The Exchanges

Q Where did your drive come from? Like, what were you like as a kid? It seems very abnormal that a 16 year old at Foot Locker would be so driven and motivated.

A I loved it. I loved working from a very, very young age. I was a bit, my wife says this about my son, and I think I was the same way. I was a man of action with no plan. I remember I really wanted a skating rink in our backyard. We had like this tiny little backyard and my parents are like, no. So I was really stubborn. I'd go and I'd start taking little, you know, like the, the sour cream container, uh, uh, I'd wash it out and put water in it and start dumping it on the lawn and dumping it on the lawn. And my parents are watching me do this and they're thinking, what is he doing? But I kept doing it and I kept doing it. And for hours on end, I'm dumping one little sour cream container worth of water on the back lawn. And my, finally, my father's like, this is crazy. The kid's never going to build a rink this way. And, you know, but then they started helping me, and then my brother started helping, and then here we are as this family, uh, with our hoses out there spraying the, the, the back lungs. Sure enough, we have a skating rink, you know, and, and I was a bit like that as a kid. I mean, I, I wanted to work before I was allowed to work. Uh, I had a paper route at a very young age. I went on, and I worked at Wendy's. I was the fry guy. I think the breaking point for me was I had to take out the garbage, and I was a small little fourteen-year-old, so, you You had to throw it …

AI assessment note: “I loved working from a very, very young age.”

Q Talk to me about David's Tea. Where did, so, so I'm guessing like after university, you followed Emily to Boston?

A No. So Emily didn't get into Boston until much later. Um, we had a lot of ups and downs together. Emily, uh, didn't get into her, her PhD program at first and was going to go do something else and then decided to wait and reapply to McGill PhD and, and then got in. So we were in Montreal. After we both graduated McGill, we, we were living together in a tiny basement apartment in Montreal, and I started a concept called Fitting Room Central. While most of my friends went off to, uh, Goldman Sachs or Procter Gamble, um, I, I developed, so because I had worked, I worked in the buying department in Le Chateau for a few summers, and I, I sold, as I was telling you, running shoes and clothing a little bit as well. So I understood that business, uh, certainly at a, a base level, uh, And I developed a concept called fitting room central because when buyers would buy clothing, remember when you, when you're in clothing or anything with inventory, your biggest risk is your inventory buy, right? You, you, you're deciding what to buy in a season. You're hoping it sells, but you're deciding in advance, you know, what you think people are going to like. So often what large clothing companies will do is they'll test. So they'll, if you have a hundred store company, let's say you'll buy for five or 10 stores and see how it goes there before you take the inventory risk of, of buying for the, th…

AI assessment note: “No. So Emily didn't get into Boston until much later.”

Q time. If you've ever checked out from a store and thought that was so easy, chances are it was ShopPay, which is the internet's best converting checkout, up to 36% better compared to other leading commerce platforms. Go to shopify.com slash Shane now to grow your business no matter what stage you're in. I want to start with what's the biggest lesson you've learned over the past year and why?

A Really that entrepreneurship is in many ways a personal journey disguised as a business pursuit. And what I mean by that is so much of it is managing your own psychology. You know, everybody talks about playing the long game, right? But it's easier said than done. There are so many swings to the game when you're building businesses. There's the lows are so low. The highs are so high as well. And it's learning how to be able to tolerate those lows. So I started this podcast with, with, uh, Harley Finkelstein's president of Shopify, a really good friend of both of ours. We interviewed these, we're both Jewish. We interviewed these old Jewish guys who don't have a social media presence there. All of them are over 70. And they've had these incredible careers and had enormous impact. Not just building businesses and becoming incredibly successful, but also in giving back to their communities and their philanthropic efforts. A podcast called Big Shot, and they talk about the swings, the ups, the downs of their career, but it's in montages, right? Like it's, it's like watching a Hollywood movie, you know, something that is actually two minutes is actually five to 10 years, and it's, it feels like a lot longer when you're in it, living it, and so I really, I Over the past year have really put a lot of emphasis in trying to manage my own psychology and get better at when I have a crappy…

AI assessment note: “entrepreneurship is in many ways a personal journey disguised as a business pursuit.”

Q Can you make somebody care or do you hire people that naturally care?

A I had a mentor that used to talk about this. He'd call it will versus skill. Sometimes they have skill, but they don't have a will, and sometimes it's vice versa. You get people who really care and work really, really hard, but can't really move the needle because they just don't have the skill. You can teach skill more than you can will. I do, I do believe that you caring about your work is something that no one can teach you what to do, but I think sometimes you develop the, the Bug for it, right? If you, you develop a love for what you do over time. Um, so sometimes I think it is about patience. You know, I don't know that anybody can, can teach you how to have a spark and a sense of urgency, but I do think you can cultivate someone's spark and their sense of urgency, but ultimately it's on the person themselves to, to, to really tap into what makes them get up in the morning and want to achieve.

AI assessment note: “You can teach skill more than you can will.”

Q What are the lessons that you wish you knew then about money that you know now?

A First of all, money doesn't buy meaning. Number one, you have to, money can help facilitate a lot of things, but you, you have to know who you are and what you want. That's really, really important, and that has nothing to do with money. Buying nice things is, is going to be fleeting. I think we all know this intuitively, and yet so many people do this, and I'm not saying don't buy nice things. It's always nice to buy nice things, but it's important to understand that in and of itself is not going to give you Meaning a really nice car or a nice watch or a nice house or whatever. It's going to be cool for, for a minute, but, uh, eventually it's going to go away. I think I once heard this from a friend, you know, the secret to life is, uh, something to do, someone to love and something to look forward to. Money can help facilitate parts of that, especially the something to look forward to, but, but you have to tap into deeper meaning on, on what it is, uh, what gets you excited on an ongoing basis. For me, it's building businesses. But I wish coming out of that experience of, of making money and becoming financially independent, I wish I'd taken a little bit more time to think about how I wanted to do that and where I wanted to do that. I think I was a bit too, I felt I needed to get back in the game very quickly. I, I think I, I, I set an artificial timeline. Like I think someti…

AI assessment note: “First of all, money doesn't buy meaning.”

Q And where's it like harder now and different?

A To contrast it, when I started David's Tea, uh, there was no Instagram. There was no Shopify. You had server rooms, and if you want to build a website, you know, you called a website guy, like, right? That's how we used to build websites. You found a friend of a friend who is usually a kid who knew how to build a website in HTML. And the store, a physical retail store is much more about distribution than it was discovery. I mean, it was about both, but nowadays you don't need a store to distribute, right? Um, e-commerce was a tiny, tiny percentage of the business back then. It's exploded on the scenes now. So it was very different. I think the space is much more competitive now. There's a lot of products out there that claim lots and lots of benefits, but I think some of the fundamentals of building a business haven't changed. So, you know, everybody loves to talk about what's changing and disrupting, but I think it's also important to look at what doesn't change and having a great quality product. Doesn't change, and I like to put my energy into that, and one of the things I love about tea is that it's so timeless. Tea has been around for hundreds and hundreds of years, and drank in cultures all over the world for different reasons. It has proven benefits versus some of these other products that come on the market that, that make claims that have not been studied. It's obvious…

AI assessment note: “I think the space is much more competitive now.”

Q Did you recognize that you were depressed? How

A Oh yeah. I was really depressed. Like, like I went through, you know, I don't, I don't talk about this often, but I was, I was in a really bad spot. And it was a weird thing. Like I felt guilty about it. Cause like, wow, what right do I have to be depressed? I just, I lived, I just had the dream that everybody plays for, which is an exit in a major company and financial independence. But I, I was, I was very upset. I had some health issues and it's hard to know whether the health issues were from the, from the depression or the stress of building it or, or just, You know, what came first, the health issues and the depression, but no, I had to, I had to, uh, develop better habits in my lifestyle. I had to develop a better perspective on life. Um, there was a lot of stress. There was a fair amount of internal, uh, uh, fighting in the company between my original partners, the private equity group. It wasn't an environment where everyone was just focused on the customer and adding value for the customer. And there's, there was a bit too much, uh, uh, in internal conflict, which is one of the reasons I felt it was time for me to move on. And I think I never had a chance to process all that and, and deal with that. And, and I had to really understand when it no longer becomes about the money, you really have to think about what you're doing and why you're doing it. You take away that…

AI assessment note: “Oh yeah. I was really depressed. Like, like I went through”

Q What would you say to somebody who's depressed right now?

A There is no shortcut for the work. Period. There's no magic pill. There's no magic elixir. It's about habits. You have to do things even when you don't want to do them. I, I don't know where I, I heard this story, but I think it was a guy who had survived the, the internment camps during the war and where they were being tortured. And, and he said that it was the people who, uh, lost hope that, that didn't make it. It was the people that had hope, but not expectations that did, right? So they knew they'd get out of there, but they didn't have an expectation on when. And I think depression is, is like that as well. You, you have to get up and go for that run, even though you don't want to do that. 20 minutes, sit, uh, you know, breathing exercise, even though you don't want to work on your eating habits or your, your, you know, your, your, your rituals, whatever they may be. I mean, And it's all kinds of different rituals in your life. It's important to develop. I'm using the word ritual loosely here. Routines, habits, whatever you want to call them. When you're in a dark place, they're even more important. I mean, it's really easy when you've had 10 hours of sleep and, and the sun is shining and it's, and it's warm outside. It's really easy to go for that run or, or, or put on that smile or whatever it is. Like, you know, that's, that's where it's easy, where it's hard. Is it's…

AI assessment note: “There is no shortcut for the work. Period. There's no magic pill.”

Q Talk to me about the annual thing versus daily. How do you use that? You do action daily. How do you set that and sort of measure progress and consistency while keeping your eye on the annual sort of timeframe?

A When you're building a business, the amount of decisions you have to make is coming at you a mile a minute. It's, it can be like trying to drink through a fire hose. I think you develop an intuitive sense of it. I don't know that I, that I consciously sit there and think of every decision and ask myself, is this a monthly decision, a daily decision, a weekly decision? I think I, I usually ask myself, uh, without consciously doing this, two things. One, Is this something that I can recover from easily? Meaning if I'm wrong about this, what's the impact of it? Two, what's the risk of doing nothing and waiting for more information? More often than not, the answer is wait and get more information. Certainly on big decisions, like to go in a different direction with the product, to deviate in a, in a big way from your marketing efforts, um, usually there it's, it's try and get more information, try and get more information, try and get more information. Things like you're out of stock and you got to pressure a supplier to ship it faster. That's where the sense of urgency comes in and you're really, you know, you start to pound the table and, and, and get people moving. And there's a lot of those, right? There's a lot of little decisions in a day where if we can do a little bit more to, you know, ship that extra order, handle that, that last customer service request, um, those add up…

AI assessment note: “I don't know that I, that I consciously sit there and think of every decision”

Q I feel that. What's missing most in life right now?

A That's a tough question. I cheated before this interview and looked at your notes, and I saw that question, and I wasn't sure how to answer it, and I'm still not. I think it's a really difficult question to answer. I think the answer is nothing. There are lots of things that I want, but there are few things that I truly need that I don't have right now. I think what's missing is just more, more life, more embracing the journey, More being able to take it all in without feeling less than like a, you know, like a failure. More being able to just appreciate all the good that's in life versus constantly, ah, um, perseverating on, on, on what's difficult or missing or bad. Life is short and, and it's, it should be celebrated. It should be, it should be elevated. And I think There are lots of things I want to do and accomplish. I mean, I definitely sit down once a year, and I write out goals, and I write out one-year goals, and three-year goals, and ten-year goals, and, um, but then I kind of like to say to myself, and, and, and let's say I achieve none of them, right? Because you always have that sort of fear, like, what if it doesn't work? What if I can't? What if I'm not that good at this? And what if I can't, right? And so what, I got three healthy kids, Uh, I, I got a, a, a great marriage. I've, I've made enough money. I've, I've, you know, and so what? And, and I know that, tha…

AI assessment note: “I think what's missing is just more, more life, more embracing the journey”

Q How does it feel now to watch that flounder?

A Not great, and I've, I've, I actually tried to buy it back at one point with Bain Capital. I've moved on. I mean, I, I, I, I wish David's Tea well, and, and I'm very excited about what we're doing with Firebelly Tea, which is my new tea company. You know, while I was developing David's Tea, I always had a private stash, right? What sold at David's Tea were these heavily flavored teas, and that's just what the market wanted, but my palate developed because I, I would drink it every day all the time, right? And, and, and I would travel these incredible tea regions, and I would, I would meet with our tea blenders, and, and I'd learn kind of how to create an amazing tea in the right combinations of different ingredients, and as, when I left, I started to realize, wow, you know, I love tea. I love creating teas, and I love creating the products that go around with it, and I would curate these tea collections for my friends. I mean, Harley, um, who's the president of Shopify and a close friend, uh, I got him really into tea, because when I first met him, he's like, you know, I'm drinking way too much coffee. I'm not sleeping well. I get the jitters. I get headaches. I'm like, well, why aren't you drinking green tea in the afternoon? He's like, I never thought of that. I'm like, oh my God, green tea is amazing. He's like, wow, it's kind of bitter, right? I'm like, well, yeah, because …

AI assessment note: “Not great, and I've, I've, I actually tried to buy it back”

Q Did you feel more like you fit in more?

A The way the stories, as I got older, the way the stories were told to me was like an episode of succession. You know, my, my, my family built a business called Peerless Clothing, and, you know, it was filled with this one being mad at that one, not talking to this one, and feeling slighted, and it was basically three brothers. The oldest one started it with the dad. The middle one came in with the elder one and was kind of the inside guy. The elder one then, then once he had made it, Decided to go to Japan. And in those days when you went to Japan, it was like bon voyage, right? Like there was no, we're talking that we're in the forties and fifties right now. And so my, my grandfather got brought in. Uh, he was a tall, uh, salesman type guy and the business was not doing well at that time. And, and they brought it back, uh, together and peerless clothing for, for people listening was they, they manufactured, they're still around today. It's a, it's quite a large business and they manufacture clothing for, you know, Pierre Cardin, Hugo Boss, and Calvin Klein. And anyway, my grandfather ended up, ah, the middle brother, ah, died, and there was a fight over shares, and long story short, the son of, of, of my, my grandfather's eldest brother, who was adopted, ah, came in and ran the business, and actually did an incredible job with it, and, and, and took it to a whole new level. Ah…

AI assessment note: “the way the stories were told to me was like an episode of succession.”