Why Founders Should Prioritize Personal Development with Shopify's President and Felicis

Okay, well, thank you everyone for being here virtually. We can't see you, but hopefully you can see us well. We're so, so excited to have both Harley and Aydan here again virtually at Zaster with us to talk about a topic that's, I mean, very, very near and dear to my heart, very important to me, the topic of what we call founder development, but essentially why It is so critical to invest in your own personal development as a founder, as an entrepreneur, whether you're venture-backed or not. And I assume that there are many, many founders in the audience watching today. So quick introduction on myself, and then I'll introduce Harley and Aydin, who really truly need no introduction. But my name is Dasha Maggio. I'm a partner at Felicis Ventures, top-tier early-stage venture firm. I lead our founder success function. So founder success is— you can think of as analogous to customer customer success in any sort of operating company. But for us, founders are our customers, and the mission of this function is to ensure that we are consistently exceeding their expectations. I also launched our 1% Founder Development Pledge back in 2018, the first of its kind in the VC industry. And this is simply our commitment that on top of every first check Felicis writes, we allocate 1% of that check's value in non-dilutive capital for founders to spend on their own development. So think executive coaching, therapy, leadership programs, and more. So that's a very quick background on me. And as I said, Harley really needs no introduction, and you can read sort of the full spectrum of his accomplishments online. But he's currently the president of Shopify. We all know and love Shopify, I hope. But 15 years ago, roughly, Harley actually started as a very early merchant on the platform. And since then has just had an incredible impact on the company across many, many roles, spinning up new functions and lines of business, including serving as COO. And Harley is also very vocal about the importance of work-life harmony and founder mental health and wellness, which is why I'm so excited that he's joining us today. And Aydin Sanket is my partner at Felicis. He is the founder of Felicis. Was a very early Googler early in his career, started out as one of Google's first product managers, worked on many, many critical international sales deals for the company. And then after leaving Google, became one of the original super angels before there were micro VCs, before there were mega funds, before all of that, and has since built Felicis into the firm that it is today. Has an incredible track record that I can't go through through fully today, but has appeared on the Midas List several years in a row thanks to the privilege of backing companies like Shopify, Adyen, Twitch, Credit Karma, to name a few. So with that, we have about roughly an hour, a little less than an hour, and please ask questions throughout as they come to you. But, you know, we could talk about this for a long time, this topic, so I will jump right in. So Harley, first question will be to you. You have written at length and spoken at length about how lonely and challenging the entrepreneurial journey can be. And in a recent article that I saw, you cited that roughly 7 out of 10 entrepreneurs, either directly or indirectly, are affected by mental health issues. And again, you tweet about this, you speak about this. So maybe just to start, just to give folks in the audience some context, why is this topic so important to you?

Yeah, thanks so much, Dasha. Thanks for having me. And Aydin, for those who don't know, Aydin is a huge part of the Shopify story. He was our first investor, and he's just been a consigliere, a mentor, and a very good friend to me and Tobi and to Shopify. So a great honor to be on this panel with him. The thing about mental health that I don't think a lot of us talk about, particularly those of us that are entrepreneurs or that are entrepreneurial, is that we sort of feel like we have to do everything ourself. And that's sort of the best part of being an entrepreneur, but also sort of the worst part is that we become incredibly resourceful, incredibly resilient because we have no choice. A couple of years ago, I began to talk about the fact that I've had anxiety since I was a kid. When I was a kid, no one necessarily characterized it as anxiety, but now that I kind of know what it is, it's become clear to clear to me that what I had ever since I was like 8 or 9 years old was a feeling of anxiety. And so as I began to sort of learn how to manage it, whether it's through mindfulness or it's through, you know, my green tea— I'm actually fast, I'm doing an intermittent fast right now because Mondays, that's just how I get back into the swing of things after the cloud or the fog of the weekend— I began to share, almost add like these little breadcrumbs of like, okay, well, hey everyone, if you feel anxious, try this. Or hey, just so everyone knows, like, I'm having a rough day right now. Here's how I feel. The more that I shared the more that I got people reaching out to me through DMs, email, even like a tweet saying, "Actually, I feel the same way." And so I began to share more and more of it. And the more I shared, the more people kind of raised their hands and said, "Oh, me too." And so we began to kind of create these little informal conversations about, "Hey, what works for you? Okay, that's great. I'm going to try that as well." And something as simple as mindfulness. For a long time, I was told I should try meditating. And it just didn't stick. And I think what I was trying to— I thought by sitting down and doing a 10-minute guided meditation, I would sort of find enlightenment or something like that. I was putting all this pressure on myself to win at meditation, to win at anxiety mitigation or management. And it's just, it's not like that. And so the feedback loop that I've been given for the last, particularly last 3 or 4 years or so since I began to share more of it is there are so many of us in in technology, but just frankly founders, entrepreneurs, people that are kind of in our space that feel the same way. And it feels like entrepreneurs disproportionately have a higher likelihood of, as you sort of pointed out, 7 out of 10, of having some sort of affliction around mental health. And the more that I share, the more that I think I help myself, I also help others. And I think for a long time, there was a bit of this bravado in business that was the stronger you come off, the stronger you are. And so if you show any weakness, then your investors, your customers, your business partners, your colleagues are going to think you're weak. It literally is exactly the opposite, that the more you share, the more vulnerability you put out there, the more strength you show. And so it's been an interesting journey of sharing this with the world. And then I had a couple really amazing moments in the last couple of years, and some of them were professional, like May 2015, taking Shopify public. It was an amazing moment to stand on the New York Stock Exchange, and Aydin was there and watched us do this. It just It's for an entrepreneur, there's nothing better. But then 2016, I had our first child, and 2018, our second child. And so as I sort of have not just developed as a leader, but also as a dad and trying to be a better spouse to Lindsay, to my wife, I've also shared some of that as well. And so I'm trying to live a little bit more out loud than I think most people do. And the benefits of it have been huge, I think, for me, but also it feels like I'm able to I'm not trying to suggest that I'm solutioning anyone's problems, but if I can provide them with a couple different tips or tidbits of things that worked for me, it may work for them as well. And it's been a very valuable journey for me.

That's great. Thank you for sharing that. Yeah, I think so much of this is— it's opaque, right? It's invisible, right? Our inner worlds, what we're experiencing, it's not just for founders and entrepreneurs, but for all of us. We can't see it. And so the only way to kind of normalize and ensure that others can relate and know that they're not alone is to share it. So as you said, it sounds like it's been incredibly beneficial for you, but also a gift to so many.

I hope so.

Yeah.

Yeah. Aydin, I'll go to you, and then I want to come back later to something Harley mentioned about anxiety, so preview. Aydin, as I said in my introduction, we launched the Felicis Founder Development Pledge about 3 years ago. And since then, well north of 50 founders have taken advantage of the program. So again, doing things like using it towards executive coaching or therapy or various leadership programs. So, and as I said earlier, like we were the first VC to do this. It was pretty unconventional, I'll say. So I'm curious and I think our audience will be curious to hear as a top-tier investor, as a leader, as a human, why did you support this initiative and then tell us about the impact that it's had since then.

Yeah, I mean, I think this is a topic that is also very near and dear to my heart because I have kind of seen it not just with Harley and Toby at Shopify, where they've done amazing things early on, maybe when the company was not well known, but having people around you that are mentally supporting, you know, kind of cheering you on, giving you perspective that you are on a good path. And if there's something challenging, just to help you think about it, I just do I do think that we live in kind of a weird age where everything we read in the news is all about these extreme successes. We talk about outliers. Venture is, you know, an industry full of outliers and everybody is under this extreme pressure to be an outlier themselves. And it's just really tough day in, day out. And the reality is that the journey to success is not straightforward, right? Like there's a lot of zigs and zags. I not only experienced it with Shopify, I've experienced it with Google as well. Like early days, like most people have never heard about it. I would call people to come work there and like people would not return my calls. And I'm sure like the same was true with Shopify. It's like, you can't build a company like that in Ottawa. Now we have the proud moment to say, yes, you can. And not only that, but it could be worth north of $150 billion. It's so nice to be able to prove the naysayers wrong. I think what it kind of comes down to, and I remember this very vividly, Dasha, when you and I were calling the founders, there is so much of a stigma and pressure to look successful and to only talk about the things that are up into the right and the extreme good things. It does not give us the room or space to say that, well, there might also be things that we're worried about or thinking about or concerned about. And in fact, this brings me to a wonderful concept that I learned from Harley and Toby, this concept of trust battery and keeping them charged. And what, what we noticed is that a lot of things in venture, especially between the investor and founder, was a little bit mechanical and at arm's length. And everybody talked about being on the board, But I'm not sure that's directly correlated to whether a founder truly trusts the investor and sees them, him or her, as a mentor and somebody that they can have an open conversation with. And this is really critical because, first of all, you know, we all know that the companies go through these really hard cases. And I think where you can really make the difference is if you can openly talk about them. And not only that, but sometimes also about yourself. And I think what Harley was alluding to that I will double-click on is is it takes a lot of energy to basically show success or put these layers of COVID to basically protect your own vulnerabilities. And that energy could also be very well deployed to actually solving the problems or the anxiety or the worries we have, and to know that there are people that care about it as much as you do. And so when we— and the reason why I'm mentioning it is like every founder that we wanted to, you know, ask about this, it would, I think, take at least 5 turns and multiple drinks and, you know, until they finally relax and said, well, listen, let me tell you, I don't think my issue is for somebody to come help us with a deal or one single hire. The bigger issue is that I just wanna be able to have trust with someone so I can truly open up and talk about the hard things. And so what we have seen is, you know, when we announced this initiative that, hey, like, that's where we're going for. And because it was built on founder feedback, it is extremely well received. And whether people use it or not, everybody mentions it, everybody cares about it, which basically lets me know that we have hit a vein and it is something that all the founders talk about. And then the last point on this, like, I'm an avid tennis player and listen, tennis is one of the few sports coaching is not allowed. And you've seen what happened with Serena Williams. And imagine like how critical it is. You look at other sports, everybody has not one but multiple coaches from fitness to mental health to other stuff. Well, if the athletes need it and we consider ourselves performance athletes as founders, then why not coaching for the founders, especially if your investors are paying for it? So there is no guilt, there's no stigma, it can only help. And like Dasha and I say, you know, our goal is to make the founders, you know, unbreakable. So that's, that's where we're coming from and we're very excited where it's going to go.

I love that. That's such a cool initiative, really is.

Thank you, Harley. Yeah, we're obviously biased, but as Aydan said, the feedback over the last 3 years and hopefully going forward will be positive. Because I mean, we talk about this internally too, and you know this very well, right? If your leaders, if the people building the company are not, as Aydan said, unbreakable hopefully, but solid, it's kind of, you can pour in all the strategy, all the tactics, all the additional hires that you want, but it's sort of a crumbling foundation.

It's also, it's interesting because, I think some of the best founders and entrepreneurs that I know, and I think that both of you know, there is a sense of resilience that they have, right? It means when times are getting tough, they can push through, they can see things that other people don't see, they're able to manage a great deal of stress and pressure and inputs. But the flip side of that resiliency is that it often makes it incredibly challenging to say stop. I need some help, or to say, I need a coach, or I need a mentor, or I just need a break. I need to take a couple days to just recover. It's been, you know, it's been full on all the time. And one of my favorite expressions is, you know, make no small plans, because I think it's such an important thing for founders and entrepreneurs to think about, this concept of everything you do should be with great ambition and with great, um, uh, with great energy, and, and, and to do it to a point where more— most people would turn back The best founders, the best entrepreneurs, they keep going. But again, that creates a sense of when I do need help, I don't often know how to ask for it because I'm so used to this, to being resilient. In fact, in many cases, I'm told your resiliency is your superpower, your energy is your superpower, your ability to manage all these types of stresses and pressures is your superpower. Well, that might be the case, but that doesn't mean that you as a founder or an entrepreneur at some point don't just hit the pause button and say, "Stop." I need some help right now. And I think the more we talk about the fact that every great entrepreneur, I think that all three of us know, at some point they got help, they spoke to someone, they got a coach, they got a mentor, they started meditating, they go for walks, they play video games when they're, you know, really, really stressed, need to clear their mind. That's a part of it, although we don't really celebrate that in the same way that we celebrate the tenacity of company building.

Yeah, well said. I'm not going to get the quote right. I And I won't attribute it to the right person, but what I hear you saying, or the way that I interpret it, is your genius is right next to your Achilles heel, maybe. It's like the same side of one coin. I'm curious, Harley, for you, was there a specific turning point, breaking point in your journey at Shopify, or more broadly, where, again, you decided to go down the path of coaching, which you've written about, or mentorship or something else?

We did coaching. I don't remember this. We brought in our first coach in 2008. 2011 into Shopify, we were probably 20 people. Felicis had just funded our Series A along with Bessemer and FirstMark, but we were really early on. And it was our original CTO who had heard about the concept of coach, and we thought, "Hey, this is such an interesting idea. There are people here that are natural born leaders, but no one here is born a good manager." So initially, the coaching, the integration of coaching into Shopify was really around management. If you manage people, you should have a coach. And so even, I think, before we hired a CFO, before Russ Jones joined, who was our original CFO, I think we had coaches on staff prior to having a CFO. And I think even a CMO. That was a really— that really sort of changed our perspective on the fact that, okay, this is a major part of company building. It's not just building the right products or commercialize the right things or building the right growth vectors or growth funnels. We need to make sure that our leaders have the capacity to keep growing. And one of the things that has always been sort of culturally, if you work at Shopify, it's obvious, but even from the outside, people have sort of mentioned this to me, we have this concept of requalification for your job, that every one of us, certainly myself and certainly Toby looks at it this way too, we have to requalify for our job every year. That in itself is difficult, but requalifying for your job at a place like Shopify, which is growing so rapidly, means you have to disproportionately grow faster than the company. That is really tricky. And so there's almost no way to do it on your own. I mean, some people can do it, but very few people. So the idea of actually building your own sort of personal board of directors, again, whether it's people in your family who you look up to have been helpful, or friends or mentors the way Aydin has been to me over the last decade or so, you build your own board of directors, but having that coaching is really important. And for me, when it all culminated was Bailey was born, our 5-year-old was born in 2016, Again, it was almost a year to the date post-IPO. We were sort of in our fourth, sorry, our fifth quarter being a publicly traded company. If any of you that have had newborns, you know how incredibly challenging it is. My wife at the time was also launching an ice cream shop. She's an entrepreneur. She had this ice cream company called Sunday School, and so she was launching her business. I was trying to lead Shopify. The baby was here. It was madness. And what I began to do was I found myself at times feeling really manic. And the manic feeling, the way that it appeared, it appeared as a hustle or it appeared as being incredibly hardworking and getting shit done. But it wasn't like that. There was no focus to it. It was just do whatever you can as quickly as you can. And that's really when I got a lot more serious about things like mental health and things like my anxiety. I remember after the IPO, Daniel Dubot, who now works at Shopify, he'd called me, he wasn't at Shopify at the time, he called me and said, "Okay, Shopify just went public. You now have a responsibility to pay it forward from an angel investment perspective." Basically, if you have any success whatsoever as an entrepreneur in our industry, you better pay it forward. You should figure out who are the next entrepreneurs and founders that you want to back. I began to write checks. I began to start angel investing, not necessarily as a return on investment or a financial decision, but more that I felt this, "Okay, you're right. Someone gave us a chance when we were small and no one cared about us. I need to do the same thing." But I expanded that definition of pay it forward from an angel investment perspective to I also need to pay it forward from a mental health perspective, that if I'm finding things that work for me, I need other people to know about it. They don't have to follow, they don't have to listen to me. My advice is worth what You're paying for it, which is nothing. But moving away from coffee in the afternoon, afternoon, like literally after lunch, to green tea has given me this calm alertness that coffee never did, and I'm far less jittery and I sleep much better. Okay. That's one thing that's really good. Meditation. I got a meditation coach that helped me get through the tough part of meditating more consistently. I don't have a meditation coach anymore because I'm able to do it on my own. So there are all these things that you probably could read in a million blogs, and 100 different books, but I was sort of experiencing it and sharing it in hyper-real time. And one, it made me feel a lot less lonely that I was going through it by myself because I'd get notes from people all over the world saying, "I'm also drinking green tea in the afternoon. I'm also hiring a meditation coach," or, "I don't have a meditation coach, but I'm doing more guided meditation as opposed to timer-based meditation." And that journey, that mindfulness journey or that anxiety management journey is I'm still on it now. I still have days where they're not good days and I do feel manic. And that's sort of when I have to take a step back and kind of recalibrate a little bit. And I don't think— I used to think that made me weak. I used to think that made me— I used to question whether or not I could handle this. I feel less like that because, again, the more you talk about these things with people, particularly people that I really admire, I realize we're all going through it. It's just some of us talk about it and other people journalize it.

Yeah, well said. You alluded to something earlier, which is I think a lot of founders, entrepreneurs, people, investors— I'm going to put investors in here, and I don't know, I'll ask you in a second about how investors are really not that different in many ways from founders. But Harley alluded to something that I think many of us don't pause and ask, which is, are we succeeding because of this resilience or hustle or whatever it is, or despite it. Yeah, in spite of it.

Um, so that's, that's the double, you know, that's the double-edged sword of entrepreneurship, which is that the resiliency and the tenacity that has allowed us to push through these things that frankly most humans just don't want or, or cannot do also don't allow us to be vulnerable. And so I think when you combine, you know, and, and this gets better, this gets easier as at least for me, as I, as I've sort of got older, as I had children, because, you know, there's— things are put in perspective at 4 o'clock in the morning when your newborn is, you know, throwing up on you. You begin to have a different appreciation for all these things and a different perspective on all these sort of things. But for me, it hits a little differently because Shopify is, is truly like the perfect company for me, for Harley. My family are immigrants to Canada from Eastern Europe, from Hungary. They didn't call themselves entrepreneurs, but they sold, they were egg merchants at a farmer's market their entire lives. When I was 13 years old, I started a little DJ company, as you folks know. It was my way of making friends. It was my way of being independent. So the fact now that there's 1.7 million entrepreneurs who rely on Shopify, also reminds me that what I'm going through, even though I may be going through at a different scale or different level, they're all going through it as well, whether it's day one at their company or they just raised their first round of financing. And so because more than anything in the world, I want Shopify to be the world's entrepreneurship company, I'm starting to think a lot more about what do entrepreneurs need? And yes, it is tenacity and it is resilience and it's hustle and it's being really focused, but it's also the ability to sort of create and cultivate a community of people around you who can help you through those tough days. And again, that doesn't mean you're sad, it doesn't mean you're bad, it doesn't mean you're a bad founder, bad entrepreneur. It actually means you're just being really honest about something that most people are not honest about. And I think that as you begin to explore some of these things, your own self-identity and your own anxiety levels and how something makes you feel, you're not necessarily— One of the things people used to say about about me is I was like the Energizer Bunny in the early days of Shopify. And I was a little bit— I didn't love the fact that over time I felt like I was less of the Energizer Bunny. I was just being a lot more honest with myself. And I used to sort of pretend like I was always happy and everything was always going really well. And I find now I'm able to be a lot more authentic about, this is a good day and this is a bad day, and here's why this was a good day and why that's a bad day. And then from there, I can sort of curate how to have more of those good days and less of those bad days. And there are still days that I'm like, I'm just overwhelmed. And I now have more tools in my tool belt to get through that.

Yeah. So Aydin, let's come back to you. I left a little breadcrumb earlier about how I think, in my opinion, investors and founders, I mean, we're really talking about the human experience. We being investors go through some of the same struggles. I mean, at Felicis, at least, we are still building our own startup, a startup venture firm. And you spoke about the trust battery, and obviously it takes to people in relationship to power the trust battery. Tell us more about why you think there's still this sort of stigma or difficulty on the part of founders to share and open up to investors. And put differently, like, what's the role that investors play in creating kind of that safe environment? How do you do that with the founders that you work with?

Well, I mean, look, I think I'm going to touch on a different aspect of it. And the reality is, look, when you're the leader of a company and you're the founder, You feel like you just can't tell anyone, like you're the rock that everybody depends on. Well, how can the rock be anything but a rock? You can't be vulnerable. You can't show any cracks. And then investors, I mean, they just invested in you and they expect you to succeed. How can you tell them that things are not working because they're going to judge you? And then how can you go back to your family and say, you know what, like, I'm working really hard? Your wife is like, dude, like, I— yeah, like, I love you, but like, I don't care. Like, I'm doing my own thing. You were not at home when the kid like threw up a couple of times, whatever. And so like, I feel a lot of times it's just kind of a different kind of loneliness where you're like, I just don't have anybody trusted to talk to really. And I think one of the things that we've done is like remove the stigma. Like, you know, I think one of the great advantages of starting a venture firm from scratch, we were just like our founders, right? Like I tell everybody, like we had 50 nos before we got the first check. The first time somebody said yes to us, we were, I think, on version 109 of our deck. In fact, I still have that version. And it's not like I started with something else. I just was not good at storytelling. I tell people I had to watch, I think, 200 episodes of late night show with David Letterman just to be funny. Turkish people are not like great storytellers or funny. So like, people were just like, who the hell is this guy? Like, he thinks he can be great in VC. And same thing, like when we talked to Shopify, we're like, holy crap, there are all these like VC firms, 10 to 100 times larger than us. But the one thing people forget, there is also heart, right? Like people, people at some point, like, use their mind, but they also use their heart. Like, you can totally see who somebody truly cares. And I had this moment of one of my smaller investments that had, like, some exit, and we were in a closing dinner, and there were 10 investors, and I thought, I'm like the 9th, like, largest investor, and I'm like, nobody's gonna talk about me. And I was the first person to get called out because there was a critical moment when the founder really needed help, and we just did it. We didn't even think twice about it, right? I think where we're trying to go with this is that just because an investor is on the board, just because an investor wrote the largest check, doesn't mean that they're necessarily the trusted partner of the founder, right? Like, that's why we say, like, we kind of like more than the actual returns or the return numbers, we measure our success by NPS. And if the founders truly feel that they found a trusted partner, and I don't think that is like a button that you press, you have to earn it. And I've learned that with my kids. So Harley gave the example, and I'm like, wow, like, I noticed that with my kids it is the exact opposite of programming. You give them a command and they absolutely not only do that, they might often do the opposite. But whenever I was consistent in doing something with them, then I noticed that they would open up to me after they seen that, like, I did that over and over and over again, that they're like, wow, like, there was a routine and they can trust me and I'm gonna hold it, right? And that also meant Conscious choice of like not going to a lot of conferences where I could be like with peers that will cheer me on. I'm like, screw that. I'm actually going to take that time and be with my family and make a hard choice. So at the end of the day, what we notice is that what the founders need more than anybody else is like, can I really trust you? Like, do you really— can you really show me that you care about the company as much as I do? Yeah, like we love your check, but what I also really need you is when that tough moment happens, like help me. And a lot of times, like, the point of the quote sometimes is, look, we all have like bad days, and sometimes a string of bad days. You just want somebody to come and tell you there is light at the end of the tunnel, and why, you know, like, why is this gonna work out even though it's been failing like 20 times miserably time and time again, that the 21st time might be success, and to just not give up and just feel like somebody believes in you. Because when things are not going right, I think we have this perception that nobody's going to believe in us. The family is going to think we're a failure. Our coworkers think we're gonna failure, our investors think we're gonna go failure, and the reality is that's happening on a regular basis. It happened with Google, it happened with Shopify, even though things did work out at the end, nobody saw the moment where, you know, Harley and Toby were losing sleep, nobody saw the times when, you know, Larry was 10 o'clock at night in the office sweating the small stuff, and still saying no to 99 things and designing hardware so that the company like could, you know, continue and do things that were really unique. Nobody saw that. Like, no, no press writer wants to write about that. They only want to capture the moment of excellence, write about it, and say that is the truth. And yet that is like 0.01% of the truth. The 99.99%, when that was being made, that is not attractive. When somebody was having a breakdown, somebody was like, I don't know, like yelling profanities or something, is not captured, but it is a part of the reality. And I just wanna like take the stigma away that, hey, it doesn't happen at the very best companies or outliers. Trust me, it happens at every company with every leader. And so why we're doing this is so that people can open up and can have like this escape valve.

It's interesting because I think most founders and most entrepreneurs, when they're vetting investors, venture capital, angels, early stage, late stage, I don't know, even I guess at some point private equity is now getting more involved, excuse me, in private companies. And they call me and they ask, "Okay, tell me about this investor." It's the same couple of questions, okay? Do they need a board seat? Liquidation preferences? Valuation? How quick were they in terms of the turn of documents? Were they able to close fast or was the due diligence period longer? I would say for every 100 calls that I get about vetting investors, 1 or 2 maybe ask, "So what happens? What's the dynamic like?" when things don't go well? Or how have they supported you on your own journey of becoming a more seasoned leader at your company? These are some of the questions actually that I think as a founder, as an entrepreneur, you should be asking. Yes, you want to know about how are they in terms of, are they going to vote with the founders? Are they going to take— do they need a board seat or is it a board observer seat? Liquid— all these things are important, right? How quick can they close? Good. All good questions. But I think you need to add another layer of abstraction to that, which is, tell me about a time where, you know, things were rough for Shopify. How did Felicia show up? And I would say, well, you know, Felicia showed up in a supportive role. How can we help is, you know, a very, at least in my circles, sort of the famous Aydin line. How can we help? He said, that's what he says all the time, no matter like whether you're hiring a leader or you're, you know, you're trying to figure out an international marketing strategy. So I think that is a new way or a new vector that everyone that's watching this, if you're evaluating investors, you should ask those questions too, because we're not talking about dumb money versus smart money, which frankly is way too binary and doesn't really capture the relationship. The people that you bring onto your cap table, even though it's a financial transaction, they're going to be part of your story. The people that came onto Shopify Series A are still people that are part of the Shopify story even today. In a very meaningful way. And that was 11 or 12 years ago when we first took money in our Series A. So adding a new— I think the question to ask if you're going to vet these investors with other founders and other entrepreneurs that have taken money from them is, it needs to be more than simply what happens after they write the check. It has to be about, how do they show up? How do they add value beyond just financial, cutting a check or sending a wire transfer to you? Because a lot of people can send you money, The difference maker is, can they send money and can they also help you on your journey? Because there's going to be tough nights, there's going to be tough periods and tough quarters, and that I think matters a great deal.

Yeah. I have a saying that relationships are really the atomic units of companies, and I think it applies to cap tables to— Totally. —throughout the organization. And yeah, thank you for saying that because you're right. I think the distinction between You know, dumb money, smart money, as you said, is binary. But something that I think I speak for both Aydan and myself, we really, really admire about you, Toby, Shopify as a whole, is just how embedded growth mindset is in the organization, right? Like, you know, you mentioned requalifying for your job and just, yeah, I mean, it is so pervasive.

And so, yeah. That term, by the way, is so interesting, right? Like for a long time, we never actually had a term for that. We would talk about someone's appetite for growth, but Carol Dweck, who I think was the one who coined the growth mindset, fixed mindset thing, naming things really matters. And by naming it, I love my dad, he's a great guy, but my dad does not have a growth mindset. If I asked my father, "Hey dad, let's go learn to play the guitar together," he'd say, "I'm not musical, I'm too old." My grandfather, who is about to turn 90 years old, if I said, "Hey Zaidy, do you want to go learn to play the guitar?" His answer would be like, "You damn right I do. That sounds like a lot of fun." Now, it's nothing against my dad. Once you understand those people, once you're able to spot people with a growth mindset, and there's great ways to figure that out, you can ask about different elements of their life that was very challenging and how they overcome it, you see evidence and glimmers of, "Oh, that's a growth mindset there." But the idea of growth mindset isn't just about learning new skills, whether you transition from a private company to a public company, now you got to get good at investor relations or you have to get good at earnings calls, but there's also the growth mindset of As your role and your job gets bigger and more complicated, how are you going to react to that? Are you going to basically use a preexisting set of tools, a preexisting tool belt, or are you going to continuously add more tools to your tool belt over time? And by the way, that means you have to get really, really comfortable with being uncomfortable. And that sucks. Humans don't like that. But that's sort of where the magic happens. Yeah.

I wanted to chime in because I think I think one of the subtleties that I wanna talk about, and I wanna make this also a little bit even more open, there are a couple times when Harley and Toby called me up and asked for things and I'm like, oh shit, I have no fucking idea how we're gonna do that. And so I also wanna shatter this preconception that, oh, when we have a successful investment, it all happened because we had a formula, we looked it up and said Shopify is a great investment. Some other very notable firms took a simple formula and said, you know what, we've seen success only happen in Silicon Valley, and because we've never seen it happen in Ottawa, let alone like another city, like it just can't be done. So I think what happens is people take these shortcuts, and yet, you know, this is a business where we make the impossible possible. Like Shopify created this platform where many people thought a new platform like this can't be created. Like we created a venture firm where people said these 10 things, like they absolutely don't fit in, can't be a great investor, and we changed it on its head. And so I remember one time like Harley is like, well, we want to get connected to this person. I'm like, we, I think had 100 calls like go like in a week just to kind of make that one connection. Cause I'm like, I can't, I can't fail Harley, right? Like, and Toby. And so everybody thinks, oh, like we just did this because it was just like a button we press and it happened. And so we just didn't give up, right? Like, and we were there and like also do it at the time that it's needed and like make decisions. Like there were so many like trials and tribulations that we go through. When we make the decision where there's a lot of risk, when there are people skeptical and you have to look at it and say, I'm actually risking like losing our LPs' money and people thinking we're dumb and stupid, but only if it works, like you're proven right and people look at it at that time, well, of course they wrote the check and it was a straight shot and it so is not. And so all I'm saying is like, I think one of the really important things, people that listen to you well and also think out of the box, Because anybody can follow a formula, but you want to see people can also give you context and the right kind of ability to see around corners rather than saying, oh, like 10 times it happened this way and this is the 11th time it's going to be that way again. And it's just not as simple as that.

It's almost like, you know, I don't expect my investors or anyone in my life to know the answer to every problem that I have. What I hope for is that the people that I've surrounded myself with will do whatever they can to sort of help ascertain that answer, help find that answer. And sometimes it works, sometimes it doesn't work. There's a very famous Shopify Felisa story in the early days that we needed to substantiate to the world, this is not mental health related, but it's a great story, that we needed to substantiate to the world that Shopify was not only a good product for small business, but that big businesses can also use it. And I told Aydin this, this is like 2012 or something. I was like, "We need some big brands to use Shopify." And through sort of magic and relationships and sort of connections, I think a month or two later, Rovio, which at the time had the biggest game in the world with Angry Birds, launched their plush toy store on Shopify. And no longer did I have to sort of convince people that Shopify worked at scale. I just showed them the Rovio store. And I love that story. Thank you.

And by the way, the opposite side of that story, which was pretty crazy too, the Rovio CEO had a similarly like stressful moment where they're like, holy crap, we're about to launch these amazing plush toys, it's 3 weeks before year-end and Christmas, and we don't have an e-commerce store. We just need like a magic trick here. And I remember Harley and Toby putting their best engineer on this and making it happen. So I think that's again, like a situation where it wasn't like, oh, we knew like Rovio all along and we knew Shopify all along, and it was very obvious to make that connection. So that's why, like, if you're hungry, that's why we call this engineering serendipity, that you never know, like, Like if you have the hustle and hunger to chase, like you gotta be there, like it's almost like you don't know where the pass is gonna come from, but you gotta be there where the puck is going. Like I have to use a Canadian hockey analogy, and yes, it makes you look great as a player, but you were also there. You kind of anticipated where the puck is gonna go and kept an open mind that, hey, there could be something really interesting here. So it's just wonderful when that happens because it's not expected on either side. And deserving people end up getting a great outcome. So it's probably most favorite part of our job.

Yeah, and a theme that I'm hearing, especially in what Harley is saying, but in what both of you are saying, is just the importance of community, tribe, other people, right? We're social creatures and things that look like magic coming out of a box are actually very, very stressful, whether you're a founder or an investor, whoever you might be. Just to make that explicit, I think something that I'm hearing in this conversation is whether it is a coach or a founder who's a peer or a founder a few steps ahead or just someone who, again, who you trust and with whom you've built at least some sort of rapport and connection, it can be— not it can be, it often is incredibly terrifying to be the first to say, yeah, I'm really struggling or I'm afraid. but the benefits, you know, can, can really compound over time.

One quick thing to add there, and I think this was really relevant because I listened to a podcast with Harley and Toby, and then there was a question from the audience is that a lot of times advisors will give you a simple piece of advice, like kind of like a transaction token, but the very best coaches and advisors will give you a framework so you can actually learn and make your own decision. So I remember like, and I don't know if this was the first coach at Shopify or later, but there's a personality system with 9 types, and it was really critical in assessing how the different people at Shopify like match each other and like work together. I mean, the same was true for us, and like when we went through coaching ourselves, or when we tried to work with our founders, it's not like there's an answer A or B. Like I know everybody's looking for that magical answer, but look, like I just want to give you the framework so that if you're in this situation again, it's more like, look, figure out the formula by which you can derive the answer rather than get to the answer. The formula and the context and the framework is so much harder. And number one, it also shows how good the advisor is because anybody can give you an answer, but to give you the true framework and explain how it works is, I think, 100 times harder. So sorry, I just had to say that because I do think that it's a very important nuance and often you don't read about it or you don't see it anywhere.

[Speaker:JASON M. LEMKIN] Yeah, the framework is the Enneagram actually. And the reason the Enneagram has been so valuable to us is, you know, when I was in business school, we learned about Myers-Briggs and there's a bunch of sort of things like that personality classifications, just none of them resonated. And then, so what's neat about having people and coaches and community is you can say, look, I tried Myers-Briggs, it didn't work. I think I'm an ESTJ or something. I tried this other one, it didn't really work either. But actually with having this community, to use your term, Dasha, like you actually get this chance to try new things and eventually stumble on a thing called the Enneagram, which is 9 personalities. And the key for us is not just actually that I know that I'm an Achiever and Toby, I'm a Type 3 Achiever, Toby's a Type 8 Challenger. It's how do Achievers and Challengers best work together. And so for example, like, you know, if you're talking to me, if you come in with great excitement and great, you know, passion about something, I'm gonna listen to you. Toby will listen to you if you've thought of all the things that he's already thought about in that, you know, 30 seconds. And so he's gonna say, what about this, what about this, what about this? And if you thought about all those things, then he's gonna listen to you. You. But until you get to that point, and so having that common language to say, that sounds like this, or that is that, that has been very valuable. And that's actually the benefit of coaching too, as Aidan puts it.

Yeah, yeah. Well, I don't know, are smiling because we know one another's types. And we have the, I would say, the exact same experience in working together. And I think that, again, to make it explicit, you know, in, in this umbrella of founder development, personal development, I think, thank you, Aidan, for bringing personality tests or frameworks. Regardless of what you choose, I think that is a great, you know, potentially tactical and specific takeaway that folks can, can use from this conversation of just, you know, try something. Because, you know, if you keep an open mind and, you know, to Harley's point, experiment and treat it as a lifelong journey, these frameworks, especially when you're working with someone, can really kind of open up these blind spots and give you a new language for understanding yourself. So I'm watching the clock, and I have a couple more questions, and we'll work in some Q&A. But it goes without saying, you both have incredibly demanding, fast-paced, stressful roles, as we've discussed, as leaders, as parents, and so much more, where lines are blurring between work, non-work stuff. Harley, I mentioned earlier in your introduction, you've talked about work-life harmony. So maybe starting with you and then going to Aida. Harley, what does work-life harmony mean? What are you actually doing to enable it?

[Speaker:JASON M. LEMKIN] There's some obvious things that I've tried to do over the time that has been very valuable. I'll share them here, knowing that it may not work for everyone. But one thing that I— prior to Shopify, as I mentioned, I was practicing law for about 10 months, hating it. And one of the things I hated most was there was this feeling, this inherent feeling every Sunday night. It was like, I know that there's a term for it now, Sunday scaries, which I didn't have a nomenclature for it, but Sunday was by far the worst day of my week because Monday was coming, and Friday was the best day of the week because the weekend was coming. And I remember when I left law and I sort of rage quit law, I didn't just leave the law firm and join Toby, I was like, "I don't want to be a lawyer. I don't want to be near lawyers." To me, that particular law firm was the antithesis of entrepreneurship, which was, it's not completely meritocratic because some of us are born on second or third base and others are not, but it was the closest thing I could find to a true meritocracy. and I love that about entrepreneurship, and law was not like that. So one of the promises that I made to myself early in my career, in my early 20s, was whatever I do next, I want my Sunday night to feel like my Friday night. I want my Saturday morning and my Monday morning to be fairly indistinguishable, because that to me was— it meant it was a proxy for there is no balance, there is no separation in work and life. It's all kind of together, and ideally it's in harmony. Okay. The danger of that is obvious. The danger of that is there is no separation. So if after this talk right now, I feel like going for a walk the dog with my wife, I'm going to go and do that if I don't have anything in my calendar. It also means that Saturday afternoon, sometimes I'm in my office or I'm taking a call and that's okay too. The difference is though, by not separating those two into two different buckets, but rather incorporating it is that it doesn't feel— I feel like this is a far more long-term sustainable rhythm, or as I often say, the beats per minute of my life can go a lot longer. I'm operating at very high beats per minute, very high frequency. I can go a lot longer because I'm not necessarily looking forward to the weekend or looking forward to a— I'm able to curate a balance and a harmony that I think works really, really well. I think that a lot of people, myself included for a long time, separated, "Well, this is work and this is life." The problem with doing it that way is that that we're going to spend, if you're a founder, you're an entrepreneur, you're leading a company or a firm, you're going to spend 80% of your time, quote unquote, doing the work side and 20%, if you're lucky, doing the life side. That seems ridiculous. I mean, that's a crazy thing to even say out loud. But by combining these things in a harmonious way and saying, look, Wednesday afternoons, that's my thinking time. It's in my calendar. No one can book me there. And I may do my thinking time at my office, or I may do it I'm sitting in the park or I may doing it going for a bike ride. It, to me, it feels like I'm able to sort of balance things a lot better. And that's the reason why I like the idea of, and it's not my concept, but I like the idea of work-life harmony rather than work-life balance because I think balance is something that if you're a hard-driving entrepreneur, it's very difficult to achieve, but harmony is a little bit easier to achieve, I have found.

Yeah, words matter. Okay, I had a different way of asking the question and I want to hear the answer too, is just how do you measure you measure success, right? Maybe work-life harmony isn't your term, but how do you measure success today?

Yeah, I mean, I think success is very simple for me. I'm gonna like relate it more to happiness, but I think it's doing something you truly love and doing it with the people that you love. So I think like to Harley's example, like I noticed that when I'm doing the stuff that I'm doing at Felicis, you know, I'm working at night, I'm working on weekends, and I never like have a dread of doing what I'm doing. I do it because I truly love— even when I'm in the middle of like some family thing, I get a text from the founder, and I think like just the thought that, hey, I could do something that's gonna help them, that they appreciate and will thank me for, it's just like a reward in itself, right? And then I also think that to get to a point that if you've been consistent enough, like Jeff Bezos has this like great answer to success as well, but like, hey, doing doing something hard, but like 100 times in a row. And I think Shopify has shown how that can be done. And so I think when that happens and your peers recognize you, it's something really great. But I just wanted to like leave one thing that was top of mind, which is, look, everybody's looking for right answers, but nobody thinks about asking the right question, right? Like we always like in a problem, oh, am I in the right relationship? Like, how is this person gonna like me more? How am I gonna find my next investor? How am I gonna fundraise? Or, oh my God, I just don't have time because I have this meeting coming up. But nobody says, oh, is this meeting important enough? Like, you don't realize that you can just say no, just don't take the meeting. Or you're trying to like figure out how you're gonna get this person to like you more instead of asking the question, what is the right person for me? Only to realize that this is not even the right person, so you shouldn't even care in the first place. Or you're looking for investors versus like Hey, you just really want the check, but like you also really need some kind of advice. And that's what kind of Harley was alluding to. And I think most of us have to go through these experiences where it kind of like, we have to crash the wall a couple of times only to realize, hey, like we always thought it could be done one way, but there is another way if we only bothered to ask it, so. I love that, well put.

Yeah, okay, we'll do one final question, can be a quick answer, it doesn't need to be related to founder development. We'll start with Harley and then we can go to Aydin. If you had to put one single message up on a billboard for every founder to see, what would it be? And Harley, I'm guessing you might say arm the rebels, but—

Well, actually, I was thinking arm the rebels or make no small plans, which is something that I believe in. But actually, more and more, I think it'd probably just be breathe. Just take a breath. Like, just sigh. Because I have found that, like, if you're a founder, are typically and usually going to be hardwired to make no small plans, to try to turn over, destroy the status quo, arm the rebels against the empire. But actually, something that I just wish I would have known a lot earlier was just breathe. Okay, Aydan.

Well, I have to choose two words, so I'm going to go with that, and I'm going to say choose positivity, because a lot of times Sometimes, you know, I don't think we think enough about the people around us, either our friends, our coworkers, you know, anybody around our life who has an influence, and even ourselves, like when we're in stress, you know, we don't even realize what kind of like a body language or tone that we have. And I noticed that, you know, positivity is contagious. So, if you want positive outcomes, try to be positive, try to have a positive demeanor and surround yourself with positive people. Again, it's a choice whether we realize it or not, so choose positivity.

Nice. Okay, I think we'll hopefully get Harley some time. I don't know if you have time for a walk, but just some breathing room. So thank you, Harley, so much for being with us. Thank you, Aidan, for being with us. And hopefully thank you everyone too who joined as well. So we will let you enjoy the rest of your day and enjoy the rest of SASTR.