Beyond the Build: Bold Commerce’s Fast Failures to Success

Welcome to Beyond the Build, a new series from Shopify, where we share stories behind the Shopify ecosystem. A platform where founders, developers, and innovators come to build for more than 1.7 million merchants worldwide.

In this episode, host Fatima Yusuf sits down with Yvan Boisjoli, the co-founder and CEO of Bold Commerce.

Bold Commerce is a software development company that provides industry leading ecommerce solutions for the world's most innovative brands. What started out as a side hustle for a group of friends in 2013 turned into a huge Canadian success story. Today, Bold has grown to over 385 employees over 90,000 customers, and just recently raised $27 million in funding.

Watch the interview below, or read on for the transcript.

Growing up with the entrepreneurial spirit, and with Shopify

Fatima: Bold has been with Shopify for a very, very long time, you were one of the OG companies to build on Shopify. Take me back to the very beginning. What inspired you to start the business and what made you decide to invest all that energy into Shopify, which at the time was probably not very well known?

Yvan: I like to think we're one of the OGs. I think back to all the people that we used to hang out with in 2012. It's been a wild ride watching Shopify grow since then. I don't know how many people know this, but all the [Bold] founders grew up with this entrepreneurial spirit, like parents who all owned their own businesses.

We all had this aspiration to build our own companies. Not to go into the weeds of life prior to Bold, but we had these really interesting stories of how we all tried to build our own products, our own business.

Bold, to me, is really four different people with four completely different strengths coming together. Whenever I advise people who are starting a business, the first thing [I say] is to find those people that complement you. Don't shy away from bringing the right people in, they're just going to make you better. That, to me, is what Bold is. You look at the four people that came in—all different walks of life, all have different skill sets, but every one of us had a passion to build a company.

That's really how it started. We all failed at our prior [entrepreneurial] tries. Bold actually started with an ecommerce store. We were ecommerce owners. We were merchants. When the idea came to us, we were already on Shopify.

Jay is one of the founders. He actually owned an ecommerce store called Supreme Archery, and he came to us and asked, "Hey, I'm on Shopify, there's this opportunity to use APIs and build some apps on top of it and make my store more money. Are you guys in?" 

At the time we were all trying different things and we didn't shy away from the extra workload. And it was like, let's try this thing, what's another project. It was a side hustle.

I believe when we were talking about joining Shopify, maybe the numbers were outdated, but on the website, I think Shopify had around 20,000 merchants at the time.

Some apps in the ecosystem, it was all more backend and integration apps, no apps were there to make you more money. There was nothing like that. It was all integrated into QuickBooks, or integrated to your backend systems. We flipped it on its head a little bit on how to approach building products in the ecosystem. Really what we tried to do is just make more money for our store, so we started building one app at a time.

The goal: Build apps that will pay for a trip to Mexico

Fatima: When you think about the full stack that you see in the ecosystem and the different categories—everything that's connected to helping merchants reach customers or sell on the front end of that experience—you guys were the first in a lot of those areas.

Yvan: Yeah. Our first app was Upsell. The reason we picked Upsell was because we thought it'd be simple. We were just like, you buy a product, we'll push a different product. We thought of a little pop-up, which is a pretty simple way to start learning about the platform and get out there.

But the APIs weren’t what they are today. They weren't designed for that front end experience. So it was a little hacky, but we ended up doing it. It took a lot longer than we thought. It's not like it took us too long to get something out, but as we started learning and improving the product, we were like, okay, well this is a little bit hacky but this works.

We got through it and from then on, we realized, “Wow, we can really impact how our merchants succeed.” That was really what fuelled it. Once we saw the results for our own store, we wondered, what else can we do? Product Discount was the next one. I believe Quantity Breaks was the third one. It just snowballed from there. [We kept asking ourselves:] What are the products that we can build to help our stores make more money? 

Fatima: I mean, it's pretty incredible. Also, at the time there were 20,000 merchants. Now there's 1.7 million merchants. The market size feels a lot more obvious, but what was it at that time that made all four of you decide that it might be 20,000 merchants now, but this is the platform we want to double down on? This is where we want to invest our entrepreneurial energy.

Yvan: So, true story. This is how it actually went down. I think it partly has to do with the fact that we all had a passion for building a company. Regardless of what the outcome was, the question of how big it can get wasn't really what was driving it. It was like, “Hey, we can make an impact in this market.” And we were thinking about how to make our store more money.

When we started it, we actually talked about the size of the platform. It was 20,000 merchants. How fast can it grow? How fast can we grow on it? We decided to do it because we said, “You know what, if it could pay for beer money, or we can pay for one trip a year to Mexico, that'd be worth it.” That was it. That was all we were expecting.

We wanted that trip to Mexico. We're from Winnipeg, so we want to get out once in a while. That's how the conversation went. From there—I mean, obviously the platform kept on growing—but what made us focus solely on Shopify at the beginning was our first trip out. We had started development in April, 2012. Back then, Blair invited us to Shopify headquarters. This was January, 2013, so we'd been building for about eight months. There were about five apps in the app store.

I call it the “Blair Beckwith effect.” That experience from when we went to Shopify for that first time. We were sold on Shopify at that point. At that point, we were talking about, “Hey, what other platforms should we move our products to?” Seeing the entrepreneurship within the company. Built great relationships, and seeing where the company was going. 

When we left Ottawa, we came back to Winnipeg completely sold on Shopify. We knew this was it. We had to focus on this platform. That was really the beginning, why we focused solely on Shopify from then on. 

The four founders: Going into business together “eyes wide open” 

Fatima: So after that trip you’re full steam ahead. Now, it’s quite uncommon to have four tightly knit founders. How has that dynamic been? What’s the secret sauce for maintaining successful relationships between four different people?

Yvan: Going back to [the idea of] bringing people that complement your skill set and elevate you, for anybody thinking about building a company, you have to be true and honest with yourself. You have to understand what you bring, your skills, and you have to find partners that complement you. That's by far the best move we ever did.

"You have to find partners that complement you. That's by far the best move we ever did."

That’s the reason why I think all the other ideas we had before never actually amounted to anything. It was a great experience, but it didn't really do much. What really came together with Bold was we were all bringing something different and unique. But it's hard. It is hard. We were friends before we started Bold. Happy to say, we're still friends, but you go through a lot.

You go through a lot as partners, as people building a company, you don't always agree. I actually liked the fact that we were four. It forced us to always get three people on board whenever there was a disagreement. It pushed us to argue the point more, which I think was good. It helped us stretch a little bit more.

When you go in, everybody has to be committed, passionate, and willing to put as much effort as the next. It's like a marriage. You take it for what it is. Sometimes it's about building that relationship, and with a long-term relationship you have to go in with that mindset. You have to build a long-term relationship. It's not, “I'm going to bring you in as a partner and then I get pissed off and it's over.”

"Everybody has to be committed, passionate, and willing to put as much effort as the next. It's like a marriage."

If you go in with that attitude where you realize that you're going in for the long-term with these people, you have to make it work. You'll have arguments and those arguments are great. You need to have those arguments. As long as everybody respects each other and pushes everybody to just elevate. It's about bringing everybody up, and then you're doing it for the right reasons. I'm thrilled that we are obviously still friends and not to say it was a rough ride, but it's difficult. 

You just have to go in with eyes wide open, that this is somebody I need to build this business. We won't always agree, but respect each other and we're going to make this work. That's really how you have to approach it.

Bootstrapping a portfolio of apps for 20,000 merchants

Fatima: Your strategy has been to have a portfolio of products as opposed to really investing in one key product. What was the motivation behind that decision? And when did things start to take off?

Yvan: You have to appreciate where we came from. We were building products for a user base of 20,000. After the first year it was 40,000. The more apps we had, the more chance we had to get more users. Companies are coming in now with one focus. They're going to be the best of breed in that industry or that app.

You're coming into a market of 1.7 million merchants. There's plenty of room. We came in at a very different time than everybody else. The strategy we had actually worked for what we had to do at that time. For somebody coming in today with that strategy, it will be way more difficult because now you're competing with a lot of best of breeds, and all of these different buckets that we're in.

I believe that's why we became the company that we became, where we had at one point, 36 different products in the Shopify App Store—now we've got about 20. [We had to reflect and ask ourselves], what are we focusing on? What are we going to be the best at? That's really the shift, the focus that we had to make: what do we want to be known for? We had to make some hard decisions for sure. That's part of the innovation that we built, which is great. Understanding that to innovate, you have to fail, and when you fail, you move on, you sunset [certain products] and you build something better.

"To innovate, you have to fail, and when you fail, you move on, you sunset certain products and you build something better."

When did we think we were succeeding on something? You know what, to be honest, I think we always felt that way from the start. We were bootstrapped from the beginning. Not to say we were making tons of money, but we were paying our salaries and we were growing and we were hiring people. We always felt, “Wow, we're onto something big.”

It was probably three years in which we realized we can be more than what we're doing. We built an identity of, “We build apps for Shopify.” About three years in, we were like, you know what? We could be leaders in the ecommerce space, and we can really help merchants succeed in the different areas we focus in. So three years into the business, we started talking about whether we wanted to be a lifestyle company.

At that point, we made that call to go all in. Let's feel this thing. Let's put all our money back in. Again, it was bootstrapped. All the money we made—every dollar we made—we put right back into the company. It just fueled our growth from there. 

Then as we started to realize that we needed help. With four founders, I always say our AGMs were a bottle of whiskey in the basement. That was how we operated. We knew we needed to step up to get to that level. At that point we saw an opportunity to continue growing and we brought in investors and an independent board, and obviously the company has been maturing since then.

Bold’s next phase of growth

Fatima: Awesome, and you totally could have opted to stay bootstrapped. It's interesting because when people look at the ecosystem today, there's so much venture capitalist (VC) activity happening between investments and acquisitions. But there's also a healthy amount of companies that are just profitable businesses that haven't raised money, that are doing really well, creating a lot of value. That's completely a path that can be taken—and successfully—especially in the world of SaaS.

Yvan: I wish for every founder to have a bootstrapped company. If you could learn those experiences, then when you go and raise money, you will be ready for that. That's one road I'm happy we went down. I don't think we went down this path on purpose. We're from Winnipeg. The exposure to VC or to capital, you don't really get it here. There's no real stories of other companies doing it. We were winning by winging it in this city, where there's nobody really to look up to.

"I wish for every founder to have a bootstrapped company. If you could learn those experiences, then when you go and raise money, you will be ready for that. That's one road I'm happy we went down."

Back in 2012, there weren't any companies [just like us]. We were doing it on our own as we matured and started talking to people outside of Winnipeg. As we started getting familiar with that world, this decision became a little easier. 

Fatima: What's ahead for Bold? What are you most excited about in this new frontier that you're in?

Yvan: I think it's about surrounding ourselves with the best people. We've expanded our office. We've got some amazing talent coming in from Austin, Calgary, and Toronto now, to round out our team, which has been great. We kind of took the same steps as Shopify. I like to think we've been highly influenced by Shopify through our culture.

We were the first ones to move with Shopify to Shopify Plus. We started maturing as a company from making that transition from SMB to enterprise. I'd still say we're going through that transition. That's the part of the business that we've been working on. To take that next step into enterprise, we've brought in some great talent. That's going to be an area that we're going to be focused on in the future. Stay tuned for that. We're already doing it, but we’ve got a lot more interesting things happening in that space.

So, [we’re] hopefully helping the SMB market, but also as you scale, being there for you during that journey, and helping large enterprise and retail. That's a space that's pretty exciting right now, too.

The new normal of ecommerce technology adoption

Fatima: We've got a lot of new developers interested in the Shopify ecosystem, lots of folks building companies. What advice would you give those who are looking to join the ecosystem today? 

Yvan: I don't know if there's a more exciting space than building ecommerce products in the technology space [due to] the amount of acceleration in user adoption of technology. COVID-19 has changed that game. 

What a consumer expects now is so different than what it was a year ago. How they behave, how they want to shop has changed since a year ago. There's just so much opportunity that's actually just opened up in the last six to 12 months. 

I keep saying this, but somebody needs to innovate the whole curbside pick up system, because there's a proper way of doing it and nobody's doing it right now. Getting bad produce, having stuff swapped without really knowing what was swapped, then getting home and it's like, I don't even know what this [order] is.

There's opportunity [for improvement]. Then there’s the [brand] interaction. Now, the brand's interaction with the consumer happens online. There's the small window where you're actually interacting with somebody dropping your food off into your vehicle. What's that experience like? It's probably the worst experience. They just open the door, throw it in, you get home and all your groceries are piled up in the worst way possible. Then your bread's flat and you're like, what? That's the experience that they're leaving their consumers. 

Who knows what's going to happen with curbside pickup once things open up. I think curbside is going to stay. It might be different from what we expect, what we know today. Anyways, my point is there's opportunity out there. More opportunity than ever, with everything happening. 

The advice I give everybody is, just start. Put some code down, launch a product, talk to a customer and just start. Learn, and then get better and iterate. That's really how you get things going. The only people that don't succeed are the ones that never actually start.

"The advice I give everybody is, just start. Put some code down, launch a product, talk to a customer and just start."

Fatima: I completely agree with you. COVID-19 fully accelerated what was already inevitable. The future pulled forward faster. A lot of these behaviors are here to stay. And I agree with you, there's really never been a better time to build because there's just so much happening in our industry. It’s incredibly exciting. 

Yvan: The habits will stay if we build a proper experience. If the experience they're getting today is bad produce, squashed bread, and whatever, you don't trust curbside. You're not going to want to continue doing that. There's an opportunity there to build, curbside is just one example. The point is there's opportunity for these habits to definitely stay and improve.

Before, when you had to get user adoption, you had to convince them that this was the better way of doing things. Consumers have experienced all of these new technologies now. It's not a matter of, “Hey, this exists.” It's a matter of, “Hey, this is actually a better experience than what you're used to. Come use this over here.” 

It's recognizing that there's lots of opportunity to improve those experiences. A lot of these behaviors are going to stay for sure, as technology continues to support them.

It all starts with a little bit of hustle

Fatima: We all know there's a lot of pivots in entrepreneurship. There's a lot of failure before you see success. Is there a story that comes to mind like that where something maybe didn't work out, but then it triggered something that ended up being a lot better?

Yvan: The best attribute that Bold has is our willingness to fail. [You can] even look at all the products. Like I said, we had 36 different products on Shopify. They didn't all succeed. We tried some, we failed on some, we decided some of them just weren't growing as fast as they needed to, to support the product or the idea. We weren't scared of trying things. From that—a lot of people don't know this—but we actually started seven different sister companies. 

We had a WiFi marketing product we tried. It didn't really have legs, so we put a halt on that. We had Flocker.tv, which was bringing ecommerce to Twitch streamers. We spent so much time trying to crack that market [but] we decided to fold it. But if somebody is going to do it, and somebody's going to figure it out, it's a market that has potential.

We just couldn't do it. We spent two years doing it and we just ended up squashing it. It's one of those things you just come to realize. That's the other side, a part of innovating is understanding what's working, and when it's not. Sometimes you don't have the right idea, the right team, etc. There's a whole bunch of factors why startups fail.

Fatima: Sometimes it's really hard to know when that moment to sunset is, right? It can be very difficult for founders to let go of a product or idea that they really thought could work, that they’ve put a lot of time and energy into. 

Yvan: An entrepreneur is always on the cusp of figuring it out. We're always almost there. You know what, I think with the experience that we have today, we probably would have approached it very differently too. There's probably a few of those ideas that if we tried it today, based on our experience of raising capital [and] bringing in different talent, they probably would work, to be honest. And so now it's opportunity cost. What is it costing us to focus on that versus something else? That's what we're always measuring. Your only limit is time at this point.

Fatima: The most important thing is to focus on the most important thing. That's what Tobi [Lutke, Shopify co-founder and CEO] always says. Figure out what the most important thing is. That’s what founders have to focus on.

Yvan: Yeah. We have all these other sister companies that didn't work. But kickbooster.me is another one that's going strong. It's a crowdfunding tool. We're big into the crowdfunding space. A lot of people don't realize that that's a Bold sister company. Yeah, check it out. It's an affiliate tool for crowdfunding campaigns. We're helping store owners become successful and transition over to ecommerce once they're successful in the crowdfunding space. There's just so many ideas out there and it’s really a matter of getting going and proving them out.

Fatima: It's been such a pleasure hearing all of your stories and having you. Are there any words of wisdom that you want to leave viewers with before we end off?

Yvan: I think I've talked about a lot of it, but really for this audience, which is probably entrepreneurs, people that want to make something happen, it really starts with you just putting something down and getting it out. 

You've got all the excuses in the world why things don't work and you won't actually know until you start. Talking about why I feel like we were successful. I felt like the things that I was scared of as an entrepreneur, [my co-founders] Jay [Myers], [Stefan Maynard], and Eric [Boisjoli] filled those gaps for me.

If you've got a fear of failing because you're not a public person and you don't want to be doing marketing or support, find that person that will. If you find the right group where you all complement each other, from there, you'll learn. Worst case scenario, you learn.

I tried nine different products before Bold. Every one of those experiences helped me get to where I am today. I don't regret any of them. It really just starts with a little bit of hustle.