Gareth du Plooy (Shopify and more)

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David Noël-Romas: Welcome to the Manitoba Business Podcast, featuring interviews with business leaders and entrepreneurs based in our wonderful province. I’m David Noël-Romas.

You’re about to hear me “geek out” a little bit. Longtime listeners will know that I’m a software developer and that I have a business which develops custom software. Today’s interview guest has accomplished what every software business person aspires to: building cool stuff that lots of people use, and getting bought out for a bunch of money.

However, before we get to the interview, I want to switch gears for just a second. The Manitoba Business Podcast is completely free to listeners, and always will be. I support it with money from my business, and never ask for anything in return. However, this year, in the spirit of these holidays, I do have one request.

Ever since starting this show, I’ve been struck by the generosity of the guests. Certainly for agreeing to come on the show, but also for the volunteerism and philanthropy they demonstrate. It inspired me to examine how I could do something similar in my own life, and for the past year I have been contributing as a volunteer board member at the Manitoba Conservatory of Music & Arts.

The Conservatory has an outreach program that does a lot of good in our community by giving inner city kids access to instruments and music lessons that they otherwise wouldn’t have. And it makes a huge difference: it’s a positive way for them to spend their time after school.

I want you to consider donating to the Music Equals program this year. We’re doing a special promotion for companies and organizations right now, where you can hire an ensemble to perform at your holiday party and proceeds go to support the kids. It’s a great opportunity to practice corporate social responsibility while adding a special touch to your party–and these are some of the best musicians in the city.

Of course, you can also make a personal donation, and all contributors will receive a tax receipt.

The website to visit if you want to support inner city kids this Christmas is www.mcmapromo.com. Again, www.mcmapromo.com

Alright, now let’s get started. Without further ado, here is Gareth du Plooy

[to Gareth] All right. Well, Gareth, thank you so much for taking the time.

Gareth du Plooy: Thanks.

David: Can we start by having you tell us a little bit about who you are and what you do?

Gareth: So I am Gareth du Plooy. Work in Winnipeg for a company called Kickbooster which is a small startup. That’s some of the people behind Bold Commerce started here like a year ago. Previous to that I was at Shopify, and before that doing kind of my own stuff, random projects and went to U of M before that so yeah.

David: Cool. So then let’s rewind a little bit to before Shopify. Well, actually before we get to that what do you do for Kickbooster? Like what’s your sort of day-to-day type?

Gareth: Yeah. I’m basically just the sort of software lead on the project. So it’s a software as a service like SAS product that basically lets people…it’s like affiliate marketing for Kickstarter campaign so Kickstarter…there was a couple other like crowdfunding campaigns.

David: Like Indiegogo?

Gareth: Yeah, Indiegogo and like a couple others that we basically integrate with, that allow people to basically market those campaigns, and like generate leads and help people like convert to actually like funding these things. So yeah, I’ve only been there a couple of weeks so like learning a lot of stuff and it’s…

David: For sure.

Gareth: Yeah, it’s been fun.

David: Cool, okay. So you’re a programmer. You went to the U of M and for computer science, right?

Gareth: That’s right. I was in the co-op program. So yeah, I think it was five years total but basically half through the program you start doing work placements every six months so yeah.

David: Perfect. And so you graduated or maybe while you were doing your co-op and you started getting to the workforce, what was the first thing that you did?

Gareth: So I did a couple stints at the city of Winnipeg while I was doing my co-op program, and then I ended up at a company called Northern Blower, which is a fan company based in Transcona. And there I…

David: Okay. I’ve seen them. I always wonder what they did. They are a fan company, okay.

Gareth: Yeah. That’s what they do. They make fans like some of the fans are like $700,000, like they do like…

David: Wow. Like industrial for factories and stuff?

Gareth: Yeah. They’re like big as house, like pollution control, like paper mills, like all kinds of stuff. They had very small IT department maybe one or two of us. But the person I worked under there was…I think at that point in your career when you first leave school, the people that you come in… Like such an important time like the people that you interact with and the choices you make in that first couple of years, it just can be hugely influential. And I work with the smartest like software guys I’ve ever met there. So yeah, that was a pretty good experience.

David: What kind of stood out to you or what kind of things have you kept from that, in terms of you know the smart guy that work with? What were sort of the standout pieces of it?

Gareth: I don’t know. I think honestly just seeing someone that has a lot of hustle in like their approach to solving problems, and even just particularly like certain software development paradigms like ways of thinking about problems and stuff like…when you work in a field like in a technology field that you have to constantly be learning. So like…but there are definitely just some sort of patterns or behavior that you pick up younger, which is like get to kind of carry throughout your career.

David: Yeah. Now for the benefit of people listening, I feel like I could take a stab out of it, because you and I have similar technical backgrounds. But what does a fan company need like an internal software department for?

Gareth: So a lot of it was like for these fans have different sort of engineering needs. So this fans needs to blow a certain amount of air, or certain amount of pressure, or certain amounts of power. And so the software that basically there is all kinds of like configuration that needs to happen when people are trying to like sell these things in different industries. The other thing we did was basically wrote a CRM, which kind of was tailored to like this industry. So when people are like placing orders and like all that kind of stuff, it’s all a lot of very specific components. Some of these things have like 1,000 parts to them. So like just kind of managing all that data yeah for like…they have a sales force that goes all over like North America selling these things.

David: Really?

Gareth: Yeah. That was kind of like we built the CRM to kind of like manage that data.

David: Sure.

Gareth: I was there for maybe a year and a half or something, so yeah, that’s good.

David: Okay, cool. And then what next?

Gareth: Then I moved to Los Angeles for no particular reason.

David: Just because it seemed fun?

Gareth: Yeah. So we moved there and I ended up working…that’s kind of when I first I guess was introduced to mobile, where this was back when people just had like the Motorola slider phones.

David: Yeah. What year would that have been?

Gareth: two thousand six.

David: Okay. So like a year after Facebook kind of started happening?

Gareth: Yeah.

David: Even 2006 Facebook was still in its early days. You know there was definitely no Twitter those early days. There was no Uber, definitely no Shopify.

Gareth: Yeah. No iPhone. Like this was like kind of right after like T9 texting phones. Like there was like flip-phones, then we kind of had the ones that would flip up and there was a style with single screen. So the company I worked for was a medical company that sent doctors into people’s homes, that people that couldn’t make it into like clinics or whatever. And so basically it was like a medical records system that was web based. But it worked off like WAP, which was kind of like a wireless markup protocol type thing.

David: Right. It was sort of like…

Gareth: It’s like stripped down HTML.

David: Yeah. Sort of like you’d have with a normal browser, except strip down for these weird kind of phones?

Gareth: Yeah, exactly. So did that for like a year and then moving to LA was never like a…well, meant to be like a permanent thing. So just went there and had a good time and like good experience and moved back.

David: Was there anything that you sort of think that you took with you from your time in LA?

Gareth: I think that was actually the first time that I led a team of people. So maybe there were three or four people, and I did like really bad. I just had no idea how to like set expectations or like help people structure their work day. Like it was just…and I look back at that time, I think like with most experience if you don’t look back on anything you’ve done, and kind of cringe it the way you did it, then you’re not learning. So yeah, that’s like one take where I got I think.

David: Sure, all right. And then you came back?

Gareth: Yeah. And then back and I started…I worked for a company in Winnipeg called Online Business Systems. So they are a consulting company based on Winnipeg. And kind of around…I worked there for a year or two and I think the iPhone came out a year or two into me working there. And I was doing some consulting for businesses through them and stuff. Yeah, when the iPhone came out basically, a friend of mine Andy Oliver and I started…we made an app called Sneaker Junkie, which basically was…it took a bunch of like…Andy is like a big sneaker guy, like the kind of guy with like 400 pairs of shoes in his closet. So we basically took a bunch of blogs, and took the RSS feeds from those blogs and kind of preprocessed them all into like a single feed, and basically put them in an iPhone app. and we charged like a $1.99 for it.

David: So for anyone who doesn’t understand those acronyms, basically you ended up with an app that had like just a stream of pictures of shoes. It was like an Instagram for shoes that you can comment on and you just scroll through pictures of shoes?

Gareth: Yeah. Literally just scroll through things people wrote about shoes that day.

David: Cool.

Gareth: This was kind of like when the iPhone 3GS came out, which I think was the first…there was the iPhone which just had the Apple apps on it. And I think when the 3GS came out that was when Apple opened up their App Store to third-party developers, and people started kind of diving in there. So yeah, we made an app and we…it actually ended up doing like…some people bought it and we were kind of surprised by that. And so based on that it was encouraging enough for us to make a bunch of other apps that were very similar. And yeah kind of like did that for like six months or so, and kind of from there decided that I was gonna try to…

David: You were basically building Pinterest before Pinterest was there.

Gareth: Yeah, basically. Just like a horrible slow strip-down like Pinterest that you couldn’t actually pin things.

David: A read-only version of Pinterest.

Gareth: Totally, yeah. And so like I learnt a lot of stuff like doing that, and again looking back at that time when you look at the things we made and you just like cringe. But you know it was like a stepping stone.

David: What was the most cringe-worthy one?

Gareth: Just like we did…what did we do? We did celebrity junkie and like…I think we did like a dog app for people that love all the cool dog…there is like dog blogs.

David: Of course there are.

Gareth: And so we just like pulled down a bunch of pictures of dogs but people bought it.

David: Was it called Dog Junkie?

Gareth: No. It was Dog Lover.

David: Okay.

Gareth: But people bought that stuff, and it was like at least we show that we could like ship something. That’s the thing as I think a lot of people like whenever get past that first step of like just literally getting something in the app store. So we decided to do that and it was a little bit of a market…

David: Well, especially at the time getting something into the App Store was kind of more of a hurdle than it even is today I would say.

Gareth: Yeah. There was no documentation or like community of like support and stuff to figure out. It was just you were…the only people that kind of knew anything about like development for IOS, were like old school Mac developers. So people that had been developing for like Mac computers for like a decade.

David: And at the time Mac computers weren’t sexy yet. Like they were sort of in…

Gareth: Yeah. The iPhone was in the process of making them cool again. So yeah, it was like not a lot of knowledge out there. Now there is way more kind of frameworks and it’s a lot easier. No, it’s not easy but it’s lot easier to get like an app launched and out and stuff. So it was very like early days for like old stuff.

David: Yeah. So you were exercising your shipping muscles, and you got some apps into the App Store and you made some money, right?

Gareth: Yeah. It wasn’t like life changing money, but it was enough to make one realize that you could make a full time living out of this. So it was like paying a mortgage.

David: Totally. Did you quit your consulting gig at that point?

Gareth: So at that point I quit my consulting gig, and kind of decided to go off and kind of try to do my own things. So that first year I think I made about 30%, something like what my salary was the year before. But when I look back at the time I don’t have any regrets. Even at that point I remember thinking like that was like a massive getting the amount of money that I have for myself and my family. But I had more fun that year than I had you in previous years. Yeah, it was totally fun. So I actually from there just did like a bunch of kind of smaller consulting jobs, and had a couple of products…kind of one main product that I worked on for like a year and a half, like primarily during that time.

David: So how long, I mean I’m fast forwarding a bit because I know where the story goes like it ends up at Shopify. How long after you quit in Online Business System before you went to Shopify?

Gareth: It was probably a good three or four years.

David: Okay. Three or four years kind of basically working for yourself, right?

Gareth: Yeah.

David: And doing some smaller apps and working on this bigger thing that we’ll get to in a second.

Gareth: Yeah. I feel like for the last 10 I’ve just always had something. Something on the side whether I was doing it full time, or whether I was working somewhere else, or whatever just like that as an idea. Well, it was not initially an idea. It’s like me trying to solve a pinpoint in my own life that I’ve been working on. So yeah at that time yeah I did consulting for a couple years, and I had a product called All of Wiki Offline, which lets you download all of Wikipedia on your phone.

David: Is that still around by the way?

Gareth: I took it off the App Store like a year ago. just because it wasn’t…it was one of those things where if you’ve made something and you like put it out in the wild, and you’re not actively…it’s not making enough money for you to justify and investing more time into it. You just don’t want it out there because you look at it and you kind of cringe and you like don’t even…like in the fear of like name…

David: Sure. And especially as sort of design trends evolve and operating system changes and stuff.

Gareth: Yeah. So to maintain any kind of like product like over the long haul, it’s like a lot of effort and if it’s not making enough money to justify that effort then you just…you try to support the people that have bought it in the past. But yeah I took it down like a while ago. Like same thing for I wrote another app called Receiptmate, which also I kind of have and I took it off the App Store like maybe six months ago, just because if you can’t look at something and be proud of it, you just don’t want it out there.

David: Fair enough. Okay. So you had a bunch of smaller apps. You were doing some consulting. And then you started working on something bigger, right?

Gareth: Well, it didn’t seem big at the time. But yeah, it was like another pinpoint that I had, so I moved to New York in 2010 and around that time…

David: Just for fun? Was that kind of similar to the Los Angeles thing or?

Gareth: Yeah. Kind of. So I ended up working for a magazine that was trying and transition from print to digital. So back then basically everybody saw kind of iPads and iPhones were kind of coming and more and more people were spending more and more time on them, and a lot of the print industry was trying to figure how to like continue with their revenue models into like digital. So everyone was like actually paying developers to write their own custom apps, you know if you’re like the New York Times or whatever you have your app, and you pay like an in-house development team to build that. So it took a couple of years for like the industry to kind of mature for there to be like platforms where you can publish this kind of stuff.

But back then everyone was just like hand-rolling their own stuff, trying to figure it out. I was there trying to do that during this time.

David: How did you get into that by the way? Were you looking for something or did they find you?

Gareth: No. I just emailed this one magazine that had a job open. And just there weren’t very many people doing iPhone stuff back then. So it was like yeah you got to developers to like do it.

David: Cool.

Gareth: Yeah. So at that time I was in New York and my friend Nils Vik here in Winnipeg, he was visiting me in New York, and he was talking about how he was gonna open a coffee shop, but he wanted basically to have a terminal on the…like a terminal of the coffee shop that just didn’t look like terrible. And I had kind of recognized some of that pinpoint, because during that time…like maybe a couple of years before that I’d opened The Albert Diner with some friends. and so I had been tasked with like figuring out the point of sale situation, and it was terrible like all these terminals look like they’re from like flight of the navigator, and they were like sitting on your desk, and they were like the worst thing ever. And they’re $5,000 and barely work.

So that industry was like pretty terrible at that time. So I kind of knew what kind of sucked about the current versions and stuff, so I decided to kind of try to make one basically based on iPad. Yeah, and so I basically just spent probably like maybe six months kind of just coding it, while I was living in New York. So kind of the front-end on iPad and wrote the backend service, and kind of had everything up and synching and stuff. And so basically at the end of that time as I was getting closer to moving back to Winnipeg, it’d been about a year. I was getting close and closer to launching it. Had it working at a few shops in Winnipeg, a place out in Toronto, a place in Calgary. And I realized that the thing that I made like people actually maybe wanna use this thing.

So I kind of got hold of a business partner, and that just kind of didn’t work out based on kind of like priorities and stuff, and I just kind of got frustrated very quickly and decided to basically like sell it, and kind of see if anyone was interested in it, and kind of just move on to something else.

David: Sure.

Gareth: And so basically, I had actually sold it to a company based in Seattle. And so like the papers were signed and I was gonna fly out there in two weeks to show the developers how it’s gonna work and all the stuff. And basically as I was like…like I was about to get off from my desk in New York to fax these papers back to these people. I had a friend from Shopify that contacted me and ask me like, “Did whatever happened to the iPad you’re about to ship?” I was like, “Oh, funny thing I like literally I’m about to fax these papers back to these people.” And he goes like, “Hold on. Just give me five minutes.” So I’m like, “Okay.” So he comes back online five minutes later and he’s like, “Can you be in Ottawa tomorrow morning?”

So I’m like, “Okay, sure. I guess.” Like Shopify I didn’t even know was based out in Winnipeg or based out of Canada. So like I Googled Shopify. I’m like, “Okay I kind of know who these…I’ve heard of these people before.” And so yeah, I basically just went there and kind of demoed it to Toby and Cody. Yeah and that’s kind of how I ended up at Shopify.

David: And so Shopify acquired these products then?

Gareth: Yeah. So they acquired the product and basically through various kind of processes turned…like we kind of rebuilt the Shopify point of sale, kind of from scratch based on the one that I had built, expect the back-end was basically obviously Shopify. So yeah back then Shopify basically had their ecommerce solution, which was like online, and they kind of wanted people that have brick and mortar stores to also be able to like you sell a t-shirt, and you sell it online and it’s all pulling from the same inventory, and you’re kind of just using one system to do all that. So yeah. From there we basically like we had the first kind of alpha version running across the street at Parlour Coffee. And so that was like really valuable to us.

I think we had it running at the plug-in gallery actually as well. And we learnt a ton of lessons. Like you learn a lot like, when you’re kind of in a room and just working on like something like a point of sale system, you kind of write the software, and you’re kind of sitting there at your desk, and everything is clean and tidy. You’ve got the iPad right there and you can kind of build this thing the way you think it should work. And then you go into an actually like store, and like the Wi-Fi doesn’t work. There is not enough cables for all the things, like their computer. Like they got all kinds of like wires you can’t figure out what’s going on. Like it’s such a valuable thing to have like actually places to test the stuff in the wild. Because you cannot reproduce like anything you’ve designed and built.

Like even like the user interface, like it’s so valuable to have basically that first one or two kind of like stores willing to like run your software, and give you the chance to kind of like make it work and fix all the things. So yeah, that was like pretty valuable having them.

David: No kidding. Okay, so I wanna unpack that a lot. Well, let’s start with because this is something that I was initially curious about. You had this point of sale system that you developed while you were in New York, and you decided you wanted to sell it. And then how did you go about finding that initial acquire, the folks that in Seattle?

Gareth: So that kind of was more of a serendipitous thing like they back then, there were people in the States like Square was kind of like the big player that had like the square swiper, which is like…

David: They were just getting started at that point too, right?

Gareth: Yeah. They were only around like maybe a year or two maybe.

David: Okay. I’m sorry I interrupted you. For the benefit of everyone listening because everyone probably doesn’t speak startup easily the way we do. Square, they’re the guys like if you go to a flea market and someone pulls out their phone with a little white thingy plugged into it, and then they swipe their credit card that’s Square or one of their competitors.

Gareth: Yeah. So there were several people in States doing that. Square was kind of out ahead of everybody. I don’t remember, I think this one was called Phone Swipe. So it just looked very similar as like this black kind of dongle that goes on the top of the phone. So they basically wanted an iPad sort of point of sale system to run their payments through. And I was actually looking for a swiper that I could sort of plug in to my app and actually run the payments. Because what I was doing was you’re sitting in a terminal and you sell coffee. You punch one coffee into the thing, but then let’s say its $3. You have to them pick up the debit or user machine, punching $3 and hand it to the…so it’s not the solution should be.

David: For sure.

Gareth: But there wasn’t really a way to tie the hardware in back then. So basically they had an API that you could actually like hook this thing into your app, and run the payment through. So I actually contacted them to try to and sort of fixing bugs in the SDK that they gave me. And through that relationship they were like, “What are you building?” I’m like, “I’m building this point of sale thing.” They’re like, “Oh, really? How does it work?” So it just kind of like I had kind of always been in contact with them so yeah.

David: Cool.

Gareth: It was definitely, I think if I would have tried to go out to seek out people to try, it would not have worked out, because I’m a terrible salesman. I have no idea of the channels I should be going through to get that stuff. Yeah, so that’s kind of how that worked.

David: That’s kind of not fair though that you had two sort of serendipitous buyers come and find you.

Gareth: Yeah, very much. Well, the way I ended up at Shopify was a friend of mine Chris Lobe had helped me with some of the design for Cashout and he was…

David: Okay. Cashout was the name of the point of sale?

Gareth: That was the name of the point of sale system yeah. And he had helped me with some of the design and he had been working for Shopify, as well kind of just around that same time I started so I think he had talked to them, and so that’s kind of how that happened but.

David: Very cool. And so Shopify, there are people listening to this podcast who have no idea what Shopify is. And so maybe you could talk through what it is now. What it was at the time when you found them, because it’s grown significantly and what it is now.

Gareth: Yeah. Shopify is basically a platform that lets you sell anything. I’m gonna sound a person from the marketing department right now.

David: Awesome.

Gareth: Just I don’t work for them anymore. So this is actually me telling the truth because I’m not being paid to say it. But they are basically a platform that lets you sell kind of anything anywhere, and like run your business. So traditionally that’s been basically ecommerce. So they let people run online stores. And it’s not a brand that’s known very well because is the technology that runs behind…

David: Right. It’s like an underlying platform. If you wanna run an online store and you don’t know what you’re doing you would just… well, that sounds bad. You can use Shopify if you know what you’re doing, but it’s so good that you could also use it if you don’t know what you’re doing.

Gareth: Yeah. A lot of the brands and stuff people buy, anytime you’re buying something online, if it’s not from Amazon or like Walmart, there is a good chance like Shopify stores like the technology behind that platform. So yeah, that’s kind of basically what they do. At the time they were like 60 or 70 people or something. I remember walking into their office the first time, and there were you know a couple of rooms full of people, and my initial thought was just I’m here like so late. I’m like the last person to the startup. I’m like the new guy. Like I missed the boat. And then you know four or five years later there is like a couple of thousand people work there.

David: A couple of thousand people and then an IPO, right?

Gareth: Yeah. So there was an IPO.

David: You were “late” but you were getting onto the rocket ship.

Gareth: Yeah. And I think like that tendency is always there for people to come to any sort of business and think well, I’m like the last because I’m the last person here. I find usually you know if you’re involved in like a good situation then like down the road, you know, there will always someone that’s been there longer than you. And so people like come into a situation like that looks like already the company is pretty big, like you have an opportunity to still be part of something that could be possibly like 10 times bigger. So that was definitely the lesson there. I still would see that when I like was up to Shopify like a month or so ago. And new people would start. And I think you’d kind of get overwhelmed by, “Oh there is so many people here. This is so big.” But I think the important thing is for people like that to remember like two years from now, you’ll be saying, “Oh, remember when we were here and there was only like 1500 people or whatever.” Like yeah that’s just people share the perspective on that.

David: Right. No kidding. And so when you came to Shopify they were only doing online stores, and basically the reason that your system was a strategic acquisition for them, was because it allowed them to have merchants who had say an online presence and a physical retail presence, and they wanted to be able to use Shopify to basically manage both. Is that right?

Gareth: Yeah, exactly. So we actually ended up…to me to some extent I still consider the thing that I made a failure, because it wasn’t sort of in its original vision to kind of carry it down to the world. Like the actually product itself was a failure. I learned a lot and also it’s also like the greatest success I’ve had. Because I ended up at a company like Shopify which is like invaluable to be part of that company at that time, and that was like amazing. But basically when it was acquired I basically…I remember like you know a few days before that I kind of panicked, and like tried to clean up all code before other people started looking at it. I was like, “Oh, gees I wrote this all like 4:00 in the morning, like I’m a total fraud.”

But when I got there we basically spent the first six months, kind of, writing the mobile portion of Shopify, so that it didn’t actually have like a full on proper mobile app to basically manage your store. And so kind of once we allowed the foundation for the framework, then we started building the point of sale, kind of, rebuilding it with some components from my plan.

David: Got you.

Gareth: So it was kind of like part acqui hire part use some of the technology. But yeah, just more getting someone in that kind through the process of like building this thing for people.

David: Totally. Very cool. And so you were at Shopify for four or five years, something like that?

Gareth: Yeah. I think four and a half, coming up on five or something in spring.

David: What was your role there, your function there?

Gareth: You know I don’t even know. It was just developer. I was developing stuff, getting stuff done like coding. So yeah, I did mobile stuff for quite a while, like for a couple of years. And then ended up transitioning to more of like the web kind of like back-end stuff for a while. Like dealt with like a lot of the taxes, the way the platform calculate like does the tax calculations and calculate shipping rates and all that kind of stuff.

David: Now US, shipping to the US from Canada, do you charge different tax or don’t you?

Gareth: Taxes on the shipping?

David: Yes.

Gareth: I don’t know. I should know but I could find the code that actually could tell you if you do or not.

David: It’s a question that’s come up for me recently. I couldn’t find the answer.

Gareth: The problem is that this kind of stuff like you’re taking like a really complicated like world, and trying to like codify it with like computer code, and it’s like it’s so hard. For every kind of problem there are some sort of like software as a service to solve that particular problem. Like there are SAS companies that only…they are like tax calculations for your ecommerce company. So like you set up all the rules in there. You are running an ecommerce platform. You call it to them for taxes or like shipping. There is like a niche for everything that’s actually like not even a niche because the market is like so big. But yeah, it’s fascinating.

David: So you stuck it out at Shopify for a while…

Gareth: Well, not stuck it out but I…

David: You enjoyed it.

Gareth: I loved it, yeah. It’s amazing.

David: I don’t know, poor turn of phrase. But you ended up…what was sort of your rationale behind leaving them?

Gareth: So yeah, I mean for me it had been you know coming up on like four or five years. A large part of that had to do with the fact that I was working remotely, and I think remote work can be very fulfilling and it’s like definitely the way the world is going, and it’s like a very…I think a lot of people like we’re lucky that the world is like going in a way, where we have lots more communication. There is a lot more opportunity even now no matter where you live. You can kind of participate in this kind of work. But for me it had a bit of a shelf life. Kind of you know I have an office downtown that has a couple friends work out there that don’t work for Shopify, and kind of share that space. And then I work at my house but just kind of year in year out only communicating on Slack. It’s kind of…yes, Slack is the sort of internal messaging tool that we use for…well, a lot of companies now use for communication inside their companies.

I think eight hours a day is too much time to invest long term, and not building personal relationship with people.

David: For sure.

Gareth: And so I kind of just got to the point where I kind of…and through various life circumstances I couldn’t really move to Ottawa. So yeah, that’s kind of why I kind of just made the choice there to try and make sure I would try and do something else again.

David: Yep. Fair enough. Did you find that like I can imagine that the change in culture from a 50-person company to a 1500 person company, would also sort of affect the way they felt you fit into it. Does that have a factor?

Gareth: Yeah. You know what? I actually…I can’t even say that the culture really changed that much. And a lot of that just comes from like the leadership of that company is very…like we didn’t just go out and hire like a professional you know CEO, with like white teeth and like a tan to kind of like be the company. Like the person that founded it is still there and a lot of that comes permeated down. He’s like a technical guy, like technical founder.

David: He wrote the first version himself, right?

Gareth: Yeah. And he was like a big kind of contributor to like the open source community and he is still well respected like the tech world. But so I don’t think that really the culture changed. I just think that the certain things changed simply with size. So you’re not gonna know absolutely everybody anymore. You’re not like…so that part of it I think just has changed, the fact that you are now working for a company that’s quite a bit large than it was when it first started.

David: Yeah.

Gareth: But yeah, no I think it was…I don’t know if the culture really itself changed. I think like the problems that you are addressing are now larger and larger, that requires more and more communication and to try to be as effective, like to try to be effective you need more communication and that requires kind of more face-to-face time with people.

David: For sure.

Gareth: I think that kind of for me was one thing I found a bit challenging, but it’s not insurmountable I don’t think.

David: Yeah. You sort of…I don’t wanna put words in your mouth but I felt like you sort of downplayed a little bit the way that you were brought into Shopify. Your acquisition there you called it maybe an acqui hire, which is sort of a term for basically just hiring someone or giving them a higher bonus essentially. But the truth is you did quite well through it all. At the end with Shopify as I feel you did well as my understanding. Did that have an impact, in the sense that like you probably weren’t purely motivated by salary near the end of your time with Shopify.

Gareth: Yeah. Like there is also so in my case like I got stock like…I got basically my part wasn’t required for decent amount of like shares in the company, which then you know over the period of like you know they invest over four years, and then we actually end up making it to an IPO. So everyone that had been around kind of since early days like did pretty well. And it’s actually been interesting…I’ve actually like learned a lot about how the market works, just watching that process from the inside. There was always like a lot of sort of people in companies like this that kind of enter this phase of the company…a lot of the concern is, “Okay, all the people with all the knowledge, they make less money and then they leave, and then you’re kind of stuck with this company.”

But if companies are concerned about that, like you should be building a company where people aren’t working there for the money, right? Or like for like this reward, and maybe the people that are leaving right as soon you know they cast their stocks out, then maybe those aren’t the people that are like super invested day-to-day anyway. So it’s kind of an interesting. like I think some companies you probably heard of like Amazon, they…and I think a couple of companies in Winnipeg do this where they offered to pay people like five grand, to like every year you get an offer of just $5,000 on the spot to leave. And so kind of make sure that people are there because they are actually engaged and they like want to do that.

David: Yeah, interesting. And so you didn’t feel that…you didn’t sort of feel any I guess boredom or there was no lack of motivation there.

Gareth: No. It was amazing. like I think also too something I’ve learnt is like the people like when you are kind of like this rising startup company…well, there is a few things that happen, but one of them is like you basically do get like the cream of the crop. And so the people that you are surrounded with are pretty amazing, and I think if for a lot of younger people coming into a company that you kind of don’t have the context that you’re surrounded by incredible people, and that won’t always be the case.

David: For sure.

Gareth: So yeah, I definitely like try to have some perspective there. And that’s kind of one of the things I was…like one big reason for me like to not leave would be that you’re no longer surrounded by these amazing people, which when you’re kind of working for yourself, you really have to go out and seek best practices, and kind of really make an effort to be constantly improving yourself. Because you are not surrounded by, right? Like you just volunteer the same habits, and like not ever change the way you do anything. So that’s to me is like kind of the biggest, but other than you know the friendships and stuff that’s been built over the years. But one of the biggest downside is like you now have to actively go and seek amazing people that are not just kind of put there for you to learn from.

David: Does Shopify do a lot of remote work stuff?

Gareth: Yeah. They do and they actually do it really well I think. Like they have some people in Vancouver. There is an office in States in like San Francisco. There is people in Europe that do like opps stuff. So I think every company’s come to the realization that if you want to basically scale, and build like a serious long-lasting company, you have to…not like actually embrace remote work and like make that part of like your core thing. With engineering sometimes I think it’s difficult if the DNA of your team is not remote. Like you need to make a more of an effort if you have sort of a core group of people in one geographic area, and then one or two satellite people. It requires more effort on both people’s parts to like make that work.

David: And that’s the case in Shopify’s case, because it have headquarters in Ottawa that’s a big office.

Gareth: Yeah. They do that and so then they have like some of their people working.

David: And what are sort of your take with…I mean I think you are right. I think more and more businesses are sort of being for better or worse, it’s the new reality is that you have to be able to embrace remote working, and to couple that with trying to build the company that people aren’t there for the money. How do you do that?

Gareth: Like how do you kind of get people to kind of embrace like remote work and…?

David: Well, how do you get people to be really bought into what they are doing. Like its one thing you know and a bunch of remote mercenaries, it’s pretty easy to imagine. But a bunch of remote workers who are bought into the culture in the meaning of the company, it’s something a bit different, right?

Gareth: Yeah. I think the way to do that is like especially I think when people first started the company, you do need to spend like a lot of face-to-face time. Like when your onboard people, like get them to the main office, get them in front of people, spend a couple of weeks with them there.

David: Did Shopify do that?

Gareth: Yeah. When you come and you spend decent amount of time, you just kind of soak up some of the culture like learn things, like meet people etcetera. So that there is kind of that base connection that you have to work off when you start working with everyone. And then the other thing I think if possible is to do like frequent trips, and like kind of make it there as much as you can.

David: How often do that happen with Shopify?

Gareth: For me it’s like every six weeks.

David: Okay. Is that common with the remote workers or…?

Gareth: I don’t know. I don’t really actually know enough about the way the rest of the remote stuff is run. I know people came like kind of as often as they could, so it’s also like a very like there is Toronto, Montreal, Ottawa. And so I think there is definitely a lot of movement of people between offices there.

David: Sure, cool. And so now you moved on from Shopify and what’s the…you mentioned a bit earlier Kickbooster.

Gareth: Yeah.

David: And we’ll get to that in a second. Is there anything else on your plate as well these days or?

Gareth: Yeah. So I’ve been also kind of just hacking on a thing.

David: Perfect.

Gareth: Yeah. I’m never…

David: It’s not a point of sales system, is it?

Gareth: No. It’s not that. I just feel like one trait that I don’t like in people, is when they talk about things that they’re in the process of doing, when they haven’t actually finished them. Because it’s like yeah, everyone is working on something, right? Like everyone is working on like the next great like American novel. Yeah, I am kind of working on something that lets you do like easy online registration forms. So I kind of had this problem for I like a year ago where I had to sign my kids up for stuff, where just like I took sailing lessons in… Like the signup forms is the worst thing in the world. And there are platforms out there that do this type of stuff, but they are just too complicated. The other shoot too low. It’s like a Google form that doesn’t have payment or anything. Or they shoot too high and they are like team snapping all these systems that let you configure all the stuff, and like sports management stuff. My theory is that people want something where they just…they want to create a form, figure out who’s paid and just have it all work. Like that’s all they want.

David: For sure.

Gareth: So my plan is to try to test that hypothesis. So that I’ll be like shipping that like the next month.

David: Very cool. And that’s just you? It’s just a side project?

Gareth: Yeah, pretty much. There is like a couple of people like a designer, and staff that’s helping me out and stuff. Yeah, I’ve just been kind of quietly working on that on the side to kind of flex my creative whatever.

David: For sure.

Gareth: Yeah, so we’re all gonna see if that has any legs but.

David: Awesome. Well, you have to keep us posted on that. What about Kickbooster? You mentioned a little bit at the beginning it’s a sort of an add-on to Kickstarter and Kickstarter platform.

Gareth: Yeah. It lets people do affiliate marketing for their crowdfunding campaigns. And so yeah, there is a lot of stuff happening where you just join forces with another company in the States. and it’s kind of one of those things where when people start stats businesses, you go kind of from an idea in the first step, which a lot of people don’t get to is they call like product market fit, where it’s like you actually find a cohort of the population that actually wants to use your product. And so like once you get…you spend a lot of time just experimenting and stuff until you kind of like hit that. And so they definitely hit that like early and way out of the gate. And so they kind of have a lot momentum of what they are doing.

David: Awesome.

Gareth: So yeah, I believe in doing in a couple of weeks. So I’m just trying kind of like trying to soak up everything, and like be that annoying that just asks more and more questions every day until you’re like no more.

David: How big of a team is it there now?

Gareth: It’s like six people.

David: Okay, cool. Did you know you were gonna do that when you left Shopify, or was it kind of like it happened after?

Gareth: No. I think I just like took a leave of absence from Shopify for like a couple of months. Because I wanted to kind of like ship my side project and just take a break. I got married. I went on a honeymoon etcetera, worked on the house.

David: Awesome. Congratulations.

Gareth: Thanks. So kind of during that time I kind of just started just meeting up in my house with a few people that kind of were involved, and then they kind of talked about what they’re doing, and it just kind of like snowballed. It just made realize that maybe now would now would be a time to just try to see if I can do something else.

David: Totally, cool. And so what’s the five-year plan for Gareth? What do you sort of see in the future?

Gareth: Well, I don’t know. I think I will hopefully always be working on something like newish or basically…I feel like in my life, I’m just like always looking. Like I still feel like I haven’t had a huge win. I feel I’ve like made a lot stuff and some of it has people who have use some of it hasn’t. but just to really like be involved in something from the very beginning that a lot of people end up using, as like something I’m always striving to do. And so I think some of the things I’m kind of involved in and I hopefully, I think some of those will get there. But something that I think like if people wanna go like to the lifestyle of like being an entrepreneur, like if you wanna make money it’s like literally like the lowest probability like hardest way to do it.

David: Totally.

Gareth: And so when you kind of go down this path of like deciding…I don’t know if people decided or whatever. But you become kind of like a bit of workaholic. You really get it and you have a lot of passion for what you do. You need to be able to come…if you go through all this effort and you build this thing that’s in your brain, that you know, you wanna build. And the whole thing just wholly flops and nobody uses it, and you spend like a year doing it. That needs to be like okay and satisfying, and you need to derive pressure for that. Otherwise it’s too much of a risk to try to think that this is something that’s gonna like make you a bunch of money or like something. And so that’s fully…it’s not my expectation with thing I do, but I’m such a skeptic…not a skeptic, but I just like I have no faith at anything I do will ever work out. And then I just go at it and like if it does, then great. Like I was there with an idea and it was super fun, and if not it’s just one more learning process. And I feel like through all almost all the things I’ve done, at least I can say that I tried to build something, I shipped it and totally learned from it.

David: Yeah. I mean that idea of sort of expecting everything you have to blow up in your face, it lines up with some of the conversations I’ve had. I think I mentioned this to you before. But I did an interview with Barb Gamey, and the way that she phrased it was that she felt like she’s been faking it until she made it the whole time. And it’s because, it wasn’t because she you know was misrepresenting herself, but it’s because every step of the way you feel like what you’ve accomplished is 10 years at best. And that the next thing that you’re trying to do could be the unraveling of it all.

Gareth: Yeah, totally. Exactly. Like walk in that line. Obviously there was a point in which if you have like…if through some Christmas miracle your business ends up being successful. Like you get to a point where okay you are like, “Yeah, I actually built the thing and people are actually using it.” So like you know there is obviously another set of challenges that come with the business like that. And that can be just as exciting trying to grow it from there. But I have not ever had that type of product that just like…yeah. So I’m just like that would always be kind of awesome. I guess it’s kind of like…it’s not like feedback. It’s kind of vindication that this thing that you thought was important, and you thought that you built it right actually is. Yeah, that would be kind of cool if that happened.

David: No kidding. It sounds like you got a lot of opinions sort of about how to start something, and about you know the attitude that you should take toward creating things. Are there people either that you’ve known personally, or that you sort of look to from a far who have influenced your thinking on that?

Gareth: I don’t know. I think that’s something that I think it’s actually difficult in Winnipeg, is like a lot of the Winnipeg’s history…we just don’t have a lot of really dynamic, like at least from tech stuff or like people…like we aren’t really surrounded by tech entrepreneurs here.

David: Right. Not to the extent of a place like Silicon Valley.

Gareth: Yeah, exactly. That’s one thing you kind of learn is that it’s very…it’s a cultural thing. Like people start businesses because they see other people do it. And they see they have an up-close view of the difficulties of it, and the reward and how exciting it can be when you are with a group of people making things, that’s very infectious. And like if you are not actually surrounded by that it’s tough to make that mental leap.

David: Totally.

Gareth: But yeah, I think like in university I had a friend. My friend Dan he was one of those older old-school app developers. And he totally had products that people bought and used. And he kind of worked for himself and that just kind of blew your mind. And like you make something and then you put it up, and someone literally will just give you money for that thing.

David: An internet person.

Gareth: Yeah. A person you’ve never met will actually pay you $10 for this thing you make, and that just goes in your bank account. That is mind-blowing. and it is mind-blowing when you…like coming out of high school you are like okay, gonna do university degree, gonna work for this company that already exists or like this thing. If you don’t think it’s possible, then you would never try. So yeah, but there is definitely people have kind of like…yeah, people like that where it’s…to me it’s not the huge billion dollar startup people.

David: Right. It’s not like Steve Jobs but it’s like…

Gareth: Yeah. It’s more like just people that I met and just seeing that run quietly go about running their awesome businesses, that not that many people know about, but are like solving real problems and doing really well. And those people don’t really get the attention. And I think that’s why I’ve had at least one or two successes in the past, is that like I never…I went into it not expecting a huge success. It was never really shooting for the stars. But just trying to make a small dent in the universe. I think that’s like the Ruby on Rails guy, like DHH or whatever. He has a…

David: Yeah, David Heinemeier Hansson from 37signals, now <a href=”https://basecamp.com”>Basecamp</a> for those of you who don’t know.

Gareth: Yeah. He has a kind of a thing where he makes observations on how people are always trying to be like the next billion dollar startup, but instead of just kind of made a dent in the universe, which is like build a thing that people are willing to actually use and pay for, and scale that out slowly etcetera. I would never be the type of person that would like have an idea, and then get a bunch of VC funding, and stuff. Mostly because I don’t have the ability to do that. I just don’t know how to sell that stuff. That’s just not in my psyche to like make huge bets and stuff, and like do that kind of stuff. I’m just more like kind of tinker away, solve a problem that I personally have, and then scale that out and see if other people maybe have that problem.

David: Cool. One last question and it’s something that I ask almost every guest. Book recommendations. Fiction, nonfiction, whatever.

Gareth: I read Ben Horowitz book, I’m in a blank…

David: “The Hard Thing About Hard Things.”

Gareth: “The Hard Thing About Hard Things.” That’s a good book to me. and I like it because Ben Horowitz is…he’s kind of like comes a little bit from the old school-ish Silicon Valley era. So it’s like he’s seen a lot of stuff. He’s kind of around the internet boom. And he is not like a super charismatic whatever, his just like, yeah, there’s just so many things in that book that I just read twice because it was really great.

David: Yeah. I thought the same thing. I wasn’t sure if I would like it. but because kind of like you are not crazy about the VC back model, and Ben Horowitz is a venture capitalist but yeah.

Gareth: I genuinely hate business books, like books about business. I’m just like, “Oh.” Roll my eyes but it’s just like…

David: There is a lot of platitudes often.

Gareth: Yeah, exactly. It’s mostly like people that somehow got rich, and then are trying to get even more rich by talking about how to get rich. but that book I really like.

David: Cool. All right Gareth. Well, thanks so much for taking the time.

Gareth: Yeah. You’re welcome.

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