S03|03: Building Symend, Overcoming Challenges, and Creating Impact with Hanif Joshaghani

Hanif 00:01
It's not that entrepreneurship is awesome and rewarding. Or by the way, the downside of it is that it’s challenging and tough and mentally draining, and it pushes you. I think those are the bonuses. I think if you're not pushing yourself and challenging yourself in your life, then you're not really living, you're just existing. 

Leah 00:21
Hello and welcome to season three of The Founder Mindset, brought to you by ATB. I'm your host, Leah Sarich, and I'm delighted to be back for another season of talking to Founders about what it's really like to build a company from that first big idea. If you've listened to previous episodes, you know I was a journalist for over 20 years, so I'm more curious about why anyone would ever want to become an entrepreneur, not so much about the business model, product market fit, and so on. I want to understand why entrepreneurs keep going, why they think they're the ones to solve a massive problem, and why they want to make a real impact in the world. And if you're here, I bet you want to know why, too. Let's find out. Joining me today in the studio is Hanif Joshaghani, Co-Founder and CEO of Symend, a FinTech company that uses behavioural science and AI to help large companies like telecommunications and utility giants personalize their customer engagements, guiding them toward paying their overdue bills and more positive financial outcomes.

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Leah 01:24

Hanif, did you like that? I wrote that myself.

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Hanif 01:26

That’s a really good description.

Leah 01:28
It's so nice to have you here in the studio. Thank you for making the time. We really appreciate it. I know you and I have talked about this in the past; it was a few years ago now, but I would love for you to share your journey into actually becoming an entrepreneur. I understand this goes way back for you.

Hanif 01:44
It does. It goes back to this thing where I perform the best when I'm most closely aligned to outcomes, which an entrepreneur ultimately is. More than shareholders, more than executives. It’s like you have this one-to-one relationship between the work that you do and the outcomes that you gain. That goes back to my first entrepreneurial endeavour. I was in high school in New York, on Long Island, and I would take the train to Manhattan and buy fireworks and fake bags and glasses. I did it because I was on a scholarship and I didn't have money. I was in a very wealthy environment where I was one of the few people who didn't have money, and I wanted to keep up with my friends. So I would then make the trip to New York, into Chinatown, then come back and sell to the well-to-do middle-class kids and rich kids in Long Island. That financed my ability to hang out with my friends without having my hand out. That was my first hustle. There were other ones—I built an online bookstore to compete with Barnes & Noble when I was in college. We would buy used books as people graduated, inventory them in warehouses, and set up a SKU and barcode-based online catalogue, without a license from the school, you are selling syllabuses and notes and stuff like that, and Barnes & Noble got really upset and told the administration. It was at the University of Chicago, and they put a cease and desist on our business after two quarters.

Leah 03:24
That's gotta be a bit of a badge of honour, though. 

Hanif 03:27
Yeah, it was pretty cool. My favourite one, and I think that was the one that poked the bear, was we had this one ad we posted all over the dormitories, which was: “Who is Barnes and who is Noble anyway, and why haven't you met them? Sounds shady to me. You know us. Come buy books from us.” It was crazy. We made money for two semesters, then they shut it down.

Leah 03:56
They shut it down. I love it. Did I also hear something about how you helped your dad sell cars?

Hanif 04:01
Yeah. My dad was a mechanic, and in the summers and my off-seasons when I wasn't at school, I would always go back home. He eventually started a dealership, but before he started a dealership, he had a side hustle on top of, not a minimum wage job, but close to it, he would find cars he could fix up and then sell them through the newspapers or by parking them in front of the house. Then I worked with him on the cars. We had classics like Corvettes and Jaguars, and everything up to Mercedes. What we figured out by accident was that I'm really good at selling. The way that happened was… he had branched out, and one of the cars he had out front was a really old Mercedes E-Class, and he had to run to the bathroom. We were renting a room on top of someone else's house, so we didn't have much. He hadn't been able to offload the car. And this was a world where he would park all of his savings in one car, try to flip it, then put it all in the next. It was a very high-risk turnover endeavour to build a bit of a nest egg until he had enough to buy a dealership. He hadn't been able to move this car. It was the most expensive car he'd bought yet… it was all Nissans, Sentras, and Accords, and all of a sudden we’re getting into this Mercedes E-Class, and he had to run to the bathroom. He told me to talk to these people, and they were, I think, Ukrainian or Polish immigrants. I remember this. And before he came back out of the bathroom, I had sold the car. I wasn't even trying to sell it at first. I was talking about how, of all the cars my dad had done, this is the one I loved sitting in, because it just makes you feel special. I talked about the experience of it, and then the guy sat down, looked at his wife, and said he would buy it. I said that if I were in his shoes, I would definitely do it. And so he did it. My dad came out, and the buyer said, “Your son convinced me, I'm going to buy the car.” The deal was struck, they signed the paperwork, went to the DMV, transferred the titles, came home… and my dad was not sentimental, so there were no congratulations. But the thing that was clear to my Mom, observing this in the house from the window, my dad came back into the house, and my mom said, “You should let him sell the cars from now on.” That was another big one for me, when I think about it. Actually, think about it. It was wild. I mean, there was a point at which, and this actually explains a lot… There was a point at which my dad and I couldn't walk into a restaurant without looking at the number of people entering and exiting, what everybody was ordering and being like, could we make money here? It was just that our lens into the world was a P and L lens. It's just… that's the way it is. It’s like a version of the Matrix where everything you see is code. In our world, everything we saw was business. It's like in the lens of business, how does this make sense? And that just became the way I was taught to think, I guess. 

Leah 07:16

It's in your blood. 

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Hanif 07:18

Yeah, yeah, it really is. And you know what? Like my dad, we came here with nothing. We lost everything because of the war and revolutions, and camps, and he didn't have a degree to rely on. And within a couple of years, he'd gone from like heavy-duty mechanic to saving enough money to… his first car we flipped was an old 80s Nissan Sentra… to having his own dealership, and he just relentlessly… There was no clock on, clock off. Hustle became a way of living from the moment you wake up to the moment you go to bed. And of all the things that my dad taught me, I think that's the thing that I carry with me the most. And I'm still like that. There's no endgame, there's no downtime, there's no balance. It's just, it's almost like you're wired and you've been groomed to think about life as a hustle? Yeah, that's a huge part of how I've developed into the person I am today. So I think in some ways I was always going to be an entrepreneur. In some way, I don't think there was any other future for me, honestly. 

Leah  08:26

Wow, that's a great story. So it was in your blood to think in a certain way, and that clearly led you to entrepreneurship. When you start seeing the world that way, I can understand how that makes you do exactly what you're going to do as an entrepreneur. But I think if I've got this correct, you told me once that you actually went into investment banking first.

Hanif  08:45

Yeah, I had scholarships through university and grad school, and coming out of there, I had a strong view that I need credibility and experience, and that I'm not ready… in the thing that high school and university really taught me, because it got me out of my bubble of like, poor income—you know, those immigrant communities and stuff like that, was what the world… because my definition of entrepreneurship was the guy that owned the car wash back in the day, and then you go to high school, and you go to college, and you're hanging out with people, where their lens into the art of the possible and what the world is, what entrepreneurship could be, is on an order of magnitude different. And I just needed to learn more. And I became very convinced of that, and so I went to university. I worked in a bunch of hedge funds in Chicago. I did an MBA. I worked in mergers and acquisitions. I worked in corporate finance. I put in enough time to determine what my core competencies, from an academic perspective, are, and to really narrow the scope of where I want to spend my time, and the next logical step after that was entrepreneurship. I think another really important thing that I learned about myself working in big companies is that companies that are primarily driven by—where success is equally or greater tuned towards political navigation of the org. versus just raw execution, I fail in those companies. I like to think analytically. I was a great banker, but most of my friends who are still good friends with me from investment banking, will back me up on this—I was a terrible investment banker in terms of the kind of investment banker that the bosses would want to promote and advance, even though, from a subject matter perspective, I knew what I was doing so, I didn't really ever fit into this kind of big company. I wanted to just execute, and so, yeah, once I had done enough, I left and started my first company. I think that was around ‘09. And the rest is history.

Leah  11:03

There you go. All right. Well, that takes us to Symend. So tell me about where you came up with the idea for Symend.

Hanif  11:11

It was a convergence of two things. One is like these memories that I carried forward from when I was a kid, kind of intersecting with an experience that I'd had after one of my exits out of a company that I'd helped start, where I was kind of just attending conferences, reading and learning and trying to plan my next move. I was at a conference, and we were talking about the kinds of things… one of the conference planners was a good friend of mine. We're having dinner, and we're just reminiscing about the… we had two different conversations. One was about what I should do next, and I needed to be inspired, and I needed to no longer be just opportunistic, but something that, like, really deeply resonates with some sort of North Star that I can really passionately get behind. And then separately, we had a separate conversation later in the dinner where we were like reminiscing about the old days and poverty and all the terrible things that we had to survive to get to where we were and how that made us stronger, tougher individuals. And the intersection of those was this thing around delinquency and this idea that, and I studied behavioural economics at the University of Chicago, and so I understood the idea of triggers and motivators and imperfect decision making away from the utility curve as people get cognitively fatigued. And so there were all these concepts that I was academically aware of, and then they resonated academically, because I was able to map them to the way things had happened in my childhood, when we were poor and we got bills and people would harass us. And instead of nudging you towards solving the problem, it actually forced you to, like, put your head in the sand, like, the ostrich effect, where people put their head in the sand, they freeze up, and they start to make bad decisions. Right? Even today, if I'm cognitively impaired and I've had a long, really difficult day, the likelihood that I'm going to be able to face head-on a really difficult problem, a challenging problem, is very, very bad. And it's the inverse of that is why people say in the 5 am club, you should tackle the hardest things first, and so I knew about these things, and I was able to map it to this problem of… I was reminiscing about the old days and how bad delinquency had impacted our lives to the point where even today, I have this negative visceral reaction to bills because of the bad experiences of bill collectors in my childhood. And so I kind of just came up with this idea. And I was bouncing it around with my friend over dinner. I couldn't sleep… all-nighters and planning and then consumer research reports. And the more that I dug into it, the more I became clear on a thesis that behavioral science, which is the science of understanding people cognitively and then being able to translate that into product design, communication design, these types of things that help influence behavior and nudge them towards doing a certain thing, that has existed as an academic discipline since the 80s. It's been introduced into consulting practices in places like healthcare and finance, but it's never been productized for communication at scale. And if you could do that, then you can nudge people towards having the empowerment and the self-agency to solve their problems without hitting them over the head and giving them these really terrible experiences that can carry with them for decades. And so that became the thesis, and surprisingly, solving it technically turned out to be really, really hard, and we've made a lot of mistakes along the way, but we've also done a lot of amazing things, and we're building a great company. But what I will say is the North Star of productizing behavioural science so that it could be deployed in a very personalized and effective way to inform the way customers behave about their bills, that central tenet has remained pretty consistent since the starting days.

Leah  14:53

You know, what I'm hearing from you is this notion of, like, that real personal mission. You know, this understanding that this really blows when people have to deal with this stuff, and I know how to fix it, and I'm going to take this deeply and personally until it's done, right? 

Hanif  15:12

Yeah. That's kind of… I mean, and then we're on a good track. We've collected, we've helped customers pay off over $50 billion of past due bills on our solution now, USD, so I guess 75 Canadian. We've helped customers resolve over a quarter of a billion past due delinquency episodes on the solution. At this point, we work with some of the largest brands in the world. It hasn't been a straight road. It's been one where we've made some… I've made and the company's made some mistakes along the way, and we've had to learn and harden it. But what we've also figured out is that what we're trying to solve is really, really challenging and difficult, and we are now, because we persisted at it with focus for so long, we've gotten quite good at it at this point. I'm really proud to see where the company is. 

Leah  16:08

I think you're underselling it just a little bit there. Some of those numbers are pretty amazing, but let's talk about how many employees do you have these days?

Hanif  16:13

At our peak, we were like 300 people. Today, we're less than 100, just shy of 100.

Leah 16:19

Yeah. And, how much money have you raised? 

Hanif 16:21

About $150 million.

Leah  16:22

Oh, that's awesome. And, yeah, you mentioned this. But, like, huge clients, global clients,

Hanif  16:29

Yeah, yeah, multinational banks, telcos, with over 100 million customers. You know, we're launching new products into the market. One of the new products is insurance products, so that if you lose your job or or you fall ill and you can't keep up with your bills, even if you're a gig worker, you can make a claim, and then the insurance company will actually pay your bills, so keep you in good standing until you get back on your feet. So it's called Symend Prevent. It's actually… again, it's like, we build this platform to nudge people, but the North Star was to help this kind of vulnerable population. And we're like, “Okay, what else can we do?” And so it was a natural extension of our trying to increase the surface area of solutions we can bring to bear to help solve the North Star problem that we were going after in the first place. The reception in the market's been really good so far. 

Leah  17:18

Oh, that's so exciting. Yeah, I love this for you guys and for the customers, obviously. But as we know, when you're building a company, and you sort of alluded to this a couple of times, there's always one or two or several do-or-die moments, pivotal moments when you're like, Oh man, I don't know if this is going to work. It'd be great if you could just share one of those moments, and then we'll sort of talk through how you moved through it.

Hanif  17:38

I think I made a couple of big mistakes, but they all kind of vector into one thing, which is, when we raised a lot of money, when we started, like, early, early through the first three or four years, we're shooting lights out. And, you know, triple-digit growth every year. And just like, you know, darling of the city and all that, and the big, big raise that we did was early COVID, we brought in new investors. The board was effectively recomposed. And one of the things that we arrived at was that we need more experienced senior leadership in key roles that could help scale the org from the 40-odd people that it was at the time to the two to three hundred that it needed to be. And the people that we brought in were just not the right… They were they're great. I have nothing bad to say about them in terms of they’re good people. They were very skilled. They're very knowledgeable, but they fell short in a couple of key areas that ultimately hurt us badly and created a pretty big reset for the company as a result. One of them was that they weren't scrappy, early-stage builders—big company guys—so they didn't know how to… they had experienced directing war from the back, but they hadn't experienced trench warfare themselves. And maybe they'd done it some time ago, but they were no longer in that place, and the fact that they weren't in that place means that they weren't builders. And when somebody isn't a builder, and you put them to a really difficult task, and the company isn't fully formed and mature in every way, what the default position that I've seen most commonly people fall back into is—hire a ton of people, right? You haven't even figured out the patterns yet. You don't know what to scale into. You don't really know what kinds of people you need to hire, but you have this problem, and you're on a time crunch, and there's the VC pressure and all these things. And so you end up hiring and bloating out your organization before you really solve the patterns that you can then scale. You get the scale before the pattern. That was one of the things, and the other thing was, we're solving this very complex thing for a very complex use case in a very complex environment of enterprise customers. And they didn't spend nearly enough time understanding our solution, the problem, our customers, the use case, before they started to really ramp up and hire and things like that. So, a stupid example, you end up with a bunch of sales guys that are selling to an audience of experts, and they're not experts themselves, and that falls flat every time. And so there was a bunch of that that happened, and unfortunately, now I've learned, in hindsight, that a key takeaway for me is you have to be very, very judicious about hiring. You have to make sure that you're hiring to the current needs, not the future needs, which means make sure that if you're still in the pattern recognition early scale time, and you're not in a mature business, hire builders. Don't hire people and validate that they're builders. And if you get it wrong, which you know, hiring is a coin flip. You know… 2/3, 1/3, on a good day… Have an understanding of what needs to be true for this guy to make it for 90 days past 90 days. What's got to be true for him to be let go quickly? Have a view of that set expectations, clearly, explicitly, quantitatively, and if it's not working out, don't doubt yourself. Just fire faster. I think the graveyard of startups is littered with people who didn't fire fast enough, but it's not littered with people who fire too fast and maybe got a fire or too wrong. It's far more expensive to give the benefit of the doubt to the wrong person than to maybe, once in a while, fire someone that could have worked out with time, right? If there's an asymmetric relationship there… and we hesitated. The guys had a lot of experience. We're like, well, what if it's us and not them? We should give it more time. So we hesitated to fire. And then what ends up happening is, the more senior you hire, the longer you leave that bad hire in place, the bigger the surface area and the depth of the thing that you need to undo. And then you combine that with long sales cycles, and you've got to reset the pipeline. What that means is a one-year mistake is really a two to two and a half year mistake by the time you fix it. And that was the thing that we went through. I mean, we were on the other side of it now, I mean, we flew really close to the sun trying to get on the other side of it. 

Leah  22:31

So we'll talk about what you've learned from that experience in a second. But what I want to get a little bit more curious about is how it actually felt for you as the Founder of the company, as the Co-Founder of the company, how did it feel to you to all of a sudden, go, oh no.

Hanif  22:47

I cried. It was gut-wrenching. It really dawned on me that there's a huge problem here. When we had a sales kickoff meeting, it was like 40-50 people on the sales kickoff. And they flew everybody into Calgary. It was like a hugely expensive thing. And I was sitting there, and everybody's like, rah, rah. And all I could see was this incredibly expensive org and the quota attainment against… there's just such a big mismatch. And I walked out of that meeting, it's like… I called my CFO, Ali, and I was like, “What have we just done?” I had a visceral reaction to seeing all those people in the room. It was that day immediately that he and I huddled and said, “We have to fix this fast,” and we set the plans in motion to undo it all. It was a visceral reaction. I could feel it. And then I started to execute and fix it. And I was able to peel the onion back and figure out that there was so much building and figuring out that still needed to be done. My penance was to go and be the head of sales myself. Pretty much 80, 90% of everybody that was hired over that surge, we had to let go, and I had to get back into the front lines. Sell it myself. Understand what works, pattern it out, make it consistent. I didn't hire another guy to lead sales until I had been able to confirm… That's a Founder-led sales motion. I could train at least a couple of guys to do it, right, so I could validate that it could be done by others. And then once we start to see the pattern that it was more than just me generating a pipeline, only then were we like, Okay, I think we're ready to exit Founder-led sales again. And that process from that SKO to the time that I hired a VP sales was almost three years,

Leah  24:41

Wow. So you learned a lot from that moment? 

Hanif  24:45

Yeah, and it was penance. I was on the road for the last three years. I mean, the new guy has been great. He's only been there for 90 days, but for the two and a half years that I basically went in, this was my fuck up. It's my job to our shareholders or our employees, to our customers, to fix it. And I stayed on the road for probably 200 days a year for two or three years straight. Because, again, the problem is rebuilding a sales pipeline can happen at the speed of the buying process by the clients, and if you're selling large ticket, seven-figure deals to people that are doing annual planning, the laws of physics of the market you're selling in will determine how fast you can rebuild that pipe. It took me a full two years to get back to the point where we had really good momentum with large logos. 

Leah  25:40

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Hanif  26:06

I think you need to have a very, very analytical and thoughtfully designed idea of what are the signals that clearly indicate that I'm ready to exit Founder-led sales and hire a CRO and hire large sales teams, because I've checked these boxes—there's a pattern, and I've been able to script it out, and I can train at least two other guys to be as 80% as good as me. And yet, there are these key elements that you need to validate. And if you're not there yet, then stay in Founder-led sales mode until you have it. That was a really big lesson. And the other one was this thing, I don't know if you remember, Bezos used to do, where he would write these articles that painted a picture of the future of a thing. And I now start to do that. It's like before I get into anything, whether it's hiring, or a new product or whatever, I write out, what are the things that need to be true in 90 days or whatever, where I validated for myself that I should double down and keep going, and conversely, what are the things that need to be true, where I've made a mistake and I need to fail because it's all well and good to say there's a difference between one-way doors and two-way doors, but that becomes a mute point if you're not decisive about walking back through the two-way door, right? And so I think that people make this mistake of, the first thing you need to decide is, is this a one-way door or a two-way door? And what does that mean about the analytical framework and the level of delegation and all of these things, and making that decision? But the other side of it is, if it's a two-way door, what are the conditions that need to be met for me to walk it back, and you need to be very, very disciplined around that, so we weren't disciplined around that. We are disciplined about that today. It's okay to fail at things. The thing is, like…

Leah  28:12

I don't like that word fail as I don't think that makes any sense in the entrepreneurial landscape. For me, it's just an opportunity to learn.

Hanif  28:18

Yeah, but it's like, you’re just being decisive… we're in the process right now of shutting down some key markets and doubling down into others, and the less mature, less experienced Hanif of three years ago would have been like, well, that's a setback versus that's just the iterative process, being an entrepreneur and you got to try things. Famously. Again, I go back to Bezos. He's one of the guys that I really try to study. You know, for every one Amazon Cloud, how many Kindles and things are there that have just completely failed? Have there been phones and this and that? You just have to learn to have a strong framework for how you decide to do things. Don't linger on to saying “Yes,” but be very decisive about when something isn't panning out, and let it go, and don't get emotional about it.

Leah  29:06

Yeah. And I would say, listening to your story, trust your instinct. Because you knew it. You felt it in your gut.

Hanif  29:13

Yeah, my CFO and I were both… within a month of hiring this guy, we were sitting around like, does something feel off to you? And we're like, yeah. And we go to the board and we'd have these conversations that'd be like, Oh no, I think we should give it more time, and then we give it more time. And then a month later, Ali and I were just sitting there having a drink together again. I'm like, This just doesn't… we doubted ourselves. Honestly. We did. We took in a lot of money. We'd never scaled something on this order of magnitude, and that self-doubt really hurt us. There are two places where you can really, really make bad decisions. One is when you doubt yourself, and the other is when the need to make something happen clouds your lens and not your objectivity. You need something to be true, so you almost data mine the facts towards making the decision in almost a predetermined way, instead of just being very objective about decision-making. I think those are the two things where you can get yourself in trouble,

Leah  30:12

Yeah, but look how much you've learned. And now here goes the company. I love it. You talked a little bit about this and alluded to it about how much travel you did over the last couple of years, but I am really curious about how being an entrepreneur affects your life outside of work, because, as we know, being an entrepreneur is not a nine-to-five gig. So what does that look like for you?

Hanif  30:34

It ebbs and flows. I can tell you when I'm at my best, and I can also acknowledge that I'm not always at my best. The thing that I really started to realize, and I do commit myself to it, but I've fallen off the wagon once or twice, is a deep commitment to… I don't really believe in work-life balance. Yeah, that's not me. And I don't burn out because I'm doing what I love. You know, I get fatigued physically, and I need to rest. But that's not the same as burnout, right? And the only time that I get stressed, like the guy who used to coach Michael Jordan, there's a famous video where he's like, stress comes only about situations that you haven't faced. And the minute you face them and start to have a plan and start to execute against the challenge, then that's just the situation that's not stress anymore. So stress comes from the inability, either because you can't or you won't, to look at a situation or a problem and just tackle it. That's what causes stress. So the thing where we were moving in the wrong direction, and I wasn't dealing with it, caused a lot of stress. The minute Ali and I were like, we know we have a plan, and we sat down, and we had clarity of thought about the direction that we want to go. The stress went away. It was still intense, and it was high octane and all of those kinds of things, but it wasn't stressful, per se, and I think the only thing that fatigues me, truly, is the lack of sleep, and the other one is stress. And so what I've learned is, as long as I deal with my problems head-on, I'm good, yeah. So that's one. The other one is physical fitness. The brain is just a muscle, and it's connected to all the other muscles in your body. And you need the energy and the mental clarity to execute. I've fallen off the wagon where I've eaten crappy for a stretch, and that's definitely a thing that I need to do better. Nine out of 10 times, I'm pretty good about it, but I don't think I've missed the day in the gym in 10 years, not one. Even if it's a shitty workout, I go in there and they do three sets and a couple of burpees and walk out, I go for a 10-kilometre power walk or whatever. If I go two days in a row without the gym, I start to see it in my mental health. And I will say for sure, and I can say this about myself, when I'm in really good shape, I do better at work than when I'm not. And so that's the other thing that I think is really important to make time for. And the final bit of it is the family life side; you have two choices. There are two vectors of things. One is finding a way to make time for your family. And every person's conditions on how much time they can make and what those demands are are different, and they have to find a different line between that and their job. So I'm not going to sit here and say what I figured out is a good rule for others, because I think it's very personal. I happen to be in a position where I have an incredibly supportive... I married well. I married really, really well. And I married, most importantly, when I see myself compared to other entrepreneurs, where this works or it doesn't, I married in between company three in company four. So I'd already had a decade of entrepreneurship under my belt, and I knew exactly what this life was about. And I was very explicit with my now wife at the time, even after the first or second date, I was like, I just need to draw this out for you. You need to understand what you're getting into, because I can see myself catching feelings here, and this is getting serious, and before we go too far, you need to understand, because there are things… This is who I am. There's no changing it. And so I was very honest with her about it, and so she knew exactly what she was buying and walking into. And the bargain was struck early. Where I've seen people struggle, like not everyone, some people can adapt, but I've seen a higher proportion of people who struggle to make the work-life thing work, where their lifestyle when they started their family was one thing, and somewhere along the way, they got the entrepreneurship bug mid-flight, to their family life, and then they flipped it. That is a lot harder to manage. Obviously, sure it can be done, but I think that's a harder thing to navigate than what I have to navigate because I was fortunate enough to both find the right spouse and a big part of that was because she chose this life as much as I did, and so she's been amazing at it, and an amazing partner. And I can also confidently say that a big part of what makes me keep going and taking on the world and everything else is her. We make it a really, really good pair, and she gives me strength. And so I actually don't think I'd be nearly as successful without her. So I don't think it's a trade-off. I think it's an enhancement, honestly.

Leah  36:11

That's really nice to hear. You know, we've talked a lot about the challenges of being an entrepreneur. I also want to take a moment to reflect on what you love about being an entrepreneur.

Hanif  36:20

Winning deals. Oh my god. Like I remember this. We had a really, really great meeting with a massive auto lender in Texas, and walking out of there, I don't remember the walk from the building to the car; it felt like I was floating. It's the greatest high, getting, closing deals, winning. You know, even to this day, the prep, the root Q and A, what if they say this? What if they say that? Let's dossier every individual. The prep work that goes into what we do to win deals is incredible. And I love that part of war gaming it out. And I love winning. And honestly, as much as I hate losing, I think the ecstasy I feel and I experience from winning is because of how it's positioned against the losses. Right? If all you've ever had is like Allegory of the Cave, if all you've ever felt is winning, you don't know what to compare it to. If all you've ever had is wealth, then I think that people who've been poor enjoy wealth much more than people who have been born and raised into it, right? I think people who have only experienced darkness enjoy the light a lot more than people who've only ever seen sunshine. So I think very similarly, loss creates that positioning and that point of reference for the wins. And so I lean into the pain and I lean into the losses, because I know that there's always a win on the other side of it, and I know that it's all part of the journey. It's not that entrepreneurship is awesome and rewarding… Oh, by the way, the downside of it is that it's challenging and it's tough and it's mentally draining and it pushes you. I think those are the bonuses. I think if you're not pushing yourself and challenging yourself in your life, then you're not really living. You're just existing. To live is to challenge yourself and to suffer, and to push the boundaries. Anything less than that, you're just floating through life. You're not really living it.

Leah  38:42

Oh, I love that. And clearly you love it too, because you're also an investor and you're a mentor to a lot of other entrepreneurs. Tell me a little bit about what you like about doing that kind of work.

Hanif  38:51

When you find the right entrepreneur, there's a friend of mine, Dan Erhard. He's a great example of it. When you work with the right people, and you feel at least partially responsible, in a limited way, for giving them the guidance and at least some of the tools they bring to bear to kind of win as well, it's a great feeling. It can be very frustrating as well. Because when you have an entrepreneurial lens, you're a consummate optimist, you have this burning thing going on inside of you, and you project that into others, and it took me a long time to appreciate that not everybody is wired the way I am, because you want to see that in others, right? So it's really frustrating when they let you down, and they're not like that. It causes an incredible amount of frustration for me. The only expectation that I have of the entrepreneurs that I invest in is to be irrationally committed to what they're doing; everything else you can work on, right? But if you don't have that grit, that ability to lean into pressure and to outwork everyone, and to have that passion, if you don't have those things, you can't build on it. Those are the foundations. But when it's there and you start to have that Vulcan mind meld with these guys, it's a lot of fun. So that's the part that I like the most. And honestly, there's a sharpening of the knife that happens as well. My primary concern is Symend, and I don't involve myself in anything. It's like the mark your own orbits effect. I don't involve myself in anything that doesn't either have some sort of network effect benefit that flows back to Symend, or is sharpening my knife analytically, or in some capacity that makes me a better CEO there. And I try to be very, very disciplined about how much of my time I allow those things to take. I used to not be good at that, right? But I've increased that discipline quite a bit because, again, I took a lesson out of our own playbook, which is that you can only put so many hours of high-grade analytical horsepower to work a day before you're cognitively impaired, and then you can't make any more good decisions, right? I can't afford to have it where I take some of those units and allocate them to other things if Symend needs those units, right? So, I try to be very conscious of how much time I put towards these other things now, and I've dialled it back quite a bit from when… again, learn and iterate. I used to get excited a lot. I still get excited a lot, but I am very, very disciplined about the kinds of things I involve myself in, but also how even the ones that make check the boxes of sharpening the knife and network effect, even then being like, this is how much budget I have for these things. And if I'm fully utilized on my budget, then something has to come out for another thing to go in. I have to do that. 

Leah  42:06

You have to, you have to protect your time, I hear you. The other thing that I'm really curious to talk to you about is this notion of creating positive human impact in the world. I have an idea that probably goes back to that first story that we talked about right out of the gate. But how do you think about creating impact in the world with Symend and even personally?

Hanif  42:27

Yeah, so I do a bunch of philanthropic things today. I sit on the board of the Alberta Children's Hospital endowment. I sit on the board of Opportunity Calgary Investment Fund. My family and I do a lot of charitable giving every year to the less fortunate. Symend does the same. So those are some of the things where I've been involved. When there was this big drive to resettle Afghanis and Syrians, we were I played a role there. I'm on the Business Council of Canada. There are all these things where I try to give back. I want to do more, but I don't have the resources to do more, but I see an opportunity to do significantly more over time; one of the greatest things that I have been fortunate enough to benefit from, and I'm sure other ecosystems have this, but from my experience, Calgary has this at a level of abundance I haven't seen in other places. Those who have succeeded because of Alberta, because of Calgary, have this incredible patriotism towards this province that almost supersedes their patriotism to the nation. I would say, they're Albertan. That's how they identify, that's how they think. And they are incredibly invested in helping this province and helping the people that are here, and I was the beneficiary of that when I got here, because a lot of doors opened for me, and I was able to parlay that into a pretty great career so far. I'm trying to do my part, to give back to the things that I mentioned, and I want to do more, but I think that's probably the place where my loyalties lie the most, and I want to do more if I can. So that's the place where helping other entrepreneurs, like I was helped, and then trying to reinvest into this nation and this province that's giving me so much, I think those would be the two key areas. And it's funny, as wealthy as Alberta is—I think per capita, we're the wealthiest province in Canada, by far, and sadly, over the last decade, I think that a lot of the other parts of the country have moved in the wrong direction. Hopefully, it gets better. But even in Alberta, as wealthy as we are, we had this thing at Symend where we were buying Christmas packages for families. I think we got up to like 500 families or something. And we would pull out these lists of what they could pick to get into their care packages for these underprivileged families in Calgary. And I thought it would be toys and turkeys and things like that. And you know, we have the highest per capita income of any major city in Canada with the lowest taxes, lowest cost of living, highest opportunities for employment and yet… this isn't Cuba, this is Calgary… it was toilet paper and bed sheets and aspirin and tampons, and it just… I really broke down when I saw the list, and I was almost a little bit ashamed, because I felt like I'd forgotten. I don't need to go that far to find people who still struggle in a way that I just didn't think would be that pervasive where we are as a nation. So there's definitely more we can do, and hopefully, with time, I'll do more. 

Leah  45:48

You’ve already done so much, 

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Hanif 45:50

But it's crazy, though, right? 

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Leah 45:52

Yeah. I mean, it is a real wake-up call.

Hanif  45:54

I didn't think that would be toilet paper, and bed sheets and school writing books and pencils were the number one things that families were asking for in Calgary. Somewhere along the way, I think we have missed the mark as a society, if with the amount of wealth… if this was happening in Cuba or Brazil, I get it, but for the amount of wealth that we have, the fact that that's still pervasive… I believe in capitalism. I want to be a billionaire. I believe that that's a good thing. I don't think that's a dirty word, but when you have things like the richest two men in the United States have more money than the bottom 50% that's a level of extreme. If that exists, while at the same time people can't afford bed sheets, there is an equalization that needs to occur that I think we're missing the mark on, and I don't believe in socialism. I don't believe in these things. So I don't know what the right answer is. I just think that, you know, as a society, we should be doing better if there's people that both people have jobs, you know, one's working in Walmart, and another one at McDonald's, and they can't afford toilet paper at home. I think we've missed the mark, if that's the case here.

Leah  47:16

Yeah, there's work to be done. No question, and I can see how passionate and emotional you are. 

Hanif  47:22

It was just a weird… Yeah, I wasn't expecting it. Honestly.

Leah  47:27

I do want to point something out, though, Hanif. The work that you're doing with Symend, that work is life-changing for that end consumer, right, like that person who can't afford to make these payments, you are changing their lives by pointing them toward a better financial outcome.

Hanif  47:27

No, I know it's just I think that whatever my life looks like on the other side of Symend, because I'm not going to be the CEO of this company forever, I think a big part of it will be finding a way to give back that is really oriented towards training people to fish, versus giving them fish. But nevertheless, like you know, Canada should, by all rights, given our resources and positioning and education, by all rights, we should be one of the most prosperous nations in the world. And if we aren't at any point in time, I think the only people we can blame is ourselves.

Leah  48:26

Work to be done. Yeah, as we wrap up these conversations, I always ask the same two questions. You are the Co-Founder of Symend. You're writing the story for your company. How do you hope that story goes?

Hanif  48:37

My biggest North Star is the quarter billion customers treated ends up being a billion. If where I hang it up is—there's a billion people out there who have passed through on their bills, and we help them, that's a big accomplishment. And along the way, there will be a lot of sacrifices, there'll be a lot of unexpected things, but as long as we continue to deliver and compound on that North Star, I think that's the most important thing.

Leah  49:07

Love it. Love it. And then finally, you know, you are a Founder. You're a Co-Founder of Symend. How do you hope your own personal story goes?

Hanif  49:15

I think recently, I had a really big moment in my professional career. I got inducted into the Alberta Business Hall of Fame. I think again, there's no number, there's no amount of money. I think when I finish and I hang it up, the things that I helped create persist and continue to deliver value when my kids are grown up and when the community has grown and expanded. And if that's more than just Symend, it's Symend and other things where I've helped or invested or guided, I think that'll be a really great outcome. And then beyond that, while I've done small things in terms of philanthropy, I don't know what that thing is. It will require a lot of my time, but I do want there to be one landmark thing that defines how I end my life from a philanthropic perspective, that survives me. Maybe an educational school for the gifted, or gifted immigrants, I don't know, something like that, but there's got to be something that I can do that survives me on the philanthropy side. I just haven't started thinking about it too much yet.

Leah  50:27

Early days. Hanif, thank you so much for this conversation. 

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Hanif 50:30

Happy to be here. Thank you.

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Leah 50:37

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