In our latest series, you’re invited to sit in on Eric Janssen’s Hustle & Grit course, taking place virtually at the Ivey Business School. Each episode explores an entrepreneur’s journey, their key learnings, and questions from our eager, aspiring student entrepreneurs.
In this episode, Andrew D’Souza Co-Founder and CEO of Clearbanc shares stories and lessons learned as he transitioned from a career in consulting, to tech sales, then tech executive, and finally to founder of a now iconic Canadian scale-up.
D'Souza addresses: why consultants make great entrepreneurs, what sets apart the people who cash paycheques from the people who write them, and how to build a world-class team.
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The Ivey Entrepreneur Podcast is sponsored by Connie Clerici, QS ’08, and Closing the Gap Healthcare Group, Inc.
On this new series of the Ivey entrepreneur podcast, you're invited to listen in on the guest visits my Hustle & Grit class taking place virtually at the Ivey Business School, Hustle & Grit is a course that we created to teach you everything that you didn't learn in Business School, in Business School. In it, we invite world class innovators and entrepreneurs to talk about topics like motivation, how to learn what to prioritize, and even how to be happier. In these episodes, you'll hear live audio from my classes, because honestly, there's just something different about the energy, excitement and honesty taking place in a live classroom environment. Get comfortable, grab a seat and don't worry, unlike my real class, I won't cold call you enjoy.
Andrew and clearbank are the epitome of how you could do more together than you can alone. Please join us in welcoming this incredible leader to our class. One Michelle describes as a visionary coming soon to a classroom near you.
do you think,
Man, that's awesome. I don't think I've ever been introduced like that. That is a that was great. Also, you can when you don't have hair, you have to really like to experiment with beard styles. And so you can see my you can see the evolution over the years of the different beard styles for different seasons. So
I'll say like the only the only improvement on that video would be just to show your face and how the beards change over time.
Yeah, exactly. It is it has evolved. Like it has evolved with my career. It's been something that I've experimented with aggressively throughout, throughout.
Well, where does this podcast? Where do we find you now? Are you back home in Toronto? Are you still on the road?
Yeah, so we we, we attempted to take a vacation, we realized we were working remotely, we can talk a lot about remote work. I'm sure we'll get into that here. But we try to think of vacation to Barbados, which was a bit of a challenge is like this is it's a crazy time. And we're coming into q4, which is the busiest time of year for us as a company. So we got a couple of days actually off. And then we work from here for most of last week, and realized that we were actually working pretty effectively from here. So we decided to extend our stay a little and so we'll see. So you're catching me in Barbados here. So if you see a mosquito flying around the screen, that's where it's that's where it's coming from.
Good good for you guys. I do want to talk about sort of making making life work as an entrepreneur and taking the time that you need. So we'll talk about that a little bit later on. The group did some digging on your bio there, Andrew. And since these are maybe a little bit different from the normal groups that you talk to on podcasts, and in some of these interviews, these are, you know, fourth year university students, so they're always super interested in hearing like, the how you got to where you were, and when talking to people who are not so far distance from where they are today, I think it'd be awesome if you wouldn't mind starting with, like your entrepreneurial if that is part of the story, upbringing, and sort of where you got to where you are today.
Yeah. Like, I don't think I had a very different life. And probably most people on this call, you know, grew up, you know, born in India moved to move to Canada when I was quite quite young. And, you know, being part of an immigrant family, it was just sort of this idea that, like, you just had to, we had to figure out how to make, how to make things work. And so a family was very supportive. But like, overall, if I needed to, if I wanted to buy CDs, or go to the movies, or hang out with my friends, I don't know if you guys don't know what CDs are. But, you know, if I if I wanted to, to buy anything, I didn't figure out a way to earn a living so or earn, earn it. And so, you know, called the Mississauga news, which is where I grew up and convinced them to let me let me start the paper route. They weren't delivering my neighborhood. So that was the first step. And then there's flyers, like, you know, as I would go around and deliver papers, I put a flyer as being like, Hey, I'm, you know, 10 years old, and I can, you know, babysit or dog walk or mow lawns or tutor your kids on math, like started started doing that. And that, you know, that was always sort of part of part of my, my life and career. And then I studied engineering, really, because I love cars, like I, you know, I was really saving up for a car in high school, thought I was going to build and design cars loved it studied engineering, really with that goal in mind. And then, you know, even through university, I went to Waterloo, and so there was a co op program. So every, you know, every four months, I would go and work. So I worked in Orca GM, I learned that I loved I loved building stuff, like I was working in robotic automation and, and the manufacturing plant, but I just felt like you were so far away from the decisions are getting made about the company and the direction. You know, being a play, you know, I'm in a plant, and then worked on a bunch, you know, did a bunch of different interesting engineering roles, did some work in investment banking, worked at McKinsey for a little bit. And the consulting world was interesting in that you're involved, you're around the strategy, right? You get to see sort of why people make decisions and the strategy behind it, but then you're so far away from the actual building. So I figured that I think what I realized In a pretty roundabout way is, if you like being part of setting the direction and being part of the strategy, but you also like getting your hands dirty and having ownership and accountability, the only way to do that is in very small companies. And so that was what, what motivated me to get involved in sort of the startup and entrepreneurial world. Because, you know, that's the that was the, that was the opportunity for, for me to do that. And so that's when I moved up to San Francisco. And, you know, ended up joining an early stage startup. And and, and that was, you know, that was the beginning of my journey here.
So why is it it seems like I've seen commonalities with entrepreneurs, people who go on to do some pretty big companies, at least in my social circles seem to start out as consultants, like so many people start out in the consulting world? What is it about consulting, you think that draws people that are either entrepreneurial, or builds a skill set that allows people to be good entrepreneurs? Yeah, I
mean, I, I don't know if so I guess there's a, I don't know if there's a correlation or causation here. I think there's just a lot of consultants. And so some percentage of consultants end up going and becoming becoming entrepreneurs. I do you think there's a few things that I learned, one was just getting up to speed on a new industry or a new business very quickly, like, you know, you're on a four week project, you don't have three weeks to ramp up on it, like you have, you know, an hour and a half to like, Okay, let me let me, let me figure this out. And then I think there's something about the pace like at McKinsey, basically like, okay, we had a 70 hour meeting, and then it was okay. 7am believe that meeting, okay, there's attending a meeting with a client, what are we going to do between 730 and 10? And then after the 10am, there's a 1pm? Is it literally like, you're getting four iteration cycles of work done. And it's not like you're following a prescribed roadmap, you're sort of learning, you know, as you're going. And that's basically what a founding team does, right? When you start a company, you're sitting in a room, you're like, Okay, here's our, here's what we think the market wants, how are we going to learn and de risk this assumption as quickly as possible? You know, even if we've got to take find some shortcuts, you know, we're not going to do as much building where to do some more selling and building, talking to customers and things like that. So, you know, I find that really effective teams operate sort of like dedicated consulting teams, because they just have they remove all the other constraints and just like, Okay, if I can get four iterate for learning cycles, or four iterations done in a day, then I'm moving at, you know, to way faster speed than what most companies are able to. Hmm.
So but you didn't go right, from consulting to starting your own thing. You joined some startups before that, right?
Yeah, I you know, I think this is one of the this is one of the, the secrets of consulting firms is they, I didn't have the confidence, I probably had the skills but didn't have the confidence to go start my own thing rather than begins because I felt like okay, well, yes, I've had success. But really, it was because I had the McKinsey brand name, right. And I think this is where like, a lot of people use that as a crutch, like, okay, I couldn't really do this myself, you know, I had to have, you know, something else behind me. And so that was when I when I thought about, you know, joining a, an early stage company, and I ended up meeting, meeting an investor in Tomas, who was head of growth at Facebook at the time, and ended up starting a fund called social capital. And he'd invested in a number of companies. So I was either gonna go join his team at Facebook, which was a big company at the time, and like, 1000 people, and I think, you know, financially would have been more lucrative for me to join pre IPO Facebook, then join an early stage startup and end up failing. But from a learning perspective, I think I think it was a deliberate
choice. You were optimizing for learning.
Yes, right. Exactly. Exactly. So that was an It was a company called top prospect. It was cool. I mean, and it was one of Andreessen Horowitz, his first seed investments, and we had a bug, we had a great roster of investors, I learned that great investors don't necessarily make a successful company, you know, despite what they market. And, and then I learned, I think the biggest thing, and this is this is, you know, the beginning of as what I thought about building, what we built for clearbank, is, I realized that all of these founders in Silicon Valley that you read about in TechCrunch, and you read about in the Wall Street Journal and stuff, they're no different than entrepreneurs anywhere else in the world. They just happen to have access to capital and access to, you know, media really like they're, you know, they're friends with people who will tell their story. But, you know, I met the founders of Instagram, when they were still bourbon before they pivoted to build Instagram, I met the founders of slack before when they were still building tiny speck, which was like a mobile game that didn't work before they pivoted to slack. And everybody's just trying to figure it out. And I think that was one of the interesting things. Like I always thought my friends that were starting companies out of Waterloo, were like, somehow different than, you know, these people that I would read about, and then I met them, and I was like, No, there's actually not that big of a difference. They just have, you know, its proximity, and a lot of ways and so that was a big part of the mission for clearbank was you can we can we reduce that barrier of proximity or social circle? Like Did you go to Stanford with this person? Or does your father know the right person to get access to, to that opportunity in that capital, and that was been part of the motivation.
Cool. So I want to try this. quickly into our class today is about teams, and leveraging teams and how to do more with teams than you'd ever be able to alone. So how did you set clear bank up from the very beginning from the right? mission, vision, values, culture? And if you don't mind, I'd love to go into the specifics, because a lot of these, this is arguably the most entrepreneurial group at Ivy. Yeah. And they've had no sort of conversations around the ambiguous talk of like culture in big companies. But like, literally, when it's you and Michelle, are you in a few partners in a room at the beginning? What did you do to start off on the right foot and set the right culture from day one? Yeah, I
mean, it was it was pretty intense. Like we, you know, we started, we got into Y Combinator, we all moved down to San Francisco, we lived in a house together. And we did that for the first eight months of the company. And that sort of set the foundation for the way we work, because we basically just worked at like, we worked at the speed of the customer. And we worked at, you know, it was that consulting, sort of like what I talked about that iteration cycle. The other important thing is, our customers are founders, right. Our customers are entrepreneurs. And so what we what we found really early is, we have to think of every person who joins our team as being a founder, like we need, they need to be like, I don't if you guys have read the loo lemon chip Wilson's book, but like, when they hired people, whether those were store associates or people in head office, they hired their customer, right? They hired people who are into fitness and athletics, and you know, this lead yet, like yoga and all of this stuff at that early, early days. And when you hire your customer, like you just like, it's a huge, huge advantage, right? And you're just like, you don't have to do all of the like customer discovery where everybody just innately innately thinks and breeds and empathizes it. And so, so one of the important tenants for us is like, we need to hire founders and like that can take different forms. That can be somebody who started a nonprofit, that can be somebody who started a club, that can be somebody who wants to be a founder, or comes from an entrepreneurial family. But the way we think about it is everybody has their founder story, right? Like, this is actually part of like your interview process. And your onboarding is like, okay, let's talk about like, what is your, you know, what did you found? What did you build? What do you want to build, right? What, like, clearbank is going to be part of your entrepreneurial journey. But you are, you should think of yourself as an entrepreneur, and we may be your launching point, we may be, you know, we've had people who have started companies, you know, raised some money, and then failed and join our company, we've got the entire spectrum. But everybody thinks of themselves, as you know, we're a company built by founders for founders. And so that's a big part of it. And then yeah, we can go into, you know, the specifics around like, our culture and values and stuff like that. But that's, that's one of the big foundational elements of, of who we hire and how we, how we treat them. And so did you.
It's funny, like, the example that I used in class, and the example everybody talks about is Netflix and their culture, Doc, right, the fact that they actually wrote it down. But I think I read an article from Reed Hastings saying that, like, yes, of course, it's important, but that alone can make you a successful company. And like, do all the other stuff, you have to do the other stuff first. And then you can put time into thinking about the culture. So it was weird to hear that from even from the Netflix founders. So did like when when did you guys actually say like, these are the values? like did you did you pick a time and literally, like, write them down and put them on the website or print them out and stick them on the wall? Like, what did you tangibly do to say, this is what we stand for? This is the mission.
Yeah, I think I think I remember one time, we started doing these retreats twice a year. And so the first day sort of happened organically, we were very small, we we ended up getting an opportunity to move the whole company to the Yukon for a few weeks, like the Yukon government had to like a sponsor and started a startup in residence program, like the US was cool. And we did a little off site while we were there. And and that was the first time we wrote down our values was probably like, I don't know, a year, two years into the company. And it was really just writing down what we were already sort of doing naturally. I've never believed in like writing aspirational values, like, you know, the values don't don't align with what's actually going on. And nobody, nobody pays attention to them, or nobody believes them. And so what we really, you know, I think, maybe the way, the way I reconcile, like, you know, reads quote, there is like, being a founder or being an entrepreneur, you get to choose what you work on with who and like, in what way, right? Like, that's the, there's a lot of negative stuff about starting a company, but the positives are you get to choose your day, right? You basically get to choose what you work on and who you work with, and what type of environment that is. And so, you know, that was really what we did was like, hey, what how what, what do we like to work? what way do we like to work we so we, the way we describe our values is it's evolved in the description a little bit, but we call it swear swa IR. And so speed is the first one. It's like what we just we want to we want to move very quickly. And it's exactly that like if you know if you can do something this afternoon. By Why wait till next Tuesday, winning is the W and it's not about us winning, but it's actually about this idea of, like, if I'm entering a new conversation with you, with my peer, with my manager, with my customer with my partner, whoever, I need to first establish that I want them to win. And I'm, you know, I'm here I'm entering into this conversation or this discussion or this proposal, because I'm on your side. And if you don't establish that, then even the smallest thing, like if I, if you, if I think that you want me to win, then you can actually say a lot of harsh stuff to me, and I'm going to take it in, I'm going to take it with, you know, the best intentions. And if I think that you've got a different agenda, but it doesn't matter how nice you are, to me, I'm not going to trust anything you say so, so establishing that that is very important. The third is authenticity. And it's basically just like, say what you feel like, and you may not need to like, it is really about when something feels wrong, just saying that something feels wrong, and feel and be okay with that. And being able to be to be real with each other around that. And that comes from winning, if you feel like somebody, if you feel like somebody is on your side, and you can establish you're on their side, then you can actually be yourself and be like, hey, I want you to I want you to be successful. But coming out of that meeting, something didn't feel right. You know, I didn't like I didn't like when you said this, and we need to we were continuing to, you know, encourage that integrity, which is not about morality, but really about doing what you say you're going to do. And so it's like, you know, for football fans out there, like, if somebody says they're going to be in a certain spot out there, and they're going to run the route, then you can throw the ball expecting them to be there. If you need to wait until they're in the position where they need to be before you throw the ball, it's going to get intercepted, or they're going to end like so. So that's the idea of integrity as ever, if everybody says what they're going to do, and then does what they say they're going to do, you can move much faster as a team. And then the last one are is responsibility, which is, is really like taking Extreme Ownership of things. And again, sometimes we conflate responsibility with blame. And it's like, oh, you're responsible for this project failing, or you're responsible for us missing a number. And it's actually we want to, we want to remove that. And it's really about responsibility thing you take. So you can take, you know, people can take responsibility for something they care about in the world, even if they're not, you can take responsibility for climate change, right, you can take responsibility for social equality, doesn't mean you're to blame for it. But this is something that I'm going to take responsibility for it because it matters to me. And so those are the those are the values that we talked about as a team. And you know, so the way we operate.
Oh, good. So you seems like you already operated by those things. And then explicitly wrote them down at one of your offsites. Yeah, seems like, seems like that's what happens at those like, it's always at an offside. Like you need to actually build in time this just hit pause and stop sprinting and just like think for 30 seconds about what you need to work on the business versus in and all the time. And it's usually, in my experience, it
was always at the off sites where you actually worked on the important but not urgent things. That's it. And it's like, if we reflect on how we work, one of the things that we really like that we want to preserve as we scale, right, and that was sort of it's like, Hey, you know, we're 10 people now. Like, when you know, when we grow, what does that look like? So now at 202 50 people were like, Okay, well, like, do we have those things? And some of those things have eroded and we have to actually go back and be vigilant about about, you know, Brandon back. And then as we continue to grow, it is it's the same, the same concept of like, how do we, what are the things we need to actively preserve in our culture? Otherwise, you just sort of devolve back to the main?
Yeah. Can you talk about talk about cadence for a second then and the importance of team because it sounds like one cadence is that you have you've got these spy that twice. Annual offsides? Do you still do that fairly regularly?
We do. I mean, we haven't done them since January this year. We missed our summer one. So we're trying to figure out how we how and when we can bring them back. But yeah, we've done that now. For the last four years. Company, and then cadence around. I know you have cadences around daily stand ups and end of the day all hands Do you still doing those? Yeah, so so we always did a Monday morning kickoff, the whole company. And Friday, we used to do drinks and demos, which was basically like, demo what you built and grab a drink. And we continue to do that. And we use have everybody in the company demo. And that sort of started to take a very long time and consume a lot of drinks. So we've we've carved it down a little bit, but it's still the same cadence. And then every one COVID hit me up to 5pm close, you know, end of day sort of sync up just as a touch point for the whole team. We did that for the first couple of months when we first went remote. And then it got to be a lot and so we've we've we have a 5pm every other Wednesday where we bring in like a guest speaker we do more of like, you know, Town Hall type thing. So there's three touch points, or there's two checkpoints a week and one every other week now, the whole company. And then each team individual teams have their own sort of rituals and cadences. And daily stand ups and things like that as
well. The drum beat to keep things going. Yeah. So you've established or you wrote down those values. Can you talk about your hiring process for how you bring in your people? I've got to know Steven Tofino, your head of sales and a bunch of people on his team, and I love, he's got his own sales playbook and his philosophies about how he thinks about building his team. But I think you've done a pretty good job of sort of defining what the interview process to make sure that the people that you're bringing in are either the founders or sort of aligned with the values that you guys think are important. So what's your what's your process to make sure that you're bringing in the right people?
Yeah, I you know, and we've tried a bunch of different variations. I don't know if we got it perfect, perfect. But I think we're, we've got a really good hit rate on the caliber of people that we hire, and that cultural and values fit. So we do we get, we have everybody submitted video, which is a little bit weird and awkward for folks, but it just gives us like, a much, much quicker, and especially in today's environment, where you're interacting with everybody over over video anyway, it just gives us a very quick glimpse into the personality and you know, the energy and enthusiasm and it doesn't like, I get that some people are, you know, introverted or extroverted and may feel, you know, made it may not present as well, you know, in that video, and we don't want people to do it like to overproduce it, it's just, uh, you know, pick up your phone, just talk to us as a human being of like, why you're excited about our mission, and why you're excited about joining, you know, the role and joining the company. And that just, you know, I think that's, that's really what we try and suss out through the entire interview process. You know, we got we do the technical, we make sure that you've got the skills to do the job, we actually feel like for a lot of jobs, we can we can train the skills, if there's real mission alignment. And so if people are people can articulate why they're excited about our mission, why we're uniquely positioned to solve the problems that we're aiming to. And then we figure out sort of like, do they have that? Do they have that sort of X factor of being able to run through walls and move very quickly, and in a much more sort of chaotic environment? I think it's been, you know, we're still very much a startup, right. And I think startups go through phases of a product market fit is not like a, it's not like a destination, it's sort of like a state or, you know, it's like a, you find it, and then you lose it a bit. And then you expand, you expand what you think of market, and you have to go continue to refine it, we continue to operate in that way. So Stephen is I love CDs, like, he is the, you know, he comes in with like a plan and a playbook. And I've constantly pushed him out of his comfort zone and be like, that's great. But like, now we have to throw it away and start over. And we've got a really good, good working dynamic to be able to do that. But yeah, it's been, it's been a lot of fun.
So do you guys have specific questions? Or do you? Do you run them through scenarios? Or how do you actually suss out whether they're the right people?
You know, I think it like we really try and understand is why, like, terms, like, understand people's life stories, right? Like, what decisions did you make in your life? How did you feel about those decisions? And what, you know, why did you make them and how did you like, but at the end of the day, our interview process is designed to help, you know, we and we've had this feedback from people is like, Oh, actually, like, I either didn't get the job, or I realized that the interview process, I actually don't want this job, and I want to go work in a different company. And so that should be what it should, that's kind of what it should feel like is helping you understand what you're really good at what you're really passionate about, and whether this is going to be the place for you to win, right? I mean, if you go back to the value of winning, we want everybody who interacts with the company, everybody who applies to win, regardless of whether that means you join our company, we want you to end up in the best possible place for you. And so that's sort of the guiding light of our interview processes, right, like so it's not, there's not like a specific sort of question I see them might have like, actually some sales specific stuff. But from our recruiting process we're really trying to understand is like who you are as a person, what motivates you what your what your, you know, what gets you up in the morning? And will you get out of bed every morning to do the job that that we're hiring before? Yeah, got it.
So we move on, say there, they're hired in the company, they get on boarded. How do you think about giving them the right feedback or cadence around feedback? We had a conversation before you came on about radical candor. And the idea of it's actually in everyone's best interest to be able to have those uncomfortable conversations. Is there a way that you guys thought through how to make sure that you give each other open and honest feedback so that you can be better?
Yeah, it's, it's something again, it's one of these things that we we we get really right and then you sort of lose a little bit and I think, if you don't have a good foundation of trust than radical candor can be very, can be received very poorly. And this is why you know, again, we go back to these values of like, the combination of winning and authenticity is really radical candor, radical candor, Or the, quote, word of radical candor can be used as a weapon very easily. And like an excuse to be like an asshole. It's like, hey, yeah, like, you know, like, that was a dumb You know, you're you're an idiot, I'm just trying to be I'm just just radical candor, right, like, and so people will do that sometimes. And that's why we need to actually the foundation has to be, you have to establish that you want this person to win. Right? And they need to believe it before you can give people any feedback. Like your first job is, Hey, I'm on your side, right? The reason that I'm telling you this is because I actually watched it. And so like, this is when when we've had to exit people, like, it's been exactly that. It's like, Look, we could keep you here, right? And we could continue to coach you. And we can continue, but like, you're not winning, like and I want you to win. And I don't see a world anytime soon, where there is a role where you can win here. And so like for your messages, here's the type of role, right? Like, here are the strengths that I see. And here's the role where I think you're going to be incredibly successful. And like that's actually different than the environment that we're moving towards, that we are right now. And, you know, we don't always get it right. But that's what we strive to have in every conversation. And every sort of like coaching conversation or feedback conversation is around like, Hey, here's what I've observed. And like, people can disagree. But look, here's what I've observed, right? Like, if and if I'm observing this, then maybe other people are. And that's sort of the that's the tactic that we use around getting that getting that radical candor right
now, there was a comment from someone in the class here that brutally honest often ends up becoming more brutal than honest, you know, like that, to your point, the excuse of radical candor is just your free rein to be a total jerk to somebody. That's not that's not, not what it means that I mean,
I've been following you Your, your journey on LinkedIn, a bunch, Andrew, and I know you get asked a lot of questions about this. I went Actually, I was up early this morning, and I went way back to think seven years ago was your first LinkedIn post, I went back, wow. And I've been watching how it evolved. Like, I think it started, I don't know, like a lot of us were first starting to test out LinkedIn, you're like, sharing other people's news with no comments in it, then like, hey, then you start to share your own news, then you started to share, like, Hey, we're hiring for people. And then I found one of your super early videos, just starting to vocalize some of the things that are going on in clearbank. Have you found like, sort of maybe you could talk to these, some of the students here who maybe aren't used to posting some of these thoughts, feelings sort of document don't create type of idea as they're going? So what's your experience been? And starting to share some of those things? And what are some of the positives and negatives of it?
Yeah, it's been, it's been a fun journey. It's sort of, you know, I used to, I used to do a lot of writing. And I think, like, reading helps me clarify my perspectives on things. And whether that strategy with its culture or hiring, like putting your stuff out, there actually forces you to take a stand and take a position on a topic and what we've been doing, and I found, when we were very small, I had a direct relationship with everybody, right. And so everybody kind of knew, like, they knew who I was, then it was on my mind, they knew, like, when I would say something, what that you know, the context around that, or what I was going through, like, I might have been distracted, I might have been frustrated, or might have been tired or whatever. And as we started to scale, it became harder and harder for us, for me to have that sort of one, you know, one to one or two way conversation with everybody. And so we you know, in our all hands, what we'd start to do, you know, in our in our all hands meetings is, you know, we'd ended with like Michelle and I would talk about like, Hey, here's what we're thinking, right? Here's what's on our mind. And it could be something about the business, it could be something about the world, what's going on, and how, you know, how it affects us as human beings. But we just sort of ended with like a thought about like, Hey, here's what you know, here's something that, you know, I realized over the weekend, I was reading a book, or I was listening to podcasts. And this is what I realized over the weekend. And here's what I took from it, and I'm gonna share it with you, because it might be useful for you in your week. And that was really the motivation. And then our social media team was like, Hey, can we like start to, you know, have you thought about sharing some of this stuff externally? And that was really what they you know, so it was really taking that broadcast, I realized that my job had been become more and more of a broadcast, at least, to most of the team. And so taking that and just externalizing it, and it Yeah, it was definitely scary. At first, it was like, you know, I don't know how people gonna react. Am I gonna get canceled? Am I gonna you know, like, is he like, I'm gonna say something I regret and other people gonna go back seven years in my posts and be like, Why did you say that? Why small? Yeah, exactly. But, but at the end of the day, I think it's been a really rewarding experience. It's been great for us from a recruiting standpoint, because people understand sort of some of the rationale and the people behind behind our company. And it's been helped really helpful for me, it's been like my version of journaling. She's just like, Okay, let me let me put out my thoughts out there and either a video or text and, and see, you know, how people react and start a conversation.
Yeah, like you, I think some people do, at least I get, I think through writing, you know, if I if I actually sit and put the time into writing something down, and frankly, I have probably 100 times more notes privately than I ever write publicly, but I think by actually putting thoughts on paper or digital, even on my computer, and so if only just to clarify my own thinking around some issues has been super helpful for me, I'm not as frequent or as high quality of a poster as you are, but it's just helped me my clarity of thought.
Yeah, yeah, it's, I think it's a very good exercise. And it's something that I, so it's hard to find the time, but I think when I do, it's like, I find it very rewarding. And I think I, the more, the more I use it as an internal sort of exercise, instead of it being like a performative exercise, which is, I think, what a lot like what a lot of social media is, and what you know, you're naturally when I'm, you know, we're naturally sort of tend towards is like, I've got a it's got to be fully polished. And it's got to be thought through and every angle and all of that stuff. And when really, it's just like, I'm you're sharing myself as a human being right? And then, you know, yeah,
when I looked at, I have no didn't do the data to support it. But if I look at the ones that you film yourself versus the ones that were like, have a higher production value. I don't I don't I think actually the ones that are just more candid, get more responses. I don't know if you find that, or it just seems like the ones that you're literally holding your phone and just, here's the thing on my mind gets way more reactions or responses than the ones that are professionally filmed.
Yeah, yeah, I think you're right. I can ask our social media team on that. But I think you're right. I think we I think that you get way more responses and engagement when it's like, Hey, I just thought of this. And yeah, I posted.
Yeah, and your team goes, Oh, God, he didn't run that by me. Yeah. So you got, I get that you're still you say that you're still a startup. And in a lot of ways, I'm sure you are, however, your 250 some 200 some odd people now. There is a post that you had about five months ago, where you say it's the the job of the CEO isn't to keep everybody happy. And I was wondering if you could maybe elaborate a little bit more on what does the CEO of a 250 person company do? And what what is your role nowadays?
Yeah, you know, change, it changes, like, pretty frame, it's certainly changed on like a, you know, monthly or every few months for me, for the last couple years now, at our stage, you know, I think one of the important things I found is I still like, setting the like product, direction and strategy. So being like, hey, how do what are the what are the invest? What are the bets that we're placing? And how much are we willing to invest to? To learn, like, what we're what we're really trying to do is say, okay, our product strategy is we're expanding, you know, we're expanding into new markets, we're expanding into new product offerings, what's the shortest path to first figure out? Should we be playing in this market? Should we be offering this product? Right? It could be a market segment, it could be geography, it could be market size, or customer type, or it could be a new product offering? How do we make those investments and, and in success? How did those tie together? Like, how do we make sure we're not just a conglomerate of disparate products, but actually, like there's a cohesive strategy around it? And how do I remove the constraints I think a lot of people have. They're like, Oh, well, we couldn't do this, because we don't have enough people, right? Or we couldn't do this because there's a financial burden, or there's a legal regulatory burden, or there's a, you know, some other technical barrier. And I think many startups assume constraints. And what we want to do is choose our constraints. So it's like, Okay, look, we're gonna push the constraint and say, Okay, well, no, that's illegal. So we can't do that, right, or like, that's like, that would cost us $100 million. So we can't do that. But like, let's actually actively say, that's the constraint instead of, you know, and then and then everything else is is unconstrained. And so we can solve the problem around that. So that's the strategy part of my job. But I would say that the more important part of my job is the people side, which is just like, putting people in the right roles, and actually making sure that all of our people are, are actually in the right. shells. We just got off another podcast, that thing.
you know, I think I think that's, that's the, that's actually maybe the most fun is like, think of like building a company as a jigsaw puzzle, or building a team and an organization around like, hey, you've got a jigsaw puzzle, and everybody's like, a different piece. And it's so satisfying when you when you fit the right person in the perfectly right role, or when you design the right role around somebody's specific skillsets and what they're uniquely qualified to do. And it's constantly evolving because the needs of the company are evolving. And so, you know, like shuffling around roles and responsibilities in organizations. It's a very fun and satisfying part of my job that I think I'll probably always always love doing.
Yeah, well, she's in the background. So it made me think Give it how did how did you guys put up those roles nowadays? Like what you do product and people? is Michelle focused on sales partnerships?
Yeah, I'd say like, you know, we're we make a pretty good team. So when, like, will will tag team a lot of stuff that are really important. So like very important partnerships, very important fundraising efforts, very important hires. But for the most part, like Michelle's like, superpower is just building external relationships, whether that's with media, or journalists or partners. And I think that's like, that's one of our incredible strengths. The other thing that she's really good at, she's gonna, like, keep me honest here.
I was just right in front of you. So you better I know, they're right. Are we good
at something, she's also just a wonderful human being. But to see you guys, podcast, recording. So So anyways, her other real strength is, is she can like, she could smell smoke, right? So if you think about our different backgrounds, I had always been the person at all my company, even before I was a founder, I was a person raising money. And so like, that was my job was tell the story, raise capital, and I'd always been part of venture backed startups. So it was like, go go go biggest possible vision, you know, like, make a bunch of mistakes along the way, we burn capital, like, you know, we trade trade capital for speed. And Michelle was bootstrapping over previous businesses. And so she's always the one that's like, hey, this seems this seems wrong. So she also looks over, like financing stuff. And she's basically like, hey, this seems weird, like, these numbers don't line up, like our payback period is too long here. And so she's really good at sort of like smelling the smoke. And then we come together and sort of solve the problem. And then yeah, what I love doing is the product vision, the direction and then the people and organization stuff, and putting people in the right roles and setting them up for success. And so those are the were the areas that we sort of break down on, but there's a lot of overlap. There's a lot of trade offs, you know, depending on depending on what the company needs, or what time is,
it's, uh, I love what you guys are doing. And everybody on the team that there's like two companies that seem to be have a really good stranglehold on talent right now in Canada, it seems to be Shopify and clearbank. And I see more and more names, the names getting updated, have, I've joined clearbank, or I've joined Shopify. So whatever you're doing, if people are the most important thing, it seems like you're just getting all amazing people, everybody that I talked to you on either the recruiting team or the sales side, they're just just a great team that's in it like they are so in it with you guys right now. So you you've got a great, you got a great thing going, it seems at least from the outside,
now. Appreciate it. Appreciate it. It is. That's good. That means that's good company to be in for sure. And I've been super impressed with, with what what Shopify is done until we get an Adobe in early from the very early days, and they've done it done an excellent job and building their team. And, and then you know, when you when you have the right people in the right roles, and you're pointed at the right market, you know, good things happen. Right. So we've we've taken certainly a page out of their book in terms of how we how we think about building our team.
Yeah, great. Well,
I want to save some time for questions from students. So Alex, I haven't I haven't opened it up yet. But what do you see has been voted the most here that we should ask Andrew,
one question that has a lot of reactions is Felix's question? I feel like? Do you want to ask it? Or I can ask it?
Sorry. One sec. Yeah, I guess my question, you worked both professionally industry as a consultant, and then also, obviously, starting your own company. And I guess probably why my question got a lot of reactions was the way that I worded it. As a person that's both been an employer, employee and an employer. What do you think truly sets apart? Those received paychecks and those that write them?
Um, that's a good. I mean, look, I think, what sets apart the people that receipts are good, it's a good, it's a good question. I think it's a journey, right? And I think through if you talk to most entrepreneurs, they float in and out of those, and like, to be honest, we all sort of like, you know, like, I have a board, and I have investors, and I have customers, right? And like, without all of those, like, that's my paycheck, right? And so it's really about like the level of risk appetite, the level of it's, it's, it's like the level of conviction and risk appetite that you have. So if you if you're like, Look, here's a thing that doesn't exist in the world that I need to go and create. And I'm going to go, I'm going to go build it no matter what, then your job is then to evangelize and find other people who are going to come along that journey, as customers as investors as employees and as team members. And that's really what I had a clear rank was like, a high level of conviction that founders and entrepreneurs you know, like, the way that capitalist information and opportunity is allocated to them is really unfair in today's world, where there's much more data and And sort of like the nepotistic world of like venture capital, or banks or whatever, it shouldn't exist anymore. So that was the conviction. And we thought, you know, I thought we were, as a team, and as a founding team, we're really well positioned to go solve it, to me why I didn't have that conviction on other things. And so what I did was through that process, when I did get excited about a business, you know, I was really excited with education technology. And my mom was a teacher, my grandfather was a teacher, I saw the impact that technology will have in the classroom, or with the context, I mean, early in my career, and, and I met the team at top hat. And like, I was like, Okay, this, this could have a major, major impact. And so then it was just about, you know, you know, I think it's, it's almost always easier to find somebody else who's solving the same problem you're incredibly passionate about, and then just join the cause, then try and start something new or to try and start a sort of copycat. So I would say, the only time that it really, really makes sense to start something new, is when you have the level of conviction about something specific in the world that you want to see that isn't being worked on? Or is it being worked on the way that you think it should be? And you think you're the right person to go do it. And I think that's, that's probably the difference, and that that happens at different points in people's lives and careers. And sometimes you go back, you know, so I could imagine myself and future state being like, hey, actually, you know, I'm excited about joining somebody else's vision. But But I think, you know, I don't think it's a I don't think there's like you're born one way or another Right. Yeah. Nice. Thank you. Alex, what
else is in there?
Is he do you want to ask your question?
Yes. Um, thank you so much for coming to speak just today. Andrew, I think you kind of answered half of my questions. I'm just going to modify it a little bit. But I'm just wondering, in your recent rapid expansion of clear banks team, how have you managed to instill and maintain a consistent culture?
Yeah, I and look, I don't think I've done a perfect job. For sure. Like we've you know, we've we've focused on growth too much and, and haven't been as vigilant but I think it's, it's, it comes down to like vigilance. Right. It's like just being honest with yourself, I think it can be very, like it's a it's a, it's a big ego hit to realize that your culture is is devolving right or like is even one dimension of it is not going in the direction that you want. So it's hard to admit sometimes. But that's like the first step, right of like, admitting you have a problem, and then be like, hey, like, you know, that we used to operate in this way, we all liked it. And now we're starting to see whether it's politics, or bureaucracy, or gossip, like all of these things that can work their way in and are, you know, natural ways that humans evolve in groups that you kind of want to actively fight against sometimes. So step one is like calling it out, like, hey, look, this is happening, getting to the root cause of why it's happening being like, yet, like taking that ego head of like, yeah, you know, I presided over us, you know, losing this or losing partially losing this dimension of our culture that was important to us. And so taking responsibility for like, Okay, how do I, you know, how do we fix it, and sometimes it's a few conversations, sometimes some people that, you know, we're with you, for part of the journey are no longer good fit for the next phase. So a lot of times, it's changing the way that I interact with the organization and sort of looking internally. But I think it starts with just being very, very honest about the current state of the culture of the company, and the trajectory of the culture and the dimensions of the culture that may not be going in the direction that we want and correcting and quickly.
Well, thank you so much.
Yeah, for sure.
keep you on Alex.
Hey, Andrew, thanks for coming today. So I've heard that a great way to incentivize early performance is to share ownership with your initial team members. And I'm wondering if this is something you did at clear bank? How did you decide which really team members to give ownership to?
And was it effective and motivating the team? Yeah, I mean, our philosophy has been like everybody should be an owner of some some capacity. So it depends on obviously, like, it's reflective of how much risk you're taking on the business or what stage you're you joined, and then sort of what you're, you know, what, what the impact is of the company and so like, in what role and what impact but, yeah, we've been, we've been a big proponent from the very beginning of everybody having some stake in the company and some some sort of stock options. We continue to continue to do that, as we've scaled, obviously, the level of ownership, you know, reduces as the company grows. But, you know, our hope is that it's still a very good investment for people because, you know, there's still a lot of growth to do as a company. We've we've only scratched the surface of what our, you know, ambitions against our mission are.
Do you want to ask your question?
Sure. So my question was, I noticed from that initial bio when the team's introduction of you that you are an investor. So what I wanted to know is there a specific characteristic you look for in the teams or the companies that you Invest in that you believe translates to future?
Yeah. So it's a really good question. I think there's so there's two ways like, we started clearbank to take the bias. So let me start with let me start with the way that I invest, like all of the investments that I've made have been of people that I've known, like, for years, right. So Mike Kachin, and I worked together at McKinsey, we both moved down to San Francisco, pretty soon after each other stayed friends there, move back to Toronto, within about a year of each other. And we would chat as he was starting wealthsimple. And so I didn't really like didn't really matter what he was going to do. When he when he said he was gonna start a company, I was gonna invest in him, Alia, to retail, we actually shared an apartment in Toronto, when I was commuting from San Francisco to Toronto, he was commuting from Waterloo to Toronto. And so same thing, he was like, Hey, I'm racing around. And so I was like, and basically, what I would do is help them help them find investors, and then write a small check into their, into their companies. So, you know, it was all sort of personal relationships, which was my angel investing. But then I think what I realized was, when we started clearing, Michelle, and I were like, should we start another venture fund, right, and you know, because we like investing, we like supporting entrepreneurs, and then just realize that, we would just be perpetuating the same thing, if we were, if we were to build another VC, it would be, we would be investing in people that we knew, right? And we'd be building relationships, and we'll be limited to our network, and you know, the profiles of people that we meet that we get to know, and our sort of limited exposure to the world. And so what we really wanted to do is take a completely different paradigm and say, let's just let the data do its job. I don't care what your background is, I don't care what you know, like, what you look like, or what school you went to where you grew up, I don't care what your product is, like, you know, we've got people that have like, hair extension products, and like sex toy products, and all like, you know, like, like, but look, if you've got a great product, and your customers love your product, and you've got an efficient way to find them, then like, why should I have to pass judgment on it, we should just be able to fund you. And so that's been been, you know, part of the mission. And so we try to separate that. So my personal investing is people that I you know, trust implicitly, regardless of what they work on betting, betting on the people, and then through clearbank, it's it's all data driven. And it's just about like, you know, do you have a good business, regardless of,
you know, your background?
Andrew, your question? It's getting a lot of reactions.
Yeah. Hello, Andrew. Thanks for joining us today. My question was, are there any criticisms that you've received on the clearbank? model? And how would you respond to those criticisms? So one that I was thinking of is, since you're you're not taking equity, you're just taking a percentage of revenue until the investments returned? Plus that I think, six to 12% fee? Has there been criticism that you might be taking, like a short term, kind of like cash squeeze approach to the businesses you're investing in? Rather than, like a long term value approach? Yeah.
I don't know if we've gotten that exact question. But I think I think it is certainly part of the model that like when when people do have an opportunity to invest in a short term opportunity to invest in marketing or inventory, then then we can be a very effective solution there. Our goal is to be a long term partner. And so what we try and do is actually, you know, we almost want to create capital, in like a SaaS product. So like, every month, we keep your, your budget funded. And so that's a big part of part of our goal is, you know, it's not just a short term capital injection, it's actually part of a plan that we establish with our customers. But yeah, I mean, look, I think one thing that we realized is, is actually, you know, there's a lot of opportunity, and there's a lot of customers who we'd love to have a longer term relationship with. And so we're starting to develop and design longer term products, for us to really establish a partnership. I think for you know, when you're designing a risk capital product, like when we built it, you know, we had to do very, very short duration, like when we started, we were funding Uber drivers for like, three or four days at a time. And then we're funny Airbnb hosts for like, a month at a time and our funny ecommerce businesses for about six months, and now we're starting to fund software companies for a year or two, like, so we're actually starting to, you know, and it just allows us to continue to build on our model and evolve it. If we had started by saying, Hey, we're gonna do a five year, you know, equity investment or, you know, five year term loan or something like that. It would have taken it like, it's really about the speed to the speed of learning that we're trying to optimize.
I thought it was interesting. You just mentioned it briefly, that in your infancy, your team actually lived together in San Francisco. And I was curious on kind of the impact that that had, whether it was really instilling those kind of team family values, or did it pose any challenges for you and actually ever getting to have a shred of work like,
balance and navigating that?
Yeah, I mean, I think
it was a look, I mean, I guess, when you're starting a company like I think I think there's very little like work life balance that, like, I think you just have to sort of agree that like, we're gonna, we're gonna be all in on this. And it was fun. Like, the nice thing is, we all everybody was all in, right, everybody was really excited about what we were doing. And so we would still, like, we'd go out to dinner, and we'd go out and explore, we, you know, I live in San Francisco before most of the rest of team hadn't. And so we would go and explore, and we go for drinks. And like, you know, we wouldn't just sit down and work all the time. But we were always kind of on, like, we were always sort of like talking about stuff or come You know, bouncing around ideas. And to be honest, it's even my life now. Like, you know, I'll it's not it doesn't feel like I'm working all the time. But I always have ideas. And I'm always like, I'm calling people, like, you know, whenever, like, my team will randomly get calls from me at like eight or 10pm. And it's never urgent, so they don't have to, if they're not in the mood, like they know what it's about. They know, it's because I had some crazy ideas I wanted their their thoughts on, if they're not in the mood to chat about it, or they're not able to, it's fine. But like, that's just the way that I think, you know, I'm wired. And I think a lot of founders are just like, they care so much about the mission of what they're doing that they can't really turn it off. Now I think it's important to have a balance and like be healthy and have friends and all of that other relationships and but I think like the idea that you can just shut off yet. It's probably a bit of a fallacy, to be honest.
Gonna get you out of here early. Andrew, we really appreciate your time. More than generous. I know we're heading into q4 super busy, but I thank you for coming in. Appreciate your time. Enjoy some vacation, man.
I will appreciate it. Thanks. All right, take
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