Jeff Stober, the exacting owner of the Drake Hotel, has exported his quirky brand of twee all over the city. Now he plans to conquer the rest of the world, one tchotchke at a time

Jeff Stober, the exacting owner of the Drake Hotel, has exported his quirky brand of twee all over the city. Now he plans to conquer the rest of the world, one tchotchke at a time

Jeff stober is colonizing Queen West. Over the past four years, he has stealthily bought up four buildings east of the Drake, his boutique hotel at the corner of Queen and Beaconsfield: the old Lot 16 dive bar, the Queen Star Chinese restaurant, a vintage furniture shop called Nicknacks and a used appliance store. He’s transforming those buildings into the Annex, a massive expansion to the original Drake. When it opens in 2018, the new space will add 35 rooms to the property, plus a grand lobby that integrates a new Drake General Store.

The Annex is the culmination of a relentless long game for Stober. He’s an intensely focused guy who has his eyes simultaneously on the details and the big picture. He’s always hustling, always plotting, always 10 steps ahead. His drive is impressive, and a little scary. In late September, Stober invited me to sit in on a meeting while he finalized plans for the Annex in a boardroom off the Drake’s Sky Yard patio. Everywhere he goes, he brings a council of senior staff, who gaze at him in earnest equipoise, hanging on to his every word. This meeting was no exception. There was John Tong of the design firm Tongtong, Stober’s long-time partner who oversaw the first iteration of the Drake and designed Stober’s Forest Hill home, as well as his Soho loft. There was Bill Simpson, the glad-handing Drake head of operations. And there was Denise Carter, who’s been Stober’s straight-shooting assistant for the past 25 years and basically runs his life.

The Drake Hotel as it currently stands on Queen Street West (Image: courtesy of The Drake Hotel)

Tong presented renderings for the new lobby, and mentioned the influence of the Dover Street markets in London and New York. Stober erupted in a gleeful belch. “HA-LLLO!” This is what he says when he’s excited. It’s a verbal tic that’s half Peter Sellers and half Looney Tunes. The staff smirk when he does it, like it’s the quirk of a dotty uncle, but there isn’t a person in the Drake universe who doesn’t want to get a ha-lllo! out of Stober.

And yet when Tong suggested large columns for the new lobby and store space, there was a tundra of silence. Stober finally spoke. “Seems like a lot of ego. No. Doesn’t feel right.” Fifteen years ago, when Stober purchased the hotel, he fought off accusations of being an interloper, an evil gentrifier, inauthentic—so he’s particularly sensitive about integrating into the neighbourhood. Stober plans to connect the two buildings by a covered bridge, which will be designed to look like a train car. Ha-lllo! The penthouse owner’s suite will mirror the loft Stober owns in Soho, with garage doors leading from the bedroom to the living quarters. Ha-lllo!

Later, while looking at renderings for the hotel’s new ensuite bathrooms, Stober zeroed in on a sketch of a shower with an exposed pipe. “Why would you expose a fragile pipe? That’s a non-starter. What happens when people have sex in the shower? They’ll rip it off. They’ll burn themselves on it. No. I have zero interest in that. Next?”

Stober’s exacting taste has determined the Drake aesthetic, which balances old and new, high-brow and low, earnest and ironic. He’s a fastidious micromanager and a demanding boss whose staff worship him no matter how hard he pushes them. And he’s always pushing. Last year, when he needed to buy a new chandelier for the Drake lobby, he made his chief curator, Mia Nielsen, call five design firms and put them all through an RFP process; he assessed the options with Tong every week for nine months, but nothing was good enough—and he still hasn’t had his ha-lllo! moment.

He has a slight build and hums with the pent-up energy of a teenage boy—he flits decisively around the hotel, eyes on everything, greeting staff with a hug or a double-cheek air kiss. Stober oversees more than 450 people across his Drake empire, and yet he’s the final arbiter on every important decision (which, in his mind, includes the installation of a new chandelier). He dresses in the uniform of an affluent urbanite: a deliberately threadbare motorcycle jacket, slim-cut jeans, cashmere hoodies and a leathery whiff of cologne. Only his greying crown of fuzzy poodle curls betray his age (he’s 56). Despite his manicured appearance, Stober is goofy and spirited, quick to compliment his staff on their work, and just as quick to note a crooked frame or a chipped tabletop or demand an answer for why he saw a negative review on TripAdvisor (yes, he reads the comments).

The bones of his spaces are familiar to any Canadian who grew up playing board games in a rec room: he uses lots of raw wood, and red brick, and warm brass, and scratchy wool. That mix is particularly attractive to the 25- to 40-year-old demographic, the generation caught up in today’s quick churn of manufactured nostalgia. Stober has a knack for marketing that kind of stuff, and he’s made a fortune off of it.

This past August, around 35,000 people came through the Drake. At full occupancy, the 19-room hotel accounted for just 600 of them. The rest were locals. Stober has created a space that’s casual and playful, with art not just hanging on its walls but integrated into its skin. So kids guzzling Pabst in the basement club feel just as comfortable as condo developers sipping scotch at the bar.

Stober has a second hotel, a restaurant and eight stores in his portfolio now, but he isn’t satisfied. In addition to building the Annex, he’s aggressively expanding the Drake General Store and developing an impressive wholesale range of in-house designs that are being carried by international retailers. And his development team is scouting locations for new hotel properties across Canada and in the States. His lofty goal is to bring Queen West to the rest of the world.

Stober is a chaotic documentarian. In the late ’90s, he started collecting ephemera from his travels and shoved the bits and pieces into a three-ring binder, a beast of a thing barely held together by duct tape. It’s the DNA of the Drake brand. In it are band flyers, magazine tear sheets of Betty and Gerald Ford’s Palm Springs house in the 1970s, newspaper clippings about street-style photography, postcards from the Viceroy in Santa Monica. There are articles about the Ace Hotel opening in Portland, about the burgeoning art scene in downtown L.A., about the re-emergence of Shoreditch in east London. There are Post-its in Stober’s precise, left-leaning block letters, describing old-fashioned photo booths and vending machines and art books and bike-sharing programs and sex-toy menus in hotels. (The Drake is the only place in Canada to offer one.) It’s the collection of someone who has obsessively studied the art of hipness.

In its chaos, it’s also a living artifact of Stober’s manic mind. When he’s seated at the Drake café, dry almond-milk cappuccino in hand, his eyes are everywhere, taking in who is sitting in the restaurant and who is walking by, and calling out rapid-fire greetings to passersby, like Kevin Drew of Broken Social Scene and Jeffrey Remedios, the CEO of Universal Music Canada. He speaks in long, uninterrupted soliloquies. It’s a challenge to hold his attention and embarrassingly satisfying when you succeed.

Stober isn’t on Facebook or Twitter or Tumblr—he’s a social media resister. He has an old-model BlackBerry, but he mainly uses it to call and text; he doesn’t even have a data plan. He spends most of his time offline, reading and answering emails for only an hour each day. Stober values immersive, personal experiences over digital ones. Especially when it comes to travel—he greedily collects Air Miles the way most people collect Instagram likes. In the second half of 2015, he visited New York three times, and travelled to L.A., Paris, London (for the Frieze contemporary art fair) and Miami (for Art Basel). He builds the itinerary for every trip—it’s a chore he tackles with relish. Wherever he goes, he never stops hustling: in every city, he cozies up to concierges, interrupts strangers on the street to compliment them on their outfits, and asks the cool-looking couple at the bar which galleries are worth a visit.

Stober, age 10, in Montreal (Image: courtesy of Jeff Stober)

It’s not that there are blurred lines between Stober’s work and personal life. It’s that there are no lines. Stober’s closest friends are his senior staff. His romantic life is the subject of much swirling speculation among the gallerists and creatives of Queen West. He’s never been married and has no children. He says he’s dating someone, but won’t tell me who. His constant companion at art openings and fundraisers is his best friend, Anne Penney, a handsome divorcée with a halo of ringlets and sky-high cheekbones. They got to know one another as neighbours 20 years ago when they lived on the same street in Forest Hill, and now she works part-time in the Drake General Store.

Stober has an unusually close relationship with his parents, whom he unironically calls his “besties.” David and Ellie frequently travel to Toronto from Montreal to spend time with their son. David, who is 85, had a stroke two years ago that caused temporary paralysis on one side of his body and left him bedridden. Stober hired two full-time caregivers to rehabilitate his father. He’d call him, sometimes multiple times a day, to motivate him, coach him, and straight-up harass him to get up and walk. He’d yell at him like he was his boxing cornerman, “C’mon, David!” The caregivers filmed his father’s progress, and when David eventually began to walk shakily on his own, Jeff gleefully showed his friends and staff the footage.

In the 1950s, Stober’s dad ran a few women’s clothing stores in Mount Royal, a middle-class neighbourhood in Montreal. It wasn’t an easy business, and David worked six days a week, most nights coming home after 10 p.m. Their first son, Stephen, was born in 1955; Jeff followed in 1959. He and his mother would spend their weekends together, picking their way through garage sales and antique markets.

Stober, bottom left, with his mother, Ellie; his father, David; and his older brother, Stephen (Image: courtesy of Jeff Stober)

Stober was a precocious kid. When he was around 10, he was taking public transit by himself to see the Expos at Jarry Park. He would go on week-long canoe trips in Tremblant Park, where he slept in army tents with wooden platforms. “There’s nothing more soothing to me than the sound of rain on canvas,” Stober says dreamily. “I need to hear the natural sounds, I need to see the natural light.” Even today, he romanticizes that period in his life, the adventures of an urban kid travelling into the wilderness—then commercializes it with balsam-scented bath products at the General Store, camping pop-up parties in the Sky Yard and an ode to rural escapism at the Drake Devonshire. The family would also travel every year to Maine or Cape Cod. “That’s when I became fascinated with motels,” says Stober. “The swimming pools. The neon signs. The maid service. It was all so glamorous.”

Like many kids, Stober had a paper route, but that wasn’t enough to keep him occupied. By 16, he was moonlighting as a football referee. He also started a window cleaning company; he designed the flyers, set up the booking sheets, and used the money he saved to put himself through undergrad at Western, where he earned a BA in creative and administrative studies.

After graduation, Stober moved to Toronto and interviewed for several sales and marketing positions. He quickly realized that his natural people skills were better suited to entrepreneurship. In 1981, he started his own headhunting company called Sabre (it was later renamed Contractors’ Network Corporation, or CNC Global). Stober was 22. He had no money or connections, but he wanted to be his own boss. That took chutzpah. “I was trying to convince big corporations that I could recruit senior IT personnel, that I was an industry expert,” he recalls. “I couldn’t cross my legs in meetings for fear of the client seeing the holes in my shoes.”

Stober on a family vacation in the ’70s (Image: courtesy of Jeff Stober)

Stober followed a strict regimen. He’d work until 9 p.m. and spend the two hours before bedtime the same way every night: 30 minutes to prepare dinner and eat, 30 minutes to go for a walk, 30 minutes to make social phone calls, and 30 minutes to read the paper or watch TV. He treated every one of those moments like a vacation.

By age 26, he had money to play with. He bought a two-storey semi on Carlaw in Riverdale, and eventually traded up to a detached house in Forest Hill. He’d already been buying street art, cheap $5 prints mostly, and when he started making money, he added more expensive paintings and furniture to his collection. He was also travelling a lot, buying handmade dolls wherever he went. They were affordable, they’d easily fit in his backpack or suitcase, and they were quirky and playful. He’d arrange them in tableaux on the living room table while his friends sat back with their cheap beers and watched him quizzically. But Stober liked the weirdness. To this day, every guest in one of his hotels is greeted by a whimsical felt doll staring up from the bed.

In 1998, at the height of the first tech boom, Stober sold majority interest in CNC to a New York–based investment group called KKR and made a small fortune. He spent six months in the spring of 2000 travelling through India and Nepal, then came home and hired John Tong to renovate his house. He’d bring Tong on buying trips to New York, where the two would spend time in hotel bars, Stober intently absorbing all of Tong’s design vocabulary to describe what was happening architecturally in the room, the use of light and space and decor. He added bobbleheads and Three Stooges figurines to his doll collection. And he kept buying art—mostly photographs and paintings by emerging artists.

A suite at the Drake (Image: courtesy of The Drake Hotel)

Stober had time and money and freedom, and he was itching to build something from the ground up again. He and Tong were obsessed with California culture (“everything cool starts on the West Coast,” he told me) and dreamed up a multi-programmed place that combined everything they were interested in: art and yoga and sushi. In 2001, he heard that the Drake Hotel was up for sale. Stober was familiar with the neighbourhood—he’d been buying art from Clint and Jamie of the Angell Gallery, from Stu at Spin Gallery and from Paul Petro for years—and he loved the tree-lined streets and Victorian houses.

The Drake had been a flophouse for decades. When Stober toured the property, there were dirty mattresses stacked up in corners, and used condoms and needles everywhere. Stober brought members of his staff on a walking tour of the space, and everyone thought he was nuts. Not only was the place a dump, it was five kilometres from the core. Who would book a hotel this far from downtown?

So Stober hired a spiritual healer to read the Drake’s energy and vibrations. She told him what he wanted to hear—that the bones were great and that the place wanted to grow and evolve and go where he wanted to take it. “Her read was that the building had some blockages and in its last incarnation was a little unloved,” says Stober. “And that was completely consistent with my own gut reaction. That’s what I love about old buildings. I have to surrender my ego at the door. It’s older and wiser than me, so I might as well come in and get swept up in the energy.” Stober likes to sound insouciant, even flaky, but the move was more complicated and more calculated than he lets on. He wanted the building, and he wasn’t going to stop until he found someone to confirm his hunch.

He paid $860,000 for the Drake in October 2001 and immediately started dreaming up its future. He pictured a Toronto equivalent of the Chelsea Hotel, where creatives would live and work and form a community. He wanted it to be part salon and part social club. He believed, in that wide-eyed California way of his, that there was a curious culture seeker in everyone and it was his job to provide a venue. It didn’t take long for that exhausting idealism to be tempered by the reality of fixing up a derelict dive in a hostile neighbourhood.

A few months after the purchase, Stober was in Scottsdale with his parents when he got a call from his assistant, Denise Carter, whom he’d brought with him from CNC. She said a pipe had burst and there was six feet of water in the basement, drowning all of the files, the computers, the plans, everything. By the time Stober was back in the city two days later, Carter, ever the pragmatist, had ordered a sump pump, strung up clotheslines and hung the salvaged documents to dry—it looked like a funhouse laundromat. The flood was but one of a dozen setbacks and headaches. The neighbours were cranky; they sneered and hissed and decried gentrification. Construction on the hotel hadn’t even started when a big snowstorm hit. Someone spray-painted “Shovel your snow” on the building. “It was an eye-opener for me. After years of working in a downtown tower I was craving a street-level experience. Let me tell you, I was getting it.”

At the Drake with his interior design team, from left: Alison McQuaid, a hotel designer from Design Agency; John Granger, Stober’s head of development; Anwar Mekhayech, the principal of Design Agency; Kateryna Nebesna, an architectural intern at Tongtong; Jeff Stober; artist Michael Awad, who serves as Stober’s architectural consultant; and John Tong, the principal and founder of Tongtong

In 2004 the reigning interior design style was crisp, clean and contemporary. The Drake’s signature mid-century modern look wasn’t a thing yet (Mad Men wouldn’t premiere for another three years). The hottest reservations in town were at restaurants that took a meticulous, cerebral approach to cooking, like Avalon and Susur and Rain. Brooklyn was still sorta PG (that’s pre-gentrification), more egg creams and Spaldeens than artisanal pickle shops and tattoo parlours. Hipster, in 2004, was somehow equated with Ashton Kutcher in a trucker hat.

Stober believed a hotel was the ideal venue to unleash his new aesthetic. Hotels are innately mysterious and alluring: at any moment someone is sleeping, someone is taking a shower, someone is writing the next great Canadian novel, someone is having sex. Stober tapped that enigma. He knew from his travels that people were moving away from choosing hotels based on the thread count of the sheets or the pillow menu. He believed a hotel should be a conduit to its city, and it should reflect the city back. The Drake was making a bold statement: Queen West is cool, Toronto is cool, and Canadiana is cool. Today, it seems as though four out of five new restaurants that open have a mounted buck on the wall, or salvaged wood furniture, or a fussily Victorian cocktail menu, or throw cushions in plaid or denim or some other Canadian Tuxedo material. Back then, the Drake was it. And the city ate it up.

After the recession hit, Torontonians craved intimacy. Communal tables became a thing and sharing plates became a thing. The handcrafted, small-batch movement spoke to our collective mistrust of big business, big banks and big institutions, and our wistful desire for a simpler time. Nostalgia is a powerful tonic—one that Stober capitalizes on in every outpost of the Drake brand. It’s a sanitized version of an idealized history, where patchwork memories filter out the mundane or negative emotions and create a whole reality that never was. Research shows that nostalgia counteracts loneliness, boredom and anxiety. It makes people more generous to strangers and more tolerant of outsiders. In our increasingly isolated, urbanized, digitalized lives, nostalgia becomes more and more seductive. Stober knew the public was primed to buy what the Drake was selling.

The first Drake General Store brought to life, and monetized, Stober’s fascination with cleverly ironic, beautifully crafted, slightly ridiculous objects. In 2008, designer Carlo Colacci and his business partner, Joyce Lo, set up a pop-up shop next to the Drake Hotel on Queen West. Shared, their line of Toronto-made T-shirts spun from Supima cotton, had already been a hit in New York, Los Angeles and Hong Kong, but they couldn’t get traction with Toronto customers. Stober, who loved the fact that Colacci and Lo controlled the manufacturing process from start to finish, asked them to put together a proposal for a permanent retail concept that would unite their clothing and his idea for a hotel gift shop.

The Drake General Store in Ottawa (Image: courtesy of The Drake Hotel)

The General Store opened that year. There are log-shaped travel pillows and cashmere sweaters emblazoned with the CBC logo, adult onesies festooned with Mounties and 14-karat-gold-plated Slinkys. Stober sent Colacci and Lo on buying trips with the mandate to make the shop a 750-square-foot tour of the world’s coolest shit. It worked. Within three years, the General Store had expanded to Rosedale, to Yonge and Eglinton, to Ottawa, to Vancouver. Across Canada, Stober’s aesthetic was stamped on totes, tuques and trinkets.

Within a few years, Stober already had his eye on the Financial District. He opened the Drake One Fifty restaurant on York Street in 2012. It was like the Drake without beds: a Canadian brasserie tweaked slightly for a more conservative crowd. The clubby restaurant was designed by Martin Brudnizki, who’s known for properties like the Ivy in London and Soho Beach House in Miami. Inasmuch as Stober adjusted his aesthetic for the bankers and money managers, he was also bringing Queen West to the core: on summer Tuesdays, Drake One Fifty takes over the adjacent parkette for a mini–night market, offering high-brow street food from neighbouring restaurants. It will come as no surprise that Stober loves parkettes and rhapsodizes about how they create beautiful little moments of green between blocks of urban grey. If a buttoned-down finance manager can dip his tie clip into a hipster oasis without moving more than 50 paces from his Bay Street tower, everybody wins. Especially Stober.

The Drake One Fifty brasserie at York and Adelaide (Image: Dave Gillespie)

Jeff Stober is not a designer or an architect or an artist. He knows he has neither the skill nor the aptitude for any of those professions. He’s the dictatorial dreamer, that guy who envisions a rustic world of selvage denim and salvaged wood, and hires other people to bring it to life. He indoctrinates his staff into the Drake brand, edits their progress along the way and constantly tests their mettle. Stober doesn’t seek conflict—in fact, he craves consensus. He solicits opinions from everyone on his staff, from social media managers to dishwashers, about what makes a great hotel bakery, or if the café should install cold-brew coffee on tap, or if a barbershop would be a good addition to the Annex, ultimately giving most weight to what his senior staff recommend. But there’s never any question of who’s in charge.

The pavilion of the Drake Devonshire in Prince Edward County (Image: courtesy of The Drake Hotel)

Stober proved that the Drake could succeed beyond its Queen West bona fides. A bigger gamble was whether it could land outside the city proper. The Drake Devonshire, which opened in 2014 in Prince Edward County, sits back from the property line, tucked into a corner, surrounded by other residential Wellington properties. The building was once a foundry, then a nursing home, then a B&B. It gets bigger toward the back, where there’s a pavilion with a loud, colourful, floor-to-ceiling mural by Brooklyn artist Faile, a pop-up craft market, a dining room with panoramic views over Lake Ontario and a glass cube portable where kids play Ping-Pong.

Like the original Drake, the Devonshire has revolving installations by local artists, as well as permanent pieces, like a sculpture in the atrium that mimics stained glass but is actually made with vintage Japanese tissue paper. The hotel is a brilliantly Stoberian simulacrum of rustic nostalgia, equal parts cunning and childlike: the Canadiana counterpoint to Martha’s Vineyard.

“When I first visited the county I was like, oh my god, this is so familiar to me,” gushes Stober. “This is how I spent the best parts of my childhood. It’s the perfect landscape with the rolling hills. It’s the perfect lakeside village. It’s big sky. It’s Sandbanks—obviously, duh. Best beach in Ontario.” Stober and his team looked at many properties and even bid on a large farm, but the deal fell through. When the Devonshire property came up, they had already spent well over three years scouting in the area. He bought the property for $1.3 million—less than you’d pay for a house in Riverdale—and began the process of converting it into a 13-room guesthouse with two extended arms that pivot out from the central, original chimney, paying respect to the foundry. His team had attended 25 local meetings to befriend the Wellington crowd, answer their questions and address their concerns about a flashy group from the city setting up in their sleepy township. Stober had to prove to the neighbours that the evolution of the Devonshire into an avant-garde Canadian farmhouse was a good thing. And with that relentless enthusiasm, he did. Today, just like the hotel on Queen, most of the restaurant and bar customers are locals, and the rooms are booked months in advance.

(Image: Christopher Wahl)

The success of the Devonshire taught Stober that if he and his team put in the time to scout the right new location, and got the locals onside, he could send his Queen West baby around the world. Two years ago, Stober lost a bid to operate a boutique hotel in the landmark Northwest Tower in Chicago’s Wicker Park. It was down to two final presenters: the Drake and Grupo Habita, the respected boutique hotel operators who run the Hotel Americano in N.Y.C. and 13 properties in Mexico. They lost out on the bid, and Stober took it pretty hard—he was sure this was their time to make that cross-border leap. But no matter. His development team is constantly checking out properties in Detroit, San Diego and other American cities. Back home, there have been murmurs among his team about a second Drake Hotel location in Toronto.

In order to expand his brand, Stober has had to place faith in his staff, to trust them to execute a vision that he’s had since he was a kid. Only now is he sure that the right people have been inculcated. Mia Nielsen, his chief curator, remembers a trip to New York with Stober a few years back. They were sitting at a bar drinking negronis when Stober suddenly turned to her and, with laser focus, said, “I need to know that you’re really in this, that you’re really committed. Because I’m ready to take this thing to the next level. You think we’ve done a lot over the last couple of years together? It’s nothing compared to what is going to happen.” That intensity is a seductive force. He used it to turn a tiny recruiting firm into a multimillion-dollar corporation. And he used it to turn a party hotel on Queen West into an empire.