Tokyo Smoke founder Alan Gertner (and ex-Googler) has mastered the pursuit to happiness. An encounter at a Ghanian voodoo ceremony inspired him to leave behind a skyrocketing career in corporate strategy for a journey of self-discovery. He refers to this chapter as the TimeOn project, where he scored and tracked how he felt about each activity he took on, using metrics of happiness and meaning.

Despite the profundity of this experience, he remains humble and lighthearted about it. “It was basically a giant Excel spreadsheet,” he says. “At Google and in my twenties, I had optimized for winning at work. Now, in my thirties, I really want to optimize for winning at life.” He applied the project’s insights to his next venture, the coffee-clothing-cannabis lifestyle brand Tokyo Smoke, which spotlights marijuana like it’s never been before: with beauty and carefully crafted utility. Sitting in the flagship location—textured with Asian aesthetics, Californian cool, and a distinctively European approach to enjoyment—there’s little doubting his success. Read on to learn just how he got there.

#ROGUESTORIES: Alan Gertner, Tokyo Smoke

With the TimeOn project, you took a very quantified approach to discovering what makes you happy. Can you tell me a little bit more about that journey?

I worked at Google for more than six years—effectively, the longest thing I’d ever done. As I looked towards my next path, I really wanted to understand not only what made me happy, but what would make me feel more fulfilled. Happiness is short-term, somewhat tangible, and more manageable. I was looking at something broader.

I’m not necessarily a believer in leaping into the void. Sometimes we confuse a lack of structure as the key to our happiness. If only I could just be on a beach, escape this 9–5. But when most people win the lottery, they lose all that money without a plan.

For me, it wasn’t about freeing me from the shackles of the workplace. It was more about creating a project that would help me understand happiness and fulfilment for myself. I called it TimeOn. My friend and I had joked about the interesting quirk that is the concept of time off. Why do people covet that off time the most?

#ROGUESTORIES: Alan Gertner, Tokyo Smoke

It’s weird that being ‘off’ is a good thing.

Right. What am I turning on, and what am I turning off? Why do people think their best selves happen then? That… sucks. So I decided to go out and do all these activities that I hadn’t been able to do, due to working during my entire twenties. I worked as a back-country ski tour guide in Japan for four months. My friends and I had bought a twenty year-old TOAD, and we drove from London to Mongolia. While doing these activities—fun, exciting, and crazy activities—I would track how I felt in a spreadsheet. Every morning I would get up and compare my scores, dependent on what I’d done, who I’d met, what the weather was like, anything I could get my hands on. I was going to use that to help me figure out my next path.

A lot of my findings were reasonably expected. But that didn’t make them any less powerful. I discovered early on that when I take on big challenges, I feel more fulfilled.

One example took place during my time in Japan, when I realized a group of beginners and their guide had gotten lost. It’s minus 30, not particularly sunny, not a particularly good place for that to happen. It turns out they’d skied into a valley. We took some guesses, hoped for the best, and worked through it.

When I woke up the next day and did my usual scoring exercise, I realized there was a pattern: It wasn’t like I’d felt much happier, but it was really fulfilling to play a material role in something difficult and challenging. I noticed this early on, and it stayed true throughout the exercise. I wanted to use these broad insights to inform my next opportunity.

Have you always been this aware of differentiating between happiness and fulfilment?

Not at all. I was a stupid twentysomething like everyone else. While working for Google in Singapore, I had a boss who was endlessly more thoughtful and intelligent than I was. He was a great and challenging mentor to question my path of happiness and fulfilment.

I remember distinctly a conversation we had about promotion. I wanted to get promoted quickly. He asked me why it mattered; it was because I wanted to beat everyone else. He then asked me whether or not it mattered if it happened later, and I said, ‘then I don’t care about it at all.’ If I’m not going to beat everyone else, then it’s effectively irrelevant to me. I remember that so well because of how silly and linear that thinking was.

One of my better skills is my ability to focus. If I could focus my energy on one thing, why not have that be fulfilment? Why not have that be a goal that brings broader and richer satisfaction than more money?

“If I could focus my energy on one thing, why not have that be fulfilment? Why not have that be a goal that brings broader and richer satisfaction than more money?”

We think we only learn lessons once, and we retain the moral of those lessons. But there are also ways you relearn them as you get older.

I remember those moments. While I recognize those are moments that pushed me over the edge, there is a long build-up. There needs to be continued reinforcement for those lessons to stay relevant. Otherwise, we move onto new obsessions.

Also, people are busy. More than ever, we have endless distractions. Why think about the reasons behind my happiness and fulfilment, when I can just reach for my phone and get some base-level joy out of that?

How has your relationship with technology changed since leaving Google?

When I was at Google, my relationship with technology was very strong. Google was starting to get more self-aware of the virtues and downfalls of its increasingly interconnected employees. We were just starting to begin our meetings by requesting people to put down their laptops and phones. I was optimizing for winning at work, which meant if I got an email late at night, I’d respond. Technology was part of my toolkit for success. I was deeply aware of how I could use technology to highlight how hard I was working, or communicate clearly.

When I left Google, I tried to be more conscious of the downsides of technology, and how it impacted my happiness and fulfilment. Once you break that bond with technology, it becomes obvious that you’re able to cultivate more pockets of stillness, where you can have more clarity of thought. When you’re constantly bombarded with information, it makes it harder to think clearly.

Having said all of that, I started a business, and I’m on my phone all the time—almost more than I ever was. I’m more aware of how the internet perceives and impacts our brand, which was not something I thought about at Google. There is a fairly linear relationship between the time I put into my business and its success. I try to be especially conscious of it in the morning, and before I go to bed. I’m now much slower to responding to emails—as in, I don’t respond immediately. [laughs] If it doesn’t appear to be urgent, then I don’t treat it as such. It’s better that I spend the time building my business.

I love phone calls. They’re clear and to the point. Emails are much easier to misread. You would wonder: why did they put an exclamation mark? I put an overly long amount of time into writing my emails, but I’m getting better at seeing what successful, older people do—which are emails that have no grammar in them whatsoever, all lowercase, no hellos. It’s like it came out of their brain, and immediately into my inbox.

“When you’re constantly bombarded with information, it makes it harder to think clearly.”

Tokyo Smoke’s mandate seems to be ushering marijuana to a modern age. Why marijuana? What’s your relationship with it?

A lot of things about marijuana and psychoactive substances is that they alter our mind and allows us to perceive things differently. I have lots of love for marijuana’s ability to do that in a safe and manageable state. But while it’s a part of who I am—my social interactions, my decompression process—it doesn’t define me.

#ROGUESTORIES: Alan Gertner, Tokyo Smoke

What kind of role do you think marijuana plays in the modern professional’s life?

Do you think drinking is a positive part of the modern professional’s life?

Sure. It’s great for socializing—helping us have conversations that we may not be having otherwise.

Right. Life is hard: It’s full of challenges and stress. I imagine that in some ways, it’s only going to get harder. We’re more anxious than we’ve ever been. Technology has made that worse, by giving us a window into the best—and only the best—parts of other people’s lives. I have a lot of love for cannabis’ ability to help us manage that.

That isn’t to say that I think we should smoke pot, or drink alcohol every day. But I do believe it helps us be thoughtful and open our minds.

How has your average pot-smoker evolved? What are the different demographics that have arisen over the past few years?

22% of Canadians report smoking marijuana on a regular basis. That’s reported use—which means it’s likely higher than that. If that’s the case, at least a quarter of the country consumes cannabis on a regular basis. Because of that, it’ll be impossible for me to define that group. It’s just society. It’s like trying to define what the segments are in coffee—at this point, pretty much everyone. The coffee-drinking population is probably very similar to the smoking population.

That’s the amazing part about marijuana legalization. We’ll be the first G20 country to have legal, recreational marijuana. It will have incredible scale. Because our population is so diverse, I’m very excited.

“We’ll be the first G20 country to have legal, recreational marijuana. It will have incredible scale.”

That’s a great point, and I’m now trying to think of the Starbucks run equivalent to legalized pot.

It’s a very mature decision for a society to make. It’s an incredible embodiment of freedom and choice, and I have so much love for that.

#ROGUESTORIES: Alan Gertner, Tokyo Smoke

Can you tell me a bit about GREEN: The Rise of Modern Marijuana?

Marijuana can be beautiful. And it can be stitched into the fabric of society. It can be revered and aspirational. But if we look at history, we’ve got a long way to go.

We had this idea to create events or experiences that will help demonstrate what modern marijuana culture could look like. This is how it happens now: You get a prescription from a doctor. You then get a package from Canada Post. You open it up, and there’s pot inside. What goes into that? We wanted to demystify it, so Canadians can understand the love, thoughtfulness, and security that goes into it. It’s not cowboys in a field. It’s a precise process. Our [product] partner is a multigenerational business. Historically, they grew tomatoes. Now they’re growing cannabis. That’s amazing.

Not long ago, pot carried the image of illegality. The future of marijuana culture is going to need a bit more transparency, in the same way we now care about what goes into our food and the other substances we consume. We wanted to bring that to life. Tokyo Smoke will continue exploring these ideas in the cannabis landscape, and there are lots of ways to demonstrate this. Conceptually, I have lots of love for beautiful edibles. Infused dinners. We tend to think of cannabis as this counterculture. If you have this beautiful dinner, that tastes incredible, that really helps change perception.

I believe firmly that the cannabis flower, and smoking joints, will only be a marginal part of modern marijuana. Modern marijuana is going to be defined by non-combustables: the vapour pens, the edibles. Sometimes I think of joints like cigars: People still smoke them, but they’re smelly and take forever. Yet it still exists in tobacco culture. Joints have a similar role; there’s something historical and ritualistic about them, but they’re not exactly practical or good for you. I’d like to continue the dialogue and [enable] more experiences that help people understand what’s coming in the future.

#ROGUESTORIES: Alan Gertner, Tokyo Smoke

How does Tokyo Smoke’s product research process happen?

We do a lot of it in the U.S. The country has a number of very developed marijuana markets. There are some great data platforms out there. I have a deep love for this product called Headset, which is a company that works with marijuana dispensaries to collect data. They aggregate it and provide reports back to them about what’s selling well, whether or not people are preferring pre-rolled to chocolates, and so on. The industry’s evolving so quickly, but it’s so easy to have no idea what’s going on. Maybe in Colorado, people prefer an energizing experience. Or in Washington, people could prefer something more calming. It’s fascinating to think about.

The Tokyo Smoke brand brings to mind so many different cultural influences. As a seasoned traveler, what steps do you take to ensure you’re making the most out of each trip?

As a gateway to perception, travelling’s great in helping us understand different ways and viewpoints of life. It’s simple, but I love staying at Airbnbs. It’s much closer to existing in the way that someone who lives there would exist. For the most part, cities are their most alive at their most local. If you’re a tourist in Toronto, the CN Tower feels like a box you have to check off. But if you go to Parkdale, and have a Tibetan momo, it’s a totally different experience.

For me, the best travel tool is my network of friends. They’ve already done the work, and they’ve discovered. For the most part, we have the same likes, so I can trust the kind of colour they’re going to give me when I go someplace new.

#ROGUESTORIES: Alan Gertner, Tokyo Smoke  Photography by Gloria Chik / @ROGUESTORIES

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