Tokyo Smoke: Can This Toronto Head Shop Make Pot a Premium Product?

Alan Gertner’s headquarters are in an alleyway, an archetypal location for a drug empire.

But vernacular can be deceptive — Gertner is no ordinary drug tycoon and this is not your average alley. A cluster of impeccably dressed men and women (think crisp white shirts and blue blazers, leather pants and designer sunglasses) stand outside the shop, built into a crevice between two bigger spaces on Toronto’s Adelaide Street West. What Gertner has created here is an upscale concept shop for marijuana paraphernalia that feels a little like what Monocle or Kinfolk would design if they got into the weed business. The exposed brick walls are stocked with items like walnut prep trays, quartz pipes, and gold rolling papers. Eventually, once the government green lights the sale of recreational marijuana, the company will sell that too, four different strains (branded “go,” “relax, “relief,” or “balance”) depending on the type of evening you’re after. For now, they’re selling well-crafted cappuccinos, a smattering of minimalist clothing, and decadent incense and home decor items. It’s smart without seeming sneaky, clever without feeling dishonest. After all, it’s right there in the name.

When 32-year-old Gertner speaks, sharply and with relentless energy, people listen. It’s a little prophetic, like a modern-day pied piper, if the piper is wearing a hand full of silver rings and the pipe is a $13,000 stainless steel bong designed by architecture firm Partisans (a product collaboration that debuted at the shop in April). Gertner is a man on a mission, to create “the Grey Goose of cannabis.” “If you think about Grey Goose, they introduced premium spirits to the world. The reason we have Patron and Casamigos is because we have Grey Goose,” he says. “It’s in a really nice package, with a beautiful story. With thoughtful experiences, you can build a brand. That’s what we want to do. For the whole world.”


He’s not kidding. In the next year alone, the company will open shops in Montreal, Calgary, Vancouver, and Seattle. They’re developing a partnership with Central American boutique hostel chain Selina Hostels that could see Tokyo Smoke counters inside Selina lobbies. They’ll release a dozen products under their own brand — marijuana-infused bath bombs, $275 leather stash bags with a lock and key — and a dozen more in partnership with others. Where they can’t sell weed — which is most places, including their flagship store — they’ll sell the experience instead. But the question remains: is there really a market for the type of luxurious evening Gertner is describing? Or is premium pot an oxymoron?

In mid-April, Justin Trudeau made good on a long-held promise that he would take steps to legalize marijuana in Canada. The Liberal government tabled its Cannabis Act in the House of Commons, a bill that will make the substance legal for recreational use in the country as of next year. In doing so, Canada joins an ever-growing list of countries where marijuana is legal in some form, including the Netherlands, Colombia, the Czech Republic, Portugal, Uruguay, and parts of the US. That means 2.7 billion people now live in a country that has decriminalized marijuana. Analysts talk of billions of dollars of untapped market share, and according to surveys the public perception of potheads as stoners with the perpetual munchies who can’t get much done is falling away. If the government’s policies swing the right way — if Trudeau decides that pot can be sold in private stores, for example, that means companies like Tokyo Smoke stand to make a killing by getting in early.

Alan Gertner was raised in Forest Hill, a wealthy neighbourhood in Toronto, by April, a stay-at-home mom, and Lorne, a lifelong entrepreneur and former president and owner of women’s apparel manufacturer Mister Leonard. Alan was a smart, dorky kid — his summer plans included attending computer camp. As a ten year old, he’d go around the neighbourhood handing out business cards that said “computer specialist.” (Best payment he ever got for a job? Leafs tickets.) Alan’s father was also one of the earliest investors in the medical marijuana market, as the co-founder of the first publicly traded cannabis company in Canada, Cannasat Therapeutics, which incorporated in 2004. It was a venture, Alan says, that his family “wasn’t exactly shouting from the rooftops.”

Alan Gertner, Tokyo Smoke

In Grade 13, his father flew him and a friend out to Vancouver to look at the residences at the University of British Columbia. One day on the trip, he said the trio would need to pay a visit to a friend on Vancouver Island. They walked in the door, and Alan tried to conceal his shock as he passed a garbage bag full of marijuana on the way. But something had clicked. “Having had no conversation with my father about any of this, I remember that moment of exposure flashing through my mind as, ‘What the hell?’ It was a good moment of clarity about how marijuana is part of people’s lives on a scale that I never really thought about.” Deloitte estimates that close to a quarter of Canadians use marijuana on a regular or semi-regular basis, and another 17 per cent would consider trying it once it becomes legal. “It’s by no means a subculture. It’s millions and millions of people.”

Gertner ended up enrolling at Western University’s Ivey Business School, taking a job at management consulting firm Oliver Wyman in New York after graduation. He loved the city, its racing pace and density. But when Google posted for a job on its new global business strategy team, he applied, got the job, and moved to San Francisco. Eventually, he’d rise to head of the company’s Asia Pacific travel vertical team, based in Singapore, making more money than he knew what to do with. “It got to the point where it was, oh, cool, I guess I can save up and try to buy a Ferrari,” he says, “but I don’t care about that. That’s not motivating to me.”

By the time the company sent him to Ghana to help build infrastructure for high-speed Internet, in 2015, Gertner was ready to make a change. It would be the last project he worked on at Google; he quit his job and flew to Japan to backcountry ski, picking up work as a guide and intending to take some time off.

“A dealer doesn’t really have an incentive to curate an experience for you. We do.”

That’s also when he started The Spreadsheet. After he left the company, he explained, he wanted to see if he could quantify happiness. He was used to working in data — virtually swimming in it — so he thought he’d apply what he knew to what he didn’t: life fulfillment. Every day when he woke up, he’d rate the previous day out of ten, using a number of categories including happiness, meaning, and energy levels, and tracking details as scrupulous as weather, how many people he’d met, what they talked about, and how much money he’d spent, among other factors. “I wanted to try to work out what winning at life meant,” he says. He kept The Spreadsheet for six months. His conclusions? That happiness is taking on big challenges and cultivating community. He came back to Toronto, where cannabis had gradually become the substance of choice after occasional family dinners at the Gertner home. He and his father began to bat around ideas for what a retail marijuana experience could look like.

It wasn’t until shortly after Tokyo Smoke’s opening in 2015, when Gertner was standing on a ladder taping a burst pipe shut while a torrential stream poured down on him, that he considered that maybe this wasn’t such a good idea. Early on, investors, friends, and even family discouraged him with all manner of arguments: the country isn’t ready; the market isn’t there. “The war on drugs is not over,” he says. But last year, Gertner noticed a change. Where before people scoffed and closed doors, Tokyo Smoke was able to raise $3 million in venture capital in late 2016 alone. The spark had finally caught.

“How are you?” one of his colleagues asks. “I’m fabulous! How are you?” Gertner exclaims, as he pulls off his quilted brown boots, waves his hand in the air. He untangles his turquoise scarf from around his neck, and begins making phone calls. Gertner looks a little like an extremely well dressed professor, in round gilded spectacles and a Klaxon Howl tweed blazer, leather and brass and silver bracelets lining his wrists. He responds to favourable information with an effervescent “Cool!” His vibe would most accurately be described as a cheerful Tasmanian devil on Red Bull. The Tokyo Smoke office is painted white, aside from a stack of red lockers along the wall. A rickety fire escape that runs along the side of the building is the quickest way down. It’s an open-concept, no-shoes office. No one looks over thirty. Everyone is attractive and well dressed and exquisitely groomed.

He’s pelted with questions every moment he’s not on the phone, from how his meeting with one of the company’s lawyers went that morning to whether one of his employees can borrow his father’s Mercedes that’s parked downstairs to what he thinks of the squid ink that’s just arrived on the desk of his product developer, who intends to use it to dye rolling papers black to make them — of course— more luxurious.

Gertner’s personality is at odds with the stereotypical stoner. In fact, the company’s language is precise and every employee follows suit. He signs his emails “high regards.” An upcoming ad campaign is sleekly named “altered states.” Their new company magazine is called “Hi.” Marijuana is cannabis, always, and there is no mention of any of the lingo associated with stoner culture. While Gertner admits to enjoying a toke or two, and declines to say how much exactly, he also explains that right now his life is a revolving door of meetings, phone calls, and events. When I ask what he does for fun, he pauses, almost stumped. He spends time with his longtime girlfriend, a Pilates instructor named Emily. And he spends every Sunday in silence, typing away on his laptop in his rented home on Toronto Island, talking to no one as a way to recharge.


From the start, Gertner says, the company has been committed to operating legally, a promise that’s caused no end of headaches. He speaks to lawyers every day, having them vet marketing materials, and taking the high road as illegal dispensaries keep sprouting up on Toronto streets last year. Instead, Tokyo Smoke has launched four strains of marijuana, or purchase via their website, for Canadians with medical marijuana prescriptions. Think of the undergrads you went to school with who lit one up every afternoon. Now, they’re working jobs in engineering or tech or finance, flush with money and lives decorated with designer apartments and bespoke suits. Gertner thinks that their weed use has grown up with them, and wants to cater to those desires. “Why would that culture exist in alcohol and not in pot? Why would it exist in coffee and not pot? In clothes? If someone drinks Sam James coffee and drinks Bellwoods beer, what’s their marijuana option? A dealer doesn’t really have an incentive to curate an experience for you,” he says. “We do.”

On April 20th, or Cannabis Christmas, it rains all day in Toronto — a bit of a buzzkill but a predictable hazard when you hold your most important holiday in the spring. The team at Tokyo Smoke has extended me an invitation to their 4/20 party. Last year, there were 80 people on the list. This year, there are 600 and more than 50 of them are standing outside a bar called Miss Thing’s in Toronto’s west end, waiting to get in. It’s such a perfect conjuring of what Tokyo Smoke is aiming to do that it could be an ad for the brand. Floral skirts on skinny blonde hipsters and blazers on well-groomed dudes spill out of a dark bar, the scent of marijuana hanging thick in the air. I spot a prominent Toronto stylist — dressed in a full-length black studded cape — in the crowd. I think of something Gertner said earlier that week: “I really believe the train has left the station. We can give people a new perspective on something old.” I press my face up to the fogging glass, watch the crowd inside sway to its own rhythm, and feel a little like I’m looking into the future.