Legal cannabis use is on the rise around the globe and at the forefront of selling it is Alan Gertner, the co-founder and CEO of Tokyo Smoke. A lover of technology and design, Alan led a $100 million organization at Google before venturing into his new boutique legal cannabis business. He also supports programs that empower the greater startup community, the cannabis movement, and future generations of people pursuing their passions, including his own TimeOn project.



In This Episode

In the pursuit of happiness, Alan Gertner instead found meaning. He left his dream job at Google to pursue his passion in creating a modern cannabis lifestyle business called Tokyo Smoke. His goal is to create a safe space for those who are seeking to legally consume cannabis. In this week’s episode of Modern Ontrapreneur, he sits down with Ontraport CEO Landon Ray to discuss his involvement in the massive cannabis movement, his strategy to combat big competition, the importance of honesty in the entrepreneurial space, and more.

Topic Timeline:

0:58 Lifestyle Brand Inclusive of Cannabis

Legal cannabis usage is on the rise and, with it, an opportunity is born.

2:45 Meaning > Happiness

Try to orient your life and career around things that make your life more meaningful.

4:15 Tokyo Smoke and The Cannabis Revolution

Following in his father’s footsteps.

5:15 Focus On a Singular Thing

Life can be full of distractions, but Alan will bang his head against the wall until he finds the solution.

6:09 Tell Honest Stories

You have to go beyond commerce to touch the lives of the consumer.

8:10 Where is The Movement Heading

Using other industries to predict the future of cannabis

9:38 Be “Starbucks”

Taking cannabis to the masses

10:33 New Opportunity Breeds New Competition

Strategic planning when the major corporations descend on the market

13:03 The Responsibilities of a Modern Entrepreneur

Believe in what you do, and be honest.

We think if we build a platform that’s about education and not necessarily about sale, we can build a much strong community that can be somewhat more resistant to big businesses.

– Alan Gertner

Show Transcript

LR: Welcome to Modern Ontrapreneur. My Name is Landon Ray, and today I have Alan Gertner, who is the co-founder and CEO of Tokyo Smoke, which is a modern lifestyle business that is inclusive of cannabis. A lover of technology, design, and everything in between, Alan is a proven leader in strategy and operations, and he recently led a hundred million dollar organization at Google. An angel investor and advisor outside of Tokyo Smoke, Alan supports programs that empower the greater startup community, the cannabis movement, and future generations of people pursuing their passions, including his own TimeOn project. Thanks so much for being here.

AG: My pleasure. Thanks for having me.

LR: Awesome. So tell me what a lifestyle brand inclusive of cannabis is?

AG:  Yeah. A couple years ago, we decided to start this business. We thought a lot about what’s happening in the marijuana movement in the entire world. Very quickly. Marijuana is becoming legal in lots of places, overnight, and a lot of people consume cannabis. But they don’t just find …

LR:  Do they?

AG:  Yeah, a lot. In Canada, about a quarter of Canadians consume cannabis on a regular basis. The numbers are not so different in the US.

LR: No wonder they’re so nice.

AGYeah, exactly it’s why we’re so kind. It’s so easy there. Same percentage of people consume wine on a regular basis so it’s this huge market.

LR: Right.

AG: But these people, just like wine drinkers, you don’t define yourself by your wine consumptions. You don’t define yourself about your coffee consumption, so let’s build a brand that happens to also touch on one part of your life: cannabis.

LR: Right, but what is the lifestyle business? What is it you actually sell?

AG: Oh yeah. We have stores, retail stores; they’re cannabis stores and coffee shops. Actual coffee shops. You can buy a drink of coffee and then we sell paraphernalia and cannabis products as well.

LR: Oh, so is this like Amsterdam revisited?

AG Yeah. You can’t smoke in the cafés because people generally aren’t pro-combustion, but they’re a place in a community experience that you can go and have that you haven’t historically may have.

LR: Oh, cool. This is in Canada?

AG:  Correct. It’s in Canada. We have stores across Canada, and we’ll open in the US sometime this year.

LR:  No kidding. Very interesting. So … and you’ve been doing this for how long?

AG:  This is two and a half years.

LR:  Two and a half years. So just like … you’ve got stores across Canada, you’re just burning.

AG:  Yeah, we’ve raised about ten million bucks in the last year. We have way more than 50 employees. We’re a business, we pay payroll, it exists.

LR:  Yeah the whole … I didn’t doubt that, but that’s a lot of movement in two years.

AG: Yeah, we work very, very hard. Someone told me early on that startups were like a roller coaster. Totally believe that. I just didn’t anticipate so much vomiting along the way, but it could because we’re moving very fast.

LR: So, if you could go back a couple of years say and give yourself a hot tip based on what you’ve learned so far in this endeavor or even in your career; what would you tell your younger self?

AG: Yeah, that’s a really good question. For me my biggest learning along the way is that it’s more about meaning than it is about happiness. I think sometimes as people we’re anchored by happiness, but that’s quite fleeting. I can feel great one day and not feel great the next day and that’s not how I should try to orient my life or my business. What I should instead focus on is trying to do something that makes my life feel meaningful. That’s an internal goal I can work on as opposed to try and optimize for a promotion or making more money.

LR:  What taught you that?

AG: I worked at Google for six years, longer than anything else in my life at the time. I went to computer camp as a kid. I love technology so it’s something I dreamed about doing. Six years of working hard. I was lucky to work in San Francisco, Singapore, Bangkok, Tokyo, Ghana, great interesting places, get promoted, make more money. Ultimately I didn’t feel any more fulfilled. I didn’t feel any happier. I did what I thought I was told to do: Work, get promoted, make more money, get some pats on the back. As I tried to figure out the path that would make me happiest, I created this big spreadsheet and every day I score how happy I was, how fulfilled I felt and I started to discover things that made a meaningful difference to my life, and those turned out to be more tied to meaning than to happiness.

LR: Just for our benefit, tie the Tokyo Smoke Project to what that means for you.

AG: Yeah. So, I grew up in Toronto, but I hadn’t lived there for any of my adult life, so part of it was I wanted to move home, and Canada’s leading the cannabis revolution. We’ll be the first developed country in the world to have fully legal national cannabis next July, so that was part of why I wanted to be there. I wanted to do something where I thought I could truly contribute. Google’s a big huge company and I played some small role in that. The cannabis movement is global and many, many countries will have legalized cannabis in the next ten years, and here was a chance to contribute in a way that I thought was interesting, different, meaningful, where I thought I could make a big difference. My father’s oddly enough been in the cannabis space in Canada in the legal market, and it was an interesting chance for me to spend some more time with my family and do something I believed it.

LR:  It’s a family business.

AG:  So it appears.

LR:  So, what is the unique skill set that you have that you bring to this project?

AG:  Yeah, it’s a great question. I work REALLY hard. I think that’s really my most unique skill.

LR:  (laugh) No, it’s not.

AG:  My core skill is my ability to bang my head against a wall endlessly. I think most people don’t want to focus on a singular thing. We tend to get distracted. Our life is more easily distracted than ever before, but I firmly believe in what we’re doing. I was lucky to be a part of a time at Google where we really touch the world at a scale that few businesses do and I learned a lot there. I was a management consultant before that and learned a lot of tools to engage consumers, to teach them about something new, to help them find a path to discover something that’s new or maybe exists in their life, but they didn’t have the education that they needed in order to engage in this product the way they wanted to. But, really the working hard thing.

LR:  Yeah, really the working hard thing. So, you have a product, obviously that lots of people are interested in, but also has a stigma around it. Just like any of us, I mean I think it might be tempting to imagine that you could just open a store and it’s just going to be flooded full of people. But, I can also imagine that probably wasn’t the case necessarily.

AG:  Right.

LR:  What is it that you figured out along the way that really … Stores across the country in two and a half years, that’s crazy. Something’s working. What is it that’s working?

AG:  We tried to, instead of building an ecosystem and getting people to flock to it, we’ve tried to integrate into people’s lives. That’s why we talked about being a lifestyle business. A big way we try to do that is working with what I’ll call evangelists for lack of a better term. People who are identifiable and approachable to a normal person, who they can feel like has a life similar to them, but also uses cannabis. That’s a huge part of breaking down any given stigma. If you see someone productive and thoughtful who for all intents and purposes seems like a caring normal human being, it starts to give you a lot more insight into the way that people integrate different things into their lives, whether cannabis, coffee, alcohol, whatever.

LR:  And that has been the thing that’s had people come to your stores?

AG:  I’m not sure it’s any singular thing, but I do think a huge part of what we do and do well is tell honest stories, touch consumers in a way that goes beyond commerce. It’s hopefully a little more emotional, a little more honest. You know, when we first started the business, a large newspaper in Toronto, I wrote an article about the fact that I smoke pot. I should say a large newspaper across Canada, I smoke pot, here’s this business I’m building. I left my dream job to do this.

LR:  “I left Google,” yeah.

AG:  You know I couldn’t do anything more honest than that. That’s not a perfect article, right, because not everyone’s going to think that’s a good decision. There were definitely some articles that were, like, why would you work at Google for six years to become a drug dealer. Okay, I get that that’s some people’s perspectives, but it is the path I chose to take.

LR:  So, what is the thing that you’re banging your head against the wall about now? What is the next problem that you’re going to solve? What are you working on?

AG:  I mean, we think a lot about where this movement is going to go. We think a lot about other industries that we can use to predict the future. We think about what’s happened with coffee over the last 30 years. Very quickly we went from drinking Folgers to Starbucks to Blue Bottle being sold for $700,000,000. We went from potency, to approachability, to craft. Right, we went from black coffee that everyone in North America drank to frappuccinos to this perfect crafted cortado. So, what’s going to happen in cannabis? Is it going to follow that same arc and that same narrative? If so, how do we get ahead of that? How do we recognize that people will move from potency in a world where they might have consumed cannabis to get fucked up to a world where it’s integrated into their lives.

LR:  Is does seem like that is shifting, right. When we were kids … Well, we weren’t kids at the same time, but yeah it used to be about, “Oh my God, look how crazy this stuff is,” and now it’s about … People not really even wanting to get high at all,  like CBD and…

AG:  The majority of consumption in non-legal US states is non-flower, so it’s not even people smoking joints. It’s not even combustibles. It’s edibles and all these other products that are very different experiences.

LR:  The majority?

AG:  Yes, the majority, and it’s the fastest growing segment.

LR: Interesting. So, this is a big project that you’re taking on, going to consume a good chunk of your life. What do you imagine … How does this contribute to the legacy you’d like to leave?

AG:  Oh, man. I’m 33, so I don’t think about my legacy that often.

LR:    No, you don’t think about that.

AG:    Maybe I should. I tend to try to anchor myself in the present. We are trying to build a business that means something to people, that can be part of people’s lives, that can help provided consumer’s who are maybe canna-curious, provide them a path. We know that this is something that is going to happen all over the world, Spain, Germany, Portugal. This is going to be a global movement, and if we can be a part of that in any given way, that’s really powerful. As a company, if we set a goal, it’s to be Starbucks. I mean, that’s not that much of a revelation for any retail business.

LR: Sure.

AG:  But, Starbucks defined a modern nomenclature for coffee and they built the modern retail experience for coffee. We dream of doing the same thing with cannabis.

LR:  Sure. When I think about the industry that you’re in, you’re on the breaking wave of something that has been illegal and is about to be legal. I would presume that as soon as it becomes legal you’re going to have to be competing with Starbucks.

AG: For sure, or some variant of that.

LR: Somebody like that. How do you strategically think as a startup … Ten million bucks is cool, but Starbucks is Starbucks, right.

AG: Agreed.

LR:  How do you strategically think about dealing with the behemoths in this industry that are going to descend upon you in the next 18 months.

AG:  No, it’s a great question. One, I think it will take longer. I mean, the US is not going to legalize marijuana in the next 18 months.

LR: You’re in Canada.

AG:  In Canada, it will happen, but a lot of the big businesses are here as opposed to in Canada, not to dismiss your point. So, ultimately we think it’s about a couple of things. One, we built the strong community and we have a history with them. Being part of someone’s first fundamental experience is incredibly important. If you parallel this to lots of other consumer products, but let’s use tobacco for a moment.

LR:  Sure.

AG:  They’re not analogous products but you picked your tobacco brand and that was your brand. That was your life. That’s who you were. It’s how you identified yourself. We think there’s some power in touching and forming someone’s first cannabis experience. We think if we build a platform that’s about education and not necessarily about sale, we can build a much strong community that can be somewhat more resistant to big businesses.

I’m also a realist, and it is very possible that we could sell our business. That’s also an okay outcome. I mean, we will be on the forefront of this, and big companies own most major movements eventually. There’s effectively a very small handle of alcohol companies in the world. I mean, almost one at this point.

So, we recognize a similar thing will probably happen in cannabis. It will be the alcohol companies I bet because if you look at somewhere like Colorado, alcohol growth slows potentially with the legalization of cannabis because consumers start to have another option. An option that doesn’t affect their midsection so that’s quite a bonus for lots of consumers. You can’t eat enough Cheetos, I think, to outweigh the calories in the beer. So, you know as an alcohol company I think they’ll get into the space and we will build a strong community, and we will also be hopefully part of their approach to the marketplace.

LR: Amazing. So, we named this thing Modern Ontrapreneur to try and point to the fact that we’re at a unique moment in sort of entrepreneurial history. What do you think it means to be a modern entrepreneur? What are the opportunities that are happening now that haven’t in history? What are the responsibilities that we have as entrepreneurs today do you think?

AG: On responsibilities, I think it’s incredibly powerful for entrepreneurs to be honest. There’s been a narrative history that entrepreneurism is glorious. I think it’s a mixed bag. The grass is always greener for most people. Me and my team, we work harder than I think we’ve ever worked in big company jobs, but we believe very firmly what we’re doing. I think the modern entrepreneur can take that bet both the upside and the downside. You believe in what you’re doing, you work hard for it, and you recognize that it’s not perfect. It’s a journey and that’s the journey that we’re on. We think that sharing that story and being honest about our journey, the ups and downs, will help inform other people to be able to make a decision thoughtfully about whether they want to be entrepreneurs.

LR: Awesome. Well, thank you so much for being here.

AG: My pleasure.

LR: It’s been a pleasure to have you.

AG:  Thanks for having me.

LR: Would you mind signing our wall?

AG: I’d love to.

LR: Awesome. Thanks. That was great.

Want more Modern Ontrapreneur Podcast?

Check out the previous episode featuring Shadé Adu of Savvy Solutions Consulting.