Cody Ruberto Shares His Remarkable Journey & How That Inspired Him to Build Ridesharing for Small Towns Against All Odds

In this episode, we hear from Cody Ruberto, founder and CEO of Uride, who shares his remarkable journey of building a ridesharing service for small towns and cities across the world. Motivated by personal tragedy and the transportation crisis in his hometown of Thunder Bay, Ruberto launched Uride with just $3,000 and no business experience.

This conversation explores how his professional soccer background shaped his entrepreneurial resilience, the numerous obstacles he overcame to build the business without venture capital, and his mission to prevent impaired driving deaths in communities forgotten by major ridesharing companies.

So, what does it take to build a successful ridesharing company with just $3,000? Let’s get into the gritty details of Uride’s journey in this eye-opening interview:

Mark MacLeod:
In this episode, I sit down with Cody Ruberto, founder, and CEO of Uride. There’s been a lot written about how hard it is to build marketplaces. Imagine how hard it was to build Uber. Now imagine building 50 or 100 Ubers simultaneously. That’s what Cody is doing with Uride. He’s bringing ridesharing to small towns and cities throughout the world.

He’s got a really powerful origin story for this very deep passion. Super hard business. VCs wouldn’t touch it, but he leveraged his background and his competitiveness as a former professional athlete to persevere despite all of this. Honestly, I knew some of the story before going on the show with him, but I just had so much love and respect for him and his business after this conversation.

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

Cody Ruberto:
Good, yeah. Pumped to be here. I’m a huge fan of your podcast and, like, obviously your blog. I’ve sent you emails a bunch over the years and helped us a ton. So, yeah, excited to chat again.

Mark MacLeod:
Amazing. One of the reasons why I wanted to have you on the show is that I feel like you’re doing something extraordinarily difficult. Many of the guests that I’ve had on the show are folks who’ve completed the journey or are nearing the journey, whereas you’re just still in the thick of it. So I thought it would be cool to unpack all of that as well. So maybe just first of all, briefly, for folks who don’t know what Uride is, just maybe tell us what it is that you do.

Cody Ruberto:
Yeah, ride-sharing for small towns. So I’m from Thunder Bay. For those of you who are in Canada, in a smaller city, there was no Uber, no Lyft. People used to wait over an hour for taxis. And my background is completely different. I’m not a business person, not a tech person. I was playing sports, I got injured, saw this problem, and yeah, basically I just started giving people.

I would go out with friends, and end of the night, you’d wait an hour for a taxi. When a taxi did show up, there’d be 10 people rushing it. I’ve seen fistfights break out waiting for cabs, and people would just walk home or drink and drive, and it was insane. I’ve had friends who have been killed, and basically, yeah, also like growing up, one of my best friends at the time, his brother was driving drunk, and ended up killing someone. The person he killed was another friend of mine, it was her brother. I grew up with her whole family. So yeah, it’s, it’s just a problem that shouldn’t exist. So I started giving free rides to people after the bar.

I would do maybe two or three rounds, just kind of on my own. And that wasn’t enough to make a difference. So we just thought, you know what, screw it, we’re going to start a ride-share company in Thunder Bay to fix this problem here. There was no Uber, no Lyft. I had now a year off from soccer. I was playing soccer overseas and had a bunch of surgeries in the U.S., and that’s how it started. And then we did like a bunch of other people reaching out across Canada in these smaller towns, saying they had the same problem.

And then it turns out there are a billion people in these small towns around the world who don’t have access to reliable transportation. And so what we do is we’re trying to fix that. So we operate in all these smaller communities that are kind of the forgotten cities, like where I’m from. And yeah, we’re just trying to fix this problem.

Mark MacLeod:
A deeply personal path to you, in terms of just feeling this pain. Like, people you know and love are dying because of this gap.

Cody Ruberto:
People often don’t know the stats. There are seven times the number of deaths caused by impaired driving per capita in these smaller towns versus urban centers like Toronto, Vancouver, and places that have options.

So, transportation is a huge part of our lives. People need options. And even for like a lot of people, if you’re from Toronto or you’re from a bigger city and you go to one of these towns that doesn’t have ridesharing, it feels like you’re going back in time, right? It’s like Oh yeah, we still got a ton of work ahead of us. But yeah, I’m super excited and passionate about going and fixing this problem for all these communities around the world.

Mark MacLeod:
When I think about marketplace businesses, lots of complexity, right? You’ve got to create lots of supply, lots of demand, and then create liquidity so that the people driving feel like they’re getting enough rides to earn a living. And then there are enough drivers so that the people who want to ride don’t have to wait too long. And I feel like that’s challenging in any market. I’ve read lots about Uber getting going in different cities and having challenges with that. I can only imagine that in small towns it’s even more challenging. Tell me about how you were able to crack the code on that.

Cody Ruberto:
So the start was in a lot of pain. I started the company with $3,000 and no other money went in until we were much bigger, like in millions of dollars a year or whatever. So a lot of pain, a lot of suffering. Like, we’re a 24/7 business, and we couldn’t afford to hire any dispatchers or any other support. So, when we started the company, there were all these different things that I didn’t know.

One of our core values and a belief I’ve held for pretty much my whole life is that there’s always a way. And just repeating that a hundred times a day when I’m going through some horrible stuff. Challenges where you have no idea what you’re going to do. Continually repeating that has gotten us through so many situations where we should have died.

And yeah, starting a marketplace business with $3,000, like, trying to figure out how to get an app up and running. Like, I didn’t go to university, my background is in sports, I had no idea what we were doing, and I just cared about this problem. So the early days of Uride, I don’t know what you want to get into, but we could talk about how you started a company with $3,000…

Mark MacLeod:
Yeah, I’m actually curious to figure out how you started a company where you had to build a piece of software for $3,000.

Cody Ruberto:
Yeah. So at the start, there were a ton of challenges just getting to the point where we could turn the app on. But yeah, basically before the app, it’s like, okay, can we do ride-sharing in Thunder Bay? Like, why aren’t Uber and Lyft here? And I was checking into all this stuff, and you couldn’t do ride-sharing in our city. So they had a bylaw that prevented ride sharing. And that kind of killed that idea at the start.

Then I reached out to Operation Red Nose. I don’t know if anyone listening is familiar with it. It’s an organization that gives free rides every December. It’s all volunteer-based. And I reached out to them. I’m like, hey, if we could figure out how to like, get an app up and running, and I could kind of help sort some of these things out. Again, I had no idea what I was doing, but like, can we run this all year round? Because people don’t just need rides in December. This is a year-round thing.

So we ended up getting in touch with their head office. They thought we were a bit nuts, so they didn’t move forward. But this could have just been like an opera.

Mark MacLeod:
You probably were a bit nuts. That’s okay.

Cody Ruberto:
Yeah, a little bit. Yeah, I don’t blame them. And then from there, I just started reading the bylaws in our city, and the third time reading through it, I saw this line that limousines could set their own rates. I’m like, okay, interesting. I’m like, we could probably run with this.

Then I started calling up these limousine companies, and I’m like, hey, the first one I called, I told them, drinking and driving is a huge problem in our city. If at any time your cars aren’t being used, can we fill them with drivers, get them on the road, and get an app up and running? The first people we called thought we were nuts and hung up.

There are only two limousine companies in Thunder Bay. The next company, we went there in person and told them the same thing, and they also thought we were nuts. But I just told them, your cars are parked. So, best case scenario, this actually works and you get paid per ride that we give or whatever, and you make way more money than you’re making right now. And we get to make a difference in our city and help people get home safely. I mean, worst case, you’re in the same position you are now, and like, can you just go for this? Let’s do it. And then they ended up agreeing to it.

We made a deal, got that sorted, and then it was like, okay, how do we get an app up and running? So I started calling people, software, and all this stuff. And it was going to be around $300,000. These quotes I was getting to build an app for. And I’m like, okay, starting the company with $3,000. I’m like, I’ve got to go for these major hip surgeries in the US and pay out of pocket for all these things. And then from there, I’m like, okay, so we don’t have that money. Like, I’m sure there are people who have built rideshare companies that have failed.

Like, maybe they have products and things that they’re not using now that we could figure something out. So I just started calling every ride-share company that started and failed, seeing if we could get their code, do a deal thing, or something like that.

Then started coming across like white labels and then ended up making a deal with one company where it’s like, hey, we don’t really have any money right now, but if you work with us you can make a little bit more over time, and yeah, convince them to kind of work with us and get this started for almost no money.

And then from there we got up and running. We had a limousine partner, and we had an app that we could put on the App Store. And then we also had no idea what we were doing.

So, I wouldn’t recommend starting a business like this, but I didn’t tell anyone about it. The night before we launched, I put up a post on my personal Facebook page just talking about this problem. And like, this is a problem that shouldn’t exist. I have a year off from soccer. I’m going to try to fix this problem for Thunder Bay, and like, let’s go for it. And then that post went viral. So in Thunder Bay, viral is like you get 5,600 shares.

And people started downloading the app. It was so cool. And then the first ride came through. And then I remember going to pick this person up, and I was so excited talking to them in my car, and like, I forgot to click, drop off, and overcharge them. So I ended up just giving him a free ride.

But yeah, from there it was the start of just chaos for six months, where orders started coming in. It’s a 24/7 business. A week after we launched the CDC, I guess they saw my Facebook post, they did an article about this, and then put it out because it was weird. It’s like they said that a professional soccer player launched an Uber-like business in Thunder Bay, and then thousands of downloads started coming in, and then demand just started exploding, and we barely had any drivers.

The limousine company had four cars. So we were like trying to get drivers to fill those up, trying to figure out how to run a business, trying to figure out how to pay drivers every week, 24/7 dispatch customer support, working as a driver all the time. And then like, I think early in the life of Uride, I had to like get two major hip operations. So like micro fractures. This is the kind of thing that could end someone’s career. I knew it would make it back.

But in the early days of Uride, if you were a customer and you booked, and let’s say it’s like, I don’t know, 3 am, 4 am, I was crashing into my uncle’s basement in Thunder Bay. I crash out of their house at 3 in the morning. The whole house would wake up, throw the crutches in the passenger seat, and come pick you up. You would hop into the car, and you’d look, and they’d see these crutches. And like this person had a huge hip race, and customers used to go, Are you okay to drive? I’m like, yeah, no problem. Hop in. I just moved the crutches over so people would hop in my car and into my phone.

Again, we had no employees at this time, so my phone would ring nonstop with customers in the car. And I’d have to say, like, hey, is it okay if I pull over and help this driver? I’m so sorry. I’d pull over, help a driver with an issue, work out something if it was a customer, and then keep driving, and then make sure that I stop the trip early so that this customer doesn’t get overcharged. And it was just chaos.

And soccer was my life. So, at this point, I’m still like, soccer is my path. I’m going back to you. Like, I know I’m going to make it back from these injuries, get back to Europe. So, in between driving people to work in dispatch, I’m going back and forth to the gym and physio and trying to do my recovery for these major hip operations. So yeah, it was nuts.

Mark MacLeod:
That’s wild. I’m so curious. Like, you managed to get a couple of folks to take a leap of faith there. Was it just your energy and passion? Like, you can go for the heartstrings here with the stories about these deaths that are close to you, do you think that’s what got them to kind of take a leap?

Cody Ruberto:
For example, a limousine company was called Granite Town Cars. Nadia, she’s awesome, and yeah, she really cared about this problem, and she had also been affected by impaired driving, so that was a big part of it.

And then also the vehicles were sitting there. So it’s like when you weigh out what the risk is of trying this versus just not trying it, it’s like, yeah, I thought it was a no-brainer. So yeah, a lot of people took chances on us. And I guess the other thing, too, is we did get tons of no’s, so we wouldn’t stop until we found a way past everything that got in our way. So any rational person should have quit many times.

So I don’t know. Yeah, like I don’t want to make it seem like we talked to a couple of people, and it just kind of worked. Limousine company, let’s say it was the second one, but the app provider was trying to get a platform up and running with no money. I must have talked to probably 150 different people. Like just. Yeah.

Mark MacLeod:
Now you said ‘we’. Was there a we, or is this just you?

Cody Ruberto:
At the start? It was me. And then probably started working on this in December, January of like well January 2017. We were live by March 27th. And then by the summer, I convinced my cousin to quit his job in downtown Toronto and move to Thunder Bay, work for free, and also be on 24/7. So then there were two of us. This was a couple of months in.

Mark MacLeod:
Sounds like an awful job. I really would love to have heard the sales pitch.

Cody Ruberto:
Yeah, call them multiple times every week. He was working for like a much bigger company in downtown Toronto, and yeah, just why did he actually go? That’s a good question for him. But just kept talking about it again, we actually had like, I think I was talking to him about it before, and you know, nothing really happened. But then we had revenue, we were growing, tons of orders coming in, all this stuff.

So yeah, was he excited? I think he was pretty pumped to jump in and try it. And then it’s like, I don’t know how much, maybe I didn’t tell him everything, like how bad or painful it was going to be. We were both having no salary for I don’t know how long, probably a couple of years. And it was just chaos.

But we saved up enough to hire a nighttime dispatcher for eight hours. This was a couple of months after he joined. And, like, that was incredible because now, like, before we get the first call, it goes to someone else and then comes to us. So I started 24/7, sort of on my own, then two of us going 24/7. So that made it way easier.

And then tons of obstacles and things happened along the way, but just like, as we grew, we were able to get more people on board and start launching more cities. Well, we started having a bunch of people reach out who, like, I would drive passengers who were from Saint Marie, Sudbury, even Fredericton, and places across Canada, that would be in my car. And you need to come to our city. We have nothing. So then we started thinking about expansion, and man, it was a roller coaster. Especially in the early days.

Mark MacLeod:
When you think about product market fit, it’s very clear from the demand side that you had that right away. And if I understand correctly, in Thunder Bay, you guys had to be the drivers. It wasn’t about now acquiring the supply side the way Uber does. Is that true in all of your towns, or are you building both sides now?

Cody Ruberto:
Now we’re building both sides. And even first launched, we launched with something that wasn’t scalable. Like we’re partnering with a limousine company. Basically, they had like four cars, so we were able to drive a lot of times. Then we were able to get drivers on board.

Product market fit was horrible on the driver’s side, so we had to beg drivers to stay on the road. Like, whatever it would take. There were times when we would buy a family dinner so that the person could work. I’ve offered to babysit people’s families so they can get on the road and drive. Whatever it took to keep drivers on the road, we did.

And a lot of the early drivers really cared about the mission and what we were trying to do. A lot of the drivers today really care about that as well. But yeah, I’m super grateful, especially to the drivers. And in these early days, when it was a horrible job, they were unbelievable and helped kickstart this thing. Then, eventually, our demand started skyrocketing, so the limousine company didn’t have close to enough cars.

They started buying more vehicles. They got up to six or seven. Then we found a bus company that also had a limousine license, and they had like two cars that they kept on. Then we had to figure out, okay, demand was still going through the roof, like, what do we do here? So then we found this sort of loophole where you could lease your personal car to this bus company. You could fall under their commercial insurance and their licensing, and then get on the road and start driving.

And then we started scaling up to like 30 cars, 40 cars. And then the bus company may be a story for another day, I think there are crazy things that happen in business, but this person wanted to invest. First, they wanted to buy the company, and they had an airline bus company, all these things. And we had just started in Thunder Bay.

They wanted to buy the company, and we were like, I don’t know, we don’t really want to sell. And then they’re like, cool, like, can we invest? And we’re like, I had sort of a bad feeling about it. You meet some people, and sometimes you have these feelings where it’s like, I don’t think I should stay close to this person, and all that. And then the person ended up blackmailing us. Can’t remember how long it was, but I got healthy, recovered from surgery, and got back to Europe. We had like a dispatcher, and now I’m doing soccer and building the company, which is insane.

But, yeah, this person started putting tons of pressure where they’re like, they wanted us to sign this document to change the bylaw so that they could have their own taxi company or whatever, and lock in a number of cars. We could have a small portion of the market and lock it in. It was a really weird thing.

And he was basically trying to force us into signing this document, saying that we support it. And he’s like, if you don’t sign this thing, I’m going to make sure that I ruin your business and you guys go bankrupt. I’m going to pay journalists to write horrible articles about you. And I’ll go to the council and also pull all your cars off the road by Monday. And like, almost all of our cars were kind of underneath this person.

And it’s Friday, and like, we have this gun to our head. And I remember I was in Manchester, England, and I booked a flight. There were these developers. We needed something built to be able to get our own commercial insurance and switch all of our cars over to our own insurance. And we were sort of like, we had a bad feeling about this person. So we’re kind of working on this. But now we had a gun to our head.

It’s Friday night. So I just booked a flight that night to go meet up with. I knew there were these developers we needed to build this thing. They were in Las Vegas at this conference or whatever. So I booked a flight that night to Las Vegas, met up with them on Saturday, and made a deal with them on Saturday during the day.

They stayed and worked basically until Monday morning, and built this thing that we needed for the insurance company. Monday morning, I called the insurance company before the start of the day.

We switched all of our cars over on Monday morning to our new policy. And it was insane. So we survived and kept the business running. This person, on Monday, pulled everything. So they said, all your cars are off the road. They went to the council. There’s probably a video of this somewhere. But they went for a council, and I sent a message to all of the council and the mayor and told them everything that was happening beforehand.

So he went up and said all these horrible things about us, and just made up these things. An article came out, like a hit piece in Thunder Bay, saying we were selling drugs out of the car. They were saying there were all these assaults and things, and we were like, covering them up. Just like complete fabrications.

After we started talking, they’re like, okay, next. And he just looked around like, what is happening? And then from there, we survived. We had this new model where people could go under their personal cars and under our commercial insurance. And it was one of the crazy things. There were multiple crazy things that happened to us.

Mark MacLeod:
I’m curious, do you still have anger toward this guy? And does that fuel you, or have you just moved on?

Cody Ruberto:
Do I still have anger? I don’t think I have anger. I think that it helped us a lot because right after that, this person started a competing company and then just tried to kill us with cash. And we’re like, you know what? It’s time to expand. We need to get big quickly. We can’t get bullied by someone like this. We just focused on providing the best service in Thunder Bay for our customers and for our drivers. It gave us a lot of fire to expand, a lot of fire to fix some of these problems that we had, and we just used that as motivation.

Yeah, I don’t think I have anger now. When there are bullies and things like that, it really bothers me. And so if it’s happening to us, if it’s happening to someone else, I’ve got to know I’m the type of person that will stand up for things that I think are wrong. And, yeah, I don’t know.

I think you have to treat people well. I think in business, if you help people and you’re trying to be a good person and try to fix a problem, I think you’ll be successful. And I think that if you’re always just trying to screw people, trying to do whatever you can to make the most amount of money, regardless of the moral side. Maybe it works for some people. I think over time, you won’t be very successful.

And a couple of years later, I was… There’s like a community sauna in Thunder Bay or whatever. And like, I’m in the sauna, and I just heard someone screaming at this girl. There was someone working as a lifeguard, and the person’s probably 50. And I heard this person just screaming. I think she was telling everyone, it’s 8:45, we’re going to close in 15 minutes. So people got to kind of start moving.

And I’m listening. I’m like, I recognize this voice. So I go and I look and it’s the same guy, like, going off on this girl. Like, I’m going to go to the council. You guys are like, it’s 8:45 and you’re trying to get people out. And then, yeah, talk to him. And he said, like, hey, I shouldn’t have done any of that, and I’m sorry. So, yeah, not holding it.

I think that we should help each other. And I think in business, try to be a good person. Try to help people. And don’t be a bully. Like, support people. Even if you’re competing with people, too, you can do it in a good way.

Mark MacLeod:
This is hard, like, I’m trying to figure out how to ask this question. Like I’m trying to figure out what role being a professional soccer player and being an athlete has had on your success. It’s hard for you to answer because you don’t know what you’d be like if you weren’t that. But hey, what I’m hearing is tons of resilience, tons of positivity, and tons of energy. Anyway, to what extent do you think you’re drawing on your athletic background to run this company?

Cody Ruberto:
I think there are two separate things. So one, which is like my athletic background, like when you’re on teams, you have so many different coaches, so many different team environments, so many different ways of running teams, and all these things. So you learn a lot and you sort of figure out at least what you think works, what you think doesn’t work. So you get these ideas in your head about how you know you would kind of do things.

But the biggest thing that soccer has helped me with and like the pursuit of that career like there’s nothing that comes close that’s anywhere close to as hard as my soccer journey was. So the amount of physical pain I endured… I’ve had like six hip operations. I’ve had crazy scenarios with like 19 doctors telling me I would never play again. So all of these different things, physical pain and emotional pain, of the amount of times I basically had my dreams feel like they’re getting ripped away from me.

So it makes whatever I’m going through in business, even that situation I described, nowhere near as challenging as some of the scenarios in my soccer journey. So yeah, pain tolerance helped me out a ton. I think how much pain you can take going through the early days of a startup, I think it’s a huge indicator of success.

You can like to get through all these different things. And like every founder I talk to, they have kind of insane stories of trying to get their business up and running, and the obstacles, and any rational person should quit. So yeah, from soccer I got resilience, pain tolerance, all of that. There are other things I could talk to you about, running the company, building teams, all that, that I think are useful.

Mark MacLeod:
I’m guessing you’re pretty coachable, given that you’ve been coached all of your life.

Cody Ruberto:
Yeah. Am I coachable? I think I’m super coachable. I think that there are times when business is a little bit different, where you sort of have to. In soccer, I was kind of like a robot. If my coach wanted me to do something, I would do it, whatever it was. I think in business, especially in the early days, we’re sort of in a bubble. And then as I started, I mean I met like the guys from Skip, and then I started learning from them, and this like startup ecosystem started reaching out to people like yourself, and learning.

So that part, I think I’m super coachable, and I’m always trying to learn. I think the other thing is like our business when you’re talking to different people that maybe built billion dollar companies and are a thousand times smarter than you and like Harvard MBAs and all this stuff and they just tell you you’re like dumb and your idea is horrible and you’re just going to get killed.

It’s like you have to, a lot of times I think it’s super healthy to disagree with people way smarter than you, take the information, but ultimately you have to make your own decision.

And we’ve had things like this too, where it’s just like, yeah, we have advisors, we have different people that we’re learning from who share their ideas and their thoughts. Ultimately, yeah, I’ll try to do my best to listen to it, be open, and take the information, but ultimately make my own decision, which in Soccer was a little bit different.

Mark MacLeod:
You know, again, when I think of Uber, many differences. Like, first of all, each market they’re in is a giant, and then they use capital as a strategic weapon. And burns a hole in the ground, and would subsidize both sides to block out competition. What do you think it is that made you able to succeed without capital, or did you end up having to raise capital along the way?

Cody Ruberto:
We’ve got a couple of angel checks. So, like, after we were doing a couple of million dollars a year, if there was a new experiment we wanted to try that we didn’t have the money for, there were angel checks that came in. But what caused us to succeed? I guess for us, that same thing. Like, there’s always a way. Every obstacle we ran into, if we didn’t have money for something, how do we get the same result without spending money? We had to get great at getting free press, getting awareness, all these things with no cash.

We had to. There’s like, we experiment all the time. We tried so many different things. And there are a couple of things that you might try, 100 things, and there’s one thing that completely changes the trajectory of the company. I guess we were always used to having no money, and so we weren’t thinking about whether we had $10 million because we just didn’t.

We were in this situation, we needed to figure out this problem. How do we solve this? And, yeah, we might try 20, 30 different things until we find the solution. Yeah, we just wouldn’t stop. And I think it’s hard to kill a person or a company or whatever that just won’t quit, and we’ll just keep driving forward through every single obstacle, every problem. I don’t know if that’s a good answer, but that’s…

Mark MacLeod:
There has to be a way. Is that a company value now?

Cody Ruberto:
I repeat it all the time. And there are still situations today where we don’t know how to solve this thing. We’re like, kind of in the middle of it, and yeah, there’s always a way. Been in way worse situations in the past. We’re going to figure it out, keep moving forward, and yeah.

Mark MacLeod:
So before we went on air, we were just catching up. I asked you where you were. You’re in Guadalajara. Turns out you’re opening up down in Latin America. I’m curious, have you had to physically move to each town that you’re opening up into?

Cody Ruberto:
I think I’ve been to every single one of our markets and spent time there. Do I have to move to every market? No. Do I like being on the ground and close to our customers and our drivers, and then kind of in it? Yes, I love it. So, yeah, early days definitely we were spending a ton of time in each of our markets kickstarting them because we had no money. A lot of times, we had no employees. So it’s like you’re kind of a launcher and all that.

Now we have a bigger team, we have more people, all of these different things. But one thing that scares me is getting too far away from our customers and our drivers. So, like, I’ll do things like this summer, I went from, well, you know, like Nanaimo, Courtney Comox, on the island, like all the way out west, basically got a car and then went visiting Uride cities from the west coast all the way across Canada and then ended up like in St. John’s Newfoundland. So hanging out with our drivers in cities, taking Uride, like yeah, I want to stay close.

Mark MacLeod:
It’s amazing. So this is like all in. Like, you don’t have a family yet, right? So you’re able to just go all in, or do you have a family as well?

Cody Ruberto:
I don’t have a family. I have a partner, my girlfriend, but no kids right now. And yeah, right now I’m in the middle of it, pushing every day.

Mark MacLeod:
Are you in the US as well, or did you just go straight from Canada to Mexico?

Cody Ruberto:
We’re not in the US. We’re looking at it. In the US, there are Uber and Lyft, drivers can turn their apps on in most cities. It’s usually just not the best service in these towns. So we’re trying to figure out when we’re expanding, where do we go? Do we go to places that have nothing and need our help right now? Do we go to places that kind of have bad service and go tackle that?

For us, at this stage, it makes sense to go to places that have nothing, bring ride-sharing there, go do our best to fix this problem for them, and then over time, these cities that might have ride-sharing, but it’s a bad, shorter version of it for these small towns, go do our best to improve transportation there too.

Mark MacLeod:
So, tell me about expanding in Mexico. I feel like it’s kind of scary. For one, I need to learn Spanish. Do you speak Spanish at all?

Cody Ruberto:
Now I do, yeah. It’s not perfect, but enough to have conversations with drivers and riders.

Mark MacLeod:
Good for you. That’s intense.

Cody Ruberto:
Yeah. A bunch of other things, like tons of learning. You can just open up your first market outside Canada. There were tons of things that we had to figure out, tons of things that we had to learn, tons of obstacles. Operating in Mexico is a lot different than operating in Canada. So it kind of felt like their early days, where you needed to learn, iterate quickly, make changes for passengers, and then try to get product-market fit there. Then the driver’s side, the same deal. I could share tons of stories of trying to get this market off the ground, but… yeah.

Mark MacLeod:
What was the driver behind the decision to expand outside of Canada? Did you feel like Canada was saturated?

Cody Ruberto:
Canada is not saturated. Like, there are still a couple of cities that we’re going to launch. In our existing markets, we can grow quite a bit. But honestly, this same problem that we have in Thunder Bay, we’re in 24 cities now. The same problem that we have in our existing cities exists in thousands of cities around the world. So someone has to go in and fix this problem for them. And so, yeah, I want it to be us. And when you’re going into these markets, you’ve got to figure out the unit economics and make sure the business makes sense.

But, yeah, the main driver is I want to have an impact on my life. People who are here at the company, we want to have an impact, we want to fix this problem. And like, I think we’ve done a decent job in Canada. We can always improve and get better, and we’re going to. But this problem exists everywhere. Let’s go tackle it and fix this problem around the world.

Mark MacLeod:
From an investor standpoint, we often say, well, there’s no market until there’s competition. So I’m wondering, are there other folks who’ve popped up who’ve seen the same gap that you see in smaller towns and cities?

Cody Ruberto:
Yeah, it’s really hard operating in these areas. So we’ve had a couple of people pop up. I mean, over the years, there’s probably been 20, 30 companies that I know that have started in one city, and it kind of doesn’t work out. Yeah, it’s hard going into these cities and making it work. Yeah, there are some companies that might be in like one city or, you know, two cities, three cities, but scaling it. I think there’s one company in the Middle East that was getting up for like 8-12 cities, but that is pretty much it.

Mark MacLeod:
And now you mentioned you raised some angel checks along the way. I’m wondering, have you also raised any institutional capital to date or is it all just angels?

Cody Ruberto:
Mainly angels. Yeah, we don’t have any VCs in right now.

Mark MacLeod:
Did you try it?

Cody Ruberto:
Yeah, we tried and just got crushed. So I think the last time we seriously went out to try and raise money, I went to San Francisco for like, four months, talked to a bunch of people, and I think Uber and Lyft were really struggling then too. And yeah, I remember going into a meeting in Palo Alto, like a partner meeting, and Lyft dropped 30% in a day that morning.

Mark MacLeod:
Bad timing.

Cody Ruberto:
Yeah. So we got ripped apart. I’ve talked to hundreds of people, and we’ve just failed at raising capital. So, yeah, it forced us to get a lot more creative, and keep more ownership over the company within the employees and stuff.

Mark MacLeod:
So, yeah, I’m not surprised. And I don’t think that has anything to do with your ability to pitch. I mean, I can just imagine, first of all, your energy and enthusiasm. You talk about the kind of founder problem fit, right? You have deeply felt this problem. So, the passion is there, right? The evidence that there’s a problem is very clearly there.

And then, of course, by the way, you’re doing it, it’s not just an idea, you’ve done it, but from a VC’s perspective, I think where I would have struggled is just like, I’m not going after one TAM. I’m going after hundreds or thousands of small TAMs, and there are no synergies.

Like, I use Uber, when I’m not in the city anymore, but obviously, I use it in Toronto when I’m there, but anywhere I travel in New York, San Francisco, Boston, wherever, like London, England, all over, but always in cities, I’m using it, so it has utility to me all the time. But the chances that I’m going to be in Thunder Bay, Sudbury, Nanaimo, like, I’m just not going to be there. So it’s like you’re basically whoever you acquire as a customer in one town; they’re just going to use you in that town.

So, the lifetime value kind of per passenger is small. And this is just standard pattern recognition from an investor’s perspective, like, therefore, I can’t apply steroids and acquire a lot of them. Like, I’m maybe not in control of the velocity of growth. I have to rely on word of mouth, organic. Did any of those objections come up? Because I feel like that’s my gut reaction, putting on a VC hat.

Cody Ruberto:
Yeah. And then just like, I think the biggest one is like, Uber is just going to come in and kill you. Lyft is going to come in and kill you. That was like, probably the number one. And then also like, even if they don’t kill you, like, those businesses are struggling, and so they couldn’t understand.

I think another really hard understanding was that they were burning a bunch of cash at that point, the whole rideshare business model was sort of being questioned, and we were profitable, and these things. So they just, it was weird. And, yeah, we just got slaughtered.

Mark MacLeod:
Yeah, they don’t understand profitable businesses. Sorry, why is this black at the bottom? I don’t understand what’s going on.

Cody Ruberto:
That is interesting. And like, yeah, another thing too is like, yeah, you need to like build it market by market. I think the lifetime value of these customers is like, yeah, there are tons of people that rely solely on taxis in these towns to get to work and to the hospital and wherever, and unfortunately, it’s not a good experience for them.

So a lot of our customers use us multiple times a week and stick around for a long time. So like LTV, I don’t know actually where I could put your, like, LTV to CAC ratios. And CAC ratios will be blended. But yeah, people seem pretty excited.

Mark MacLeod:
I have been an angel investor for a long time and have invested in lots of companies, and have seen a high correlation between CEOs who send out regular updates, and those companies tend to succeed. The ones that don’t send out regular updates actually tend to fail. My theory is that the process of sending out regular shareholder updates just creates accountability and forces you to show progress each time.

I bring this up because I’m not a shareholder, but I get your updates. So, what’s driving you to send out updates? Walk me through your thinking there.

Cody Ruberto:
Yeah, I don’t know. I see you as a friend of the company. Like you sort of have been a mentor. We’ve had a couple of calls over the years, but like you’ve been a mentor through your blog, through the podcast, just like I’ve been learning tons from you, even if you don’t really know it. So, yeah, I love keeping you updated.

But yeah, what drives that? I think we first started doing them by thinking about the line versus the dot. So does it motivate us to execute? Like, I don’t know. So live versus a dot for everybody is like investors, people, if they see you at it, if they look at a dot and they look at your numbers at a point in time, there’s like way lower chance of them working with you, doing anything with you, versus seeing a line of you executing every month, every quarter, every year, just continuing to execute.

So yeah, for us, does it change how we do things? I don’t know. I think we’re pretty obsessed with executing and growing and doing what we say we’re going to do. I think that the great thing about setting out these updates is that it forces you to take a step back from the business, look at things, and that kind of laid it out raw, like the good, the bad.

You obviously want to have good things to send in these, but there are some of the investor updates where we might share things that are like, hey, this part we’re like failing and it sucks and we need to figure out here’s what we’re trying, here’s what hasn’t worked, and here’s what we’re going to try next. So I think that the process of stepping back makes a difference.

Mark MacLeod:
So you mentioned earlier, hey, I didn’t go to university as a soccer player. What have you done other than just experience putting in the reps in trying shit, failing, what have you done to turn yourself into now the CEO of a technology company?

Cody Ruberto:
From day one, you start off as the founder or CEO, but like you’re not a CEO. You have no idea what you’re doing. As the company scales, your job keeps changing. So I know you talk about this, and Tobi talks about this, like every year, you need to re-qualify for your job. So things that I do are one like yourself, you put out a bunch of content on being a CEO, and like, I’m pretty sure I’ve read every single one of the blog posts that you’ve written.

Like, yeah, other people. I’ve been so since one of the highest impact things I was in Saskatoon for a little bit, and showed up at the founders of Skip, they started a new company there. So I just like showed up there and said, hey, I’m Cody. And ended up staying there for three months, just like watching, learning, trying to absorb as much as possible, and learn tons.

And then from there, I started reaching out to people who were a little bit further ahead. And the crazy thing is, I’d reach out to people and I’d say, like, why would this person ever respond to me? Like they’re not going to talk to me. And people would take meetings, and I would learn a bunch.

And it doesn’t even have to be about the CEO overall. There are things that you need to learn as a CEO, like how to hire, whether it’s like a CFO or a VP of finance, or different roles that you like, you’re hiring someone who should be way better than you. So, reaching out to ten different CFOs and having conversations and learning and knowing what to look for.

Books, like I’ll crush through books. So every day I’m reading something and trying to learn. There are things like one thing I started doing recently, just like actually taking courses. So I took like there was like an HBS online leadership course, and I learned a bunch of stuff from there and started testing some of this stuff in the company. Right now, I’m taking a course on EQ, emotional intelligence. I think being able to stay level-headed and like actually think rationally through decisions without your kind of emotions or all these things affecting it is important. So I’m trying to work on that, and it’s something I’m doing right now.

So yeah, every day getting 1% better. You talk about this. I know Shopify. I’m like everybody at the end of each day, did I get 1% better today? I do an end-of-the-week review. Did I get 5% better this week? And when there are too many days, if there’s a day that I can’t answer yes, that annoys me. So I think maybe it’s not the best for your EQ and your happiness, but man, I want to keep improving.

I want to keep making progress. And so every day I’m trying to do it. And by the way, I don’t think I’m a great CEO right now. I think that I’m learning this level of being a CEO today. And my job’s going to change in six months and 12 months. But, yeah, I’m religiously trying to learn and get better, but those are some of the things that I’m doing.

Mark MacLeod:
Listen, man, I’ve seen the scale on your reports, and you’ve done that really without much capital. So I think you’re not giving yourself enough credit.

I connect the dots to what you’ve just described and your athletic background, because what I’m hearing is competitiveness. You’re competing with yourself every day, right?

Cody Ruberto:
Another thing I would add is my soccer journey; the other thing it taught me is that you can improve dramatically at whatever you want to do. So, if you’re willing to do whatever it takes, there are tons of sacrifices. This isn’t the best for personal relationships and things like that, but if you’re going all in and doing everything you possibly can every day on one craft, the progress over a year, five years, ten years, is insane.

So in soccer, I was riding the bench for my high school team in grade nine. I was, like, under 5ft, 95 pounds, and I just trained like an animal. My whole life revolved around it. And by the time I got to the end of high school or whatever, we won for Ontario, I made a ton of progress, then went to Europe and ended up on a team where you basically pay your own way. It was an academy, and I was the worst player. There were 26 of us. I was the worst player on the team at the start of the year.

I trained three times a day, which is probably over-training or whatever. And by the end of the year, the two of us ended up getting contracts, right? I was one of them, fortunately. And just throughout my career, if you look at me at 20, to me at 30, the improvement is insane.

And then I think there’s another thing too, like, always wanting to be the worst player on the team. So my goal at the start of every season was to be in a place where I feel like, man, why am I here? Like, everyone’s way better than me. And then just train like an animal so that by the end of the year, I’m at the top of the pack. And you do that year after year, and it just compounds.

And I think in business it’s the same deal. If you’re learning, growing every single day, and surrounding yourself with people who are way better than you over time, I think that makes a huge difference.

Mark MacLeod:
Wow. I respect and admire that so much. I don’t know if I showed up, and I was like the worst person on the team. I might just crawl under a rock. What got you to become one of the top two? Is that just self-belief? Is it just this vision? What got you to show up every day harder than everyone else?

Cody Ruberto:
Ah, what got me to show up every day again, not healthy, and I don’t recommend this for happiness or anything like that. My identity and my life were linked to me as a soccer player. So when things were going well with soccer, my life was great. When it’s going poorly with soccer, my life is horrible. It’s like the end of the world.

So this isn’t a map for happiness or anything like that. But I had this drive where I think I never felt like I was good enough. I always wanted to improve and just like, it sucks being in those situations where you’re looking around and you feel really small and you’re like, why am I here? And man, these people are way better than me.

But if you remind yourself, perfect, this is where I need to be and the improvement I’m going to have. So if everyone’s twice as good as me right now, maybe in three months they’re 50% better than me. And then in six months, they’re 25% better than me. And then in nine months, we’re kind of on the same level. I would just sort of think of it that way.

And the other thing I would do is, and this is important as a CEO, I probably need to do more of this. But I would map out every part of my game and like all my weaknesses, all my strengths, and just write a plan. I love having plans where you just need to execute on this.

So if it’s like you’re tired, it’s pouring rain out, it’s 5 am, it’s cold, you don’t want to get outside, but it’s on there. You’re getting out of bed and going and doing it. If you write something where it’s like you stick to this thing, it’s almost impossible for you not to make progress. And you stack that up over years, I think that makes a difference.

Mark MacLeod:
Nobody who achieves greatness is balanced. Can be in any field, from business or sports, to performance, or arts. Like, Messi didn’t get to be Messi by being balanced. Tobi didn’t get to lead a 10,000-person software company by being balanced. And this kind of identifying with yourself as a soccer player, I think everyone who just listened to you speak, they’re going to resonate with that, because I spend every day with CEOs, and many of them are in the same boat.

Often, when they show up, their sense of happiness is completely tied to the trajectory of their company. Now, that’s not healthy. We have to uncouple them in some ways, but it’s very common. So I think people would definitely resonate with what you just said.

Cody Ruberto:
Can I share one other thing here? Like, another thing that I think really, really helped me is like, whatever you’re doing, if you’re trying to do anything hard, building a company is hard. You know, trying to be the best in the world at something else is tough. But, like, there’s all these crazy things that happen along the way. So another thing I used to tell myself was like, okay, this challenge here, this is where another 50% of people quit. And I’m like, I get past this stage, we’re like a little bit closer. It’s not irrational, but it’s things like that which got us through so many things in soccer and business. So, yeah, gotta keep pushing, keep rolling every day.

Mark MacLeod:
All right. Have you wound down from soccer now, or is it still a part of your life?

Cody Ruberto:
I’m playing for fun. So when I’m on the road, we could go into this probably on another call. I sort of had like a midlife crisis, like, impact. All these things I was doing, Uride and soccer at the same time. And like, go to soccer, you would entertain a small group of people, and I love doing it, and there’s all these lessons from it, but the impact we get to have with Uride, like, fixing this problem for hundreds of thousands, millions of people, that’s super cool.

You create jobs for thousands, tens of thousands, hundreds of thousands, and millions of people. That impact is great. Every month, a portion of all rides goes towards helping the communities that we’re in. So I think I got super excited about the impact. And when I look at my time and where I want the majority of my time to go, I want to have an impact and want to try to make a difference, and I think Uride, I’m super passionate about it.

So it’s been about three and a half, four years since I played soccer professionally. I still play for fun. If I’m on the road, if I see a field and people are playing, I’ll go play. And…

Mark MacLeod:
Do you just, like, decimate them? They’re not former pro players, so you must just destroy them.

Cody Ruberto:
I just go pass the ball around and have fun. Try not to take it too seriously now, but yeah, that’s it.

Mark MacLeod:
Well, Cody, thank you so much. I gotta say, I knew some of the Uride stories, but I have so much love and respect for you and what you’re doing now. Having heard this story. I really appreciate you sharing it now.

Cody Ruberto:
Mark, honestly, you’ve been a huge part of it. And, seriously, you don’t know how many hours I’ve spent absorbing and implementing the material that you’ve been putting out. But yeah, you’ve been a huge mentor throughout this. I appreciate you for that.

Mark MacLeod:
I really appreciate it. Thank you. All right.

Hey, thanks for listening to 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. See you next time!