The scraps, stunts and multi-million-dollar investments behind Charles Khabouth’s empire of cool

Once inside, you will be greeted by tall, thin women with the suspender-trays worn by cigarette girls in the Roaring Twenties; they will be giving out lollipops, popcorn and artfully wrapped candy bundles. Aside from the equally statuesque bartenders and the security men (one of whom has the bulk and flattened nose of a KGB assassin) the only other staff are the go-go dancers, who’ll be wearing nothing but high heels, Bono-style goggles, long braided ponytails and glittering body paint. You will watch them (a tricky gambit in that staring would mark you as a rube) not because they are naked (well, okay, partly because of this) but mainly because they’re managing to exuberantly dance on chest-high Grecian columns without falling off, all the while wearing the pissed-off expression that people get when forced to wait in driving hail for a bus.

The patrons, meanwhile, will be a mixture of what you expected and what you didn’t expect. Uniun is expensive—it costs $750 (i.e., a three-bottle minimum) if you want to sit down—and so the crowd tends to be somewhat moneyed, the men coiffed and dressed in slacks and jackets, the women favouring ultra-short skintight dresses. Yet there will be people in jeans and T-shirts, and there will be women dressed more demurely, though they will be in the distinct minority, as will patrons above the age of 40. You will also notice that Uniun has an atmosphere—all those flashing lights, all those bottles of Veuve—that is repellent to the urban hipster, there being not a beard, dreadlock, tribal piercing or tattoo sleeve in sight. You will see celebrities: at the Uniun opening I shared space with Ben Mulroney, Mats Sundin and, surprisingly, one of the interventionists on Intervention Canada. The club is mostly empty until 12:30, the earliest time nightclub-goers deem acceptable to be seen in public. Then, as if a switch has been thrown, it will instantly fill.

As for the club itself, the bar runs about two thirds of the length of a large, rectangular room before giving way to the dance floor, which is notable in that the walls and ceiling pulsate with half a million dollars worth of LEDs, programmed to create combinations of colours and patterns in time with the music. The room has a premium sound system and long stretches of leather banquettes, and is intended to be Toronto’s exclusive stop for the sort of modern celebrity DJs who tour the world, playing short sets for dance aficionados.

The person responsible for all of this is the owner, Charles Khabouth, who has been opening nightclubs in Toronto since the 1980s and has brought an unparalleled level of sophistication to the city’s entertainment scene. If you spot him, he will likely be saying hello to the vast number of clubbers who know him personally. Yet it’s more likely you will not see him. On nights he works late, he makes brief visits to each of his 17 businesses, a roster including the Guvernment complex, a warehouse-sized venue on Queens Quay that hosts concerts and massive DJ dance parties; the upscale, intimate nightclub Cube; the grungier Queen West venue Tattoo Rock Parlour; and the sprawling lakeside party venue Polson Pier. If you factor in his eating establishments—he owns the King West resto-lounges Patria, Weslodge and Spice Route, and the Yorkville bistro La Société, and has three more due to open this year—Charles Khabouth entertains, on a Saturday night, roughly 15,000 people in Toronto, making him by far the biggest individual restaurant and nightclub owner in the city. His company, Ink Entertainment, earns annual revenues of $60 million.

Khabouth intends to become an international phenomenon. In August of last year, he launched Veld, an annual electronic dance music festival, in Downsview Park, attracting more than 20,000 people. He’s since been approached by investors to take the festival to other countries—he has three full-time staff working on that project. And the American luxury hotel chain Loews approached Khabouth in 2011 and asked him to recreate La Société in their Montreal location. It opens this April, and the plan is for Khabouth to open restaurants in Loews hotels throughout Canada and the U.S.—the next will likely be in Philadelphia or Los Angeles.

Then there’s Bisha, his eponymous condo/hotel project on Blue Jays Way (his real first name is Bechara, Bisha for short, but he changed it after his family came to Canada from Lebanon). Khabouth intends to open Bishas all over the world: though the Toronto location won’t open until 2015, every unit has been pre-sold since mid-2012. “I can say, with 100 per cent certainty, that Bisha is going to go global,” he told me.

“You mean Asia?” I asked. “Europe? South America?”

“Everywhere.”

Charles Khabouth is yardstick slim, has an olive complexion and bears a mild puffiness beneath his eyes, a product of sleeping as little as three hours per night. He’s 51 years old and separated from his wife, Libby Eber, whom he first met when she was working as a hostess at Acrobat, a ’90s restaurant he co-owned with Franco Prevedello. Eber and Khabouth have a 13-year-old son, Charlie, and a nine-year-old daughter, Maya, whose names Khabouth has tattooed along his forearms.

He starts each day by visiting whatever construction site he has on the go; when I met him, he was spending his mornings on Mercer Street, where his Japanese restaurant Ame was being refitted to become a high-end Italian eatery called Buona­notte. He then heads to the Queens Quay East headquarters of Ink Entertainment, where he spends most of his afternoons in ­meetings. He goes home when people stop returning his calls—“Really,” he says, “the only time I don’t work is when I’m with my children.” On evenings when they’re with their mother, he has a driver take him from nightclub to nightclub—“You can’t really get a feel for how a place is doing unless you’re there.”

On these nights, his day usually ends sometime after two in the morning.

Khabouth drives a Ferrari F430 and lives in an airy King West condo with a 1,200-square-foot patio that all but the most acrophobic would pine for. He knows everybody—Lenny Kravitz and DeadMau5 are friends. Despite his fast-paced lifestyle, there’s a slightly old-world quality to him. Often, at home, he’ll put on traditional Lebanese music. He never swears, still has a slight accent, and when he meets people inevitably asks, “Do you want anything? Do you need anything?” In the industry, his court­liness is legendary. Liloo Alim, the long-time concierge at the Yorkville Four Seasons, told me that “people will call Charles in a total panic and say, ‘I have to find a Birkin bag for my wife! Can you get me one? Can you help me find one?’ And you’d wonder why they would call anyone as busy as Charles Khabouth. And yet, next thing you know, he’s making some calls.” Another friend, the events producer Steven Levy, characterizes Khabouth with this story: “After my separation, I was feeling desperate and confused, and one night I called Khabouth. He immediately said I couldn’t be alone, and he sent a driver to pick me up. The next thing I knew, he’d installed me at a table at one of his clubs with a bunch of funny, happy people.”

For Khabouth, it’s a reflex rooted in his upbringing in Beirut. “Things are different over there,” he says. “People enjoy life. They go out every night, they socialize, they have a good time. Here, all anybody thinks about is paying the mortgage—believe me, in Lebanon it’s the last thing on anyone’s mind.” Khabouth’s mother used to keep 20 cigarette brands on a silver tray on the living room coffee table. That way, she knew she’d always be able to offer the favourite of anyone who happened to drop by.

The other source of Khabouth’s solicitousness is his father. “He loved to socialize,” Khabouth says, “he loved to dance, he loved to have a good time. He was probably the best dressed man in all of Beirut. I’m just like my father, actually.” In 1970, Khabouth’s father left his job as a restaurant manager to open a supper club that, at the time, had the largest patio in all of Lebanon. He went bankrupt six months later and, shortly after that, at the age of 42, suffered a fatal heart attack. Khabouth was nine years old.

Khabouth’s mother remarried, and Khabouth grew close to his stepfather. (His name, William, is the third tattoo on Khabouth’s body; it’s written across his right shoulder.) In 1975, civil war erupted in Beirut. As the conflict worsened, Khabouth and his family began sleeping in the parking garage beneath their building, to stay safe during nightly bombings. Still, they witnessed horrific acts of violence; Khabouth remembers driving over a corpse on a Beirut side street. By 15, he was being courted by the Christian militia, and he probably would have joined had he and his parents not fled Lebanon by paying a fishing boat operator to take them to Cyprus.

The operator packed 250 people on a boat designed for 18. The trip took 14 hours, and within a half-hour everyone on board became violently ill. Had the boat sunk, or been bombed by hostile air patrol, it wouldn’t have been the first time. “We were in shock,” Khabouth says of their arrival in Cyprus. “We barely spoke to one another, except to say things like, ‘Do you want to eat?’ or ‘Do you want to sleep?’ But even then, I remember ­thinking that if I have to go through this, at least I’m going to make something of it. I didn’t know what business I was going to get into, but I did know one thing: whatever it was, it was going to be big.”

Four days later, Khabouth and his family flew to Athens, and from there they took a plane to Toronto, where other family members had already settled. Khabouth studied at Overlea High School and after graduating took a job at a computer company, but he wanted work that involved dealing with people. He decided to try out retail, and quickly worked his way up to manager at a Stitches clothing store in Yorkville. One night, he and another manager were at the old Diamond Club on Sherbourne. Khabouth looked at the black walls, at the grungy decor, at the general air of dissolution, and had a single thought: I can do this.

He bought a defunct gay club on St. Joseph Street called The Manatee and spent $15,000 on renovations. He painted the floors himself. To make the walls shiny he covered them with the metal sheeting used to make heating ducts. He rented a sound system from Long and McQuade and opened Club Z (using the American pronunciation) in 1984. For two months nobody came. The third month wasn’t much better. He fell behind on his rent, and his landlord told him he’d give him one more month before evicting him. Khabouth remembers sitting on the curb in front of Club Z, head in his hands, thinking, what am I going to do? He was 22 years old and living on Kentucky Fried Chicken.

Rescue came in the form of a guy who rented out exotic animals for film work and photo shoots. Khabouth borrowed snakes and cougars, which he displayed inside the club. For Halloween, he put a tiger in the enclosure of the front window, thinking it would attract clientele. The next morning, the cat had punched a paw through the front window and almost mauled a passing woman. When police asked if the tiger was his, he thought his answer would land him in jail; no one was more surprised than he when no charges were laid.

The dailies and radio stations covered the event as a human interest piece, and the next night his club was full. If Club Z was a success, it was because those who came out of curiosity returned night after night: Club Z was one of the first to play house music, which at that point had barely been heard in Canada. “Back then,” Khabouth says, “you couldn’t just walk into a store and buy house music. I had to drive to Chicago, New York and Detroit and go listen to the music in people’s homes before buying what I liked. That’s why it was called house music in the first place—it was DJs mixing records in their own basements.”

Inspired by his success with Club Z, Khabouth rented the dirt floor basement of a warehouse space at Richmond and Duncan. At the time, the area was deserted; neighbourhood parking lot attendants packed up and went home at six and the street lights shut off at 11. For the privilege of placing his next club in no man’s land, Khabouth paid all of $4 per square foot. He then took $1.1 million and built Stilife, the antithesis to Club Z.

Whereas Club Z had an unpretentious, minimalist look, ­Stilife was rendered in high fashion by the Toronto design firm Yabu Pushelberg. Whereas Club Z had clientele with new-wave haircuts, Stilife had doormen dressed in fur coats. Whereas Club Z started with a rented stereo, Stilife had the best sound system available at the time. Whereas Club Z catered to anyone who wanted to dance, Stilife was exclusive: Khabouth gave entrance cards only to those with the requisite fashion sense or attitude.

“Stilife was the product of my being arrogant and cocky and doing all kinds of things I wouldn’t do today,” Khabouth admits. “Sometimes, if I felt like going inside for a half-hour, I’d tell the doormen, ‘No one’s coming in.’ It didn’t matter if there was no one inside. If I didn’t feel like letting anyone in, they didn’t come in.” There were huge lineups every night. Prince came, as did Madonna. The club appeared on Lifestyles of the Rich and Famous.

Two years later, Khabouth opened Oceans, a restaurant being a natural next step in his foray into the hospitality industry. Affixed to Stilife, it was no less exclusive. “I was 27 years old,” he says, “and Pierre Trudeau was in my restaurant.” His success, along with the low rents, inspired others, and soon the neighbourhood bounded by Front, Queen, Bathurst and Simcoe was home to such venues as Go-Go, 23-Hop, LimeLight, Venus, Club Max, My Apartment, Club 606 and many others. Says Matt Casselman, a real estate agent, a former DJ and an owner of the King Street dance club Industry: “First you get the clubs, which make a neighbourhood cool. Then the real estate developers follow and build condos.” (Casselmans’ Industry would lure people to the nether reaches of King West, and soon after that Liberty Village was born.)

After Oceans came Khabouth’s Yorkville invasion: there was Boa, The Bellair Café, Ivory Supper Club, Acrobat. In 1995, he purchased RPM on the waterfront and turned it into the Guvernment complex. There was The Strand Diner, Lux, Loft and a Beatles-themed restaurant in Las Vegas called Revolution Lounge. (For its opening, Khabouth sent out leather-bound invitations, unintentionally offending his vegetarian business partner, Paul McCartney. Apparently, they are now friends.) There have been so many clubs and restaurants, in fact, that when I tried to get a complete list from him, Khabouth eventually stopped and lifted his slight hands in the air, looking somewhat sheepish.

“Honestly,” he said, “it’s tough to remember them all.”

Khabouth is a master at providing an experience that people generally wish to repeat, his establishments imbued with a joie de vivre derived from a proprietary intersection of decor, a hard-won customer base and smooth service—when Khabouth lets staff go, it’s usually for evincing the wrong attitude. He’s had very few failures, and when he has it’s often because a partnership didn’t work out: he sold his share of Acrobat to his partner, restaurateur Franco Prevedello, because they “weren’t seeing eye to eye.” Khabouth wanted it to be a supper club where people dined and danced, while Prevedello was more interested in the dining. More recently, his partnership with the restaurateurs Guy and Michael Rubino failed as well; when I spoke with Michael, he diplomatically informed me there was a ­“difference in vision.” (Ame, a high-end Japanese restaurant with $25 cocktails, opened at the start of the recession. It was one of Khabouth’s few failures in timing—his instinct for a neighbourhood’s needs is usually razor sharp.)

With Oceans, Khabouth learned that it’s a mistake hiring celebrity chefs like Greg Couillard. “I’d notice that the kitchen had backed up,” Khabouth recalls. “I’d go in and find Greg in the walk-in fridge, smoking a joint.” Couillard left on short notice, taking all of the kitchen staff with him. Khabouth replaced him with Susur Lee, who lasted only a few weeks. After that, Khabouth would no longer let a chef dictate how a restaurant was run. “I just spent one or two million and the chef is telling me, ‘It’s my way or the highway’? We have to draw the line,” he says.

It’s expensive to run a nightclub in 2013: tougher regulations have increased the amount club owners have to spend on security and soundproofing; celebrity DJs expect $30,000 a night, with a handful of top-tier performers such as DeadMau5 earning half a million dollars a shot; and commercial real estate in the area has risen to about $45 per square foot, 10 times what it was 20 years ago. The only saving grace for club owners has been the anointment known as bottle service (which, as Matt Casselman told me, “was designed so guys who live with their parents in the suburbs can, for one night, feel cool”). But the greatest obstacle to success in the hospitality industry is the one everybody knows about: the public’s cruel tendency to get bored and move on.

To combat this, a nightclub owner must be as restless as his clientele, always trying something new, always striving to give customers what they don’t yet know they want. As I followed him around during the last months of 2012, Khabouth was readying to open La Société in Montreal, Buona­notte, and a Duncan Street lounge called Storys. In addition to launching Uniun, he’d also just opened his Spanish restaurant Patria in an alley around the corner from the busy King West bar and restaurant Weslodge and had finalized his deal to buy the Polson Pier entertainment complex. His is an industry that moves at warp speed, and, perhaps not surprisingly, he can suffer from impatience when events conspire to slow him down: several times he told me he must wait until Bisha opens in 2015 before he can sell the idea to investors abroad. “I know they’ll have to see it to understand it,” he said. “But I tell you: the wait’s just killing me.”

One night, after touring Weslodge, Patria and Spice Route with Khabouth, we became ensnared in traffic. For five minutes we didn’t move. “Gus!” he finally blurted to his driver. “What is going on here? You think something has let out at SkyDome? If this lasts much longer I swear I’m going to get out and walk. Here….Turn north….I don’t care if we’re going the wrong way. The thing I can’t stand is the not moving.”

We eventually got to The Guvernment, where a Vancouver-based band called Mother Mother was just finishing its set in Koolhaus, a live-act venue located within the complex. By the time we got back in the car, Khabouth was running late. “We’ll just have a quick stop at Cube,” he told Gus. There, Khabouth paused to ask a gorgeous bartender in a barely existent dress to lose her gum. We then headed to Uniun, where I parted with Khabouth outside the entrance. “Really what we’re trying to get is an older, more sophisticated crowd here,” he told me. “And how do you do that?”

Khabouth shrugged. “We only let those people in. Of course, this means that the first few weeks might be a bit slower inside the club.” He peered toward a lineup that, at midnight, was just starting to form on the far side of a black velvet cordon. “But in the end,” he added, “we’ll get there.”