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Gwen Madiba:

Welcome to uOttaKnow, a podcast that illuminates, inspires and entertains produced by the University of Ottawa.

Hello, I’m Gwen Madiba, host of uOttaKnow and a proud two-time graduate of the Faculty of Social Sciences. I am also the President of the Equal Chance Foundation, a non-profit organization that empowers women and Black communities across Canada. 

uOttaKnow puts you in touch with 91��Ʒ���ϳԹ� alumni and researchers around the globe at the cutting edge of their fields. Listen in for thought-provoking conversations on today’s trending topics.

For the fifth season of uOttaKnow, our theme is curiosity. How does it propel us to ask questions, explore new areas of interest, and move into uncharted territory? Our extraordinary alumni guests this season will be digging deep to uncover what curiosity means to them, its impact, and how it has spiced up their lives.

We are very excited to launch Season Five today with a first for the uOttaKnow podcast: two incredible alumni guests, Harley Finkelstein and Lindsay Taub, who met during their time on campus and are now married and the proud parents of two daughters, Bayley and Zoe.

Harley Finkelstein is an entrepreneur, lawyer, and the president of Shopify. He founded his first company at age 17 while a student at McGill. Harley completed his law degree as well as his MBA at the University of Ottawa, where he co-founded the JD/MBA Student Society and the Canadian MBA Oath.

Harley is an advisor to Felicis Ventures and one of the “dragons” on CBC’s Next Gen Den. He has received the Canadian Angel Investor of the Year Award, Canada’s Top 40-Under-40 Award, Fortunes 40-Under-40, and was inducted into the Order of Ottawa. He was recognized in 2021 with the University of Ottawa’s Alumnus of the Year Award.

Lindsay Taub is a child and family therapist who has been providing mental health support to children, youth, and families since 2006. Lindsay graduated from McGill University after earning a degree in psychology. She completed her master’s degree in counseling at the University of Ottawa. Lindsay currently works in a private practice at an Ottawa-based child psychology clinic, Child in Mind, where she supports children and parents with a wide variety of issues.

She is also currently serving on the board of directors of Ottawa Salus, an agency that provides supportive housing and mental health services to individuals in need. Lindsay is a passionate advocate for mental health awareness and support, and is committed to ending the stigma faced by individuals with mental health issues.

Hi, Harley and Lindsay! Thanks for joining us today. I’m really excited for this uOttaKnow podcast. It is the first time that we are welcoming an alumni couple together on this show.

Harley Finkelstein:

Thanks for having us. We’re happy to be here. It’s interesting because I do a bunch of podcasts and media, and Lindsay does her own podcasts and media, and we don’t really ever do it together. This is actually quite a unique experience for us, and of course, the cherry on the sundae of this whole setup is that we actually met when we were both students at the University of Ottawa.

Lindsay was in graduate school, I was in law school. We met there. I guess, the birth of our relationship happened at the University of Ottawa, in the Byward Market actually: at a cafe is where we actually met. This is a special one for us.

Gwen Madiba:

That’s pretty awesome.

I want to start off with a question that we will be asking all of our guests on this fifth season on curiosity as a way to set the stage for our conversation today. What does curiosity mean to you?

Lindsay Taub:

To me, curiosity means asking questions, but also being open-minded to hear the answers to the questions that you may have.

I think a lot of people get locked into their opinions and more and more, unfortunately, I’m noticing that people are not even able to tolerate another person’s perspective if it’s not aligned with their own. I think it’s a mistake. I think we need to get back to being curious and being able to actually listen to what other people are saying, because I don’t think we’re going to learn anything if we stay locked into what we believe.

That’s why, personally, I think it’s important to surround myself with people who are different than I am because we all have different experiences and we think different things, we have different opinions, and we want different things. At the end of the day, I think it’s really important that we listen to each other. That’s what curiosity means to me: being open to hearing other perspectives.

Harley Finkelstein:

One of the things that Lindsay hears me say a lot to our—we have two daughters Zoe is three and Bayley is six—but she hears me say this quite often in the context of a bunch of different things, is how you do anything is how you do everything.

I echo what Lindsay said about being open to new opinions and new perspectives but the one thing that I think Lindsay and I have baked into our psyches and our DNA is curiosity. The way that it manifests itself is actually fairly different.

I flatter my wife enough, so I don’t have to flatter her here, but the way that she thinks about plans for our family, or she thinks about her philanthropic efforts and the organizations we get involved with, she goes really deep and she tries to understand every single aspect of those things. But also, something as simple as lunch on Saturday for the kids, we think about lunch and I got really into Yakitori, which is Japanese barbecue, during the pandemic. It felt like it was a really good pandemic hobby I was really curious about. I wanted to understand the charcoal and the cooking times, and how long to soak the skewers so that you have the optimal skewer density. Once it’s taken off the grill.

Lindsay Taub: You watched a lot of videos.

Harley Finkelstein:

I watched a lot of videos, read a lot of books about it, actually, a great book on it is called Chicken and Charcoal. It’s the best Yakitori book that I found on the topic but the way that we do anything is the way we do everything. That is very deep, very intentional, with a very curious mind. What that means is we don’t necessarily … we don’t do a lot of things in a shallow way; we do a couple things in a really deep way and that’s not for everyone.

Some people prefer to be a jack-of-all-trades. I think we, as a family and as a couple, we try to go deep on a couple of specific things. Even the way that we look at philanthropy, we think about it. There’s this amazing, I think one of the best, philanthropists on the planet: David Rubenstein. He wrote a book about his family’s philanthropy and he created these rules around philanthropy. We took those rules and figured out how we can make those our own, make our own version of that, so that we can be very intentional, and we can go deep, and be very curious about four or five projects, not be kind of curious about 30 projects.

Gwen Madiba:

That’s really interesting.

You talked earlier about your romance at 91��Ʒ���ϳԹ�. Now, I have to give a shout-out to the fact that you two met while you were at the University of Ottawa, as you said, a campus romance, definitely a story that I would be curious to hear.

Harley Finkelstein:

We give our own versions of it because I’m not sure they’re exactly the same.

Lindsay Taub:

You don’t think so? Let’s see, why don’t I start, and then you can correct me if you see it differently. Harley and I met at an event; it was an Ottawa U event for grad students, law students, and med students. We both decided to go to the event. It was a speed dating event. Neither of us was particularly experienced or keen about speed dating, but we both knew the woman who was organizing the event and we felt okay, or at least I felt, "Okay, why not? I’ll be open-minded and I’ll be curious, then I’ll give it a chance."

I went and that was where Harley and I met. That’s not exactly accurate because we had met before that, but we had never met in that particular context and we didn’t know each other. We had mutual friends. Our families knew each other growing up because we’re from the same area in Montreal, but we didn’t know each other. We were both at this speed dating event and that was really where I guess the romance began.

Harley Finkelstein:

Actually, what she’s not telling you is that the way that the speed dating model works is that you write someone’s name and if they write your name, the speed dating organizers introduce you. Logic or basic game theory would suggest that the smartest thing to do is to write everybody’s name that you did the speeding with.

Lindsay Taub:

Which I did.

Harley Finkelstein:

So did I because we both think about the world in that way of how do we optimize? How do we hack this whole thing? The ideal way to run as a speed dater in the program, the best way to do it, is just to write everyone’s name, to see who he got matched up with. Interesting enough, Lindsay was the only person that I did not get matched up with. My interpretation of that was all these other people, all these other women that I was sitting down speed dating, were into me but the one person that I actually was most interested in, which was Lindsay, was not into me.

I actually sent her a message a couple of days later and basically said WTF, why didn’t you pick me? It turned out that, at least this is the story we were told, the organizer of the speeding event made some errors and was not precise in their matchmaking optimizations or operations. I ended up messaging her and saying, "Hey, let’s hang out. That’s--

Lindsay Taub:

Luckily you did not allow yourself to be confined to what was reported to.

Harley Finkelstein:

I was curious about why you and I were not connected. I messaged her and said we should go out on a date. That’s how we started dating.

Then I was doing a joint law/MBA at the University of Ottawa and Lindsay was doing her master’s in psychotherapy at the University of Ottawa. I was finishing law school and starting my MBA.

That year I ended up moving to Toronto to do my articling at a law firm in Toronto. We weren’t sure where that was all going to go, because it was still a very new relationship and I was moving… the long-distance thing just didn’t seem overly appealing, but in the end, Lindsay ended up coming to visit me fairly often in Toronto and then, in 2009, decided that we would move back to Ottawa. Lindsay was in Montreal at that point, I was in Toronto, and we both moved to Ottawa in early 2010. We’ve been here ever since.

Gwen Madiba:

I love your love story. It’s just, like, it talks about perseverance and just going for it, even when you’re told no, when you know what you want, you just go for it and that’s amazing.

Lindsay, you have a practice as a therapist providing support to children and families in Ottawa, as well as serving on the board of directors of Ottawa Salus, an agency that provides supportive housing and mental health services to individuals in need.

Harley, I know that you’ve been vocal in support of mental health in your own work as the president of Shopify.

This is an area of importance to our 91��Ʒ���ϳԹ� community, with the desire to support the overall wellness of our students.

It’s also an area where I think a curious state of mind can be helpful in talking about these issues, reaching out for support, and developing practices to cultivate well-being. I wanted to make some space to hear your thoughts on this.

Lindsay Taub:

I work in mental health, as you mentioned, and I think it’s incredibly important to pay attention to our mental health. I think that for a long time, this was very overlooked and now it’s being talked about more than ever.

Thank you for talking about it, Harley, in your work, because it’s something that everybody in my work talks about because I work in mental health, but people outside of mental health, maybe not as much. I think it’s changing, which is great.

I think we need to look at our mental health and nurture our mental health in the same way that we would nurture our physical health. We need to pay attention when we’re not doing well, when we’re feeling off, when we’re feeling sad, when we’re feeling anxious, these are normal feelings.

Sometimes it gives us a clue that something in our life isn’t maybe working as well as it could be, and it could inspire us to make some changes. Even when things are going well, it’s really important to pay attention to that. It helps us understand what we need and it helps us take care of ourselves better.

Harley Finkelstein:

It’s interesting because in Lindsay’s line of work, as she mentioned, talking mental health is a normal thing to do. You talk about how are you feeling, are you feeling anxious, or are you feeling depressed? Are you feeling one way or another?

In my line of work, which is entrepreneurship, both in running a large company like Shopify, but also just as an entrepreneur since I was a kid, you tend to push those emotions aside. In fact, I think that historically, showing vulnerability in entrepreneurship, in business and capitalism, it was connected to weakness in many ways.

Well, if this person is not headstrong, they must be weak and if they’re head weak, then they must be weak in business as well. I think that’s complete BS. I don’t think that that’s the case at all, but it just wasn’t in the zeitgeist of business and entrepreneurial circles. That has changed.

I think, now, the reason you hear myself, but many, many other people in business talk about how they are feeling, is that vulnerability now…when talking about vulnerability, it is now more of a strength. It means that you have a deep understanding of what makes you tick.

You have a deep understanding of how to be the best version of yourself and when things are not going well, because that is also part of life and business and marriage and relationships; you begin to create a tool belt for yourself in which to mitigate those issues.

Whether it’s…For me, I’ve always been fairly anxious. I know that every single morning, I need to start my day on that chair, right over there, with meditation, and it’s very simple.

It’s usually just breathwork. I use insight timer, and I just basically breathe by myself, counting breaths for 10 minutes or so. That is, for me, what I need to be the best version of myself. I know I need to go for runs. I need to go for walks with the dog. I need to spend weekends involved with my family, for me to be the best version of myself on Monday.

Those conversations just didn’t take place, and when I think about this current generation of entrepreneurs, the separation they have between work and life is far more fuzzy; it’s not this is my work, and this is my life today. There’s pros and cons to this. It’s all blended together and because we’re blending work and life together, it means that if you’re not feeling good about your life, it means you’re probably not going to feel as good about your work.

The work that you do around mental health actually, doesn’t just make you a better father or husband, it also makes you a better entrepreneur in many cases. Bringing that topic to the surface, to the zeitgeist, I think is a very healthy thing. It’s a much better way for us to operate as business leaders.

Lindsay Taub:

You mentioned vulnerability before. I think vulnerability used to be associated with weakness. I really don’t think … I think that’s changing. I think now we look at the ability to be vulnerable is actually the bravest thing of all and it’s the strongest thing of all. I think acknowledging your vulnerability actually makes you stronger in the long run.

Gwen Madiba:

Lindsay, Harley shared with us how he protects his peace and takes care of his mental health. Can you share how you do it because you work a lot in that field. You’re always taking care of others and you’re a mother. How do you take care of yourself?

Lindsay Taub:

Well, I think, for me, the biggest thing is knowing where to have those boundaries, being able to say no to things that I know are not serving me, even if it’s like we went out last night and tonight I’m too tired and I don’t want to go out and I’ve had to learn how to, this is just for myself personally, I’ve had to learn how to get over disappointing people because I have to take care of myself.

Sometimes setting those boundaries I know might disappoint people, but I think it’s okay because I need to do it for myself. I look at where I can set boundaries all over the place and that helps me stay true to myself. It helps me take care of myself.

Gwen Mabida:

Thank you, Lindsay, for the important work you do as a therapist and with Ottawa Salus, and to you both for continuing to have these conversations and to show leadership in this space.

I know that our listeners are curious to hear from you, Harley, as the president of Shopify. Shopify now powers millions of businesses worldwide as an all-in-one commerce platform to start run and grow your business.

Quite the path from its origins here in Ottawa over a decade ago, with the catalyst of CEO Tobias Lütke, starting to sell snowboards online, not finding e-commerce solutions that gave the control needed to be successful, so building one.

Harley, you have such an incredible vantage point to share from having joined Shopify back in 2010, to being an integral part of this transformation to a global leader in the e-commerce space.

What are some of the lessons that you have taken from this journey and what are you currently most excited about looking to the future of retail?

Harley Finkelstein:

I’ll start with the second part of the question because it’s a little easier for me to describe. I think right now, end of summer, 2022, about 10% of all e-commerce in the United States and Canada goes through Shopify, which is a big number.

We have millions of stores and for anyone listening, if you’re buying something on the internet and it’s a great experience and it’s not on a marketplace, there’s a very good chance it’s powered by Shopify.

I still think that while we’ve made entrepreneurship and retail more accessible, most people don’t wake up in the morning and say: you know what? I’m going to start a business today. I think that’s unfortunate. I think the apprehension is that starting a business, being an entrepreneur is scary, it’s expensive, it’s complicated. And so the thing I’m most excited about Shopify, over the next decade, is can we convince more people to try their hand in entrepreneurship?

The best example I can give you is Lindsay’s story. When she decided for a period of time to become an entrepreneur. When we had Bayley in 2016, I think.

Lindsay Taub:

Yes, you got it.

Harley Finkelstein:

We would go for walks around our neighborhood here in Ottawa, on Beechwood. Bayley was born in June. It was the summertime. We were just taking walks with Bayley in the stroller, and we would lament the fact that there was no ice cream shop in the area where we wanted to go for ice cream.

That’d be a nice thing to do on a nice summer evening, but there wasn’t one. With a little bit of, maybe, influence from me, but frankly, mostly influence from herself, Lindsay’s like, “You know what? I want to solve this problem myself. I want to go build an ice cream shop.”

She built it, what was called Sundae School, and ran it for three years until the pandemic, when she decided to return to a psychotherapy practice.

That idea, that I see a problem and I’m going to solve it myself by building a business around it, that is really amazing. The world is made better by more people, starting businesses and pursuing interesting passion projects. You think about how many people have wonderful hobbies. They make beautiful jewelry for their family, or they make the most delicious chicken soup for their neighbours, or whatever they may do.

Not all of them should commercialize that hobby, but some of them may actually be sitting on their life’s work through their hobby, and other people may want to buy from them.

Because there’s this apprehension that entrepreneurship is not for everyone, it makes it too scary. My hope for Shopify is that not only do we continue to add more stores to our platform, and add more merchant solutions, helping them with shipping and helping them with capital, helping with payments, but at a larger macro level, how do we convince more people globally to try their hand on entrepreneurship.

In my view, and I think Lindsay shares the view, entrepreneurship can be the greatest way for humans to self-actualize, for them to find their own versions of success.

In terms of the first part of the question, which is my journey with Shopify, I think you have to understand the stage that you’re in, and the stage of the company that you’re in.

My first couple of years at Shopify, I was effectively the Swiss Army knife. I was the janitor, I was head of sales, I helped create marketing campaigns. I helped great partnership programs in the app store. I think when you are early at a company, whether you’re the founder or you’re one of the first employees, your job is not to do one particular thing.

Your job is unequivocally to add as much value as possible. That’s it. If the floor is dirty … that is now a quasi-famous photograph that goes around Shopify from time to time, with me sweeping the floors at Shopify in 2010. It wasn’t that I was good at sweeping floors, I don’t think I was particularly good at that at all, but the floors were dirty, someone needs to grab the mop, or the broom, and sweep and that was it.

At that particular point, that was how you added value in that moment. In the early stages, you have to figure out how to add the most amount of value and make yourself indispensable.

As the company has grown, I think we’re the seventh or eighth largest company in Canada, for a period of time, we were the largest company in Canada during the pandemic by market cap. We have 10,000 employees across many, many countries around the world. We are, by far, the dominant player in our space in retail and commerce globally. As the company has grown, then you begin to hone your skills and figure out okay, what am I really, really good at? For me, it’s storytelling. The thing that I love doing the most is telling stories. I have been able to find areas of Shopify where I can tell stories, and that has the greatest amount of leverage and the greatest amount of return on investment through storytelling, through making sure that anyone in the world thinking about entrepreneurship immediately associates it with Shopify.

So those are two things about stage and phase of companies that I think anyone listening: if you’re thinking about how to become a valuable figure at the stage of the company and if it’s early-stage company, just try to do as much as you can to add value. As the company grows, try to figure out what is your superpower, and then sharpen that superpower skills as opposed to reducing your weaknesses.

I think in most companies, as the company grows, the leaders become well-rounded objects, like river stones. You put a sharp object in a river, over time, that water makes it all smooth and shiny. You get these river stones, which are really wonderful but they’re well rounded. At Shopify, generally, most of the leaders of Shopify are not well-rounded. We are really, really good at one or two particular things, and all the things we’re not good at, we’ve hired for. We brought in people that are better at those things than we are.

Maybe that brings me to my last point on this, which is have a really good self-awareness to know I am good at this thing. I want to become the best at this thing but all these other things, someone else is probably better than I am at it, and have that sense of self and sense of self-awareness to say I’m going to bring in people that are better, smarter than I am.

I’m going to hire people that are better, smarter than I am. That is challenging, particularly for young entrepreneurs, like I was, who have a little bit of a chip on their shoulder and have a little bit of an ego: getting over yourself really does make a big difference. It leads to, I think, finding your life’s work and building companies which are now multinational, multi-billion-dollar companies like Shopify.

Gwen Madiba:

That’s great to know that and encourage people to understand that it’s okay to ask for help and it’s okay to seek help when we don’t know.

Now, continuing on the topic of entrepreneurship, I have to say, for the two of you, it certainly seems like entrepreneurship is part of your family’s culture. Harley, you had started young with a T-shirt company, and Lindsay, as Harley mentioned, previously, you founded an ice cream shop, Sundae School, in Ottawa.

Recently, on Instagram, there was a sweet video of your two daughters with their lemonade stand, which you captioned, ‘my little entrepreneurs.’ How would you say the spirit of entrepreneurship informs your life as a family? I do think that there are many links between the entrepreneurial spirit and a spirit of curiosity.

Lindsay Taub:

Well, for me, I think I try to encourage my girls to be really independent. I want them to go and do things for themselves. If we’re out in public or something, if we’re at a restaurant, this is a good example, I try to encourage them to order their own food because I want them to have that interaction with the staff and I don’t want them to feel afraid of adults. I want them to be able to ask for what they need and to ask questions.

Harley Finkelstein:

She’s talking about Zoe, who is three years old. A three-year-old deciding what she wants to order and then placing order for herself. That may seem like nothing but that’s a big deal.

Lindsay Taub:

The only reason I do that is because I know they can handle it. My girls happen to be very social and outgoing already. It’s not like I’m pushing them so far in the other direction; they’ve already shown that they’re capable of doing these things. What I try to do is notice what they’re already gravitating to and push them further in that direction and get them to take risks in that direction. I’m not going to ask them to do something that’s very painful for them, but I’m going to push them in the area where I think they’re capable.

Then the other thing I try to do is expose them to as much as possible, because I want them to see what’s out there and then choose for themselves what they want to pursue. It’s not like I’m saying you should be entrepreneurs, but I am encouraging them to make their own decisions and to figure out what they love and what they’re passionate about.

Harley Finkelstein:

I feel like entrepreneurship is generally associated with business creation, but actually, it also is simply a way of doing things. It is highly optimized, or it’s super-efficient, or it’s not waiting in line but finding a way to the front of the line. There’s all these different ways and metaphors, analogies you can use for entrepreneurial mindset.

Lindsay Taub:

Selling yourself, knowing your worth, knowing what your brand is. Obviously, I don’t talk to my three-year-old about her brand, but … I’ll work on that.

Harley Finkelstein:

A way of doing things in her entrepreneurial sense. I just believe it is a better way to do things and even bringing it back to the University and I’m not sure Lindsay and I had the same experience, like this. I went to law school not to be a lawyer. I never had any intention of really practicing law or being a lawyer. I didn’t do my MBA so I can go work at some big consulting firm or a big company.

I went to law school to acquire skills, writing, reading, critical reasoning, debates, argumentative analysis. I went to business, I did my MBA at the University of Ottawa to acquire skills. I went to learn how to read a balance sheet really well or an income statement. I learned how to understand corporate finance and managerial accounting. All of these things, I believed what I was doing. I was paying the University of Ottawa money, my tuition, and in return, they were giving me a set of skills.

Now that’s not to say that everyone listening should not concern themselves with their grades. I was just less concerned with grades. I was more optimizing my education for myself. How much can I take from the school? How many skills can I acquire? How many more connections can I make?

I have a great relationship with a guy named Jay Hennick who’s one of the greatest Canadian entrepreneurs of all times. I met Jay Hennick through the University of Ottawa. He was one of the first people to do the joint law/MBA program. Perry Dellelce, same sort of thing, and Calin Rovinescu, who is chancellor of the University of Ottawa.

So, my version of education was: I pay you, the University, you now owe me a debt and you repay that debt by giving me all these great skills and all these great pieces of knowledge and all these great connections. The onus is on me, the student, to figure out how to acquire those things.

I think that’s a great way to think about life, in general, going back to Yakitori. Yes, it is faster and easier for me to go put a piece of meat on the barbecue using propane, but I actually want to understand it better. I want to have a different approach to it. I want my children to enjoy the process of it. I’d be curious about it.

I think we take, as a family, an entrepreneurial approach to just put everything that we do, even if it’s not about starting a business.

Even if the ultimate goal is not some capitalistic outcome, it’s a way of doing things. Even the way that the people in our lives, we are very thoughtful about who is in our lives. We believe that there are people in the world that give you energy and there are people in the world that take away your energy. The term that floats around is there are energy givers and energy vampires.

We want to spend our time with people that give us energy, that inspire us, that challenge us, that make us better version of ourselves. Those that take away energy we are going to very politely say, this is just not for us.
 

I think entrepreneurship is not just the vehicle by which we’ve been able to build our lifestyle and our life and our livelihoods, it’s also the way we approach pretty much everything in our lives.

Lindsay Taub:

As you’re talking, I’m actually thinking about a psychology concept. I think it’s important to like … I want to show our kids how to have an internal locus of control rather than an external locus of control. When you have an external locus of control, you blame everything around you for all the bad stuff that happens to you. It’s like, oh well, this just happened because this person didn’t do this or, oh well, I’m unlucky and things like that.

I think when you have an internal locus of control, it gives you back that sense of control so you feel like you can control your destiny. If you were not exposed to the right person then like, okay, so what can I do to expose myself to the right person so that I get the opportunities that I need and always just bringing it back to yourself and what is in your control?

Obviously, there are many things outside of your control and you have to accept those, but there are lots of things that you can do, and I really want my kids to feel that ownership and to know what are the things that I can control and then what are the things that I can’t.

Gwen Madiba:

Lindsay and Harley, you’re sharing so much knowledge and so many gems today, so thank you so much because I’m learning a lot and I’m sure that there are many listeners that will be learning too.

Now we have two special spotlight questions for you today from two entrepreneurs who have been part of 91��Ʒ���ϳԹ�’s Startup Garage Program as co-founders of the e-commerce brand, Unique America.

Amaan Merali is a recent graduate of Ottawa’s Telfer School of Management and Jamal Abdullah graduated from Carleton with a Bachelor of Engineering.

Jamal and Amaan, thanks for joining us on uOttaKnow today.

Jamal Abdullah:

Hello, Lindsay. Hi, Harley. It’s a pleasure for myself and Amaan to get to meet both of you today.

We actually have a question for Harley and then we have one for you both.

First off, Harley, congratulations on your achievements for Shopify. Your leadership as president and also on your new brand Firebelly Tea. I’ve actually followed Firebelly Tea’s journey since you started in COVID. It’s been really inspiring to see the president of a behemoth company like Shopify make the time to be in the trenches, like us budding entrepreneurs, and actually build a brand. I find it truly leading by example.

We’ve got a question that we’d love your thoughts on. Amaan and I, we were watching your interview with Noah Callahan-Bever. One thing that you said that resonated with the both of us was that entrepreneurship is the greatest tool that can be used to achieve whatever your vision of success is. Like yourself, a major variable that inspired us to take the leap of faith into the world of entrepreneurship was to provide for our families.

I’m actually an immigrant that came from Egypt, where my family currently is, and I want to be able to provide for them from anywhere in the world.

Now after running a painting business side-by-side with Amaan, we decided to take the leap of faith into the e-commerce space, beginning of 2021.

In one statement, our business model is built on identifying emerging demands in the online marketplace and then bringing innovative products to market, with the end goal of building a recognizable brand for those products.

Our business is currently at $2 million in yearly sales with a long-term goal of $100 million exit. Now we are aware that just in the last two years alone, the e-commerce landscape has shifted massively and that it is constantly ever-changing.

What questions should e-commerce business owners like us be asking to continue to remain directionally correct when it comes to adapting and continuing to grow?

Harley Finkelstein:

First of all, I mean, $2 million on run rate is absolutely amazing.

You hear a lot about… especially if you’re listening to podcasts like Noah’s Idea Generation one of the greatest podcast I think in the world… it’s humbling. I think episode one was me and episode two was Dwyane Wade or something. It was just unbelievable that I was the warmup for Dwyane Wade, who’s an incredible athlete and incredible leader.

But, I think, as a society, we glamorize entrepreneurship. In some cases, as I mentioned earlier in the interview, that’s a good thing because it encourages more people to encounter it. The thing we don’t really talk about is that most businesses fail.

The cool part about building a new company in 2022, and was not the case before 2015 ,was that the cost of failure is now trending as close as zero as it’s ever been.

If you try something and it doesn’t work, you try something else. This is the Ben Francis Gymshark story. Ben was selling pizzas, realized it wasn’t working, ended up creating Gymshark, which is now a multi-billion-dollar brand competing with Nike. Ben has been running it himself since day one.

So, to build a $2 million-a-year business is incredible, so just kudos you on that. I think a couple things you should know: one is you mentioned e-commerce two or three times in your question.

I actually think the future of retail and commerce and business is not necessarily going to be channel specific. I would drop the “e” immediately.

Firebelly, which is my little tea company that I have with David Segal, we built it as a passion project, as a labour of love. David, obviously, famously is the founder of David’s Tea. He introduced me to tea when I decided I didn’t want to drink coffee anymore in the afternoon. We built this thing, but we never built it as an e-commerce company.

We built it as a brand and e-commerce happens to be the most effective way and the most efficient way for us to sell to a global audience, and so we are leveraging that. We also cross-sell on Instagram. We also cross-sell on Facebook. We may decide at some point to do some brick-and-mortar sales or do some wholesale stuff. Part of the reason you’re seeing Shopify go into these spaces, whether it’s B2B wholesale, or it’s Instagram, or SNAP or TikTok commerce, whether it’s physical commerce, whether we are now powering physical stores all over the world, is because we think the future of retail and commerce is going to be channel-agnostic, it’s going to be omni-channel, permanently.

Right now you hear this term, omni-channel, which is: I’m selling across multiple channels. Ultimately, I think talking about multi-channel in the next couple of years, we’ll be talking about like a colour TV: you would never say a colour TV anymore because every TV is fundamentally a colour TV today. That’s going to be the same thing in the future: every business is going to be omni-channel, multi-channel in the future. Where you sell and how you sell won’t depend on what your business model is, it’ll depend on what your customers demand of you.

Firebelly’s customers at some point may demand that they taste the tea before they actually buy it, in the way that David created, I think, 300 stores with David’s Tea, and we will go in that direction because that’s where the demand is pulling us. That’s how I would think about the business, as well; don’t be too caught up in the channel itself, be more caught up in what your customers really want.

You didn’t ask the second question, but I’m going to talk about it anyway because I think it’s important. When you choose your company, you said you’re at $2 million revenue sales, and you’d like to have an exit for $100 million. That is amazing. What I will tell you, however, is that that also may preclude you from building something far bigger, far more long-lasting, and far more impactful at a global level. We had a lot of acquisition opportunities in the history of Shopify, where a big company was coming off for us at $10 million, $50 million, $100 million, and even a couple billion dollars.

We were steadfast. We didn’t actually take those meetings because, fundamentally, we want it to be a global, independent, publicly traded company. It is okay for you to have to talk to your investors about a potential exit.

If you go to harleyf.com/startups, you’ll see about 30 or 40 companies that Lindsay and I have invested in personally, as angel investors. We love those companies, we want to have an exit at some point if it’s possible, but I would never want to limit their trajectory simply because they have a made-up number of exit in their minds.

If what you’re saying is true, and I believe it to be, which is you’re doing this because you too want to build a great life, your family, as new immigrants. My father was an immigrant. I understand that immigrant mentality better than most people that have been born in Canada. Survival, and putting food on the table and roof over the heads of your family is really, really important.

Don’t limit that. Don’t be overly cautious with that. Because, actually, you might build something much larger that doesn’t just help your family and your children but actually, creates multi-generational opportunity. That is amazing.

I’m reading this great book now called Distilled, written by Charles Bronfman, Charles’s father, Sam Bronfman, is arguably the most important Canadian entrepreneur in the history of the country. I mean, he built Seagram. Really, more importantly, he put Canada on the map as a global powerhouse.

One of the things that Charles, Sam’s son, talks about in the book Distilled is that his father never gave him limiters, there was no governor on any project. If you’re going to start a thing, your ceiling should be unlimited. If you end up selling your company for $100 million, this is an incredible thing. I mean, $100 million is more money than pretty much anyone in the world has ever seen or made in their lives. If that could be a billion-dollar company, or that could be a company that instead of you getting acquired, that you be the acquiree, if you can be the acquirer, that would be even better. That’s one thing I would say just around that ceiling of success.

Jamal Abdullah:

That was valuable. Definitely. Thank you so much. Thank you very much. Here’s what I was expecting as an answer. This is where we go. Thank you.

Harley Finkelstein:

I like to talk too, you’re just winding me up.

Jamal Abdullah:

Love that. Love that. Okay. Now our second question is to both of you as a couple.

In today’s world, where we can be connected to work all the time, it’s easy to blur boundaries, and never really stop working on projects that we’re passionate about. As a couple that are achieving so much professionally, how do you ensure that you make time for family and friends in your life?

Lindsay Taub:

For me, it’s a priority. I love my work and I’ve definitely spend more hours than I thought I would on my work and I’m happy to do that because I really enjoy my work and I get a lot out of it.

I’ve had other jobs in the past where it’s like, oh my God, I’m looking at the time and I can’t waitfor the day to be overand that’s not at all how it is now. I love being a therapist and I love helping people and I love my work.

I definitely also make it a priority to spend time with my family. There’s certain days and times that are blocked off and I will not take clients at that time and I will not do work at that time. I will not do emails at that time. I will not attend a conference at that time, I just won’t because that time is also very, very important and when I look at my life as a whole, I see my work as part of who I am. It’s part of my identity, but it’s only one part of my identity. I’m also a wife, I’m also a mother, I’m also a friend.

I have hobbies that I pursue. I like to exercise; I like to walk my dog. There are other things that I do that, maybe they don’t sound that important, but that walk with my dog is really important. I really need to clear my head and I want to enjoy a beautiful day.

We live in Canada, it’s winter a lot, so when the weather’s nice, I want to enjoy it. I take the time to be mindful of all these things too. When I am spending time with my family or with my dog or doing something I love, which is cooking, I am aware of that time and I’m mindful of it and I’ll note to myself “oh, I’m so grateful that I’m doing this right now.” That’s how I do it. I make that time a priority and I am really mindful of it when I’m in it.

Harley Finkelstein:

One thing that is in that answer, which is worthwhile double clicking on, is the requirement of really, really good prioritization, ruthless prioritization, and scheduling. This is not a joke, I literally have walk the dog, workout, yoga, meditation, family time in my calendar, including on the weekends, and I’m sure it’s annoying sometimes to Lindsay and definitely to our friends when they are getting calendar invites for the next, I don’t know, six weeks or eight weeks, but that’s the only way I’m able to do all these things.

It's the only way that I’m able to be the best version of president of Shopify and be a good husband and a good father and a good friend. We’re building a synagogue in Ottawa now, in Sandy Hill, the Finkelstein Chabad Jewish Centre. To do all these things you want to do, which are all really cool and really exciting and none of them feels like a 9-to-5 job. None of them feels like a job, per se, but they’re all important. The only way to do that properly for us is this ruthless prioritization.

I find using a calendar is really important, even if it seems silly to put in like, walk dog with Lindsay in the calendar, but that’s the only way for us to actually live a life that is this intentional. It’s not for everyone; some people don’t want to have plans on Saturdays. We’re just not that family. We’re not that couple. We do a lot of things all the time and we’re grateful for that. That’s the life we chose.

Lindsay Taub:

I actually do look at the calendar as a whole, and if I see two nights in a row, there’s something then on the third night, it’s like: we are not doing anything that night. I don’t care what it is, there’s no way I’m going to be able to do that for myself and just for my mental load and my sensory load. I know what I need and I need to not be overbooked so yes, even though everything is scheduled, there’s also time built in for not having anything scheduled.

Jamal Abdullah:

I love that I’m taking away too main things from what you both said, which is that, you mentioned this a few times Lindsay, prioritization, and Harley, you really hit at home with that, as well as being present. It seemed like you were talking a lot about being present and being aware of when you are spending the time with your family, you’re actually there and spending time with your family or walking your dog. Then when you’re at work, you’re actually at work. Incredibly grateful for all the advice and feedback and your thoughts. Thank you very much.

Harley Finkelstein:

Thank you, guys. Congrats on all your success and keep building. It’s an amazing story, Jamal and Amaan.

Jamal Abdullah:

Thank you very much. Enjoy the rest of your day. Take care.

Gwen Madiba:

Harley and Lindsay, thank you so much for taking Jamal and Amaan’s question.

Before we end today’s conversation, I have one last question, a fun one we are going to end all our conversations with this season. What is something that currently is sparking your curiosity? It can be something completely random, something you don’t know much about, but you have a thirst to learn more.

Harley Finkelstein:

I’ll go first and then you can jump in. We’re on a podcast, so it feels a good time to talk about this although I’m not going to give any details, but I am fascinated by the connection between immigrants and cities that have a lot of immigrants and entrepreneurship. I was born and raised in Montreal, and ended up moving to South Florida when I was young, but Montreal to me is one of the most entrepreneurial cities on the planet. I believe one of the reasons it’s so entrepreneurial is because there are so many immigrants there, including my parents, my family. My father immigrated to Canada from Hungary during the Hungarian revolution and came to Montreal.

Lindsay Taub:

It’s a very multicultural city. The French and the English coexist, and so I think it attracts a lot of immigrants.

Harley Finkelstein:

There’s a lot of immigrants there, but there’s also a lot of entrepreneurial activity there. I’m fascinated by the connection between immigrants and that mentality and that philosophy and survival tactics and entrepreneurship. I’m going deep on that right now and one of the reasons I’m reading that book, I mentioned earlier, Distilled, the Bronfman story is I want to understand that better.

In the next couple of weeks, I’m trying to create a little bit of a mini podcast, which is only basically just for me and a few friends and for Lindsay, where I just interview immigrants and talk about entrepreneurship and how they did it and what they did.

That is currently right now, when I turn off to go to bed, what I’m thinking about in the evenings. I think it’s a fascinating topic and I haven’t been able to find very much on that connection between immigration and immigrants and entrepreneurs.

Lindsay Taub:

I think one of the things I’m curious about is, I almost feel like life right now is in a state of Renaissance. We’re just coming off of a pandemic. This might be a cheesy answer, but the pandemic obviously was difficult for so many reasons. Me, personally, I feel like we’re maybe starting to see some light at the end of the tunnel. I feel like a lot of us are moving on from the fear and all these things that have been holding us back, and I’m really curious to see what unfolds. We’ve seen some things happen that are not so good.

I know that there’s going to be lots and lots of good that eventually comes from it. If you look back in history, every dark period is followed by a lot of light and we don’t know yet what that light will bring, but I’m really curious about it.

I really want to see how we’ve changed as a society. I think there’s a lot of things that will never be the way they were before, and that’s okay, and how’s it going to work with the kids going back to school, and what’s the workplace going to look like moving forward? I’m really curious to see how people are going to embrace this Renaissance. What are people going to do with it? I’m excited for it.

Gwen Madiba:

Well, with everything that you both share today, I’m sure that many of our listeners will want to follow you and continue to learn from the both of you. Can you please let our listeners know where they can find you online?

Harley Finkelstein: @Harley on Instagram is probably the best place to find me.

Lindsay Taub: Yes, same. I’m @Lindsay_Taub, Lindsay with an A and my last name is T-A-U-B.

Gwen Madiba :

Thank you both so much for taking the time to speak with us today. This was an amazing way to kick off our Season Five on curiosity. Thank you so much.

Lindsay Taub: Thank you for having us. It’s been a real pleasure.

Harley Finkelstein: It’s been really fun.   

Gwen Madiba:

uOttaKnow is brought to you by the University of Ottawa’s Alumni Relations team. It is produced by Rhea Laube with theme music by alumnus Idris Lawal. This episode was recorded with the support of Pop Up Podcasting in Ottawa, Ontario. We pay respect to the Algonquin people, who are the traditional guardians of this land. We acknowledge their longstanding relationship with this territory, which remains unceded. For a transcript of this episode in English and French or to find out more about uOttaKnow please refer to the description of this episode.