Float’s CEO, Rob Khazzam, on Why Execution Matters More Than Strategy

What does it take to build a successful fintech company in today’s competitive market? We explore this question in a conversation with Rob Khazzam, co-founder and CEO of Float Financial, one of Canada’s fastest-growing fintech companies.

Rob’s journey from a private equity background to key leadership roles at Uber gave him a unique perspective on what it takes to win. He shares his insights on building a strong team culture, the power of relentless execution, and his vision for transforming the Canadian financial landscape, drawing from his experiences at Uber and applying them to the building of Float.

This is a must-listen for anyone interested in startups, leadership, and disrupting the status quo. Let’s dive right in.

Mark MacLeod:
In this episode, I sit down with Rob Khazzam, co-founder and CEO of Float Financial. Rob spent five pivotal years in a number of leadership roles at Uber, and that experience completely transformed him. He brought that relentless execution to Float, and as a result, it’s now one of the fastest-growing fintech companies in Canada, if not in the world.

We unpack all of that experience in this episode. Lots of insights. I hope you enjoy it.

Rob, welcome to the Startup CEO Show. It’s a true pleasure to have you here. How are you doing today?

Rob Khazzam:
I’m doing well. Thanks for having me. Excited to be on the podcast.

Mark MacLeod:
Yeah, much to discuss. I wanted to have you on for some time because you’re running one of the most prominent fintech companies in Canada, so there’s lots to discuss. To start, I think many folks may have followed a similar path to you, started more on the investment side, and then made the switch. And so I’d love to hear from your standpoint how that background served you, what parts did you bring with you, and what gaps did you need to fill in once you got to the operating site?

Rob Khazzam:
So I was fortunate. I got to spend five years doing investing before I jumped into operations or startups, and I’m glad I did. I think that the background was really helpful. So I did the three levels of the CFA program. I was the only analyst and then the only associate in a shop for those five years with about five or six partners that I got to work with on deals.

And so the benefits were, you get a lot of reps building models, you get a lot of reps doing work, having your work critiqued, doing it again, and understanding how to work with a bunch of different personalities. And so that was a great experience. I also got to see a lot of different businesses. So I got to look at probably a couple hundred different P&Ls and balance sheets.

A couple of hundred times a year, I get to look at least at a one or a two-pager about a business and provide input on what I thought. And for me, that’s the thing I’ve always enjoyed most, is having an opinion. I struggled in business school thinking about being in financial services or being in a sales role. I like looking at a business, looking at financials, and taking a point of view. And so that gave me a lot of experience, a lot of confidence.

As I started to formulate opinions, you’re nervous about them. By the end of my time, that five-year run in private equity, I had a lot still to learn about doing deals and businesses. But I felt that foundation was helpful, and, in the operating world, it served me well.

Mark MacLeod:
That’s amazing. So much learning. I was in public accounting doing auditing for a bunch of years, and auditing is deeply, painfully boring. And the thing that got me through it was the opportunity to learn about different businesses. It sounded like you had that on steroids. I have to say, I think it was Scotiabank you were in before this, where the description was like, I mostly did not work. So anyway, I just love that.

Rob Khazzam:
Yeah, I look back fondly on the time, and I’m grateful that I got the experience, that people there were patient with me, and that I had an opportunity to learn about businesses. And I think the last thing I would say that was most helpful about that experience, looking back, is when I graduated from business school, and when many people graduate, I think from business school, you have a perception of how the world works. Private equity, for me, broke that.

It helped me see how the world doesn’t work, and how investment decisions weren’t as simple as just what the business case and the model say. I got to see the vast difference between a stated strategy and actual execution. I didn’t realize it until I got to Uber, but it helped me formulate a view, which is strategy is easy, insights are easy, and execution is really hard.

Coming to board meetings every three months, every six months, I began to feel frustrated with the pace of execution. And that’s when the intellectual interest sort of met the heart in me, the soul, which is like, I want to do something about this.

I don’t want to keep coming to meetings, and talking about this strategy. Let’s do it, and let’s do it quickly. And understanding that that’s a competitive advantage in business was not a perspective that I thought of when I entered the world from business school. So that was a great learning experience as well.

Mark MacLeod:
I love it. Yeah, listen, man, all the value is created through execution. You can have the fanciest strategy slides in the world, but that in itself creates exactly $0 in value. So, it’s all about execution.

I’m curious, I see this a lot today with investment firms where you come in, you get some experience, and then you go out and operate like you can’t even get a path to the partner unless you’ve been on the other side. Was that an impetus for you to move, or was it just that you were seeing this and you wanted to go and fix this kind of execution challenge?

Rob Khazzam:
No, I knew I wanted to leave. I think by the time I was an associate for two years, I realized I sort of had an opportunity to keep going at that point and get on a partner track. And the firm I was at wasn’t very operational-heavy, so the partners there only came from financial backgrounds. But I was 28, and to be honest, I did have a flashback to my childhood, I had always felt this entrepreneurial instinct and also maybe this fear that I wouldn’t live up to that.

And so, to be honest, I do remember I was 27, 28 years old, thinking, this is great, I’m proud of my achievements here, I’m proud that I’m in this field. It’s not something I ever dreamed of getting into but now I want to be on the other side of the table. I want to be creating something, building something. I don’t want to be part of a firm.

Not that there’s anything wrong with it, but I want to be known as someone who makes their success through building things, building teams, and building a business. And that’s scary as hell, but it’s kind of time to do that. And if I don’t do that now, I probably never will. That was really what was going through my head.

So it was not just leaving there, but kind of jumping into the abyss and getting in the deep end and daring myself to make a change before I got too far into a career that I couldn’t leave. And I think everyone who has navigated those decisions knows as you get into your late twenties and your thirties, it gets harder and harder to make those switches.

Mark MacLeod:
Fair enough. Yeah, I made a switch at 50, but I’m not the one being interviewed, so it doesn’t matter.

Rob Khazzam:
So, at least in my mind, it felt like such a big deal. But you’re right. As you get older, you realize, like, you can always do this stuff.

Mark MacLeod:
I opened up an investment bank at 45, shut it down, and became a coach at 50. So, you know, life happens. But anyway, so you wanted it. You talked about being thrown into the deep end, which is exactly the analogy that comes to mind when I think of Uber.

And, you know, you talk about the importance of execution, and from the outside in and everything I’ve read or heard about Uber, it sounded like a relentless execution machine and something that was just deeply competitive to a fault. And so, yeah, just tell us about your experience there. Again, when I was LinkedIn stalking, I saw you were often in Europe and just like, man, that must have been really lonely. But anyway, that’s an aside. But just, yeah, what did you take from Uber?

Rob Khazzam:
Yeah, so, you know, the background is I quit my job in April of 2014 or March of 2014. I started looking for a job in New York. I met Uber and a bunch of different startups. And long story short, Uber wouldn’t hire me in New York. But I got introduced to this international launch team, and they said, look, we’re not going to hire you in the US, but we have this global team, there are 25 people on it, they get sent all over the world, you’re alone the entire time, you work seven days a week.

And I thought it was like, I thought it was sort of cheesy. The job description was that they were making something of it. But then as I went further and further into the interview, it was like, no, this is serious. Like, they’re actually like, hey, you’re going to get sent to Egypt, and then you can get sent to Pakistan, and then you get sent to Prague, and then you get sent to wherever and they were actually serious. So, like, are you ready to do that?

And, you know, you go through the interview process and they’re really thoughtful about interviewing, which I loved. And so, long story short, I joined in May 2014. I got on a plane to Frankfurt. They told me, you know, days before I joined where I was going, I had no idea what I was going to be doing. I knew the launch job. I knew that there was a handful of people I got connected to that I could reach out to.

But where I was going was really last minute. Got there, spent three weeks doing this Frankfurt launch, which was pretty funny now, looking back. And then that was it. And then it was truly my boss and three other launchers that had just started, the three of us together.

He just said, this is a map of MEA, meaning Middle East Africa. That was the region we were in, and it was like, this is where you’re going to be going. This is what we’re going to be doing for the next six months. And it involved where you’re going to be living, not to mention working at a daunting job. So it was pretty mind-blowing to think back to it. It was scary.

Mark MacLeod:
Is telling an employee you’re going to work seven days a week even legal? Is that a legal employer practice? I’m not sure that it is, yeah.

Rob Khazzam:
I mean, I don’t think it was so much working seven days a week. And I did appreciate it now that I look back on it, and it taught me something, which is like, this is all in. Like, you’re not in a job in San Francisco. Like, you’re going to be in the people that you’re going to be working with. And I got introduced to some of them. Like, some of them are on their 15th or 16th month touring the world.

And, yeah, I remember thinking, maybe this is too much. And then I’m glad I didn’t. I was lucky I had mentors who said just go for it. If it doesn’t work, you’ll figure something else out. What’s the worst that could happen? Those first few months were a great experience, and Uber did a great job of removing the ego that we all enter startups with. And I think that coming there, I’ve done the CFA. I was getting up to a principal level in private equity.

I thought it was a hotshot. You know, I got there, and I’ll never forget, like, sitting in that office during the Frankfurt launch, and it was like, okay, well, should I build a model to market size? And I was like, well, no. Right now, we have to submit these tasks to the engineers to draw this geofence and then we need a thousand chargers, a thousand iPhones, and a thousand cables.

Go to the mall and go get them. And I was like, what do you mean? Do you want me to source a supplier? And it was like, no, we need this stuff in two days. Get it, and then come back and let us know when it’s done, and we’ll cross it off the list.

And then I went and did that screen around Frankfurt for a day and a half. And then it was like, okay, we need to print a thousand cards to hand out to drivers. And I was like, should I find a company to do this? Surely someone else can. And it’s like, no, do it and don’t come back to the office until it’s done and it’s done today.

And then the next thing is we needed to find drivers. And, well, how do you find drivers? Should we get an agency? It’s like, no, walk around the streets to where taxi drivers hang out and don’t come back here until you’ve got 20 drivers. And we all did that. And then we ran the onboarding. We’d sit in a conference room, and it’s like me talking to German drivers and scanning their documents and talking to them and teaching them how to use the app. And that was the first couple of weeks, and then that was all I got.

We got that and a launch playbook, a Slack group of launchers who we could reach out to. The advice was, there’ll be someone doing what you’re doing or that has done it in the last month or two online 24/7 in all these different countries and time zones. So use this group to your advantage.

And that was what I remember when I left to fly to Eastern Europe, is I was scared shitless, but I knew I got some people I could count on that are in the midst of launches a couple of weeks ahead of me, and they’ll help. And that was, for a brief period, comforting.

Mark MacLeod:
Did you miss your ivory tower of sitting in boardrooms and, like, I don’t know, pondering spreadsheets versus going to a mall to buy 1,000 iPhones?

Rob Khazzam:
I liked it. There was a swagger to Uber. While all this was happening, there was a swagger, which was, everyone was like, well, but we’re going to win. So even then, within the first week or two, I felt swagger. Like I’m on a mission, I’m making this thing happen. When I’m walking to the mall in Frankfurt, I’m not walking slowly. I’m speeding, I’m racing. And there’s a momentum throughout the company that done is better than perfect. Get shit done.

Get moving. It wasn’t even, it didn’t even need to be said. Like, we’re going to work late tonight. The whole company was in 24/7, and I don’t mean in the office, I mean, like, they were in it. Like, there was a sense that time was being measured in hours and that was infectious. And I think that that was something that infused a lot of energy into me, even though I was nervous. And so those first few weeks, I got sent to Prague and I got sent to Prague basically to launch and I had to do it in eight weeks or so. And I was like, no, I want to do it in ten.

And they’re like, well, this other launcher did it in six. So you’re sort of negotiating for how long you’re going to get and then you go there and then you have a backlog of a hundred things to do. And I very quickly got overwhelmed and made all the mistakes you make. But that was the beginning of that journey.

Mark MacLeod:
Do you think it changed you permanently, how you operate?

Rob Khazzam:
Yeah, definitely. I think that first launch, that feeling of there’s a clock ticking somewhere and I have all this stuff to do and if I’m fierce, I can get most of them done well enough to launch. And that changed me for sure. That 18-month period was one of extreme loneliness. I was alone almost the entire time and if I was with people, it was for a day or two and then I was alone again and it hardened me.

A lot of things go wrong and you cry and you weep and you feel anxious and then you call someone at the company and they give you a tip and talk you off the ledge and then you keep going. And I think doing that over 18 months, hardened me in some good ways.

In other ways, I’ve tried to unlearn, but it taught me you can achieve a lot. You can achieve a lot by saying, no, I’ll figure it out. I remember we had a saying, we walk around these cities as launchers, and you’re recruiting people. You’ve got to hire a marketing manager, and you’ve got to get a meeting at the Ministry of Transport, you’ve got to get an office…

Believe it or not, it took me three weeks to get an office lease in Prague because of the bureaucracy in the country, I couldn’t get the legal entities or the signing authority. This is such a small thing. That was my biggest headache for three weeks.

You think you’re never going to actually overcome this stuff and you just keep finding ways to make it happen. I remember people saying again, that it was a saying famous on the launch team, which is everywhere in the world. People were telling us, it’ll never work here. Trust me, son, in Prague, you don’t want to screw around with taxis. We know what Uber is doing, but trust us, not here.

And there was this balance of naivety and confidence, arrogance, not knowing better, some combination of all of them where you just said, yeah, I will, and this city is going to launch and wait till you see what’s going to happen. And that was a great lesson to see that you can will your way to great outcomes. And Uber was time and time again just stories of willing our ways to outcomes that felt impossible, at least on the ground in the markets I was in, it felt impossible quite often.

Mark MacLeod:
Do you ever worry you are going to end up in a foreign jail?

Rob Khazzam:
There were some interesting moments. Yeah, Hungary is an interesting place. It was a really interesting part of the world. Hungary, Ukraine, and Belarus have very different approaches to these topics. American companies are unpopular enough in some parts of the world and then you add on the taxation regime, the fact that Uber is taking taxi drivers’ jobs. Yeah, we encountered a lot of resistance, but again, it hardened me.

Which, you know, Uber has great things, they have a great app, we have this great stuff, we have money, we have a lot of things, but the service is still illegal in a handful of countries. We still have people chasing us. We still have government actors and people affiliated with the taxi industry who are tied to unionized workforces trying to get in our way. And again, it was fun. I felt like I was at an SMY novel at times, but it was a blast. And again, the thing I took away from Uber was the swagger. And that’s that belief we can make something happen.

We had people showing up at our onboardings and they would intimidate us physically. And the drivers that came to sign up for Uber, what did we do? We made up a fake ride-sharing service. I made up fake Facebook communities to say we were building a ride-sharing service, but not under the name Uber. We hired security. I had 24/7 security to protect the offices. We’d put false information out there about where our office location was and there was a bit of a cat-and-mouse game which made the journey interesting and definitely fun.

Mark MacLeod:
That’s wild. Crazy. I was saying, the very first time I went to continental Europe, I went to Amsterdam and it was all lovely and friendly. And then I went to Budapest and I got off from the airport and like, the police officers are there with like machine guns.

Rob Khazzam:
One of the best parts about being a launcher was our first job was to get ripped off by taxi companies. So we’d fly to a city where Uber didn’t exist and someone like me would go there and spend two or three days doing this green light trip. And the first thing we do is look like tourists, which is pretty easy. And then they get a ride to the city center and do it with a bunch of different companies to and from the airport and figure out what the hell is going on. And you start to find the devices and the gear shifter and these little hacks.

And we did a series with an undercover journalist in Prague at the time of the launch to expose taxis. So there was all sorts of crazy stuff going on, but also a lot of people that wanted it there. I’m a student of history, I studied world politics and geopolitics a lot growing up and still do, so being there and seeing what I’d studied in post World War II, the Cold War, and then building a business there was just really fascinating.

Mark MacLeod:
I feel like we could spend the entire podcast unpacking that, but that’s not why we’re here. I want to talk about Float. First of all, for folks who are listening, just tell folks what Float is.

Rob Khazzam:
Float builds software and products that simplify the entire process of spending, whether that be on corporate cards, through wire transfers, or reimbursing your team for expenses. We offer a platform that makes that whole experience really seamless and automated for small businesses. We’ve been around for a couple of years now. We have 3,000 customers across Canada and about 85-90 people across Canada helping us build towards this mission.

Mark MacLeod:
Amazing. As I understand it, you were brought in pretty early. There were some initial technical founders, but then you were brought in. How did that all happen?

Rob Khazzam:
Yeah, so after my time at Uber, I was looking for what was next and doing what everyone does, meeting people, going for coffee, and trying to find their next job. And whether it was joining something or partnering, I didn’t know. But I was fortunate. I got a call from Jamie Rosenblatt from Golden Ventures and he said hey, we’ve got a pre-seed investment into this company.

It’s called Journal, there are two founders there and they’re looking for a third they’ve been building for a while now. We think they’re on to something, but they need a third. They need someone to lead the company, but we think there’s something great there. Why don’t you meet them? So he introduced me to them.

Over a two or three-month time span, I got to know them. They showed me what they were working on, and I told them about myself, and we talked about business finance in Canada and what it looked like. And we bonded over shared experiences that we all had as employees. My time in Eastern Europe with expense reports. I had this €150,000 expense report in February of 2015, and it led me down a multi-month process of getting reimbursed and going through this really painful process. They shared the same experiences they had at Uber and Shopify.

Mark MacLeod:
Oh, they worked at Uber as well?

Rob Khazzam:
Well, when I met them, they were the top Waterloo grads. They’re the top-of-the-class grads who chose not to get a job in New York at a hedge fund or Shopify. They chose to build something. But in their internships, and their co-ops, they did each have a stint at Uber and Shopify. And so that was the background that I had when I met them. Griffin was still in school and my other co-founder had graduated.

But we bonded over a shared passion for that problem. And they had a product. I’ll never forget, they showed it to me. They said, so you had this problem with expense reports. And then they sort of like, turned the laptop around and they showed me two things. It was an employee requesting spending from their manager on Slack. The manager shows a thumbs up and instantly issues you a single-use virtual card.

Then they created a virtual card for me and showed it to me. And they said, you can buy something on Amazon. When I saw what the product was already what they had built could do, the issuing technology and what it enabled, the bond that we had developed, that’s where it all started. Then we got together more often and then decided to join full-time after about, I think it was eight or nine weeks of getting to know each other.

Mark MacLeod:
So they weren’t in the market when you joined, you led the go-to-market launch initially.

Rob Khazzam:
Effectively, yeah. To their credit, they had done a lot. One of the stories I tell people always is what led to us working together. And I always mention the passion for the problem space. They were and are relentless, so when I met them, they said, if you’re interested that’d be great. Let us know what you think.

Let us know if you want to help out. We meet every day and they added me to this stand up and I think back to my Uber days. It was like a 08:30 a.m. stand-up, seven days a week, and it’d been going on for like over a year. And I was like, okay, that’s the kind of energy that I want to be around. Those are the kinds of people with the level of commitment that’s required to build something. That’s something that I remember fondly.

But they already had a couple of beta customers. So what they had done, they were really smart. They’d gone to Kirk Simpson from Wave, and they’d gone to a handful of other small business owners or startup CEOs or finance teams and said we’re trying to research this problem. They researched a bunch of them. They were showing them either beta versions of the product or product designs.

When I joined, I didn’t know where it would go, but I could see that they had a small captive number of companies that were giving them some feedback. So when I joined, that allowed me to evaluate over four, six, eight weeks. Is this good enough to take to market? Should we do a broader push? Should we hire our first staff now and do a broader sales build-up? And that’s what we started to do in the spring of 2021.

But they were looking for someone to come in to lead the company and that was something they were upfront about, which was we want someone to come in to lead the company, to deal with the board and investors and build up the company so that we can focus on building the best product.

Mark MacLeod:
They smartly dodged the toughest job, which is why I only coach CEOs.

Back in my operating days, I was offered a CEO role twice. When I first entered the startup world, I thought I wanted to be a CEO. I went out of my way to try and learn all these things beyond finance. And I would run HR, support, bizdev. I ran engineering for one week while my CEO was on holiday and I was so grateful when he came back because that was just a disaster. But I quickly realized I didn’t want to be the CEO. And when I was offered that job, both times I turned it down flat. So good on them, they were very insightful to pass you the hot potato there.

Rob Khazzam:
Yeah, I think it’s a rare thing for teams to not get protective and defensive over roles and responsibilities. One of the things that I felt blessed about is that my co-founders, and not just my co-founders, but all of the leaders that I work with at Float are, is that they are so passionate about winning and succeeding that it’s always about what the company needs.

And I won’t just say that. I remember in our second meeting, it was a bit awkward. Well, does one of you want to be the CEO? Did the board or your investors make you do this? And they said, no, the reason that this happened, we think that the trajectory of the company would be better off if we brought someone in like yourself. We don’t think we’re best at doing that. And we care a lot about who this person is, so they interviewed me.

They were really serious, like, great, now take care of that and we’ll take care of this, and let’s get back to work. And I think that’s a rare thing to find in teams, especially among young people. And I’m grateful that they did that and it made my entrance into the business a lot easier. And I think that was important to our success.

Mark MacLeod:
Amazing. So it sounds like these guys have an intensity and relentlessness that you were used to from Uber. So I’m wondering, what practices, values, and ways of operating have you imported from Uber to Float?

Rob Khazzam:
Yeah, a lot. Griffin, Ruslan, and I did talk about those things. We shared docs of thoughts on values and principles of working together. The things that I took and that I think are definitely embodied in flow, whether they’re directly attributable to Uber or we’ve come up with them ourselves, or people we’ve hired and our own co-founders have come up with. One is a real genuine bias for action and urgency.

I mean, everyone says that in startups, but there are levels of what that means and levels of intensity. And I think that I point to that example, the spirit of that seven-day-a-week, daily stand-up. Not to say that that’s a practice that everyone should use, but the idea that you’re daily accountable like you do a daily stand up, like, here’s what I’m going to get done today.

And then the next day you’re like, I got it done. I’m at a pretty good week. And we did that with our first twenty employees. Every week, everyone would communicate at 09:00 a.m. what were the kills or dies for that week. For them personally, what were they going to kill? Or it would kill them. A bit of a metaphor, but what am I going to finish this week? I think that attitude of getting something done every day is really important.

Also, customer obsession. I saw that from the very beginning. Ruslan and Griffin were relentlessly customer-obsessed. I’ve been deeply influenced by reading about Amazon and their shareholder letters and I think that customer obsession is really important and it’s hard to maintain as the company grows. And that was something that I saw them living and how they were. They were already in Slack groups with customers and talking to them daily and those were practices we’ve continued learning and growing.

I think this idea that in a startup it doesn’t matter how good you are, if the company’s succeeding, you have to be at least 50% to 70% better every year. On the one hand, you want to hire great people, and I’ll talk about talent density in a minute, but it’s not enough to just be great in 2021 with whatever you’re running or whatever you’re doing, the attitude has to be like I’m going to get challenged, I’m going to have an egg on my face and I’m going to need to get better because the business is going to grow and my role is going to evolve and the challenges are going to change.

And so not just a capacity to learn and grow, but evidence that you’ve done it, that you like doing hard things, and that you can take direct feedback. If I think about the humility my co-founders showed, I think the spirit at Float is one where everyone, no matter who you are, can acknowledge that they’ve got to be better in this area and I think that that’s a really important element of the development trajectory.

To keep hiring people and having them keep scaling, you need to see great competence, great pedigree, and great experience, but humility and a willingness to be vulnerable and open to learning more.

The last one is just the idea of talent density. We talked a lot about that when I joined them. They said what do you think you’ll be spending your time on? And I said well, assuming the product works and the first 20 or 30 customers we bring on use it and we raise our seed, which we figured we would do over the next two or three months, I’m going to be spending 70% of my time hiring in some cases and so will you over the next year or two.

And they thought that was crazy. And I said, oh, if we’re doing this together, you’re going to learn how to recruit properly and we’re going to learn how to interview properly and we are going to be very intentional about who we bring into the company and why we’re bringing them into the company and for what reason and on what understanding and what values we’re tied to. And that one, I think has been really important.

Not just the idea of we want to hire great people, we want talent density, but the commitment to a philosophy about how to do that. Griffin and Ruslan were very committed to that they didn’t know how to do this necessarily, but that it was really important. And that’s been a hallmark of our culture and how we’ve built the company so far.

Mark MacLeod:
I’m sure anyone listening resonates with that. Anyone who’s gotten into scaling realizes how critical hiring is and also how challenging it is. I’m curious, other than putting the reps in and screwing up, what did you do outside of that to accelerate and become excellent at hiring?

Rob Khazzam:
Yeah, I mean, at first very little, because in the first few months we didn’t have much hiring to do. But then once the product started moving and we could see there was product market fit and we could see the round was coming, we started by just trying to do a lot of outreach. What I saw pretty clearly was there was no brand and no one knew about the company.

I had a bit of a network in Canada, but it was only enough at that stage and we were desperate to hire engineers. So I showed them the operational excellence of recruiting that I had learned, which was to pound the pavement. Do you want to hire one engineer? Well, you better book ten coffees and you better do 100 outreaches.

We got good at measuring the inputs to recruiting, so we were very militant about organizing outbound and sourcing email campaigns from all three of us. We were diligent about making sure that each week we had clear next steps with candidates. I’m going to bring this person in for coffee and I’m going to do it in two days. I’m not going to wait another week. We nudged that stuff all along, but it wasn’t enough.

And we did have a lot of challenges hiring in those early days, we struggled with engineering, and then we started to step it up and do a lot more employer branding. And I think that was a decision from my time at Uber and also seeing what was going on in startups in 2021 in the US was a great opportunity to build some buzz around what we were doing. And so it was a bit counterintuitive as a startup to be doing it. I think we spent $40,000 in the summer of 2021.

We rebranded the company, the name of the company, and the website. And we also filmed recruiting videos. We filmed interviews with our first ten employees. We interviewed them about working at Float. We interviewed and recorded snippets of us talking about our product, our mission, and our cultural values. And we started working hard to get into different talent markets. So when we would post a role, everyone at the company would post it, and we’d tag people we knew.

And so getting from five people to twenty-five, that was a very intensive process of building an employer brand foundation, trying to be smart about creating a little bit of virality and branding around the people we had hired.

And then just a lot of time for me to build relationships. I took most of the senior leaders at Float, whether they met me, interviewed with me, or applied for a job, I went on walks and met some of the family members, and a lot of the senior leaders who joined Float. It took me three to nine months in some cases to recruit those people, and I still recruit a year or two ahead.

I tried to be pretty genuine about that. So as I recruited for product or engineering or different functions, I wanted to find the best, but I’m going to just reach out to the best and say transparently, this is what I’m doing, I’m trying to find someone, I’m curious if you could help me, and if you have any suggestions, I’d love to compare notes.

Half the time that led to those who were interested in learning more, or those who knew someone who may want to know more. And if you do that a couple thousand times, then good things happen. And I think that was really what those first two years for me were all about. It was mostly recruiting.

Mark MacLeod:
I love it. So the themes that are standing out for me so far are learning. Private equity, I’m looking at 100, 200 PMLs a year. I’m learning Uber, learning on steroids, and then kind of massive execution.

And you brought that massive execution to Float, and from the outside looking in, Float seems like a rocket ship. You’ve got a tier-one Canadian investor in the form of Golden, and a tier-one global investor in the form of Tiger Global. What do you attribute this kind of massive growth to? Is it just that relentless execution, or were there other aspects that are worth touching on?

Rob Khazzam:
Well, I’ll start by maybe bursting the bubble…

Mark MacLeod:
I don’t expect that. Every company’s got issues, right?

Rob Khazzam:
Yeah, Float is still an infant. We’re three and a half years in. We’re proud of where we’ve come, but we’ve got a long way to go, and staying humble and disciplined about where we are and avoiding complacency is important. But I think we’ve mainly been lucky. You need a lot of luck in startups.

Let’s count how many things aligned for us. We got financed in 2021, which is a great time to do it. I met my co-founders because I had a board relationship that had a product that they had already built in an MVP that was well-timed. And I think what we should take credit for, or at least celebrate that we’ve been able to do, but we must do it every day, is to recruit outstanding, world-class people who are passionate about solving the problems that we solve.

I didn’t mention it in the values, but you have to be passionate about what you do to succeed in startups, because anyone else would just give up. What’s embedded in all of this?

I’ve described all this work, but recruiting people who find this stuff fun and interesting and want to solve customers’ problems and want to compete to have the highest quality bar for customers and provide customer service even at 01:00 a.m. on a Friday, I think it’s been the commitment to recruiting great people who are genuinely passionate and committed to that mission and being fortunate that we have customers who have been patient with us and have shown loyalty to us because we make mistakes along the way.

I think those are the things that help you create success out of nothing and continue to double down on that as the company changes because change is always a constant. And I think that you do need to have that long-term commitment because there are a lot of good moments but a lot of hard ones. And you need to genuinely want to create a better landscape for businesses in Canada. Better B2B finance, modern rails. If you’re not passionate about that, you’re not going to go far.

Mark MacLeod:
Now tell me a little bit about the decision to focus on Canada, because the knock on the Canadian market often is that it doesn’t do something unless its peers in the US have done it. So, what made you decide to focus on Canada and not on the US?

Rob Khazzam:
I mean, we feel a real, genuine mission to serve Canadian businesses better. I mean, I was frustrated when I left Uber as an employee thinking about where am I going to work in Canada that I could make an impact that I see here, not in the US. And as a citizen, as a resident, as a voter, I think we all share a huge amount of pride and frustration, frankly, that the Canadian finance ecosystem is not working for all businesses. It’s not keeping up with the US.

There’s a real sense of pride, frankly, that we want to be the ones to do that in Canada for Canadian companies. And more importantly, we really believe that in order to do that, you have to build Canada first. It’s not just a software application layer. You do need to build really strong banking relationships here. You do need compliance programs. You do need to be close to customers.

So we saw very, very quickly that the market needed it. And we felt that, as we have seen and studied in other markets, and I studied a lot of case studies in other business industries, where you have American companies come to Canada and compete, where that hasn’t resulted in the kinds of industry change and innovation that we all read about and want to see here.

So, there’s a real, genuine pride in that. And we do believe the market is substantial. There’s $5 trillion of B2B payment volume every year in Canada. And the long-term trends around payment modernization and business banking modernization, are not changing.

No matter what happens in the next year or two in the industry, the move towards modern business banking, and modern business payments is going to happen. We want to be the ones to marshal that into the industry in Canada and to help unlock what feels like it’s missing in Canada, which is a level of innovation that transcends just software. It applies to how money moves and we are fired up about that.

Mark MacLeod:
Amazing. I have to imagine that a decent chunk of that 5 trillion is floating through Schedule 1 banks. So, at what point does it become David versus Goliath and you take these guys on?

Rob Khazzam:
Yeah, I mean, we want to offer a lot of things that the banks offer today in a manner that we think is outdated. So there’s no question we are positioned as a company that thinks there is a simpler way and looks at the way that banking today operates in Canada, the way that card payments operate in Canada today, the way that the wholesale aspects of the finance department are hugely outdated and its a source of real motivation.

It doesn’t have to be this difficult. And I see the narratives in Canada now about modern banking and real-time rails and everyone’s sitting around asking, waiting for someone else to do something. It’s like the government’s going to do it and the banks will do it and these associations will do it. To hell with it. If we can help them do it, great. But we’re not going to wait for that. We’re just going to do it ourselves and we’ll figure out how to make it happen. And if we have to build a partner, we’ll partner. And if we have to build it ourselves, we’ll build it ourselves.

And if we have to, frankly hire GPTs and humans to auto-categorize all of the manual transactions of our customers and use technology to do that, and we have to become a licensed, regulatorily compliant entity in Canada to do this stuff, we’ll do all of it.

To work backward from that experience we want to enable here, which is the ability to pay any vendor in the world globally instantly, the ability to access capital instantly, not in four to eight weeks of engagement with a bank, but through an accounting connection, through a bank account connection, through software that can read your financial statements and quickly determine what level of credit you can access and deploy to invest more in your business.

Great automation that eliminates all of the hassles of managing spending and helps finance teams across the country spend more of their time informing strategic decisions, and strategic investments.

How can we be more productive as a company? How do we grow our revenue faster as a company? As opposed to, hey, the sales team went to Nashville for a week and we got a backlog of transactions to reconcile. So, those are the things that were fired up to do. There are simpler ways to make these things happen. Canada, in my view, has to dream bigger and we have to stop settling for the service quality that we’ve become accustomed to in this country.

Mark MacLeod:
Amen. I’m all over that. Even my tiny little business, my chief of staff is in Colombia, and I can’t pay them directly. I can’t pay them through my bank. I have to do this kludgy process and send documents to his bank so that they don’t feel there’s some money laundering BS going on and it’s such a hassle.

When I was hearing you talk about your 18-month stint in Europe and just how intense that was and how you were alone, you never had time off, what came up for me was like, soldiers in theater, and soldiers in the theater do so for short periods and they come back and they have PTSD and they need to recover. And then you kind of go right from Uber right into this. And so I’m wondering, do you have PTSD? Like, what’s the state of your mind? Do you have the capacity to be happy or are you just always intense?

Rob Khazzam:
Yeah, it’s evolved. I was with Uber for five years and I had three jobs. There was the launch job, then there was the GM for central and Eastern Europe jobs, and then there was the GM for Canada. When I became the GM for Central and Eastern Europe, I had to unlearn some of that. So after that 18 months, I was still out there for two years. Now I was managing GMs and bigger businesses and working with more experienced stakeholders.

I did have to learn how to taper some of that back. Not everything is about execution. Strategic thinking is important, building trust is important, and taking the time to strengthen interpersonal relationships above and beyond the OKRs or the goals on the page is important. And I think I’m still learning that.

My time as a GM helped me soften and round that skill and also learn how to be mentally healthier. I learned that working seven days a week is not admirable and you may need to do it a bit, but you’re probably not going to show up very effectively as a leader if you’re thinking and looking and acting in an adrenaline-fueled way all the time.

So, it has been a gradual process of learning how to harness the good parts of that experience while also being more strategic over time. In my last years at Uber, the message in the company was, everybody, chill the hell out. Let’s take a step back here, get off the hamster wheel for a minute, and be strategic. What are we trying to achieve? How can we best achieve that, not just next month, but over the next year?

And I’m grateful that I’ve had that experience and worked with people that have helped me see that. So the leaders I work with now, are all in, but they also push me, and they give me great feedback about how I can be a better leader. And so those have been great learnings.

On a personal level, you also realize that the sacrifices and commitments you make in a business are real and so there’s nothing wrong with making them. But you’ve got to be happy personally and whatever that means, whether it’s dating, going to the gym, or making sure that you take time off, you need to fulfill those other parts of your life, or else you won’t show up and be the best leader you can be.

Maybe you’ll do good documents, maybe you’ll send okay emails, but you’re not going to inspire people and you’re not going to build the kinds of momentum as a team, optimistic, and positive culture that you need to cultivate if all you’re talking about is we got to hit this goal and everything has got to be intense 24 hours a day.

Mark MacLeod:
So do you feel like you have sufficient boundaries? Like, is your life sustainable?

Rob Khazzam:
I think my life is sustainable because I love what I do. I would rather be working on and doing what I’m doing than anything else in the world. There’s nothing I would rather be doing than what I’m doing. Is it a lot sometimes? Sure. And is it a lot for everyone at the company? Often, sure. But it’s worth it. We love doing it. I love doing it because we have this fortunate opportunity to build something everlasting that will hopefully be around for a lot longer than I am. And that’s special.

I could spend the rest of my years chasing an opportunity like that. So I actually feel really grateful that I’ve had the opportunity to have these experiences and to be working with the people I work with at Float. To be serving the customers that we serve is incredibly inspiring and rewarding.

So I don’t feel bad and I don’t like people feeling bad for me. I get to do something I love every day and things that are worthwhile are hard. With that opportunity comes pressure and the fear of failure. And the best antidote to the fear of failure is hustle, work, and preparation.

Mark MacLeod:
I love it. Now speaking about intensity, I only coach CEOs, especially those who are founders have more context but also more motivation than anyone else. It’s their company, their identity is tied up to it, and they are a meaningful participant in the cap table. I’m wondering how you translate that intensity to the rest of your team who don’t necessarily have that same motivation, and where if you dial it up too much they just check out and go somewhere else.

Rob Khazzam:
It starts with who you hire. And I mean we hire very intentionally, which is we only hire people who give a shit. I mean we don’t hire people who are just passively interested in what we’re doing. And if we do, they generally won’t have success or may not last very long. So I demand and expect commitment, accountability, ownership, and passion in the people that I recruit. And it makes it a lot easier because I don’t think it’s fair to demand that from someone. If they don’t want to be like that, they aren’t that committed. It would be absurd to expect it of them.

So for me, it starts with recruiting and understanding the people I’m hiring. Who you start with is probably the highest leverage decision I make as a leader. Then in terms of working with them, what I try to instill is a sense of pace, a sense of ownership, and ridiculously high standards, that no matter what progress we’re making, we can always be better, we can always grow more, we can always do a little bit better.

And to try to be the person that can call attention to when we are meeting that and recognizing it and celebrating it, and then also being willing to hold people accountable when we’re not. Sometimes that may mean pace. Like, hey, we’re not moving fast enough, folks. I know we’re on track for the quarter, but this stuff is moving at a stale pace. What is going on?

Being willing to challenge people and amp it up, as Frank Slupman would say, I think has been important, but I’ve learned a lot of really important lessons about not overdoing that. And I probably relearn that lesson once or twice or three times a year where I’ll overdo it, and then it’s an opportunity for me to take a step back and say, how was I too intense in this situation, and how did it contribute, for example, to an erosion chipping away of psychological safety?

If Rob is too intense for a month or two on accountability, I might find in the subsequent months that people are afraid to fail, that we aren’t making those big, bold bets, and that people aren’t being vulnerable. And then I look around and go, well, how did I contribute to that? How can I be better and be more nuanced in how I’m an intense leader? And that’s something I don’t think I’ll ever be done working on, to be honest.

Mark MacLeod:
No, endless layers to that onion, that’s for sure.

Maybe the last question as we start to wrap up. Fintech is generally going big or going home, and it just takes real scale for these things to work. And when I think about your category, I think about Brex which kind of burnt its way to greatness and that consumed a lot of capital, did a pivot kind of pretty far into that journey.

Just curious, have you studied Brex at all? Do you draw any cautionary tales from them? And also just because you’ve committed to this path now of capital, what do you think generally about the consumption of capital as you try and achieve a big scale here?

Rob Khazzam:
Yeah, I mean, this is one area where I’m grateful if we come full circle to the beginning of the interview, the financial experience and that intellectual curiosity and truth-seeking and financial background were really helpful, even in my time at Uber. I think that if I apply what I’ve learned in startups against the backdrop of the financial experience, it’s that there are great opportunities in technology, and you have to understand how big your opportunity is, how important is scale, depending on what business you’re in, what are the unit economics of your business?

And I think you can make really big bets. I think that one of the best things about the startup and entrepreneurial industry, is you can raise tens of millions of dollars and make these big, important multi-year investments and try things that may not work out, but where the upside is asymmetrical, where can I invest $1 million but create a $25 million revenue business? I think that that’s a great aspect of the startup industry.

There’s always the downside, which is there’s been a lot of exuberance. I mean, Float did a big series A. People would point to that if I pick one of our own examples. But Brex did have a huge round. Uber certainly had raised a huge amount of money. We’ve seen with that a lot of waste, a lot of excess, a lot of mistaking subsidies for product and traction. And so we’ve tried to find the balance.

I don’t know that we ever did it perfectly. I think we’re probably pursuing growth too aggressively and then pursuing efficiency too aggressively and trying to find somewhere in between. But the lessons from Uber were significant, and in the second half of my time there we had to unwind from a lot of the things we did that were not very smart, we wasted a lot of money, and we missed opportunities to say, okay, we’re doing this now, but this is not sustainable. We need to figure out another way to do this. There’s a more sustainable way to build something.

And I think that there are plenty of examples of that over the last couple of years. If you look at building bloated teams, running campaigns that are massively promoting and discounting products, and the erosion of your value proposition to customers, and over-hiring, we’ve made all of those mistakes as well.

But I think that those are the things that I look at and say, how can we be aggressive about the investments we want to make? Those asymmetrical bets are where it’s attractive to make a multimillion-dollar investment. Then what are the areas where we’re just not ready yet? Hey, we’re not ready to hire 70 people on our sales team. We’re still figuring out how to operate it at 25.

We want to go bigger, we want to go faster, so maybe that means we’ll experiment. But let’s not build an army of people to run a function that we haven’t figured out how to optimize yet. And I think that’s the stuff that I try to keep in the back of my mind and straddle that line of being aggressive and ambitious, but taking really that long-term shareholder mindset.

And maybe to close, I think being realistic and true to yourself about equity value per share, not valuation, not dollars raised, equity value per share that you’re creating for all of your shareholders. I think the more that we all stay anchored to that and not the valuation of the overall company, I think if you think through that lens it changes how you make financial decisions as a founder.

Mark MacLeod:
Amazing. I love that. Wise words. I’ve got to say, I’ve always said no one wins unless the common shareholders win. Yes, I’ve got my prep as an institutional investor, but if I’m exercising it, it wasn’t a win. By definition, if that investment is a win I’ve converted to common, so I love that you’re thinking about all the shares.

Rob Khazzam:
It’s just long-term value creation.

Mark MacLeod:
Yeah, I’ve learned a ton from this discussion. It could have been a lot longer. We probably could have just done an hour on Uber and then an hour on what it means to execute relentlessly inside a fintech company. We probably could have done an hour on Canada, and whether it’s competitive or not. Anyway, I really enjoyed it. Thank you so much for taking the time.

Hey, thanks for checking out the Startup CEO Show. If you’d like to connect with me, be sure to visit my website at markmacLeod.me, or follow me on LinkedIn at The Mark MacLeod, or X account @markmacleod_, and if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We’ll see you next time!