Lindsay Taub & Harley Finkelstein: How to Build a Ride or Die Partnership

One thing that I remember hearing that is super not helpful is when people tell you, 'Well, when you stop looking, that's when you'll find them.' And I mean, that is just a trap. Like, how could you stop looking? And so, just using very basic game theory, I wrote down every girl's name. I wrote down every guy's name because this way I would know who I matched with. But, funny enough, I wasn't matched with Lindsay. So, and we think it was an error. We think it was. So I actually messaged her and said, 'Hey, you know, I picked you. Why didn't you pick me? I thought we really hit it off.' And she of course said, 'Oh, I picked you also.' But that's how we started dating.

There's an acceptance of who that person is deep down. But there's also an expectation that like they re-qualify and I want to re-qualify to be Lindsay's husband next year. To do that, I have to, there has to be some growth and I can't just show up the way I do now. And I think I don't say that as a chore. I say that as maybe as a romantic challenge.

We are very grateful to be here. Thanks for having us. We don't do a lot of these podcasts together as a couple, so this is kind of fun.

Eric, that's a story we have not really told anyone publicly before. So you are getting the goods because we don't share that a lot. But actually what's interesting is that the way that speed dating works is if each person picks one another, then the speed dating organizers connect you. And so just using very basic game theory, I wrote down every girl's name. I wrote down every guy's name because this way I would know who I matched with. But funny enough, I wasn't matched with Lindsay. So, and we think it was an error. We think it was an error. I mean, this was literally, I don't know, 15 years ago at this point, maybe more than that. So, I actually called Lindsay or texted her, I think. Actually, I think it was Facebook Messenger. That's how long ago it was. I Facebook messaged her and said, 'Hey, like what the, you know, I picked you. Why didn't you pick me? I thought we really hit it off.' And she of course said, 'Oh, I picked you also.' But that's how we started dating.

I think part of those early, I mean, obviously when you're first dating anyone, you bring a lot of baggage from previous relationships, from previous experiences. I had been in a serious relationship throughout most of law school before I met Lindsay. And so this idea of getting back into another serious relationship felt kind of like the wrong thing to do. And it had nothing to do with Lindsay at all. It was just my own baggage that I brought in. And then it seems to me that there's this threshold, this particular point that happens where the dating gets to a level where you're willing to effectively, you know, clean slate all your past relationships. Like it doesn't matter that I just came from a long-term relationship that like the dynamic and the connection with Lindsay was so strong that I was like whatever happened before is sort of non-consequential and I obviously there's a spark here there's something here we should kind of figure a way to make it work. But we effectively started our relationship with me saying I'm going to be moving in a couple of months from now to Toronto to article and I don't know how that, like you know, starting a relationship long-distance model is not always ideal.

But it ended up that I moved to Toronto to article, had the worst year of my life. Anyone, I mean, you know me a little, Eric, but anyone that knows me that's watching knows that I am, you know, I've been an entrepreneur my entire life and working at a law firm, no matter how much money they were paying me, was like the worst thing in the world. I never wanted to be a lawyer. I went to law school to become a better entrepreneur. But the silver lining of my article experience was one, at that point I'd already known that there was no way I was going to be a lawyer that I wanted to go back in entrepreneurship and I was already sort of pitching Toby at the time to let me join Shopify and it was him and basically three other engineers at the time. So, one, it was that I like I found the thing that would become my life's work. And second, I found the thing that would become my life's partner, which is Lindsay.

So articles are 10 months and by like month three into the 10-month article experience, just for those that are watching in the US. So I think you have something similar to this in the US, but in Canada before you get called to the bar to officially be a lawyer, you spend 10 months working at a law firm. And in my case, I was working at a fairly large, you know, corporate finance law firm on the side, nights and weekends. I was like running my online store on Shopify. Lindsay was coming to see me in Toronto every weekend. But at that point, it was clear to me that I was going to move back to Ottawa, join Toby and Daniel and Cody, the original kind of three people that built Shopify, that founded Shopify, and I was going to move to Ottawa. And I remember saying to Lindsay, I'm going to move back to Ottawa. I'm going to get an apartment there. You should get an apartment there as well. And she basically said like, absolutely not. Absolutely not.

And I remember thinking about it. I was like, well, like I'm not willing to lose Lindsay. I didn't necessarily think that we were going to move in together yet, but you know, this feels like this can go somewhere. And those were the circumstances. It didn't make sense for me to find my own place when you were getting a place. And I remember actually the day that we went to look at condos to rent and it was like a rainy day. And at that point, I still wasn't even sure that I'd be living with you. But I was still, you know, I was coming along and trying to be really extra helpful and, you know, like showing like, hey, like this is the right thing for us. We should be living in this place together. And I guess it worked. But to your exact point, I don't remember the exact moment where at least from my perspective, I realized that this was going to work. But I do remember that.

Remember like you're now kind of seeing us, you know, we've been married now since 2013. So we married for 12 years. We've been dating now. So we've been together pretty much for 15 or 16 years. I'm celebrating my 16th year at Shopify at this point. You're sort of seeing the highlight reel, I think, of our relationship. But if you sort of go back to that moment where we agreed we decided to move in together. I had been grinding most of my life. I was, you know, I was born in Canada. I grew up in South Florida. I ended up starting a t-shirt business in college. Went to law school to become a better entrepreneur. I didn't have any money. I was paying my tuition. I was helping my family support helping my mom and younger sisters. My life was a little bit unclear. I knew that I wanted to be an entrepreneur. I knew that that was something that I felt that that was going to be some version of that was going to be my life's work, but I didn't have any money. I didn't necessarily have any big vision. This idea of Shopify, I think when I pitched it to Lindsay that I'm going to go join Toby, who she may have met once or twice at that point in Ottawa, Canada, which again, like we're not from there. I didn't grow up there. It's not exactly Silicon Valley or Miami or San Francisco or New York.

The fact that Lindsay was willing to take a chance on me at that point I thought was very telling. And I'll foreshadow a little bit what I think we'll talk about later on in this discussion. But I actually think more and more that the best relationships that we try to emulate, that we admire, this is going to sound somewhat transactional but it's not. It's actually I think a beautiful and a romantic thing. The best relationships I think are true partnerships. What I mean by that is someone presents their vision of a life to the other and the other person kind of jumps on board that journey. Doesn't mean they don't have their own journey or their own vision. Lindsay has her own life. She has her own career. She has her own, you know, life's work as well that is separate from mine, from my life. But Lindsay was willing to close her eyes and kind of jump on this journey that I tried to articulate for the both of us. And it meant move to Ottawa, this random city, work for this brilliant, crazy German programmer who was trying to, you know, build e-commerce software for SMBs. And she was in for the ride. And I remember at that moment thinking that this has all the makings of what might be a very long-term partnership. I didn't realize our life would turn out this way. Certainly, I never could have imagined any of this would have been possible. I don't think you could have either that our life would be like this. But she was kind of ride or die from the get-go.

It's so interesting you say that. So every once a month we do town hall at Shopify and I don't want to make this about Shopify but we have we do town hall and I last we just recorded our town hall and we have an internal podcast at Shopify called Context. It doesn't really, I don't need to go the details of it but we just did our hundredth episode of context and so I did a bit of a review of like all our context episodes we've done and I picked up a couple from like episode two and episode 4 and 47 and 69 you know all these different episodes and like I randomly did a bit of like a mashup, like a super cut of them. And one of the episodes that I showed Toby was the episode where I interviewed Fiona. I interviewed his wife. And Fiona talks about how they actually met playing a video game, like literally in the video game in 1999, I believe she it was. And it sort of got us on a little bit of a conversation that everyone at Shopify was able to see now which was about how it is remarkable that that early team, the very early team of Shopify, all of us were in these amazing relationships and the question that we sort of posed to ourselves was could we have built this thing which is now you know this huge multinational publicly traded hundred billion dollar company that has you know had a major impact without the support of Lindsay for me and Fiona for Toby. And the answer was no. That there's no way we could have done it. That knowing that we had some stability in our life, in our personal life, allowed us to take these very big swings, very big chances in our professional lives, that we were okay with taking big bets with Shopify because we knew ultimately we had this incredible support system. And to your point, Eric, I agree with you. I think that because of when Lindsay and I got together, the success that we've enjoyed feels like our success, not my success or her success. It feels like it is our success that she's like she's a huge part of the Shopify journey. Just like Toby's wife Fiona's as well.

Yeah, we have a bunch of, we maybe this is a topic. We have a bunch of role models in our life, different buckets. So, we have like, I maybe I've said this to you on previous interviews, but you know, I have a mentor in my life for building like a company the size of Shopify and I have a mentor in my life who I really want to, I think he's a wonderful father and I've emulated sort of his style of parenting. We also have relationship couples in our lives as well who we look at and again, we don't know everything that goes on behind closed doors, but we have a pretty good sense of how they've kind of gone on this journey, you know, good times and bad times together and we've learned a lot from them. But actually our ultimate relationship role model are my grandparents who are in their 90s and they've been married for 75 years. And what is remarkable is that 75 years of marriage, again they're in their 90s. So you know they've been ride or die for a very very long time. My grandfather will still go on a random Tuesday to go buy my grandmother flowers and they will still take a drive. This is so crazy, but my grandfather went out and bought himself a little convertible last year, two years ago. And they'll take these drives like, you know, south of the border. We live in Canada, so they'll drive to like Vermont to buy a particular cheese that they really love. And you'll ask them like, why are you, like you're 93? Why are you driving three hours for cheese? And part of it is they like the cheese. Part of it is that it gives them this sort of date. Like it's a date for them. And so we've emulated that. Lindsay and I, you know, last Thursday, like we had a, we try to have date nights a lot. We go for a great dinner, an amazing restaurant. We don't, we're not really sports people, but we have tickets to the Montreal Canadiens, the hockey team. So, we're just going to see the hockey game. We've stayed for all of I don't know, six minutes because we're not really hockey fans, but we plan whatever. But we plan these things and we're emulating what my grandparents have done because frankly, we think they've done it better than anybody.

I mean, Lind is a psychotherapist. I think that's incredibly helpful. Not to say that like everyone who's watching who's single should go and marry a psychotherapist, but I can tell you that someone that has a background in therapy is very valuable because she has nomenclature for things. She'll say, 'I think you're feeling this. Therefore, we should try like here's an interesting technique.' That has been a wonderful hack and as part of that we've like we've seen a couple's therapist for a long time and we sort of go in and out on it every now and then. I take over the therapist just for me. The couple's therapist would be like I need some time alone with Harley. She usually doesn't say she needs time alone with Lindsay. But this idea of a couple's therapist also is really great. Something that we learned from another couple friend that we have and it felt a little bit like you know the famous maxim of the best time to go to the gym is before you like need to go to the gym like you should go to the gym before you're overweight and out of shape. The couples therapist is this great tool that we can sort of implement every now and then when we feel like we're doing something or we're just not connecting in the right way over an extended period of time. We will like breach into that toolbox and say, 'All right, it's time to go talk to Katherine, our couples therapist, and we'll go meet Katherine. We'll have it out. We'll have a facilitator to it.' That I think is something that most people view as something they do after they go too far where it's so bad, it's so negative, there's so much tension. And actually, I think that that's a wonderful way to do it.

Another thing that I have found to be, actually I've never even told you this but this is so maybe I don't know nerdy or something or weird or cringe but you know once a quarter I have earnings calls and that's sort of like you know part of my role at Shopify is to be like the chief storyteller but earnings is like the moment for me to storytell to Wall Street to the media to consumers to merchants to everyone in the world about how Shopify is doing and it's really stressful I mean every word needs to be chosen properly. Every voice inflection is noted. Every hesitation is written up in some analyst report. Things like there's a lot of weight to it and I feel the weight of that. And one of the things that I don't know if you do this, you know, if this comes easy or you put a lot of time and attention to it, but I sort of feel like the week coming into earnings, it feels like Lind and our daughters like everyone knows it's earnings week and it's not like leave Harley alone or leave that alone because it's earnings week. It's actually way more supportive of that. It's like, you know, like Lind makes a special meal for me before earnings. Like it's more of a quiet night in the house. It feels like we're team Harley and Lindsay. It feels like we're team Lindsay and Harley. It doesn't feel like I'm on my journey and she's on hers and like we can have our own lives. It feels like when the stakes are really high, I feel this level of support that like the Finkelstein family has Q2 earnings and that type of support system. It sort of goes back to those early days of when we were just building Shopify that like we were able to take big risks because we felt we had the support system at home. I feel that now. I feel like it's Linds and I versus the world and like we are going to fight together to win whatever winning means in that way.