The Entrepreneur Podcast
The Entrepreneur Podcast

Episode · 11 months 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 entrepreneurpodcast. You're invited to listen in on the guest visits, my hustle and gritglass 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 inbusiness school in business school. In it, we invite world class innovatorsand entrepreneurs to talk about topics like motivation, how toe learn, what toprioritize and even how to be happier. In these episodes, you'll hear liveaudio from my classes because, honestly, there's just something different aboutthe energy, excitement and honesty taking place in a live classroomenvironment. So get comfortable. Grab a seat And don't worry. Unlike my realclass, I won't call, call You enjoy Andrew and Clear Bank are the epitomeof how you could do more together than you can alone. Please join us inwelcoming this incredible leader to our class one Michelle describes as avisionary 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 haveto really like to experiment with beard styles. And so you could see my Youcould see the evolution over the years of the different beard styles fordifferent seasons. So I'll say, like the only the only improvement on thatvideo 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'sbeen something that I've experimented with aggressively throat throughout mylife. Well, where does this podcast? Where do we find you now? Where youback home in Toronto. You still on the road? Yeah. So we, uh, we attempted totake a vacation. We realized we were working remotely. We could talk a lotabout remote work. I'm sure we'll get into that here. But we try to take avacation 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 timeof year for us as a company. So we got a couple of days, actually, often thenwe worked from here for most of last week and realized that we were actuallyworking pretty effectively from here. So we decided t extend our stay alittle on DSO. We'll see. So you're catching me in Barbados here. So if yousee a mosquito fly around the screen, that's where it's that's where it'scoming from. Good, good for you guys. I do want to talk about sort of makingmaking life work as an entrepreneur and taking the time that you need. So we'lltalk about that a little bit later on the group did some digging on your biothere, Andrew. And since these air maybe a little bit different from thenormal groups that you talked Thio on podcasts and in some of theseinterviews, these air, you know, fourth year university students that they'realways super interested in hearing like how you got to where you were and whentalking to people who are not so far distance from where they are today. Ithink it be awesome. If you wouldn't mind starting with, like yourentrepreneurial if that is part of the story upbringing and sort of where yougot to where you are today. Yeah, like I don't think I had a very differentlife 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 ideathat, like, you just had to We have to figure out how to make how to makethings work. And so my family was very supportive. But like, overall, if Ineeded 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 Iwanted Thio by anything, I had to figure out a way to earn a living andso are earning. And so, um, you know, called the Mississauga News, which iswhere 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 itwas fired, like, you know, a zai would go around and deliver papers. I put upflyers being like, Hey, I'm, you know, 10 years old and I can, you know, babysit or dog walk or Mullan's or tutor your kids on men Math, like startedstarted doing that and that, You know, that was always sort of part of part ofmy, uh, my life and career. And then I studied engineering. Really? Cause Iloved cars. Like I you know, I was really I was saving up for a car inhigh school. I thought I was gonna build and design cars, loved it,studied engineering, really, with that goal in mind and then, you know, eventhrow 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 orto GM. I learned that I loved I loved building stuff like I was working inrobotic automation and manufacturing plant, but I just felt like you were sofar away from the decisions are getting made about the company and thedirection, you know, being a plan, you know, you know, in a plant and thenworked on a bunch, you know, did a bunch of different interestingengineering roles. Did some work and invest banking worked at McKinsey for alittle bit and through the consulting world was interesting in that you'reinvolved, you're around the strategy right, and you get to see sort of whypeople make decisions and the strategy behind it. But then you're so far awayfrom the actual building. So I figured that I think what I realized in apretty roundabout way is if you like...

...being part of setting the direction andbeing part of the strategy. But you also like getting your hands dirty andhaving ownership and accountability. The only way to do that is in verysmall companies. And so that was what what motivated me to get involved insort 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'swhen I moved out to San Francisco and, you know, ended up joining an earlystage 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 socialcircles seem to start out as consultants, like so many people, startout in the consulting world. What is it about consulting? You think that drawspeople that are either entrepreneurial or builds a skill set that allowspeople to be good entrepreneurs? Yeah. I mean, I don't know if ever so I guessthere's, Ah, I don't know if there's a correlation or causation here. I thinkthere's just a lot of consultants. And so some percentage of consultants endup going and becoming becoming entrepreneurs. I do. You think there'sa few things that I learned one was just getting up to speed on a newindustry or new business very quickly. Like, you know, you're on a four weekproject. 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. Andthen I think there's something with the pace, Like at McKinsey. Basically likeOkay, we had a 7 a.m. meeting, and then it was Okay. Seven am. Believe thatmeeting. Okay, there's a 10 a.m. Meeting with a client. What we're gonnado between 7. 30 and 10 and then after the 10 8, there's a 1 p.m. It isliterally like you're getting four iteration cycles of work done, and it'snot like you're following a prescribed roadmap. You're sort of learning, youknow, 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 ourHere's what we think the market wants. How are we gonna learn and de risk thisassumption as quickly as possible? You know, even if we've got to take, findsome shortcuts, you know, we're not going to do as much building where youdo some more selling and building talking to customers and things likethat. So, you know, I found that really effective teams operate sort of likededicated consulting teams because they just have they remove all the otherconstraints. And just like okay, if I could get four iterated for learningcycles or four iterations done in a day, then I'm moving it. You know the wayfaster speed than what most companies were able Thio so But you didn't goright from consulting to starting your own thing. You joined some startupsbefore that, right? Yeah. You know, I think this is one of the This is one ofthe 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 ownthing rather than McCain's. Because I felt like Okay, Well, yes, I've hadsuccess, but really, it was because I had the McKinsey brand name, right. AndI 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, youknow, joining a new early stage company. And I ended up meeting, meeting aninvestor named Timothy, was head of growth of Facebook at the time andended up starting a fund called Social Capital. And he had invested in anumber 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 oFacebook. Then join in early stage startup that end up failing. But from alearning perspective, I think I think it was a deliberate choice you wereoptimizing for learning. That's right. Exactly, Exactly. So that was and itwas a company called top prospect. It was cool, I mean, and it was one ofinterest in horses, first seed investments, and we had a but we had agreat roster investors. I learned that great investors don't necessarily makea successful company, you know, despite what they market. And and then Ilearned, I think the biggest thing and this is this was the beginning of as aswhat I thought about building what we built for Clear Bank is I realized thatall of these founders in Silicon Valley that you read about in TechCrunch andyou read about in the Wall Street Journal and stuff they're no differentthan entrepreneurs anywhere else in the world. They just happen to have accessto 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 metthe founders of Instagram when they were still bourbon before they hadpivoted to build Instagram. I met the founders of Slack before when they werestill building tiny speck, which was like a mobile game that didn't workbefore. They pivoted to slack, and everybody's just trying to figure itout. And I think that was one of the interesting things. Like I alwaysthought, my friend, that was starting companies out of Waterloo. We're, like,somehow different than you know, these people that I would read about. Andthen I met them and I was like, No, there's actually not that big of adifference. They just you know, it's proximity in a lot of ways. And so thatwas a big part of the mission for Clear Bank was, can we reduce that barrier ofproximity or social circle like, did you go to Stanford with this person, ordoes your father know the right person to get access Thio that opportunity inthat capital? And that was a big part of motivation. Cool. So I want totransition quickly into our class.

Today is about teams and leveragingteams, and how to do more with teams than you'd ever be able to alone. Sohow 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 thespecifics because a lot of these this is arguably the most entrepreneurialgroup at Ivy. And they've had no shortage of conversations around theambiguous talk of, like, culture in big companies. But, like, literally, whenit'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 culturefrom 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. Welived in a house together, and we did that for the first eight months of thecompany. And that sort of set the foundation for the way we work becausewe basically just worked at, like we worked at the speed of the customer andwe worked out, you know, it was that consulting. Sort of like what I talkedabout that iteration cycle. The other important thing is our customers arefounders, right? Our customers are entrepreneurs. And so what we what wefound really early is we have to think of every person who joins our team isbeing found like they need to be like, I don't know. You guys have read theLululemon Chip Wilson's book. But like when they hired people, whether thoserestore associates or people in head office, they hired their customer right.They hired people who were into fitness and athletics. And you know this leadyet like yoga and all of this stuff at the early early days. And when you hireyour customer like you, just like it's a huge, huge advantage, right? You'rejust like you don't have to do all of the like customer discovery, whereeverybody just hate, innately, thinks and breathes and empathizes it. And soso 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 anonprofit that could be somebody started a club that could be somebodywho wants to be a founder or comes from an entrepreneur family. But the way wethink about it is everybody has their founder story, right? Like this isactually 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 youbuild? What do you wanna build right? What, like clear bank is going to bepart of your entrepreneurial journey. But you are. You should think ofyourself as an entrepreneur, and we maybe you're launching point. We maybe,You know, we have people who have started companies, you know, raise themoney 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 byfounders for founders. And so that's a big part of it. And then, yeah, wecould go into, you know, the specifics around, like our culture and values andstuff like that. But see, that's one of the big foundational elements of of whowe hire and how we how we treat them. And so did you. It's funny, like theexample that I used in class and the example everybody talks about isNetflix and their culture, doc, right? The fact that they actually wrote itdown. 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 asuccessful company. And like, do all the other stuff, you have to do theother 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 youlike, 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 andput 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 themission. Yeah, I think I think I remember one time we started doingthese retreats twice a year, and so the first it sort of happened organicallyway were very small. We we ended up getting an opportunity to move thewhole company to the Yukon for a few weeks. Like the Yukon Government had alike a sponsor of starting a startup in residence program, like, Okay, it wascool on. We did a little off site while we were there, and and that was thefirst time we wrote down our values Was probably like, I don't know, year twoyears into the company. Um, and it was really just writing down what we werealready sort of doing. Naturally, I've never believed in, like writingaspirational values, like, you know, if the values don't don't align withwhat's actually going on, that nobody, nobody pays attention to them or nobodybelieves them. And so what? We really you know, I think maybe the way the wayI reconcile like you know, reads quote there is like being a founder of beingan entrepreneur. You get to choose what you work on with who and like in whatway, right? Like that's the There's a lot of negative stuff about starting acompany, but the positives are you get to choose your day, right. Youbasically get to choose what you work on and who you work with and what typeof environment that ISS. And so you know, that was really what we did waslike, Hey, what? How What? What do we like to work? What way do we like towork? Eso we? The way we describe our values is, uh, it's evolved in thedescription a little bit, but we call it swear, s w A I r. And so speed isthe 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 thisafternoon, why, why wait till next...

Tuesday? Winning is the W. And it's notabout us winning, But it's actually about this idea of like if I'm enteringinto 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 thisdiscussion or this proposal because I'm on your side. And if you don'testablish that, then even the smallest thing, like if I think that you want meto win, then you could actually say a lot of harsh stuff to me, and I'm gonnatake it in. I'm gonna take it with you know, the best intentions. And if Ithink that you've got a a different agenda, it doesn't matter how nice youare to me. I'm not gonna trust anything you say so. So establishing that thateyes very important. The third is authenticity. And it's basically justlike, say what you feel like and you may not need thio like it is reallyabout When something feels wrong, Just say that something feels wrong and feeland be okay with that and being ableto to be to be really with each otheraround that and that comes from winning. If you feel like somebody, if you feellike 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 tobe 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 youknow, for football fans out there, like, if somebody says they're gonna be in acertain spot out there and they're gonna run their out, then you can throwthe ball expecting them to be there. If you need to wait until they're in theposition where they need to be before you throw the ball, it's gonna getintercepted or they're gonna in like so So that's the idea of integrity is ifeverybody says what they're gonna do and then does what they say they'regonna do, you can move much faster as a team, and then the last one are isresponsibility, which is is really like taking extreme ownership of things. Andand again, sometimes we conflict responsibility with blame. And it'slike, Oh, you're responsible for this project failing or you're responsiblefor 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, youknow, people can take responsibility for something they care about in theworld. Even if you could take responsibility for climate change,right, you can take responsibility for social equality doesn't mean you're toblame for it. But this is something I'm going to take responsibility forbecause it matters to me. And so those are the Those are the values that wetalked about as a team and and you know, so the way we operate. Oh, good. So youit seems like you already operated by those things and then explicitly wrotethem down at one of your off sites. It seems like it seems like that's whathappens at those like it's it's always at an offsite like you need to actuallybuild in time, just just hit, pause and stop sprinting and just, like, stinkfor 30 seconds about what you need to work on the business versus in it allthe time. And it's usually in my experience. It was always at the offsites where you actually worked on the important but not urgent things. That'sit. And it's like if we reflect on how we work, what are the things that wereally like that we want to preserve as we scale? Right? And that was sort ofIt's like, Hey, you know, we're 10 people now, like when you know when wegrow, 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 wehave 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 samethe same concept of like, how do we have? What are the things we need Thioactively preserved in our culture. Otherwise, you just sort of devolvedback 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 cadencesthat you have. You've got these by twice annual off sites. Do you still dothat fairly regularly? We do. I mean, we haven't done some since January thisyear. We missed our summer one. So we're trying to figure out how we howand when we can bring them back, but yeah, we've done that now for the lastfour years, uh, company and then cadence around. I know you havecadences around daily stand ups and end of the day, all hands. Do you stilldoing those? Yeah. So So we always did a Monday morning kickoff, the wholecompany and Friday we used to drinks and demos, which was basically likeDemo what you built and grab a drink. And we continue to do that. And we usedhave everybody in the company demo, and that sort of started to take a verylong time and consume a lot of drinks. Eso we we've We've carved it down alittle 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 touchpoint for the whole team. We did that for the first couple of months when wefirst went remote, and then it got to be a lot. And so we've we've way have a5 p.m. Every other Wednesday where we bring in like a guest speaker. We domore of like, you know, town hall type thing. So there's three touchpoints orthere's two points a week in one every other week. Now the whole company andthen each team. Individual teams have their own sort of rituals and cadencesand daily stand ups and things like...

...that as well. The drumbeat to keepthings going. Um, so you've established that you wrote down those values. Canyou talk about your hiring process for how you bring in your people? I've gotto 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 howhe thinks about building his team. But I think you've done a pretty good jobof sort of defining what the interview process to make sure that the peoplethat you're bringing in our either the founders or sort of aligned with thevalues that you guys think are important. So what's your What's yourprocess to make sure that you're bringing in the right people? Yeah, youknow, And we've We've tried a bunch of different variations. I don't know ifwe'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 valuesfit. So we do we get we have everybody submitted video, which is a little bitweird and awkward for folks, but it just gives us, like, a much, muchquicker And especially in today's environment, we're interacting witheverybody over video anyway. It just gives us a very quick glimpse into thepersonality and, you know, the energy and enthusiasm it doesn't like. I getthat some people are, you know, introverted or extroverted, and mayfeel, uh, you know, made It may not present as well, you know, in thatvideo, 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, Ithink that's that's really what we try and suss out through the entireinterview process. You know, we got we do the technical. We make sure thatyou'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 soif people are people can articulate why they're excited about our mission. Whywere uniquely positioned to solve the problems that we're aiming to? And thenwe figure out, sort of like, Do they have that? Do they have that sort of Xfactor being able Thio run through walls and move very quickly and in amuch more sort of chaotic environment. I think it's been, you know, we'restill 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 thenyou lose it a bit and then you expand. You expand what you think of market andyou have to go continue to refund it. We continue to operate in that way. EsoStephen is I love Steven. He's like he is the you know. He comes in with aplan and a playbook, and I've constantly pushed him out of hiscomfort zone to be like, That's great, But like now we have to throw it awayand start over and we've got a really good, good working dynamic to be ableto do that. But, yeah, it's it's been it's been a lot of fun. So do you guyshave 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, Ithink it like what we really try and understand is why, like terms likeunderstand people's life stories, right? Like, what decisions did you make inyour life? How did you feel about decisions and why? You know, why didyou make them and how did you like at the end of the day, our interviewprocess is designed to help, you know, And we've had this feedback from peoplewas like, Oh, actually, like, I either didn't get the job or I realized theinterview process actually don't want this job and I want to go work in adifferent company. And so that should be what it should. That's kind of whatit 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 foryou to win, right? I mean, if you go back to the value of winning. We wanteverybody to interact with the company, Everybody who applies to win,regardless of whether that means you join our company, we want you to end upin the best possible place for you. And so that's sort of the guiding light ofour interview process is really like so it's not. There's not, like a specificsort of question Stephen might have liked actually, some space salesspecific stuff. But from our our recruiting process, we're really tryingto understand is like who you are as a person. What motivates you what, yourwhat your You know what gets you out of bed in the morning and, well, you getout 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 geton boarded. How do you think about giving them the right feedback orcadence around feedback? We had a conversation before you came on aboutradical candor on the idea of it's actually in everyone's best interest tobe able to have those uncomfortable conversations. Is there Ah, way thatyou guys thought through how to make sure that you give each other open andhonest 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 losea little bit. And I think if you don't have a good foundation of trust, thenradical 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 ofwinning and authenticity is really radical candidate radical candor or thelike. The quote word of radical candor...

...can be used as a weapon very easily andlike 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 beI'm just just radical candor, right, like and so people will do thatsometimes, And that's why you need to. Actually, the foundation has to be. Youhave to establish that you want this person to whip right, and they need tobelieve it. Before you could give people any feedback like your first jobis Hey, I'm on your side, right? The reason that I'm telling you this isbecause I actually want and so like this is when when we've had to exitpeople like it's been exactly that. I said, Look, we could keep you hereright 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 anytimesoon where there is a role where you can win here and so, like for your bestinterest, here is the type of role where I like here, the strength that Isee. And here's the role where I think you're gonna be incredibly successfuland like that's actually different than the environment that we're movingtowards that we are right now and you know, we don't always get it right. Butthat's what we strive Thio have in every conversation and every sort oflike coaching conversation or feedback conversation is around like Hey, here'swhat 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, thenmaybe other people are, and that's sort of the That's the tactic that we usearound getting that. Getting that radical candor, right? Yeah. There wasa comment from someone The class here that brutally honest often ends upbecoming more brutal than honest. You know, like that to your point, theexcuse of radical candor is just your free rein. To be a total jerk tosomebody does not. That's not not what it means. You know what I mean? Exactly. I've been following you. Your yourjourney on linked in a bunch, Andrew. And I know you get asked a lot ofquestions about this. I went actually, I was up early this morning and I wentway back. Thio, think seven years ago was your first linked in post. I wentback and I've been watching how it evolved. Like I think it started. Idon't know, like, a lot of us were first starting to test so linked inyour, like sharing other peoples news with no comments, and it then, like uhhey, 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 videosuh, just starting to vocalize some of the things that are going on in clearbank. Um, have you found, like, sort of Maybe you could talk to these? Some ofthe 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 howwhat's your experience? Been starting to share some of those things. And whatare some of the positives and negatives of it? Yeah, it's been It's been a funjourney. It's it's sort of, you know, I used Thio used to a lot of writing, andI think like writing helps me clarify my perspectives on things and whetherthat 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 whatwe've been doing. And I found when we were very small, I had a directrelationship with everybody, right? And so everybody kind of knew like theyknew who I was. The new was on my mind. They knew like when I would saysomething. What the You know the context around that or what I was goingthrough like I might have been distracted. I might have beenfrustrated 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 allhands 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 couldbe something about the business. It could be something about the worldwhat's going on and how you know how it affects us as human beings. But we justsort 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 readinga book or I was listening to podcast, and this is what I realized over theweekend, and here's what I took from it, and I'm gonna share it with you becauseit might be useful for you in your week on. That was really the motivation. Andthen our social media team was like, Hey, can we like, start Thio? Have youthought about sharing some of this stuff external? And that was reallywhat they you know? So it was really taking that broadcast. I realized thatmy job had been become more and more of a broadcast at least Thio most of theteam And so taking that and just Externalizing it and yeah, I wasdefinitely scary. First, it was like, you know, I don't know how people reactI am. I gonna get canceled on my, you know, like it's like, I'm going to saysomething I regret. And, uh, people gonna go back seven years in my postsand be like, Why did you say that? Uh, exactly. But at the end of day, I thinkit's been a really rewarding experience. Has been great for us from a recruitingstandpoint, because people understand sort of some of the rationale on thepeople behind, um, behind our company, and it's been helped really helpful forme. 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 textand, 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 somethingdown. And frankly, I have probably 100 times more notes privately than I everwrite 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 aroundsome issues has been super helpful for me. I'm not as frequent or as highquality 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 hardto find the time, but I think when I do, it's like I find it very rewarding, andI think I mawr the more I use it as an internal sort of exercise instead of itbeing like a performative exercise, which is, I think, what a lot like whata lot of social media is And what you know, you're naturally when I'm, youknow, we're naturally sort of tend towards is like Okay, I've gotta It'sgotta be fully polished and it's got to be thought through in every angle andall of that stuff when really it's just like I'm just sharing myself as a humanbeing, right? And, you know, Yeah, when I looked at, I have no didn't do thedata to support it. But if I look at the ones that you filmed yourselfversus the ones that were like have a higher production value, I don't Idon'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 onesthat you're literally holding your phone and just here's the thing on mymind gets way, Mawr reactions or responses than the ones that areprofessionally filmed. Yeah, yeah, I think you're right. I can ask oursocial media team on that, but I think you're right. I think I think you getway more responses and engagement when it's like, Hey, I just thought of thisAndi 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 astartup in a lot of ways. I'm sure you are. However, your 250 some 200. Someodd people. Now, um, there was a post that you had about five months agowhere you say it's the job of the CEO isn't to keep everybody happy. And Iwondered if you could maybe elaborate a little bit more on what does the CEO ofa 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 monthlyor every few months for me for the last couple of years. Now, at our stage. Youknow, I think one of the important things I found is I still, like settingthe like product, direction and strategy. So being like, Hey, how whatare the what are the invest? What are the bets that we're placing on? Howmuch are we willing to invest, too? To learn, like what we're really trying todo is say Okay, our product strategy is we're expanding. You know, we'reexpanding into new markets were expanding into new product offerings.What's the shortest path to for us to figure out? What should we be playingin this market? Should we be offering this product right? It could be amarket segment. It could be a geography. It could be market size or customertype. Or it could be a new product offering. How do we make thoseinvestments and and in success? How did those tied together like, How do wemake sure we're not just a conglomerate of disparate products, but actuallylike 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 thisbecause we don't have enough people, right? Or we couldn't do this becausethere'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 assumeconstraints, 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'sillegal. 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 saythat's the constraint instead of, you know and then and then everything elseis unconstrained and so we can solve the problem around that. So that's thestrategy part of my job. But I would say, actually, more important, part ofmy job is the people side, which is just like putting people in the right roles andactually 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 Ithink that's that's the other that's actually may be the most fun is like Ithink of like building a company is a jigsaw puzzle of building a team in anorganization around like, Hey, you've got a jigsaw puzzle and everybody islike a different piece, and it's so satisfying when you when you fit theright person in the perfectly right role. Or when you design the right rolearound somebody's specific skill sets and what they're uniquely qualified todio and it's constantly evolving because the needs of the company areevolving. And so, you know, like shuffling around roles andresponsibilities and organizations. It's a very fun and satisfying part ofmy 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 guysput up those roles nowadays? Like what...

...you do product and people? Is Michellefocused on sales partnerships? Yeah, I'd say, like, you know, we're We makea pretty good teams when, like, well, tag team a lot of stuff that air reallyimportant. So, like very important partnerships. Very importantfundraising efforts, very important hires. But for the most part, likeMichelle's, like superpower is just building external relationships,whether that's with media or journalists or partners. And I thinkthat's like That's one of her incredible strength. Three other thingthat she's really good at. She's gonna keep me honest here. I know she's rightin front of you, so you better know, right? Uh, she's also just a wonderfulhuman being. Uh, but a podcast. A recording. Eso So, uh, Anyways, herother real strength is is, um she can like. She could smell smoke, right? Soif you think about our our different backgrounds, I had always been theperson at all my companies. Even before I was a founder, I was a person raisingmoney. And so, like, that was my job was tell the story, raise capital andhad 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 alongthe way we burn capital like, you know, we trade trade capital for speed. AndMichelle was bootstrapped in all of our previous businesses. And so she'salways the one that's like, Hey, this seems this seems wrong. So she alsolooks over like finance and stuff, and she's basically like, Hey, this seemsweird, like these numbers own lineup, like our payback period is too longhere. And so she's really good at, sort of like smelling the smoke. And then wecome together and sort of solve the problem. And then, you know, what Ilove doing is the product vision, the direction and then the people inorganization stuff and putting people in the right roles and setting them upfor 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 ondepending on what the company needs at what time it's Ah, I love what you guysare doing and everybody on the team that there's like two companies thatseem to be have a really good stranglehold on talent right now inCanada, 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 joinedShopify. So whatever you're doing, if people are the most important thing, itseems like you're just getting all amazing people, everybody that I talkedto you on either the recruiting team with sales side there, just just agreat team that's in it like they are so in it with you guys right now. Soyou you've got a great you've got a great thing going. It seems, at leastfrom the outside, no, appreciate it. Appreciate it. It is. That's good. Imean, that's good company to be in for sure. I've been super impressed withwith what what Shopify has done. And Toby got Toby in Harley from the veryearly 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 rightroles 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 howwe how we think about building our team. Yeah. Great. Well, I want to save sometime for questions from students. So, Alex, I haven't I haven't opened it upyet, but what do you see? Has been voted the most here that we should askAndrew. One question that has a lot of reactions is felixes Question e feellike, Do you wanna ask it? Or I can ask it. Okay. Okay. One second. Yeah, Iguess my question. You worked both professionally industry as a consultantand then also obviously starting your own company. And I guess probably whymy 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 thinktruly 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 goodquestion. I think it's a journey right, and I think through if you talk to mostentrepreneurs, they float in and out of those and like it. To be honest, we allsort of like, you know, like I have a board on, I have investors and I havecustomers right? And like without all of those like that's my paycheck righton DSO. It's really about like the level of risk, appetite, the level ofzits, like the level of conviction and risk appetite that you have. So if youif you're like, Look, here's the thing that doesn't exist in the world that Ineed to go and create and I'm going to go, I'm gonna go build it no matterwhat, then your job is then to evangelize and find other people whoare going to come along that journey. Aziz customers as investors, employeesand 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 theway that capital the way that information and opportunity isallocated to them is really unfair in today's world, where there's much moredata and on sort of like the nepotistic...

...world of, like, venture capital orbanks 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 afounding team were, really, well, position to go solve. It took me whileI didn't have that conviction on other things. And so what I did was throughthat process when I did get excited about a business, you know, I wasreally excited Education, technology And my mom was a teacher. Mygrandfather was a teacher. I saw the impact that the technology that youhave in the classroom and work with the Khan Academy early in my career and andI met the team of top hat and like I was like, Okay, this this could have amajor major impact on dso. Then it was just about, you know, You know, I thinkit's It's almost always easier to find somebody else who's solving the sameproblem 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 Iwould say the only time that it it really, really makes sense to startsomething new is when you have the level of conviction about somethingspecific in the world that you want to see that isn't being worked on Or is itbeing worked on the way that you think it should be? And you think you're theright person to go do it? And I think that's that's probably the thedifference and that that happens at different points in people's lives andcareers. And sometimes you go back, you know? So I could imagine myself infuture state being like, Hey, actually, you know, I'm excited about joiningsomebody 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 yourquestion? Yes. Thank you so much for coming to speak to yesterday, Andrew. Ithink you kind of answered half of my questions. I'm just gonna modify it alittle bit. But I'm just wondering, in your recent rapid expansion of ClearBanks team, how have you managed to instill and maintain a consistentculture? Yeah, I and look, I don't think I'vedone a perfect job for sure, Like, you know, we've We've focused on growth toomuch and and and haven't been as vigilant. But I think it's it comesdown to, like vigilance, right? It's like just being honest with yourself. Ithink it can be very like it's a it's Ah, it's a big ego hit to realize thatyour culture is devolving right or like is even one dimension of it is notgoing in the direction that you want, So it's hard to admit sometimes. Butthat's like the first step right of like admitting you have a problem andI'm like, Hey, like you know, is that we used to operate. That's why we allliked it. And now we're starting to see whether it's politics or bureaucracy orgossip. 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 toactively 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 beinglike yeah, like taking that ego hit of like, yeah, you know, I presided overus, you know, losing this or losing partially losing this dimension of ourculture 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 fewconversations. Sometimes some people that you know we're with you for partof the journey are no longer a good fit for the next phase. A lot of times it'schanging the way that I interact with the organization and sort of lookinginternally. But I think it starts with just being very, very honest about thiscurrent state of the culture of the company and the trajectory of theculture and the dimensions of the culture that may not be going in thedirection 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 heardthat a great way to incentivize early performances to share ownership withyour initial team members. And I'm wondering if this is something you dida 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 hasbeen like everybody should be an owner of some some capacity, so it depends onobviously, 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 whatthe impact is of the company and so, like in what Rolande will impact. Butyeah, we've been We've been a big proponent from the very beginning ofeverybody having some stake in the company and, you know, some some sortof stock options. We continue Thio continue Thio to do that as we'vescaled. Obviously, the level of ownership, you know, reduces as thecompany grows. But you know, our hope is that it's still ah very goodinvestment for people because you know, there's still a lot of growth to do asa 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 teamsintroduction of you that you are an investor. So what I wanted to know Isthere a specific characteristic you look for in the teams or the companiesthat you invest in that you believe...

...translates to future six? Yeah. So it'sa really good question. I think there's so there's two ways like we startedClear Bank to take the bias. So let me start with let me start with the waythat I invest. Like all of the investments that I've made have been ofpeople that I've known like for years. Right? So Mike catching and I worktogether at McKinsey. We both moved down to San Francisco pretty soon aftereach other stayed friends. They're moved back to Toronto within about ayear of each other, and we would chat as he was starting with simple and so Ididn't really like it. Didn't really matter what he was going to do when hewhen he said he's gonna start a company, was gonna invest in him. Aaliyah, TulipReally detail. We actually shared a department in Toronto. When I wascommuting from San Francisco to Toronto. He was commuting from Waterloo toToronto, and so the same thing he was like, Hey, I'm raising around. And so Iwas like And basically what I would do is help them help them find investorson, then write a small check into their into their companies. So, you know, itwas all sort of personal relationships, which was my angel investing. But thenI think what I realized was when we started Clear Bank Michelle and I werelike, Should we start another venture fund? Right. And you know, because welike investing like supporting entrepreneurs and then just realizedthat we would just be perpetuating the same thing if we were. If we were tobuild another V C, it would be we would be investing in people that we knewright, and we'd be building relationships and would be limited toour network. And you know, the profiles of people that we meet that we get toknow and are sort of limited exposure to the world. And so we really wantedto do is take a completely different paradigm and say, Let's just let thedata do it Dude, I don't care what your background is. I don't care what youknow, like what you look like or what school you went to where you grew up. Idon'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, youknow, like like but like, Look, if you've got a great product and yourcustomers love your product and you've got an efficient way to find them, thenlike, why should I have to pass judgment on it? We should just be ableto 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 Itrust implicitly, regardless of what they work on. I'm betting, betting onthe people and then through Clear Blanket's all data driven. And it'sjust 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 lotof reactions. Yeah, fellow Andrew, thanks for joining us today. Myquestion was, are there any criticisms that you've received on the clear Bankmodel and how would you respond to those criticisms? So one that I wasthinking of is, since you're not taking equity, you're just taking a percentageof 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 termkind of like cash squeeze approach to the businesses you're investing inrather than, like a long term value approach? Yeah. I don't know if we'vegotten that exact question, but I think I think it is certainly part of themodel that, like when When people do have an opportunity to invest in a in ashort term opportunity to invest in marketing or inventory than then wecould be a very effective solution there. Our goal is to be a long termpartner. And so what we try and do is actually, you know, we almost want tocreate capital and like a SAS products like every month we keep your yourbudget funded. And so that's a big part of part of our goal is you know, it'snot just a short term capital injection. It's actually part of a plan that weestablish with our customers. But yeah, I mean, look, I think one thing that werealize this is actually you know, there's a lot of opportunity andthere's a lot of customers who would love to have a longer term relationshipwith, 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 fundinguber drivers for like, three or four days at a time on we're funding Airbnbhosts for like, a month at a time. Now we're funny commerce businesses forabout six months, and now we're starting to fund software companies fora year or two, like so, we're actually starting toe, you know, and it justallows us to continue to build on our model and evolve it. If we had startedby 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 itlike it's really about the speed Thio speed of learning that were trying tooptimize Abbey. Sure, Yeah, I thought it was interesting. You just mentionedit briefly that in your infancy, your team actually lived together in SanFrancisco. And I was curious on kind of the impact that that had, uh whether itwas really instilling those kind of team family values. Or did it pose anychallenges for you and actually ever getting toe have a shred of work likework like balance and navigating that? Yeah. I mean, I think, um what it waslook, I mean, look as when you're starting a company like I think I thinkthere's very little, like, work, life...

...balance that, like, I think you justhave to sort of agree that, like, we're gonna we're gonna be all in on this ongit 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 stilllike we'd go out to dinner and we'd go out explore. We were you know, I livein San Francisco before, but most of the rest of team hadn't and so we wouldgo and explore and we'd go out for drinks and like, you know, we wouldn'tjust sit down and work all the time, But we were always kind of on, like wewere always sort of like talking about stuff or come, you know, bouncingaround ideas. And to be honest, it's even my life now, like you know, it'snot. 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 teamwill 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'sabout, they know it's because I had some crazy idea I wanted their theirthoughts 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 Ithink a lot of founders air just like they care so much about the mission ofwhat they're doing, that they can't really turn it off. Now. I think it'simportant to have a balance and, like, be healthy and have friends and all ofthat, like other relationships. And But I think, like the idea that you couldjust shut off. Yeah, it's probably a bit of a fallacy, to be honest, I'mgonna get you out of here early. Andrew, we really appreciate your time morethan generous. I know heading into Q four. Super busy. But I thank you forcoming in. I appreciate your time. Enjoy some vacation, man. I willappreciate it. Thanks. All right, take care. You've been listening to the ivyentrepreneur podcast toe. Ensure that you never miss an episode. Subscribe tothe show in your favorite podcast player or visit ivy dot c a forwardslash entrepreneurship. Thank you so much for listening until next time.

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