The Entrepreneur Podcast
The Entrepreneur Podcast

Episode · 2 years ago

32. Building a Startup for Startups with Andrew D'Souza of Clearbanc

ABOUT THIS EPISODE

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.

...thats new Siris of the Ivy entrepreneur podcast. You're invited to listen in on the guest visits, my hustle and grit glass taking place virtually at the Ivey Business School. Hustling great is, of 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 toe 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. So get comfortable. Grab a seat And don't worry. Unlike my real class, I won't call, call You enjoy Andrew and Clear Bank 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 s Andrew. What do you think, man? Man, that's awesome. I don't think I've ever been introduced like that. That is, uh 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 could see my You could 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 is involved. It is involved with my career. It's been something that I've experimented with aggressively throat throughout my life. Well, where does this podcast? Where do we find you now? Where you back home in Toronto. You still on the road? Yeah. So we, uh, we attempted to take a vacation. We realized we were working remotely. We could talk a lot about remote work. I'm sure we'll get into that here. But we try to take a vacation to Barbados, which was a bit of a challenge because, like, this is, it's a crazy time, and we're coming into Q four, which is the busiest time of year for us as a company. So we got a couple of days, actually, often then we worked from here for most of last week and realized that we were actually working pretty effectively from here. So we decided t extend our stay a little on DSO. We'll see. So you're catching me in Barbados here. So if you see a mosquito fly 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 air maybe a little bit different from the normal groups that you talked Thio on podcasts and in some of these interviews, these air, you know, fourth year university students that they're always super interested in hearing like 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 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 than probably most of people on this call, you know, grew up. You know, born in India, moved, Teoh moved 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 have to figure out how to make how to make things work. And so my family was very supportive. But like, overall, if I needed to, I wanted to buy CDs or go to the movies or hang out with my friend. I don't know if you guys don't know what CDs are, but, you know, if I if I wanted Thio by anything, I had to figure out a way to earn a living and so are earning. And so, um, you know, called the Mississauga News, which is where I grew up, and convince them toe let me let me start the paper route. They weren't delivering my neighborhood, so that was the first step. And then it was fired, like, you know, a zai would go around and deliver papers. I put up flyers being like, Hey, I'm, you know, 10 years old and I can, you know, baby sit or dog walk or Mullan's or tutor your kids on men Math, like started started doing that and that, You know, that was always sort of part of part of my, uh, my life and career. And then I studied engineering. Really? Cause I loved cars. Like I you know, I was really I was saving up for a car in high school. I thought I was gonna build and design cars, loved it, studied engineering, really, with that goal in mind and then, you know, even throw 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 a So I worked in or to GM. I learned that I loved I loved building stuff like I was working in robotic automation and 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 plan, you know, you know, in a plant and then worked on a bunch, you know, did a bunch of different interesting engineering roles. Did some work and invest banking worked at McKinsey for a little bit and through the consulting world was interesting in that you're involved, you're around the strategy right, and 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 in entrepreneurial world? Because, you know, that's that. That was the that was the opportunity for for Meteo Do that. And so that's when I moved out to San Francisco and, you know, ended up joining an early stage startup on duh. And that was that was the beginning of my journey here. So why is it it seems like seeing 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 don't know if ever so I guess there's, Ah, 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 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, a now er and a half to like. Okay, let me let me let me figure this out. And then I think there's something with the pace, Like at McKinsey. Basically like Okay, we had a 7 a.m. meeting, and then it was Okay. Seven am. Believe that meeting. Okay, there's a 10 a.m. Meeting with a client. What we're gonna do between 7. 30 and 10 and then after the 10 8, there's a 1 p.m. It is 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 OK? Here's our Here's what we think the market wants. How are we gonna 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 you do some more selling and building talking to customers and things like that. So, you know, I found 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 could get four iterated for learning cycles or four iterations done in a day, then I'm moving it. You know the way faster speed than what most companies were able Thio so But you didn't go right from consulting to starting your own thing. You joined some startups before that, right? Yeah. You know, I think this is one of the This is one of the secrets of consulting firms. Is they? Yeah, I don't have the confidence. I probably have the skills, but don't have the confidence to go start my own thing rather than McCain's. 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 new early stage company. And I ended up meeting, meeting an investor named Timothy, was head of growth of Facebook at the time and ended up starting a fund called Social Capital. And he had 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 at, like, 1000 people. And I think you know, financially would have been more lucrative for me to join pre I. P o Facebook. Then join in early stage startup that end up failing. But from a learning perspective, I think I think it was a deliberate choice you were optimizing for learning. That's right. Exactly, Exactly. So that was and it was a company called top prospect. It was cool, I mean, and it was one of interest in horses, first seed investments, and we had a but we had a great roster 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 was the beginning of as as what I thought about building what we built for Clear Bank 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 had 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 friend, that was starting companies out of Waterloo. We're, 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 you know, it's proximity in a lot of ways. And so that was a big part of the mission for Clear Bank was, 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 Thio that opportunity in that capital? And that was a big part of motivation. Cool. So I want to transition 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. And they've had no shortage 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 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 out, 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 is being found like they need to be like, I don't know. You guys have read the Lululemon Chip Wilson's book. But like when they hired people, whether those restore associates or people in head office, they hired their customer right. They hired people who were into fitness and athletics. And you know this lead yet like yoga and all of this stuff at the early early days. And when you hire your customer like you, just like it's a huge, huge advantage, right? You're just like you don't have to do all of the like customer discovery, where everybody just hate, innately, thinks and breathes 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 could be somebody who started a nonprofit that could be somebody started a club that could be somebody who wants to be a founder or comes from an entrepreneur 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 on boarding is like, Okay, let's talk about, like, what is your What did you found? What did you build? What do you wanna build right? What, like clear bank is going to be part of your entrepreneurial journey. But you are. You should think of yourself as an entrepreneur, and we maybe you're launching point. We maybe, You know, we have people who have started companies, you know, raise the money and then failed, then joined our company. We've got the entire spectrum, but everybody thinks of themselves, as you know, where a company built by founders for founders. And so that's a big part of it. And then, yeah, we could go into, you know, the specifics around, like our culture and values and stuff like that. But see, 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't make it through 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 you 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 due 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 it sort of happened organically way 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 a like a sponsor of starting a startup in residence program, like, Okay, it was cool on. 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, year two years into the company. Um, 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, if the values don't don't align with what's actually going on, that 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 of 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 ISS. 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? Eso we? The way we describe our values is, uh, it's evolved in the description a little bit, but we call it swear, s w A I r. And so speed is the first one. It's like what? We just we wanna we want to move very quickly. And it's exactly that. Like, if you know, if you could do something this afternoon, why, 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 into a 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 think that you want me to win, then you could actually say a lot of harsh stuff to me, and I'm gonna take it in. I'm gonna take it with you know, the best intentions. And if I think that you've got a a different agenda, it doesn't matter how nice you are to me. I'm not gonna trust anything you say so. So establishing that that eyes very important. The third is authenticity. And it's basically just like, say what you feel like and you may not need thio like it is really about When something feels wrong, Just say that something feels wrong and feel and be okay with that and being ableto to be to be really 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. 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 on. We need to be. We're continuing. Thio encourage that integrity which is not about morality, but really about doing what you say you're gonna dio. And so it's like you know, for football fans out there, like, if somebody says they're gonna be in a certain spot out there and they're gonna run their out, 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 gonna get intercepted or they're gonna in like so So that's the idea of integrity is if everybody says what they're gonna do and then does what they say they're gonna 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 and again, sometimes we conflict 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 wanna we wanna 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 you could 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 I'm going to take responsibility for because it matters to me. And so those are the Those are the values that we talked about as a team and and you know, so the way we operate. Oh, good. So you it seems like you already operated by those things and then explicitly wrote them down at one of your off sites. It seems like it seems like that's what happens at those like it's it's always at an offsite like you need to actually build in time, just just hit, pause and stop sprinting and just, like, stink for 30 seconds about what you need to work on the business versus in it 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, what are 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 250 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, bringing them back. And then as we continue to grow, it is it's the same the same concept of like, how do we have? What are the things we need Thio actively preserved in our culture. Otherwise, you just sort of devolved back to the mean. Yeah. Can you talk about talk about cadence for a second, then? And the importance of team? Because it sounds like one cadences that you have. You've got these by twice annual off sites. Do you still do that fairly regularly? We do. I mean, we haven't done some 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, uh, 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 drinks and demos, which was basically like Demo what you built and grab a drink. And we continue to do that. And we used have everybody in the company demo, and that sort of started to take a very long time and consume a lot of drinks. Eso we we've We've carved it down a little bit, but it's still the same cadence. And then every when covert hit, we used to go 5 p.m. close. You know, end of day sort of sync up Just 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 way have a 5 p.m. 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 touchpoints or there's two points a week in 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 drumbeat to keep things going. Um, so you've established that you wrote down those values. Can you talk about your hiring process for how you bring in your people? I've got to know Stephen Delfina, 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 our 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, you know, And we've We've tried a bunch of different variations. I don't know if we've got it perfect, perfect, but I think we're we've got a really good hit, right on the caliber of people that we hire and and the 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, we're interacting with everybody over video anyway. It just gives us a very quick glimpse into the personality and, you know, the energy and enthusiasm it doesn't like. I get that some people are, you know, introverted or extroverted, and may feel, uh, you know, made It may not present as well, you know, in that video, and we don't want to be able 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 Rolande 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 weaken, 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 were 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 being able Thio 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, you know, product market fit is not like a It's not like a destination. It's sort of like a 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 refund it. We continue to operate in that way. Eso Stephen is I love Steven. He's like he is the you know. He comes in with a plan and a playbook, and I've constantly pushed him out of his comfort zone to 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 it's been it's been a lot of fun. So do you guys have specific, like questions or do you Do you run them through scenarios like, How do you actually suss out whether they're the right people? You know, I think it like what 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 decisions and why? You know, why did you make them and how did you like at the end of the day, our interview process is designed to help, you know, And we've had this feedback from people was like, Oh, actually, like, I either didn't get the job or I realized the interview process 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 gonna be the place for you to win, right? I mean, if you go back to the value of winning. We want everybody to interact 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 process is really like so it's not. There's not, like a specific sort of question Stephen might have liked actually, some space sales specific stuff. But from our 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 out of bed in the morning and, well, you get out of bed every morning to do the job that that we're hiring you for. Yeah, got it. So if we move on, say they're 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 on the idea of it's actually in everyone's best interest to be able to have those uncomfortable conversations. Is there Ah, way that you guys thought through how to make sure that you give each other open and honest feedback so that you could be better. Yeah, it's It's something again. It's one of these things that way 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, then 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 candidate radical candor or the like. 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 you need to. Actually, the foundation has to be. You have to establish that you want this person to whip right, and they need to believe it. Before you could 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 want and so like this is when when we've had to exit people like it's been exactly that. I said, Look, we could keep you here right and we could continue to coach you and we could 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 best interest, here is the type of role where I like here, the strength that I see. And here's the role where I think you're gonna 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 Thio 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 could disagree. But it said, Look, here's what I've observed right, like if I'm 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? Yeah. There was a comment from someone 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 does not. That's not not what it means. You know what I mean? Exactly. I've been following you. Your your journey on linked in 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. Thio, think seven years ago was your first linked in post. I went back 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 so linked in your, like sharing other peoples news with no comments, and it then, like uh 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 uh, just starting to vocalize some of the things that are going on in clear bank. Um, 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 how what's your experience? Been 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 it's sort of, you know, I used Thio used to a lot of writing, and I think like writing helps me clarify my perspectives on things and whether that strategy with its culture, hiring, like putting your stuff out there, actually forces you to take a stand and take a position on the topic. What 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. The new was on my mind. They knew like when I would say something. What the 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, 1 to 1 or two way conversation with everybody. And so, 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 that, you know, I realized over the weekend I was reading a book or I was listening to podcast, 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 on. That was really the motivation. And then our social media team was like, Hey, can we like, start Thio? Have you thought about sharing some of this stuff external? 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 Thio most of the team And so taking that and just Externalizing it and yeah, I was definitely scary. First, it was like, you know, I don't know how people react I am. I gonna get canceled on my, you know, like it's like, I'm going to say something I regret. And, uh, people gonna go back seven years in my posts and be like, Why did you say that? Uh, exactly. But at the end of day, I think it's been a really rewarding experience. Has been great for us from a recruiting standpoint, because people understand sort of some of the rationale on the people behind, um, behind our company, and it's been helped really helpful for me. It's been like my version of journaling. Um, she just were like, Okay, let me let me put out my thoughts out there and either in video or text and, uh, and see, you know how people react and start a conversation. Yeah, like you. I think some people do. At...

...least I get I 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 but poster as you are. But it's just helping my clarity of thought. Yeah, I think it's a very good exercise on Did something that I Yeah, 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 mawr 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 Okay, I've gotta It's gotta be fully polished and it's got to be thought through in every angle and all of that stuff when really it's just like I'm just sharing myself as a human being, right? And, 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 filmed 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 mawr responses. I don't know if you you you find that you are It just seems like the ones that you're literally holding your phone and just here's the thing on my mind gets way, Mawr 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 I think you get way more responses and engagement when it's like, Hey, I just thought of this Andi posted. Yeah, and your team goes Oh, God. He didn't run that by me. Um, yeah. So you got I get that. You're still You say that you're still a startup in a lot of ways. I'm sure you are. However, your 250 some 200. Some odd people. Now, um, there was a post that you had about five months ago where you say it's the job of the CEO isn't to keep everybody happy. And I wondered if you could maybe elaborate a little bit more on what does the CEO of a 250 person company do? And what is your role nowadays? Yeah, you know, change. It changes like pretty. It's certainly changed on, like, a monthly or every few months for me for the last couple of 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 what are the what are the invest? What are the bets that we're placing on? How much are we willing to invest, too? To learn, like 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 were expanding into new product offerings. What's the shortest path to for us to figure out? What should we be playing in this market? Should we be offering this product right? It could be a market segment. It could be a 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 tied 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 ah, 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 constraints, 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 unconstrained and so we can solve the problem around that. So that's the strategy part of my job. But I would say, actually, 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. Michelle's just got off another podcast thing. Um, but you know, I think I think that's that's the other that's actually may be the most fun is like I think of like building a company is a jigsaw puzzle of building a team in an organization around like, Hey, you've got a jigsaw puzzle and everybody is 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 skill sets and what they're uniquely qualified to dio and it's constantly evolving because the needs of the company are evolving. And so, you know, like shuffling around roles and responsibilities and organizations. It's a very fun and satisfying part of my job, but I think I'll probably always, always loved doing. Yeah, well, she's in the background, so it made me think of it. How did how do 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 teams when, like, well, tag team a lot of stuff that air 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 her incredible strength. Three other thing that she's really good at. She's gonna keep me honest here. I know she's right in front of you, so you better know, right? Uh, she's also just a wonderful human being. Uh, but a podcast. A recording. Eso So, uh, Anyways, her other real strength is is, um she can like. She could smell smoke, right? So if you think about our our different backgrounds, I had always been the person at all my companies. 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 had always been part of venture backed startups. And 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 bootstrapped in all of our previous businesses. And so she's always the one that's like, Hey, this seems this seems wrong. So she also looks over like finance and stuff, and she's basically like, Hey, this seems weird, like these numbers own lineup, 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, you know, what I love doing is the product vision, the direction and then the people in organization stuff and putting people in the right roles and setting them up for success. And so those are the where the areas that we sort of breakdown on. But there's a lot of overlap is a lot of trade offs, you know, depending on depending on what the company needs at what time it's Ah, 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, and it seems to be Shopify and Clear Bank and I Seymour and more names, the names getting updated of. I've joined Clear Bank 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 with sales side there, 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've got a great thing going. It seems, at least from the outside, no, appreciate it. Appreciate it. It is. That's good. I mean, that's good company to be in for sure. I've been super impressed with with what what Shopify has done. And Toby got Toby in Harley from the very early days. And they've done an excellent job in building their team. And and then, you know, when you when you have the right people in the right roles on your 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 felixes Question e feel like, Do you wanna ask it? Or I can ask it. Okay. Okay. One second. 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 ordered it. A za person, that book being an employer, employee and an employer. What do you think truly sets apart those that received paychecks and those that right thumb? Um, that's a good I mean, look, I think, um, what sets apart of the people that it's a 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 it. To be honest, we all sort of like, you know, like I have a board on, I have investors and I have customers right? And like without all of those like that's my paycheck right on DSO. It's really about like the level of risk, appetite, the level of zits, like the level of conviction and risk appetite that you have. So if you if you're like, Look, here's the thing that doesn't exist in the world that I need to go and create and I'm going to go, I'm gonna 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. Aziz customers as investors, employees and as team members, and that's really what I had to clear Bank was like, Ah, high level of conviction that founders and entrepreneurs, you know, like the way that capital the way that information and opportunity is allocated to them is really unfair in today's world, where there's much more data and on sort of like the nepotistic...

...world of, like, venture capital or banks or whatever, um, shouldn't exist anymore. So that was the conviction. And we thought, you know, I thought we were us as a team and there's a founding team were, really, well, position to go solve. It took me while 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 Education, technology And my mom was a teacher. My grandfather was a teacher. I saw the impact that the technology that you have in the classroom and work with the Khan Academy early in my career and and I met the team of top hat and like I was like, Okay, this this could have a major major impact on dso. 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 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 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 in future state being like, Hey, actually, you know, I'm excited about joining somebody else's vision, but, uh, but I think you know, I don't think it's Ah, I don't think there's like you're born one way or another, right? Yeah. Nice. Thank you, Alex. What else? Easy in there, is he? Do you wanna ask your question? Yes. Thank you so much for coming to speak to yesterday, Andrew. I think you kind of answered half of my questions. I'm just gonna 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, you know, we've We've focused on growth too much and and and haven't been as vigilant. But I think 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 Ah, it's a big ego hit to realize that your culture 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 I'm like, Hey, like you know, is that we used to operate. That's why 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 evolving groups that you kind of want to actively fight against Sometimes. So step one is like calling it out. Hey, look, this is happening. Getting to the root cause of why it's happening being like yeah, like taking that ego hit 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 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 a good fit for the next phase. 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 this 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 it quickly. Well, thank you so much? Yeah, for sure. Keep going, Alex. Max! Hey, Andrew. Thanks for coming today. So I've heard that a great way to incentivize early performances to share ownership with your initial team members. And I'm wondering if this is something you did a clear bank. How did you decide which early team members to give ownership to? And was it effective in 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 are you joined And then sort of what you're you know what what the impact is of the company and so, like in what Rolande will 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, you know, some some sort of stock options. We continue Thio continue Thio 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 ah 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 are, you know, ambitions against our mission. Our, um, tyranny. Do you wanna ask your question? Sure. So my question waas I noticed from that initial bio when the teams 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 six? Yeah. So it's a really good question. I think there's so there's two ways like we started Clear Bank 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 catching and I work together at McKinsey. We both moved down to San Francisco pretty soon after each other stayed friends. They're moved back to Toronto within about a year of each other, and we would chat as he was starting with simple and so I didn't really like it. Didn't really matter what he was going to do when he when he said he's gonna start a company, was gonna invest in him. Aaliyah, Tulip Really detail. We actually shared a department in Toronto. When I was commuting from San Francisco to Toronto. He was commuting from Waterloo to Toronto, and so the same thing he was like, Hey, I'm raising around. And so I was like And basically what I would do is help them help them find investors on, 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 Clear Bank Michelle and I were like, Should we start another venture fund? Right. And you know, because we like investing like supporting entrepreneurs and then just realized that we would just be perpetuating the same thing if we were. If we were to build another V C, it would be we would be investing in people that we knew right, and we'd be building relationships and would be limited to our network. And you know, the profiles of people that we meet that we get to know and are sort of limited exposure to the world. And so we really wanted to do is take a completely different paradigm and say, Let's just let the data do it Dude, 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 like, 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, uh, you know, be part of the mission. And so we try to separate that. So my personal investing is people that I trust implicitly, regardless of what they work on. I'm betting, betting on the people and then through Clear Blanket's all data driven. And it's just about like, you know, do you have a good business, regardless of you know, your background. Thank you. Thanks. Andrew, your question is getting a lot of reactions. Yeah, fellow Andrew, thanks for joining us today. My question was, are there any criticisms that you've received on the clear Bank model and how would you respond to those criticisms? So one that I was thinking of is, since you're not taking equity, you're just taking a percentage of revenue until the investments returned. Plus that I think 6 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 in a short term opportunity to invest in marketing or inventory than then we could 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 and like a SAS products 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 realize this is actually you know, there's a lot of opportunity and there's a lot of customers who would love to have a longer term relationship with, And so we're starting to develop and design longer term products. Um, for us to really establish a partnership, I think for, you know, when you're designing a risk capital product like what we've built, 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 on we're funding Airbnb hosts for like, a month at a time. Now we're funny commerce 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 toe, 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 or, you know, five year term loan or something like that would have taken it like it's really about the speed Thio speed of learning that were trying to optimize Abbey. Sure, Yeah, 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, uh whether it was really instilling those kind of team family values. Or did it pose any challenges for you and actually ever getting toe have a shred of work like work like balance and navigating that? Yeah. I mean, I think, um what it was look, I mean, look as 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 on git was fun. Look, 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 explore. We were you know, I live in San Francisco before, but most of the rest of team hadn't and so we would go and explore and we'd go out 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, 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 for me like eight or 10 p.m. And it's never urgent. So like they don't have if they're not in the mood like they know what it's about, they know it's because I had some crazy idea 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 air 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, like other relationships. And But I think, like the idea that you could just shut off. Yeah, it's probably a bit of a fallacy, to be honest, I'm gonna get you out of here early. Andrew, we really appreciate your time more than generous. I know heading into Q four. Super busy. But I thank you for coming in. I appreciate your time. Enjoy some vacation, man. I will appreciate it. Thanks. All right, take care. You've been listening to the ivy entrepreneur podcast toe. Ensure that you never miss an episode. Subscribe to the show in your favorite podcast player or visit ivy dot c a forward slash entrepreneurship. Thank you so much for listening until next time.

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