palm Springs, London. The Belltown halfway house became a global brand because the cool it was selling was real, and the world wanted what Seattle had figured out how to bottle.

The original Ace at First and Wall still operates. It is now owned by Seibu Prince Hotels Worldwide, a Japanese conglomerate.

This is what happened in between.

Alex Calderwood, Wade Weigel, and Doug Herrick took over the lease of a 28-room maritime workers' halfway house at the corner of First Avenue and Wall Street in 1999. The neighborhood was overrun with homeless men. All three were from Seattle. All three were gay. All three were already running other businesses. They had built Rudy's Barbershop on Capitol Hill in 1993 with $12,000 and a third partner, David Petersen. They were running an experiential marketing company called Neverstop with Jared Harler, Nasir Rasheed, and Caroline Davenport. Calderwood had a stake in ARO.Space, the Capitol Hill dance club he ran with Harler, and in Sweet Mother Recordings, the indie label he ran with Harler and Rasheed. He was, in his own words, "a barber and a tattoo pimp." He had no business education. He saw a building.

They kept the rooms cheap. Sixty-five dollars a night, with shared bathrooms down the hall. They commissioned room art from a young street artist named Shepard Fairey, nearly a decade before Fairey would design the Obama Hope poster. They left the homeless men on the stoop. They named the place after the playing card that is both the highest and the lowest in the deck — "we employ that high and low principle in our hotel models," Calderwood said — and called it the Ace.

It broke into the black in its first year.

The opening was hosted by Tyler Brule, the editor of Wallpaper magazine. The whole scene showed up.

To understand what they built, you have to understand the Seattle that built them.

Calderwood grew up in Bellevue. His father was a contractor. His mother was a newspaper columnist. He did not go to college. By his early twenties he was promoting club nights at Re-Bar on Capitol Hill and selling vintage clothing wholesale. In 1985, when he was nineteen, he heard about a guy named Wade Weigel and got his number from a mutual friend. He called and asked Weigel out to dinner. They became instant friends. Eight years later they opened Rudy’s together. There are now nineteen Rudy’s Barbershops around the country.

"I don't think he ever looked at his bank balance," Nasir Rasheed said later. "What drove him was creativity and doing something amazing."

The Belltown and Capitol Hill of those years was a city you could afford to be young in. Louie Raffloer opened Black Dog Forge in 1989 in a back-alley space a few blocks east of where the Ace would later open. He paid $75 a month for a twelve-by-twelve room. Louie was dating my younger sister Liffy at the time. She witnessed all of it, and I heard the stories.

By 1991, the basement of Black Dog had become the rehearsal space for Pearl Jam, Soundgarden, Temple of the Dog, the Presidents of the United States of America. Eddie Vedder went there straight from the airport when he arrived in Seattle in October 1990, having flown up from San Diego the day after Jeff Ament called him about an audition. The bands tacked blankets over the exposed water pipes to soundproof the room.

The Crocodile opened on Second Avenue in 1991 and became the main grunge-era venue in the neighborhood. Re-Bar on Capitol Hill, where Calderwood had promoted club nights in his twenties, anchored the queer creative scene. The Lobby, Weigel's underground club in the International District, anchored another part of the same ecosystem. The goal at every party, in Calderwood's own description, was "gay and straight, uptown and downtown — we sort of collected people that were interesting."

The interesting people were coming from everywhere. The bands from Aberdeen and San Diego. The visual artists from New York and Los Angeles, finding lofts they could afford on the strength of a part-time job. Seattle in those years was a city you could build something in. A twenty-something with $12,000 could lease a Capitol Hill storefront and start a business. A blacksmith could rent a back-alley room for $75 a month and turn it into something that shaped American music history. Three friends could lease a Salvation Army halfway house and turn it into the founding property of a global brand.

Calderwood lived on First Hill, in an apartment he had taken in his late twenties. Walking distance from Capitol Hill and downtown. He would keep it until the day he died.

His romantic and business lives overlapped. His first boyfriend, in 1997, was Todd Bohannon, a twenty-year-old he met inside the same nightlife world. His longest non-romantic partnership was with Caterina deCarlo, his manager and protector, what he called his "life appointment." She would live in his First Hill apartment, on and off, for the next twelve years.

The Ace, when he and Weigel and Herrick opened it in 1999, was a hustle. "At first, Alex and I were trying to do it out of our cash flow," Weigel said later. They realized they would need investors. They cobbled together some cash for the flophouse on First Avenue that still had tenants living inside. The hotel was bare bones. "We were thinking of it as a white canvas, really plain, like a New York loft or art gallery kind of space," Weigel said. "It was very minimal."

What Calderwood and his partners added to Seattle's century-long hospitality tradition — the Olympic Hotel in 1924, Westin Hotels founded here in 1930, the boarding houses of the Klondike era still echoing in the city's old building stock — was the cool. The Ace was the cool, packaged. The reader who walked into that Belltown lobby in 2001 understood, without anyone having to explain it, that this was Seattle's idea of a hotel. The vinyl turntables. The reclaimed furniture. The graffiti elevated to fine art.

It was Seattle exported. The latest chapter in the city's long habit of exporting things the world ended up wanting.

For the first eight years, the Ace was a single property in a single city. Then the expansion began. In 2007, Calderwood and his partners took over a derelict building called the Clyde Hotel in Portland's West End and opened the second Ace. Jack Barron joined as a fourth partner. In 2009, the Ace New York opened on West 29th Street in Manhattan, and the ballroom-sized lobby — free seating, dark velvet couches, art on the walls — became a destination for creative workers across the city. Palm Springs followed in a renovated Howard Johnson's. There were Ace hotels planned for Panama City and Los Angeles.

The hotels reflected the cities they were in. Throughout his career, Calderwood supported artists before they were well-known. "He believed in people and things before other people could see those things themselves," Caroline Davenport said.

In 2011, Calderwood needed capital to scale. He got it from Stefanos Economou, a New York investor whose holding company, Ecoplace LLC, put $10 million into the Ace in exchange for a 33 percent stake. The same year, Calderwood hired Brad Wilson, a Cornell-trained hotel executive who had launched W Hotels at Starwood, as the company's new president. The money was real. The logic behind it was not Calderwood's. Calderwood was driven by creativity and did not look at his bank balance. The capital that took the Ace global came from someone who did.

Calderwood himself was, by then, living between cities. He spent extended time in New York, in Palm Springs, in Portland. But he never gave up the First Hill apartment. deCarlo was still there.

In September 2013, Calderwood opened the Ace London in a former Crown Plaza on Shoreditch High Street. It was the most ambitious project the company had ever attempted, the first major property built on Economou's $10 million. The retrofit was complete enough by opening night that the lobby filled with the same upbeat mix of dubstep reggae, bluegrass, and vintage British punk that the Ace had become known for. The bar was packed. The restaurant, Hoi Polloi, was overpriced and busy. Calderwood was forty-seven years old and at the height of what he had built.

The last few weeks of his life were consumed by the simultaneous openings. The London hotel in September. The Los Angeles Ace scheduled for January 7. The Panama City Ace, called American Trade, scheduled for December 5. He flew Los Angeles to New York to London and back. He spent the weekend before his death in the English countryside with friends.

On the surface, the last weeks of his life were a victory lap. "We both connected on Monday, and he was really happy and excited to move on to LA," Kelly Sawdon would later remember. He was thrilled by the 1,600-square-foot theater at the LA Ace. "It was all kind of coming full circle," she said. Underneath, he was operating past his limit. The man who had never looked at his bank balance was now the public face of a global brand built on someone else's capital, flying between three time zones to manage the openings of properties he had agreed to build because the money required him to. He had taken the deal he needed to take. The deal was now taking him.

The night before he died, Caterina deCarlo logged into his email from the First Hill apartment. She saw how many unopened emails were waiting.

"I saw how many unopened emails there were that day, and all of a sudden this wall hit me that he was operating past his maximum," she said. "I don't care how amazing you are. I don't care how driven you are. Everybody has a limit. I was like, 'This is going to be the death of him,' and I went to bed thinking that."

The next morning, she received the phone call that Alex had died.

On November 14, 2013, Kelly Sawdon used a master key to enter his third-floor room at the Ace London. She had not been able to reach him for three days. She found him face-down on the bed.

The toxicology report would later show alcohol at five times the UK drink-drive limit and traces of cocaine. The room was, in the Daily Mail's reporting, "littered" with bottles of gin, whiskey, wine, and Grey Goose vodka. A pipe made from a burnt brandy bottle sat on a surface near the bed. The inquest established that Calderwood had met an unnamed man at the Redchurch Bar in East London three nights earlier; that man was subsequently arrested and bailed on charges of possession with intent to supply Class A drugs. The coroner ruled the death a result of alcohol and drug toxicity.

In a 2011 interview, two years before his death, Calderwood had said he was five months sober. "You get to a certain age," he had told the interviewer, "and you get to a certain point, where you realize this is just, like, dragging me down. It's not fun anymore. I'm not enjoying it." He relapsed.

He died intestate. No will. No living heirs. His controlling 51.7 percent stake in the company he had built passed to his elderly father, Tom Calderwood, a contractor who had never been involved in the business.

The Belltown halfway house, the Portland Clyde, the Manhattan lobby, the Palm Springs HoJo, the new Shoreditch retrofit — all of it now belonged to a grieving father who had no idea what the company was worth or how to run it.

The First Hill apartment was still in Alex's name. deCarlo stayed there.

What happened next is the part of the Ace story that no one wrote at the time. The partners who had come in for the global expansion did not share Calderwood's creative orientation. They had invested in an asset. With Calderwood dead, the asset was now an estate question — and the estate was a grieving father in his eighties who had never been involved in the business.

Economou offered Tom Calderwood $200,000 for his son's 51.7 percent controlling stake in the company. The estate's valuation of the same stake was no less than $3.7 million.

Tom Calderwood refused.

In March 2015, the Calderwood Estate filed suit in New York State Supreme Court against the Ace, against Ecoplace, and against Stefanos Economou personally. The estate alleged that Brad Wilson — the company's president and chief operating officer — had colluded with Economou to commission what the filing called "a bogus appraisal that omitted key Ace assets to make Tom think Ace was worth less than it truly was." The estate sought $14.5 million in damages.

In August 2016, a second suit followed. Michael Bisordi, a former Wall Street finance professional who had taken a small equity stake — roughly four percent — in exchange for advisory work years earlier, sued through his consulting firm Tungsten Partners. He alleged Wilson and Economou had been diverting profits and that Wilson's management was "either proof of incompetence or as a result of a deliberate effort to stifle the growth of the Ace brand value during litigation with Alex Calderwood's estate, or both."

In October 2016, the Calderwood Estate filed a third suit, this one against Brad Wilson personally.

The litigation lasted four years. The brand kept operating. New hotels opened. The company kept telling the press it was growing. But by then, what mattered inside the Ace was not what the Ace was making. It was who would end up owning it.

What had begun as a Belltown hustle was now an asset fought over in Manhattan courtrooms by men who had never set foot in the Black Dog basement. The Seattle that had made the Ace possible was not in any of those rooms.

By 2023, the company was for sale. Sortis Holdings, a Portland investment firm, announced an $85 million all-cash acquisition that January. Kelly Sawdon, who had joined Sortis in 2021 specifically to bring the Ace home, was leading the deal. The same Kelly Sawdon who had used the master key in Shoreditch.

The deal collapsed in November of that year. Sortis walked, citing the loss of management contracts, the departure of key employees, and the rise in interest rates. The Ace, having been sold and unsold, sat in limbo for two more years.

In September 2025, Seibu Prince Hotels Worldwide, a Japanese hospitality conglomerate, acquired what remained. Brad Wilson, who had been the defendant in three separate lawsuits alleging he had conspired to undervalue Calderwood's stake and suppress the brand to win the litigation, became Chairman. The Ace London had closed by then, rebranded as One Hundred Shoreditch. The Alex Calderwood Fund, announced in The Stranger in 2019 as a memorial to support emerging creative work, is now a 404 error.

The original Ace at First and Wall still operates. There is still a desk clerk. There is still a sign. There are still rooms with the ghost of Shepard Fairey on the walls. The Ace Seattle is, twenty-six years after it opened, the founding property of one of the most influential hospitality brands of the twenty-first century. It is now owned by a Japanese conglomerate.

The First Hill apartment where Calderwood lived from his late twenties until his death is no longer his. The boy from Bellevue who discovered himself in Belltown, who took what the Black Dog basement and Re-Bar and Sub Pop had made and packaged it for the world, is gone. The Ace had cachet as long as Calderwood was in the picture. After he was gone, the cool went out of it. The hotels still operate. The sign still says Ace. The Seattle he bottled is no longer in the bottle.

On the staircase of the Ace Hotel in New York, the words he chose are still emblazoned. They are the last thing his friends saw when they came to mourn him there, ten days after his death.

Everything is going to be alright.

Michael R. Hatch is an investment manager based in Seattle. A Seattle native, he attended Lakeside School and has served on the boards of the U.S. Olympic and Paralympic Committee Foundation, the Seattle Symphony, the Henry Art Gallery, Intiman Theatre, Seattle Children's Theatre, PONCHO, and other civic and cultural institutions.