Sipping the Tea with Harley Finkelstein

Today we're chatting with Harley Finkelstein, entrepreneur, lawyer, and the President of Shopify. We'll be talking about the future of commerce, democratizing entrepreneurship, and career moves.


Harley Finkelstein 

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. Recently, he received the Canadian Angel Investor of the Year Award, Canada’s Top 40 Under 40 Award, and was inducted into the Order of Ottawa.

From 2014 to 2017 Harley was on the Board of the C100, and from 2017 to 2020 he was on to the Board of Directors of the Canadian Broadcasting Corporation (CBC). Harley is starring on Discovery Channel’s I Quit, a television series about hopeful entrepreneurs who decide to quit their 9-5 jobs to focus full-time on their side hustles.


Mesa is an easy way to integrate any Shopify store with any eCommerce app or service. Mesa is the only automation platform designed exclusively for Shopify and Shopify Plus merchants. By creating workflows that carry out repetitive tasks automatically, merchants can focus on their business and create new customer experiences at scale. 

Mesa has a no-code workflow builder for any action your customer takes, such as a new order or product return. Leverage Mesa's built-in features to extend your connected apps. Set up email notifications, receive forms, schedule tasks, delay workflows, or even work with files to sync data with your back-office systems. Developers love Mesa too, since they can lift the hood on any automation to customize them for total control.

Even if you're unsure where to start, Mesa's library of workflow templates helps you get set up quickly with popular tasks common to growing businesses. Or contact their team of automation experts here to support you every step of the way, 24/7.



Win back valuable lost time for your support team. Gorgias has machine learning functionality that takes pressure off small support teams and gives them the tools to manage a large number of inquiries at scale. Gorgias combines all your different communication channels (email, SMS, social media, livechat, phone, etc.) into one platform and gives you an organized view of all customer inquiries. 

Their powerful functionality can save your support team hours per day and makes managing customer orders a breeze. They have allowed online merchants to close tickets faster than ever, with the help of pre-written responses integrated with customer data to increase the overall efficiency of customer support.

Their built-in automation also frees up time for support agents to give better answers to complex, product-related questions, providing next level which helps increase sales, brand loyalty, and recognition.


show notes.

  • [01:46] Harley's origin story
  • [16:34] Democratizing commerce
  • [19:12] 2020 Retail success stories
  • [28:49] Why philanthropy?
  • [36:40] Is it too late to become a Shopify Partner? 



Rhian (00:00):
Today we're chatting with Harley Finkelstein, entrepreneur, lawyer, and the President of Shopify. We'll be talking about the future of commerce, democratizing entrepreneurship, and career moves. Let's dig in.

Rhian (00:16):
Welcome to Commerce Tea, a podcast to help you succeed on Shopify. I'm Rhian.

Kelly (00:21):
And I'm Kelly. Grab a mug and join us as we talk about all things commerce.

Rhian (00:31):
Hey Kelly, let's say I can't write code but I want to create workflows that carry out repetitive tasks automatically, so that way I can focus on my business and create great customer experiences. What would I use?

Kelly (00:45):
I recommend Mesa, a no-code workflow builder for any action your customer takes, you can use Mesa's built-in features to extend your connected apps, set up email notifications, receive forms, schedule tasks, delay workflows and much more. Developers like me also love Mesa because we can lift the hood on any automation to customize for total control.

Rhian (01:04):
Okay. I'm in. How do I start?

Kelly (01:07):
Go to that's and their team of automation experts will support you on your journey 24/7.

Kelly (01:21):
Harley. Thank you for joining us today.

Harley (01:24):
Thank you for having me. This is such a pleasure. I've known both of you for at least five years. I'm sort of using the first Unite as certainly when we met each other, but it was probably before that. And it's an honor to be on your show.

Rhian (01:38):
Well, thank you for being here. We're super amped up and we've got a question off the hop for you.

Harley (01:44):

Rhian (01:46):
Okay. So we love a good origin story, and we think that yours is a great one to highlight. Before Shopify, you were an attorney, a career switch is common with entrepreneurs. So what was the catalyst to make your career shift?

Harley (02:01):
I never wanted to be a lawyer or an attorney. I never wanted to be in that profession. I went to law school rather to become a better entrepreneur. And that was it. I had this little t-shirt business when I was in college at McGill. We made t-shirts for other universities and for McGill as well, and a mentor of mine convinced me that my t-shirt business had... He was a lot less polite about it, but effectively what he said was that the business had no competitive advantage. There was no moat around the business. And that, even though I was like 20 years old at the time, even though like I was making a little bit of money and my dad wasn't around then my mom had no money. I was supporting my sisters, my mom and stuff.

Harley (02:43):
So I had enough money to help my family, but 20 years old, if you have anything more than like $500 in your pocket, you have money. Right? It's the most amazing thing ever because you've no idea what anything costs at that point. But this mentor convinced me that this business did not have any long-term potential and that I should consider adding some assets or some skillsets to my portfolio of skills and privilege of understanding. And he happened to be a law professor.

Harley (03:14):
And of course if you ask a barber, if you should get a haircut, they're going to say yes, whether you need it or not. You ask a law professor, if you should go to law school, they're going to say yes, but actually he was a hundred percent right.

Harley (03:26):
His name is Phil and Phil convinced me to go to law school, he happened to be teaching law at the University of Ottawa. So I moved here in 2005 to go to law school. And from the second day I arrived at law school to the second I graduated, it was always about the acquisition of skills and the acquisition of any assets that would make me a better entrepreneur after law school. And it just turned out that while I was in law school that teacher business that I had there was a wholesale business selling to the universities worked really, really well in the college dynamic, meaning you don't have to go to class. You show up for the exam. If you pass you're good. Law school was not like that. Law school took attendance. Law school required you to actually go to class. Otherwise you'd fail.

Harley (04:12):
And so I needed a way to make money concurrently while being in school. And I had the really great fortune in 2005 of meeting Toby. Meeting one of the smartest human beings I've ever met. And Toby was just transitioning from selling Snowboards to selling the software behind the Snowboard business. And I became a merchant 136 or so. I always get that wrong, but it's about 136 on Shopify. And then after law school I practiced law for all of 10 months which is the least amount of time you need to practice law to get called to the bar to officially become a lawyer. It's 10 months in Canada and I practiced law for 10 months. And then halfway through, I just knew it was going to continue it. And I called Toby and said, I'd love to join you. And it was Cody and Daniel were around at that point. And I said, I'd love to join you. You three and help build the business side of Shopify. And that was it was about 12 years ago.

Kelly (05:09):
And the rest is history. I love that couple of things. One of my best friends is lawyer. And she always jokes that when she speaks to law school professors now, and if she were to ask a law school professor, she should go to law school. They be like, don't do it.

Harley (05:27):
Interesting. It's funny because I get this question a lot because I've talked a lot about how law school was very much like finishing school for me. And it was incredibly instructive and valuable but I also went to business school. I have an MBA and people asked me about that, I was like, "I don't think you need it."

Harley (05:45):
Now, I'm not saying the MBA is valueless or useless. For me though, the MBA felt incredibly pedagogical, very case study based. It did not reflect the realities of being an entrepreneur. Which is strange because it's a business degree. Whereas law school is not a business degree. It's actually a law degree, but actually I took a lot more skills from that particular curriculum whether it was... There's this term is legal Maxim. It's a Latin term called ratio decidendi. It's basically the summary of the case. It's like the lesson that you would take, if it's a 3000 page case, what is the one thing that summarize the takeaway? And that's called the ratio decidendi.

Harley (06:29):
That ability to read hundreds or thousands of pages and come up with the one line or figure out the one lesson out of all of that, that really matters. Well, that talks a lot about prioritization that allows you to very quickly ascertain what is the thing. And we're all three of us are entrepreneurs. So we know that that is really important. We get documents all the time. We get emails, sometimes 18 page emails, and very quickly, we're like, all right, what are they asking for right now? And another one was critical reasoning or critical debates that law students, frankly, most law schools tend to be somewhat, what's a good way to put this that's polite. There's a high quality of discourse in a lot of law schools. There's a lot of debates.

Harley (07:16):
And so the ability to walk into a classroom particularly where you feel like an outsider like I did and the professor says something and a bunch of you as students have to debate it. That idea of being able to debate and argue and negotiate on your toes. That was also a very valuable asset. But learning a bunch of practices or best practices about the marketing profession in my MBA. I think those were dated before they were even in the textbook.

Kelly (07:48):
I think it's an important piece of talking about just deep generalism as a whole, having these different backgrounds and applying them to whatever you're doing in entrepreneurship, as you mentioned, sure an MBA can be useful to a degree but being able to apply skills from some other facet of your life is so hugely beneficial and could be give you that leg up. I have my master's in social work. So I'm a trained therapist. I use this all the time. I never in a million years want to be a therapist but it plays out in my day to day. I am really good at establishing rapport. I'm a really good at conflict resolution, not so good at it. I still have conflict avoidance issues but my therapist is working with me on that. But I mean that degree is so useful.

Harley (08:34):
If you can pull all those things together whether you call it a polymath or whatever you decide to call that term, there's a lot of terms for it. If you can synthesize information and you can pull things that you read a month ago and an experience you had two years ago and an article you read this morning and you can synthesize all those different things. And that helps you make a better decision. I mean, that to me is how to have real impact. That to me is how to make better decisions in a much more timely manner.

Harley (09:05):
And I don't think school teaches you that in general but certainly the MBA was not this is not supposed to be an MBA thrashing session. But we started the conversation around career development. You guys use a different term but it's basically the career trajectory and where you go. And I think that what most people get wrong is that they look at their career as this linear slope. It's up into the right. It's the ladder. You go from step one to step two, to step three.

Harley (09:34):
And the most impressive people I know, the most interesting people I know, the most successful people I know, they don't look at it that way. It is not linear. It's ups and downs and sideways and eventually it all sort of trends up into the right, but it's a jungle gym and not a ladder. And I think when you use a less finite game of evaluating and judging your own career, a lot of good things happen and entrepreneurship in many ways, if you are an entrepreneur, if you're a founder you're sort of forced into thinking about things in a non-linear way, in a non finite way, in an infinite way, you sort of have to do it that way, especially if you love what you're doing, because if you love what you're doing, the goal is not to make X dollars or to have X contracts or to have X number of merchants. It's to keep playing as long as you possibly can. And that is what life's work is.

Rhian (10:32):
I love that so much. I do have one question for you because when you said you called up Tony and Tony, who am I? Where have I been? You called up Tobi. And you said I'd like-

Harley (10:48):
I'm going to start calling Tony by the way. It's an amazing so they kind of have him as Tony. I don't know why. Just it's so funny. It's great.

Rhian (10:55):
Tell him, Rhian says, hello, she's now calling you Tony.

Harley (10:59):
He's going to start calling you Ryan by the way.

Rhian (11:01):
Yup. That's fine. That's fine. That's an accepted name of mine. So you called up Tobi and you said, I want to do the thing. I want to take this jump. And there's so many folks who are afraid to make that call. They're afraid to pick up the phone and say, you're doing something rad I want to be on your team. What does it take to be on your team? And what would you say to someone who's kind of in those shoes and working through that process right now?

Harley (11:32):
That's not where you find a life's work. That's not where you find the magic. It's trying to even say it's so obvious, but you got to get out of that comfort zone. And so what I would say is that... Well, first of all, I had an unfair advantage because I was a merchant first before I joined Shopify. And so let's take a step back for a sec. We all sort of these two tracks that we're supposed to be on one track is our personal track. The other track is our professional track and people that describe what they're doing as life's work or they found their critical calling or they have been able to find this harmony with both those things. What tends to happen is the Venn diagram overlap of their professional life and their personal life overlaps not entirely because I'm not... I love my wife and I love my daughters. I'm not sure really how they play a role in my professional life, although I'm sure they have a big influence on it.

Harley (12:30):
But the goal, I think for anyone who wants to have a really fulfilling career, who wants to search for their life's work is to have as much of a Venn diagram overlap between personal life and professional life. And from a very early stage in my life entrepreneurship was more than just a way to make money. It was always a way to solve problems. It was just this magic tool that I kept in my tool bench just pulled it out until I needed it. So it started when I was a kid, you folks have probably heard this on stage at Unite, but I wanted to be a DJ. No one would hire me, oh, start my own DJ company hire myself. That sounds like a great solution. And it was. I ended up deejaying 500 parties now where those first 30 parties, very good. No, they were terrible. I would've gotten fired if it was anyone else's company, but it wasn't, it was my company. So I didn't fire myself.

Harley (13:23):
And then much later in a much more serious part of my life where dad's gone, family's broke. I pulled out the tool again. I was able to go to college, go to McGill and also sell t-shirts and make some money and help my sisters and my mom and paid my own rent. And so entrepreneurship for me wasn't only just the professional side of it. It was very personal to me. It was a way I was enabled to continue to live, to continue to survive, to not starve and not be homeless or not that I was ever worried of being homeless, but it was this great thing for me.

Harley (14:02):
And so when I was sitting in tax law class in 2006, and I set up this t-shirt shop on Shopify. It was like magic because all of a sudden, I remember, this is early liquid days, we only had, I don't know, probably 12 maybe 10 different themes, maybe less than that. It was a couple of different variants of each theme but there wasn't very much going on there. And I was able to set up a Shopify store and start selling all within the span of a couple of hours. And then the next day I started getting sales. That was magic to me. That was this like once again, entrepreneurship allowed me to solve the problem in that case in law school was I needed to make money while currently being in class.

Harley (14:49):
And so, as I was sitting there as a lawyer, hating it, I mean, law is sort of the opposite of entrepreneurship, entrepreneurship, as much as possible. It's not perfect meritocracy because some of us are born on third base and let's all check our privilege, but it's a better version of a meritocracy than the law, which is all, but legacy. How long have you been here? Who are your parents? What is your last name? What is your social network look like? Because you're going to have to get those people's clients. It wasn't a meritocracy.

Harley (15:20):
So some sitting there as an early young lawyer, hating it, all I can think about was what I really want to do. And what I really want to do was I wanted to give more people the opportunity to access this tool that I call entrepreneurship and the best vehicle to distribute more of those tools called entrepreneurship.

Harley (15:43):
The best tool I had ever encountered was this piece of software called Shopify. It was bold to call Toby and say, "Hey, I want to come work for you," but what the heck else was I going to do? That was the greatest idea that I ever had. And the reason that I think I can stay at Shopify for the rest of my life if Toby and the board will have me, is I still have not found a better way to provide more access to this thing called entrepreneurship which is access to people having a better life, people doing something they love. People sharing their gift with the world. And I think that's I feel very fortunate to have that. And I know both of you feel the same way as you both have started and now run these incredible businesses on your own. What the heck else would you be doing?

Kelly (16:29):
Being a therapist, unhappy?

Rhian (16:32):
There's nothing else I'd rather be doing.

Kelly (16:33):

Rhian (16:34):
Right now. Well, I love that. And I love that you took that courageous step of doing the thing to do the thing and to make yourself happy and to chase your dreams. And I've always really appreciated your position on entrepreneurship and the democratization of it. And as you say, arming the rebels, what do you mean by arming the rebels and how do we all help?

Harley (17:05):
Well, first you are helping and you are arming the rebels on your own independent of Shopify. But let's be clear, let's sort of define things because one of the things that is important to acknowledge is that even the term rebel is somewhat controversial. If you've grown up in a war torn country, the idea of a rebellion or rebels doesn't have the same connotation as maybe it does for us who grew up in North America where the idea of rebelling or being rebellious or a rebel is actually kind of has been kind of positive. Right? We all kind of admired the rebels growing up. The protagonist in so many of the movies and shows we watched growing up were kind of rebellious. And there's a different connotation to it.

Harley (17:50):
But what we really mean is this, for basically since the creation of commerce which is effectively tied to the creation of currency which is very very old, in order to access this thing called enterprise, free enterprise, capitalism, small business entrepreneurship, you needed capital. That was the main ingredient to starting a business, to being an entrepreneur, to creating a revenue generating entity. And capital while it's a very easy thing to explain if you give me money. You can now have the keys to your store. If you give me money, we will now give you a bank loan to go do whatever you want. If you give me money, you can now have inventory of whatever you want selling.

Harley (18:40):
So for a while time, the idea of entrepreneurship or business was limited to those that had capital. And what has changed is that now capital is not the main ingredients because the tools that are required to build a business have been democratized through technology through software. So now the question of what would happen if anyone wanted to or needed to because those are not always the same thing we're able to build a business.

Harley (19:12):
And that I think what technology has provided and our version of that is through the software called Shopify, which means that anybody that has ambition can start a business for $29, which again, it's not nothing, but it's affordable for most people particularly in the countries and the geographies that we serve, all that we need to do a better job serving other countries where $29 may not be affordable some point, but for $29 you can start a business right now at your mom's kitchen table, on the grass in front of your home at a library or a coffee shop. If this wasn't in the middle of the pandemic and that store can grow to be a multi-billion dollar company if you want it to be. And if you just want it to be a really great way to pay your bills and avoid working in a corporate job that you hate or you want to be able to give your family a place to go into as a family business as Mike D likes to talk about, from Mike D's Barbecue Sauce then that successful through entrepreneurship.

Harley (20:18):
And that is the mission of Shopify. We want to provide anyone who wants to, who needs to, with the tools that they need to actually self-actualize to actually create a real business. And we also believe at the same time that that is happening. You also have massive consolidation where the big players in retail are getting bigger and bigger and bigger. And so at the same time that we're trying to democratize entrepreneurship we also want to the consumer, basically, everyone listening, whether you're involved in e-commerce or not, that you can also buy from independent retailers.

Harley (20:56):
And so the idea of arming the rebels isn't just a slogan to create this great energy and community around entrepreneurship does that but it also reminds everyone that if we want the future of retail and commerce to be interesting and exciting then we as consumers need to support independent brands because that way the future retail is in the hands of many not the few.

Harley (21:22):
And so that's a very long answer to a very short question but since it's a podcast, we can spend a bit more time on things that I don't get a chance to often dive into, but that really is what it means to arm the rebels. And I think if you replace rebels with independent businesses or people with ambition or people that make stuff, I think giving those types of people the tools in which they can go and bring their thing whatever it might be to market to a global market that's pretty damn cool.

Kelly (21:57):
I think it's also you had mentioned helping others and providing these tools very relevant in the past year with the pandemic. You've these brick and mortar businesses who are family run for it's passed down generation, generation, generation had never sold online, suddenly having to pivot their entire model just to stay in business. And we've talked in depth on the podcast about the pandemic and how businesses have adjusted but I would love to hear maybe one or two of your favorite success stories that came out of last year.

Harley (22:29):
One of them I just think it's a really, really cool story particularly for those listening from the U.K. It's a story about a very well-known brand in the U.K. called Pizza Pilgrims. These are pizza restaurants in the U.K. and they're great pizza restaurants. If you've ever been to one it's quite delicious, but there are brick and mortars pizza restaurant that was forced to close during lockdown and almost on a dime they began selling pizza kits in the mail and they started creating this direct to consumer offer with what they call pizzas in the post. And they've had their largest day of sales, post-pandemic, not pre-pandemic. They sell it immediately. So despite the fact that all of their restaurants have to close their business's booming.

Harley (23:15):
Give you another one. There's a great company called Thich out of Toronto. It's actually, I mean, this is a hair salon. So very traditional hair salon business, of course, pandemic hits everything has to close particularly in Canada where the lockdown measures here are extreme. There's a curfew, for example, in the province of Quebec. I think after 8:30 PM, you're not allowed to be outside your house, which is about 30 minutes post sundown. So, I mean, that's a big weight on the community. So these hairstylists from T-H-I-C out of Toronto, shut these things down and they decide to start their own hair oil company. And now they're releasing hair accessories and they're expanding their product base. And they went from an entirely 100% long-term service based business as hairstylists to having this incredible hair product brand.

Harley (24:09):
Or Sassy Jones. Okay. Sassy Jones, great brand have lots of retail locations permanently closed, April, 2020. And now I think their performance, I think e-commerce is now up by like 3000% since March 2020 monthly visits have increased 200% and revenue went from $350,000 a month to $1.5 million a month. And they did more than $10 million in sales in 2020.

Kelly (24:40):
That's wonderful.

Harley (24:42):
Amazing. Right? Now, why are these examples interesting because I'm not talking about Heinz Ketchup. I love Ben my relation with Ben Francis. He's a buddy. I think Jim shark is amazing. I think join Tim from Allbirds are great. Richard from Fascia. These are great people. I'm not talking about these big, massive blowout stories. I'm talking about Pizza Pilgrims, Sassy Jones, and Thic. These stories of resilience. They have given me so much energy and so much inspiration in a time where energy and inspiration are in short supply.

Harley (25:20):
And I said this in like in June 2020, when I began to do a little bit of more broadcast media, post pandemic hitting. And I've said this on television that like, it's a tale of two retail worlds, the resilient ones and the resistant ones, and the resilient ones are kicking butt. And the resistant ones are waiting for the status quo to come back and it's not happening, but they're still waiting for it. And the most interest thing about our community, the Shopify partner ecosystem, the people that work in our kind of vicinity. And obviously both of you play a very large role in the Shopify partner ecosystem and the economy.

Harley (26:00):
We are lucky because for the most part, the merchants and businesses and brands that we encounter are mostly the resilient ones. We have this disproportionate amount of resiliency happening in and around the Shopify ecosystem. And that, I don't know if I'm allowed to swear on this, but that is cool. That means that we are for better, for worse, because we also don't want to be blind to the fact that some businesses are not, we're not able to pivot, they were not able to be resilient, but those that had that opportunity and then took that plunge to be resilient. I don't know how you can't be inspired by them.

Kelly (26:37):
I think it's also important to note those that are resistant. It's not too late to pivot. It's not too late to find that opportunity just because vaccines are starting to be distributed, in some places lockdowns are lifting. There's still an opportunity to jump into this new space, this new territory. And it is terrifying. It's hell.

Harley (27:00):
It's totally terrifying. And it's totally new and it's totally out of your comfort zone. And we're all kind of feeling that same way. And in many ways that edge of terrifying that is where things get really interesting. I did an Instagram live a couple of days ago with one of my best friends Steve Beckta and Steve is great Canadian restaurateur, he pivoted his business during the pandemic to go from having three very high end restaurants to doing these great meal kits. And he publicly said on this Instagram live that he sold 15,000 meal kits. I mean, these meal kits, it's a high end restaurant. So 15,000 meal kits is a lot of money, a lot of revenue and someone that was listening sent Steve and I note right afterwards and said, I was one of those people who, when I saw the tidal wave coming around from the shore and grabbed my talent, waited for the wave to go back into the ocean.

Harley (27:53):
I was resistant and I kept thinking, it's too late. It's June. I should have done it a month ago. Now it's August or done a month ago. Now it's November. She have done a month ago. And just because this particular person heard this short little Instagram live that we did, He was like I'm just going to start doing meal kits. And this weekend my family, my wife and I are going to be ordering from this restaurant. And they're just starting to meal kits now. And that's absolutely okay. And it's not too late. And I think it's a great point you make Kelly, which is let's remind everyone that not only are we still in a pandemic but even on the other side of the pandemic, the resiliency and the new muscles and the new experiences that you build right now will be incredibly valuable long-term because hopefully we never have another global pandemic, but if you can get really really good at thriving on change, you're going to be really really good, no matter what change comes your way.

Kelly (28:49):
Right now it's the pandemic what's next. We don't know, but something else will occur in this world. And again, we'll be presented with an opportunity to change and to adapt with it. I love that juxtaposition between a resilient and resistant, and that kind of just is marinading now in my brain. But I have a question and it's a divergence from this, and it's about you and it's about your wife and you were both philanthropists, which I think is awesome. Can you speak to us about your drive to give back to the community and why?

Harley (29:29):
First of all, let me just for those that don't know, Lindsay and I do not come from very much. We come from very humble beginnings and I'm not saying that as a flex like, look where we come from look at where we're. I mean, I didn't grow up with people that I knew that were "philanthropist." I'm not even sure what that even means, but I didn't grow up with people that were really contributing deeply to community. At least not financially because of the people that I grew up with didn't really have that sort of money. That was sort of what the people that lived in nice houses did. And so I think because Lindsay and I have clawed our way to where we are as parents, as humans, as entrepreneurs it just feels like if you have any whatsoever, any excess time or money or connections or the ability to help other people, and you have some capacity, you've had some luck in your life, pay for it.

Harley (30:30):
I remember when I think it was our series C, someone called me. Actually I'll say who it is. It's Daniel Dubbo, who currently now works at Shopify. He was the founder of Helpful and a bunch of other companies, a great entrepreneur. And he's all over Twitter as well, and intrusive to listen to this. But Daniel called me after the series C and says, "Congratulations on the series C, what are you going to do with..." There was a small secondary component to it. So I was able to take a little bit of money. It was the first time I actually had any like real money in my life. And he's like, "What are you going to do with it?" I was like, "Oh, I haven't thought about that." And he's like, "Well, there's a lot of companies out there. A lot of young entrepreneurs, a lot of founders, a lot of startups that a $10,000 check from you would be a big deal for them. One, it would give them some money, but two, it would give them some incredible motivation. It would make them feel like they're validated."

Harley (31:21):
And so early on, we started doing a little bit of that, do like angel investing in a couple of different companies. And then after that, we're like what does our community need? And the big project that Lindsay and I really doubled down on early on was Lindsay and I are both Jewish. We're not from Ottawa. We live in Ottawa. Now, Ottawa is the capital of Canada. It's a G-7 capital and there is no synagogue. There's no Jewish center in downtown Ottawa. And so we thought, well, what if we were to create a synagogue?

Harley (31:49):
The feeling that we got from that project of building something from nothing, it was reminiscent of starting a startup, being a founder of a business. It gave us so much energy except other people can share in that thing, in that project. And so we just kept doing it and we're like what else could we do? And Lindsay, when we had Zoe, our two-year-old, Lindsay had a very, very difficult birth emergency C-section very, very scary. And as the spouse, I want it to be with her and the area of the hospital for high-risk new moms and new babies had no seating area. It was just obvious that it was a bit of a mess.

Harley (32:37):
And so came home a day later and Lindsay and I gave it to their hug and we got through this, and now we have these two beautiful daughters. And we said, well we had to do something about this now. There's a problem. We need to create a space in that hospital so that during the most stressful times of people's lives and they're having their children, and these are high risk persons in some cases emergency C-sections, there needs to be a place to make them feel a little bit more relaxed, whether it's an extra couple of chairs or it's a small little family lounge, or it's a place where mom can go for a little walk or have the seat on a couch, and if she doesn't need to be in bed. And so we just did that.

Harley (33:15):
And so there is no strategy to it. The strategy is if you have the means to do so, whether it's money or time find areas in your life on a global level or on a local level and do something about that. And the cool part about that is that creates a flywheel because now other people see it, they're like, oh, that's cool what Harley and Lindsay did, we're going to do that too. And then other people do it as well. And what you end up creating is this the cycle of reciprocity where now when you have some success, other people.... And when everyone has to have some success, you immediately feel like you should contribute. And then other people think they should contribute.

Harley (33:57):
And I think that's how you build real community. That's what you build real culture in your cities. That's how you build great places for us to live. And you can do it on a global level. You can do it on a local level, but I don't know. I don't know if that's a satisfactory answer, but that's the way we think about, and we don't call ourselves philanthropist per se. It's just Lindsay and I are really fortunate. Shopify and our lives have given us these incredible things in which we can contribute to. How can we not do it.

Rhian (34:24):
I have to say Hartley that I know that one of your big donations was to Chabad and I read some articles about it and your reasoning, why? And Chabad fed me during my time at Arizona State University more times than I can count. That's something, I just think that everything you're doing is fantastic, but your donation to the Jewish community as a Jewish person is really meaningful. And I really am appreciated.

Harley (34:57):
That Rabbi whose synagogue we sort of help build for him. He used to come to see me in law school and I'm not religious. My grandparents were Holocaust survivors. So I have a connection to it. My father is now religious. He became religious in the last couple of years, but I'm not a religious person per se. I'm very much a secular Jew, but this rabbi, which just coming every Friday, just asked me how I was doing. I just thought, what a nice guy. Law school is tough. I was running a business on the side. This guy's just coming here just to see how I'm doing and he'd asked me if I want to Wrap the Tefillin, which is sort of a religious thing to do before the Sabbath, but he didn't care if I was religious or not. He knew that I was there and he just asked how I was doing.

Harley (35:40):
And so I randomly said to him at one point in law school, hey I have very little, but if I ever have enough, I'd love to help you. And that turned into six years later building the Finkelstein Chabad Jewish center here in Ottawa. And I love hearing that story that you've also been touched by them. And then in a very positive way.

Rhian (35:58):
Yes. My heart is so full talking about this.

Harley (36:04):
This got real. Right? We're supposed to be talking about like great pivots in e-commerce and ecosystem. But I think what I think this conversation actually is fairly demonstrative of the way that the three of us operate our lives which is that there is no major disconnect between professional and personal. That it's all one in the same. And we know each other through this ecosystem, the Shopify community, but it doesn't feel like it's our professional community feels just as much like it's a personal community too. That is really unique. And I don't think that's unique to Shopify, I just think that's just unique in general.

Kelly (36:40):
It is. It is. Although, I do want to actually talk about being a Shopify partner.

Harley (36:44):
Let's talK about it.

Kelly (36:50):
Hey Rhian, what can I do to help my support team be more efficient?

Rhian (36:53):
I recommend Gorgias, Gorgias, combines all your communications channels, including email, SMS, social media, live chat, and phone into one platform that gives you an organized view of all help requests. This saves your support team hours per day. It makes managing customer orders a breeze.

Kelly (37:12):
Sounds great. What else can it do?

Rhian (37:14):
With Gorgias, you can pre-write and save responses to your most frequently asked questions. You even have access to the customer's order information. So you can personalize responses with things like an order or tracking number. This then frees up your time. So your support team can focus on complex questions.

Kelly (37:32):
That sounds like a great way to also increase sales and brand loyalty. Where can I learn more?

Rhian (37:36):
To request a demo visit That's

Kelly (37:52):
Both Rhian and I have built our careers on top of Shopify, and we were both fortunate to discover Shopify earlier on, Rhian before I did, I joined Shopify community in 2014. I get a lot of questions that basically is it too late to become a Shopify partner.

Harley (38:10):
I get the same questions all the time.

Kelly (38:13):
I mean, I have my answer, but what are your thoughts?

Harley (38:18):
It's kind of amazing. Right? Because I... Sorry, I don't really understand why people ask that because the proof is in the pudding. I mean, Shopify is now 9% of all e-commerce in the U.S. We now have 1.7 million merchants, every 28 seconds, a brand new entrepreneur gets their first sale on Shopify. So actually in many ways, the opportunity is so much bigger now than it was for you, Kelly, way bigger, like in 2010, that's pre-IPO Shopify Plus was created February 14th, I think it was. 2014 it was Tech Crunch article that Darrell had written when he was a Tech Crunch. I remember it because I think it was Valentine's day and I was working that day. And me wasn't so happy about that, but it just 2014 plus didn't exist. SFN didn't exist. Shopify Payments didn't exist. Shop Pay did not exist. Cash off capital doesn't exist. Again, like there's no enterprise because plus is not even around then.

Harley (39:18):
So it's a funny thing to answer because in many ways it's the easy thing to answer. No ways was there more opportunity then. There's way more opportunity now. And you can say, well, there's more people. So the numerator in the equation is bigger but the denominator is so much bigger. We probably only had, I don't know, 80, a hundred thousand merchants then. We have 1.7 million merchants.

Harley (39:40):
So I tweeted about this a little while ago, but I mean, you folks know the amount of opportunity just keeps growing. So not only do I not buy that, that it's too late, but I actually think like the opportunity it's probably easier now than it was then because think about just from an app perspective or a theme perspective, forget the agency side or the custom build stuff, but just from an app perspective or a theme perspective, if you are starting an online business today, one of the first stops you make is the Shopify app store. The part of your process of building.

Harley (40:17):
And so if you have a Shopify app in there you're going to get seen. It will be a go-to market strategy for you. Whereas in 2014, you may have people stumbling upon the app store but it wasn't really part of the traditional journey of building a new modern retail business. I don't buy that at all. And if you don't believe me ask partners that have just recently joined. In fact, one of the things I used to love to do at Unite when we were all in person together, was you guys remember this? I used to call out random partners to stand up. And what was new was like some of the partners you knew, and some of them you'd never even heard of before. And then you find out that like they did 600 stores and they have 50 people at their company and they didn't exist a year ago.

Harley (41:03):
Shopify cares deeply about our merchants that's why we go to work every day. That's why we get up in the morning, but without our partners, Shopify would not be where it is today. And that goes for every type of partner we have. And I said this in 2015, 16, and 17 and 18 onstage at Unite, we want to create more value for you than we capture for ourselves. And it's one thing to say that you sort of talk with the Bill Gates line. But the partners that have been around for a long time actually demonstrably have evidence to that effect that we leave room on the table so our partners can participate. There's so much opportunity in that ecosystem. And it's only to get bigger.

Kelly (41:49):
It's baffling, just reflecting on my own journey. I came in as a Shopify partner, solo freelancer. I have a team of 20 now.

Harley (41:58):
Unbelievable. It's unbelievable. And I got to tell you, I mean, you and I talk offline, we're not being recorded. So you hear me say this offline to you when not everyone's listening to us, but I don't know if you fully appreciate Kelly, how much pride I get and watching frankly, both of you build these incredible companies on top of Shopify that I don't take for granted for a second, that you've selected Shopify as the platform build on top of. That your success in very many in a very real way, it feels like my success. I don't want to go all Jewish mom on you, but like fricking proud of what I've seen. And sometimes you call me and we have really tough chats about you going through something at your business or I need help on something in my business.

Harley (42:48):
And it's not always rainbows and butterflies, but when you zoom out for a second you realize what you have built. It's incredible. And I know that both of you have very much influenced a lot of people in some cases to drop out of school and start their own agency. In some cases to leave a job, they hate and start their own thing or to join a Shopify partner. A theme designer decides to build an app, an app developer decides to become a Shopify Plus partner. It's amazing. And I've been at Shopify now for about a third of my life which is crazy.

Harley (43:26):
And one of the things that I love watching our merchants go from cradle to scale from zero to being these brands that are discussed as a competitive threat in the Nike board meetings, which I don't know that's true, but I just assume some of our stores are like. I mean, I assume Noble is being discussed. I assume Allbirds is being discussed. I love that. Right? Because again, those are the rebels and the rebels are now challenging the empires like, hell yes, that is democratizing. That is the coolest stuff. But I also love watching the partners grow to be these formidable, these forces in modern retail.

Rhian (44:01):
We love being part of this.

Kelly (44:03):
Without a doubt.

Rhian (44:06):
Without a doubt. Without a doubt this has been the journey of a lifetime. And we're still just getting started.

Kelly (44:13):
We're just getting started. Exactly.

Harley (44:14):
Me too. Me too. I got nothing else to do also like, this is it for me. This is it. Like many of us, I have found that thing. And I'm so lucky that I found the thing that I want to do the rest of my life.

Kelly (44:30):
I have to say I not going to say who it is, because I want them to be able to announce it. But somebody sent me a DM yesterday on Twitter saying, this is not just to toot my own horn or anything like that, but they were like, thank you because of the encouragement you gave me, I just put it in my two weeks notice to go all in and building my Shopify app. I love those stories.

Harley (44:58):
Awesome. It's amazing. And it's cool. Right? Because you sort of, when you think of the entrepreneurs on Shopify, you immediately jumped to the merchants but what you don't understand is there's an entire layer of partners that are also entrepreneurs. They're also using Shopify. We're leveraging the platform to be entrepreneurs and to create their own ventures as well. That actually I haven't really thought about that until right now actually.

Harley (45:21):
So bear with me because it's going to be a bit of a stream of consciousness but Shopify is really a company for entrepreneurs by entrepreneurs connected to other entrepreneurs. And think about that. Right? The people that work at Shopify but for the most part, you know all them. We're all entrepreneurs, the people that we're serving merchants are entrepreneurs, the partners are also entrepreneurs.

Harley (45:45):
In a lot of cases, the consumers that care about supporting independent brands and small business, they're also entrepreneurs. It's kind of this interesting thing. And that I think is why we all get along so damn well. Which is not something that traditionally you had in business, there was inherently friction in business. Right? A lot of companies historically this is going back even like in the Gordon Gekko days. But like win-win means we win twice as opposed to I win and you win and we all kind of kumbaya. But that idea of all being in it together, I don't know, that's a special thing. It really is. It truly is.

Kelly (46:26):
So we usually end these podcast episodes with a store recommendation but I want to things up this week and ask you for a book recommendation instead because there are never too many books to add to my already started but still need to finish list.

Harley (46:45):
So I have two books on my desk right here. The first one was a gift from Lindsey Craig. Who's our director of growth and it's called Storynomics by Robert McGee, but it's basically the science behind great storytelling. And Robert McGee. I think he wrote something like 150 different screenplays of which something like 50 of them were like Oscars. They got Oscars for it. But it talks about like character empathy and the power of underdogs and the emotional arc of brand story and structure of story. It's a great one. So that's one of my pick. The other one that I'm reading right now. And I'm taking lots of notes on it's called Understanding Exposure. Do you this one?

Kelly (47:28):
No. Do not know this one.

Harley (47:31):
Okay. So I love taking pictures and I usually use this camera is my friend as my friend Chase likes to always say the best camera is the one you always have on you. But actually I wanted to explore taking better pictures. And so I bought myself this great camera, actually. Noah Mark from GymShark recommended me this camera, it's called, it's a like a Q2. So I get this camera and like looking at it and trying to figure it all out. And I'm like, I hit auto auto auto. And then I tell Noah, I was like, "Hey, I got the camera taking photos of my wife and my kids and my dog." And he's like, you are only using like 5% of the capacity of the Leica if you're putting it all on auto mode. I was like, all right, I'll put on manual mode, manual manual, take a bunch of pictures. They all look terrible. They're overexposed, they're blurry.

Harley (48:16):
And so Toby actually recommend, he's like, "Hey, there's this great book called Understanding Exposure by Brian Peterson. And it'll teach you everything about shutter speed and aperture and ISO and everything you need to know about the camera. And I'm reading it right now. And it's an amazing book. And I like taking notes. I have a pen in here, like taking notes of my books. But understanding exposure is this great book. If you want to understand, have a deep understanding of how to take great pictures. And the cool part is it doesn't really change. It's been the same thing for a hundred years. So if you understand aperture and understand shutter speed, understand ICER, like you actually now know how to take really great pictures. And so that's what I'm reading right now.

Kelly (48:55):
My husband's been trying to get me to learn how to take better pictures because I'm also very much just defaulting to my phone these days. Also just because I don't like lugging around a DSLR when I'm traveling around Europe.

Harley (49:08):
I agree. That's the problem. It's really big and it's clunky and the battery runs out whereas the iPhone it always kind of just works well. But then when you take this one photo of 50 of them for me, it's just one picture that I have of Bailey actually posted on Instagram playing in a swing set in the gym at the local park. You take that one picture like, oh, now I get it because now you're like the difference in depth and the difference in quality is so much bigger, but I'm now taking 50 pictures in order to get one really good one. So I'm trying to get to [crosstalk 00:49:43] down a bit.

Kelly (49:44):
I mean, as long as it's not like taking a picture of them, looking at it and then taking a picture and then looking at it, you're just taking a bunch of pictures and then repeat it.

Harley (49:52):
Well, on the iPhone, he was like you're taking as many pictures of you. How do you hope it goes well, and then you ended up adding a filter to it or something like that. But that's what I'm reading. What are you guys reading?

Kelly (50:00):
Rhian, you want to go?

Rhian (50:02):
Right now I'm reading Because Internet: Understanding the New Rules of Language and-

Harley (50:10):
That sounds pretty cool.

Rhian (50:11):
It sounds like a good accompaniment to Storynomics to be frank, because it talks a lot about the linguistic shifts that have happened online and how we work within that and then change the way we communicate because of it. And for me, it's very interesting as an SEO person because content is always super critical and storytelling is a major part of that. But the way we consume and communicate has changed so much even since I started working in the Shopify ecosystem. It's just been a fascinating read and I couldn't recommend it more. It's just phenomenal. It's phenomenal. Phenomenal. Yes.

Harley (50:56):
Awesome. Very cool. Kelly?

Kelly (51:00):
The book I'm actually reading right now is No Rules Rules which is about Netflix and the culture of reinvention. I am only like two chapters into it so far. So I can't speak too much on it quite yet, but I pulled this book out right next to me to show Rhian earlier. My dad gave this book to me a couple of weekends ago and it is called And-- Howe! I grew up in Michigan grew up really big hockey fan.

Harley (51:24):
Gordie Howe.

Kelly (51:27):
It's an autobiography about Gordie Howe and it's signed by Gordie and his wife. Wow. And so my dad was like, "Take really good care of this book. It is going to be a lot of money one day."

Harley (51:38):
That's awesome. It's a big one.

Kelly (51:41):
It's a Tom, but I'm excited to dig in and get that story because there's a deep connection to my dad.

Harley (51:48):
That's so cool. For one of the build a business competitions, you guys may remember this, we went to Necker Island, Richard Branson's island, and he's got this amazing library and randomly, I was just walking around. And I went to the library and I grabbed this book. Sort of some finance book, small little book, and it was written by George Soros and ended up reading it and I forgot to put it back in the library. So I took it home with me accidentally.

Harley (52:14):
And then I looked, and there was this letter from George Soros to Richard Branson in the book. And I still have it there. So every time someone talks about it, say like a signed copy of something I like to think about like this Richard Branson book that I accidentally took that George Soros owns. Wrote a personal letter to him in it. But I feel like at some point I'll give it back to Branson and there'll be like a really [inaudible 00:52:34].

Kelly (52:35):
Exactly. I remember that time I took your book. I love it.

Harley (52:40):
I'm going to be like banned from the U.K.., a decade or something.

Kelly (52:44):
Yeah. If it happens, at least you get a story out of it. Yeah. All right. Actual final last question. Where can everyone find you on the internet.

Harley (52:53):
@Harley on Instagram, @HarleyF on Twitter? Of course And I don't know. Those are the best places to find me. I'm pretty out there on the internet. But that's where you can find me. And I just want to say first of all this was a lot of fun. This is not the way I thought this was going. Couple of times I thought I was going to get teary-eyed. But this is great. And I'm grateful that you asked me to come on and I think it's really cool that you folks do this and that you bring on interesting people onto the podcast. And so. Thank you.

Kelly (53:24):
Thank you. You're one of the interesting people we bring onto the podcast.

Rhian (53:27):
Thank you so much.

Harley (53:30):
That means a lot to me.

Kelly (53:30):
We count on that.

Rhian (53:30):
Thank you. Thank you.

Kelly (53:34):
All right. Wrapping this up. Thanks so much for tuning in and thanks again to our sponsors for supporting this episode. We have a YouTube channel that I swear we are going to update-

Rhian (53:44):
We promise.

Kelly (53:45):
But you can find it at We promise. We keep talking about recording the friendly Shopify store tear down. So it just hasn't happened yet. One of us needs to offer here potentially. If you like our podcast, leave us a review on apple podcasts reviews make us really happy, and we like to read them. You can subscribe to Commerce Tea on your favorite podcasting service. We post new episodes, there we go, every Wednesday now. So grab your mug and join us then. We'll see you next week.

Rhian (54:10):

Rhian (54:11):
ClockedIn is a time clock for Shopify. With ClockedIn your team members can easily clock in and out of their shifts from anywhere. You can manage your teams' hours is they work remotely with an intuitive interface that can be used from desktop tablet or mobile. Check it out at or in the Shopify App Store.


Leave a comment

Please note, comments must be approved before they are published