Ian Mackinnon, Later Media - Founder Journey Series, Episode 8

The highly coveted technical co founder. Today on Founder Journeys we've got Ian McKinnon, CTO and co founder of Later.com we're going to dive into his experiences and the different approaches that he takes to building a B2C company versus a B2B company. We're talking about work, life, balance and what it's like building one of the fastest growing social media digital marketing companies today in later.com 3, 2, 1. Hey everyone. Welcome back to another episode of Founder Journeys. Really excited. As I say, every week or every episode I'm really excited because the people that are on this series are people that I really look up to and really appreciate and admire. Today is one of those people. Ian McKinnon. Ian is a founder multiple startups. I met him back in 2012 when he was working with his first startup Placeling at Grow Labs which is the accelerator here in Vancouver, which was co located with Launch Academy. And so I grew to to really appreciate Ian as a technical founder. As you probably have heard multiple times, every startup founder needs to have a technical co founder or somebody that can come in and really understand how to build a product. Ian's just that type of guy. He really understands the technical side of the companies but he has grown to become a full rounded entrepreneur and really does understand the other aspects of being an entrepreneur and building a startup. The latest one is exploding. It's just on wildfire later.com it's doing extremely well. Full caveat. I am an investor. I've been following the journey of these entrepreneurs that started later since day one in their previous startups and then I saw firsthand how they built later and I knew it was something that I want to get behind and support. I don't really do that very often with Launch Academy companies but later was an exception and I'm so happy that I did because it is really fit along the lines of what I like to invest in and what I believe in in terms of visual media and social media. And later is doing extremely well and we're lucky to have one of the co founders, Ian McKinnon on Today. Ian, welcome to the show and please let us tell us a little bit about yourself.

Well, thanks for having me Ray. Like you said, I'm the technical co founder and Current CTO of Later.com before that I had a bunch of other startups that got increasingly less crappy as time went on. Before that I, you know, in another life I was a student at Waterloo and did my internships at Google and then I moved out To Vancouver and a few. After working a few jobs, I started creating my own companies.

Like how did you get to where you are today? What are some of the obstacles that you had overcome? Obviously some great opportunities working at a company like Google and learning, but you made the switch to a startup very early. And your own startup for that matter, not working at another person's startup builds your own.

Yeah, I think I always kind of knew that I wanted to do startups. I started university right around the time of the dot com crash. So that meant when I was in high school I saw all of these techie people getting, you know, creating these amazing companies and getting super wealthy and then losing it all in the dot com crash. But what I kind of knew is like, well, I still wanted to do computer science. So when I started in the crash, it was a very weird time to start learning how to program because everyone was worried that, you know, these jobs wouldn't be around. There's a lot of fear and I didn't know what else I would do, so I still did it. And it turns out that's amazing because it's crazy to bet against the future. You know, tech being the future. I always knew I wanted to do startups. I just had no freaking idea how to even start. You know, when you're 20 years old and you're learning all about compilers and programming, that's great, but no one really tells you, well, here's how you actually go and create a product and take it to market. And when I interned at Google, all I could think about is how there were people who would literally kill to have the job that I had. And all I could think about was that this company is not mine and I really wanted to create my own. So if I was at the pinnacle of other places that you could work and all I was thinking about was startups, I just knew it was something that I had to do. And my journey was actually a very nonlinear one to startups because after school I wasn't really sure how to do it, what to do. I ended up going to grad school for two years, which was great. That's a very non standard approach for someone who wanted to go and create companies. Because as much as people, you know, I like the idea of startups, the idea of, you know, staying in academia was pretty sweet too. Especially when you're 24 and don't have a clear idea of what you want to do. And you also learn that other, a lot of people do create companies out of grad school by monetizing their research. That's not what happened with me. Then I had to go work a real job at another startup out here in Vancouver. But eventually, once Grow Lab came around, it kind of gave me a framework in order to start creating my own companies. But it was a long time. I didn't start my first company until I was 29. And, you know, they have this kind of myth of the right out of school person. Very rarely do you get to do that, especially if you don't come from money where you can kind of just not take a salary for right out of school and have someone finance it for you. If you don't have that, you still have this whole issue of how are you going to pay rent? So once you kind of figure that out and, you know, clear out any student debt, it can take some time. And that's okay.

That's one of the biggest fallacies is that a lot of people do assume you need to be really young and dedicating 20 hours a day living off ramen to build your startup. But the reality is a lot of the ones that are successful are entrepreneurs that are working on their second or third startup, or entrepreneurs that have come out of the workforce and they do have a nest egg that they can rely on, but they've got real life experience that they can apply to their business. Because it's not just about having a cool idea for an app. You have to execute and you also.

Have to be exposed to problems that people will pay money to solve. And when you're a student, your whole life is, or at least it was going out to bars, meeting people, worrying about class. But one of the things I always, whenever I give a talk to students, I say, don't make a product that students would care about because you're kind of the worst customers. You don't pay for anything. You're cheap as anything. You have like no disposable income. And the worst part about students is that you have a 25% turnover rate in post secondary every year as people graduate out. So the problems that you have of a student are just not that interesting. And there's a whole world of other problems out there that businesses have that once you get exposed to, you can realize that, oh, I don't have to make some huge piece of software that millions of people use. Having something that a few thousands of people are really excited about is often a better way to create a startup.

Also, somebody that's building a product that you're going to sell for 99 cents versus a product that you're going to sell for $1,000. Very, very different business models, but also the path to success, success is going to be very different. And the 99 cents you need to have a huge, huge volume of customers reusing or subscribing your product and using it on a regular basis to, to justify staying in business and continue to build the business.

And you'd also be shocked at how many businesses will pay a thousand dollars for something you don't think is that technically interesting. That is the one thing I have encountered over and over again as I'm now buying software and I see what people are charging me for something I think I could write in a weekend. But you know, the reality is I'm not going to, I'm just going to put it on the company credit card. And I think when you're a student, you just don't have that idea that for businesses certain amounts of money which are just extreme to you are nothing. You know, if you're charging less than $5,000 a year for something most businesses are just going to put on their credit card and not even think about it.

Yeah, definitely. And that's actually something I want to ask you about. Like when we talk about co founders and building startups, there's more than probably two to one ratio of a business co founders to technical co founders. And so you being the technical co founder, having multiple startups, what was your journey like in terms of finding and matching up with a business co founder? Because most of our audience probably is business co founders that are out looking for technical for you. From the technical perspective, how did you determine who you want to work with and what type of products you wanted to build together?

I think one of the things I've always kind of fought against is the idea that technical founders can't be idea people. You know, when it comes down to it, we have ideas just as well. But I think when you're looking for a non technical founder to partner with, you're always looking for someone who has some domain knowledge of whatever you're building. That's always the optimal consideration is that if they know about this problem a particular industry has that you just aren't exposed to, but they know that problem really well. They can go up there and can sell and can network. That's what you're looking for. My first co founder went with Placeling, which was a social local mobile app, which turns out to be a glorified bar finder in the end, which were all the rage back in 2012.

Hey, it worked for us. We were using it.

Yeah, I mean I liked it, but I learned a lot from it. But my co founder Lindsey, he was, had kind of a similar. On paper we looked really good as startup founders. He had done his MBA at Insead, he had worked at the Boston Consulting Group. I was a software developer who from Waterloo who had interned at Google. Like on paper we were just the ultimate pair. But the problem that we were solving wasn't one that people cared deeply enough in order to really get traction with.

And this is again one of those ones that we just talked about where your price point was more consumer based. And so you had to have a large volume of users to justify ongoing business.

Yeah. And then before you can even think about being ad driven, you have to have a huge volume. If you're a consumer. Consumer is just a tough, tough play. And the thing is that the really popular companies tend to be consumer. Like everyone wants to create the next Snap, the next Facebook, but there's a lot of those that get no traction because you have to make something that a lot of people like. And consumers tend to be very fickle. Whereas if you go to a business and say, hey, I have a piece of software that will save you a certain amount of money per year, they almost have to buy it because they are so relentless in terms of cost cutting and optimization that if you make business a slightly bit more efficient, they're going to have to buy whatever you're selling. Whereas consumers can be fickle and flaky. Might use it, might see some use, might not. It's a much harder game to pin down.

Yeah, definitely. And so as you've gone through various startups, your current one is massively successful and you are a very senior position cto, a lot of responsibilities. But you also just recently had a baby and I know you do a lot of mentoring in the community. You also help teach at Leidos Labs, which is a coding school here across Canada. How do you balance everything? What's work life balance for you as a founder?

Well, I didn't do all those things at one time for starters, because. Yeah, so I was an instructor at Lighthouse Labs because I think teaching more people to be developers is the solution to how do I find a technical co founder. There just is always going to need to be more technical talent. And as much as I went through a very traditional background of, started coding when I was 15 and went to a computer science program, not everyone needs to be that. Most of the developing we do day in and day out doesn't involve deeper knowledge of compilers and machine learning. It's very useful to have those in certain verticals. But it was one of my ways of giving back to the Vancouver tech community was being an instructor at Lighthouse Labs. And I had to stop when later started getting bigger. And, you know, once you've taken an investment, you can't really have side hustle.

So definitely investors don't want to see that.

Yeah. So right around the time that our seed round closed and once your check to us cleared, that was a time that I told, okay, I've got to go all in on this because, you know, and also competition was heating up. When you have something that's moving, other businesses are going to take notice. So that was the time when, okay, we have to be all in on this and really make a go of it. As for mentorship, one of the nice things about COVID is made very easy to mentor people without any travel time. And one of the things I really hope that we get used to is the idea of these kind of zoom meetings to get things done. Because for someone who has a baby like me, it's just really easier to kind of pop into another room, spend an hour having a zoom conversation with someone than going out to coffee. We do that thing of whose turn is going to pay and all this as if my time is, you know, really, you know, the coffee kind of offsets my time. You know, it's just a lot easier to kind of do things over zoom. So it's really helpful to kind of talk to people that way. And it just makes it a little easier because I can babysit the kid while I'm. I shouldn't say babysit my own son.

Parents.

It makes it really easy. Yeah, it's easy to be a parent. I am a co parent of this little one. It is a lot easier to multitask these things if, you know, I just have to be there in case of fire while I'm helping some other company or doing my own thing. These are also benefits in Covid.

Like you said, these are not your core business you've got later, but you're trying to help other entrepreneurs. You're trying to give back to the community, but also enrich yourself by helping others. And I know personally, like, I learn vicariously through others while I'm mentoring. Like I always say, if in a mentoring relationship, I should be learning more than I'm giving out, because that's why it's worth my time to do so. And when you, when you have to do these in person. Well, that's not just that 30 minutes, but it's also that transition time from weaning off of what you're doing to traveling to wherever you need to go, traveling back, and then getting ramped back up to do something. Whereas Zoom meetings and being able to be flexible with this just makes it so much easier to do those side.

Things because I can do it from home. I don't have to make sure my wife doesn't have anything on the calendar. It just integrates so much easier to other things. And actually, I got a lot of benefit out of being a Lighthouse Labs instructor. Because if you're an instructor or a TA for a year, it really supercharges your network because you're meeting, you know, 20 new software developers every couple of months, do that for a year, and then once they all graduate and they've been out in the real world for a few years, you now have this network of software developers that is, you know, that is so much bigger than you'd ever get by working at a local company. So it was just a, you know, super way of supercharging my network was by being a TA and instructor at a coding boot camp.

Yeah. And when you do have a little bit of legacy in your company, there are certain tech stacks and systems and processes that you have ingrained to your business. But teaching and mentoring, talking to other startups gives you an opportunity to learn vicariously through them of new tech stacks or new ways of doing things that you can't implement in your business but you, as a technical person or even as an educated person want to stay on top of. That's a great way to do that.

Also, teaching becomes important because for every non standard tech stack we use, every new employee has to learn it. So the ability to onboard new people in teaching are very similar. And it's always good to be if you know, because I feel like we're the only company in Vancouver that uses Ember JS rather than react. But I don't hire based on that. I just train people on Ember and after two weeks they're fine. So as long as you have within your company that culture of up leveling training in people, it's always a good skill to have.

That's actually a good segue into. Another topic that I want to talk about really quickly is you guys are based in Vancouver and you have a very large team that's remote around the world, but you didn't fall in line with the whole mantra of you have to be in Silicon Valley, you have to move to Silicon Valley. You guys were successful building a company out of Vancouver. Granted, you do have a workforce in London and Toronto, and I think you do have some people in the Bay Area as well. But you didn't have to headquarter out of the Bay Area. What's that like as a founder pushing against that mantra of you have to be in the Bay Area?

One of the things that has really changed a couple of years before we started raising is that American investors got very comfortable with the idea of investing in Canadian startups. I actually think you're our only Canadian investor that we have on our cap table. Most of our money came from the Valley. Again, they're in a relentless pursuit of returns and if they can get higher returns outside of the Valley, they will. There is a lot happening in the Valley, but by the nature of what we do, social media management, there's social media managers everywhere. There was nothing special about the Valley, aside from Twitter and Facebook being headquartered there. But that really doesn't mean much for what we do. We didn't really. We could be headquartered anywhere for what we do. It's just Vancouver is a great place and has a history of making social media management companies.

And you guys are now probably one of the top dogs in the industry and just happen to be headquartered.

Yeah, depending how you count. Yeah.

What does the get shit done attitude mean to you? That's obviously been the mantra at Launch Academy and you were there virtually from day one. And so you've seen the gsd, the get shit done attitude, grow and evolve into our culture. What does it mean to you?

Get shit done to me means finding a way to unblock yourself. There's always going to be hurdles. There's always going to be some challenges. And get shit done is a way of either getting through that obstacle, through sheer grinding it out to finding some clever solution around it, or finding some way of making do without. And I think a lot of people realize they might see some kind of challenge and it just might seem so insurmountable that they don't realize that there might be other ways of doing it or just not doing it at all. Just always kind of moving forward and finding some way of just pushing forward however you can and not letting something block or be depend waiting for someone else to unblock something for you.

Yeah. And you guys definitely live and breathe that you of all people, I've seen overcome a lot of challenges over the years.

Yeah. It gets interesting as the company gets bigger, because that hacker ethos doesn't scale too well as the company gets bigger. And now we have to worry about software development processes. But early on, it's all you have to do.

Yeah. Well, I remember the challenge you guys had at Place Link as a B2C company, and then Flock and Swarm trying to introduce a whole new concept of interactivity and real world environments. And then now look later. Ian, this is an awesome, awesome conversation. I want to kind of wrap it up with two specific questions for you. The first one is you as a founder. What is a tool or an app that you have found to be instrumental in your career? Whether it's a personal side of things or in the work life, what is something that is indispensable for you?

On the work side, it's kind of lame, but Slack. I know that it's employee communication, but all the integrations, all of my software systems, all the notifications are coming through Slack. On the work side, that's just how I know about what's going on with our system, with our customers, with other employees. That's the command and control center for later engineering. On the personal side, there's an app I like called Streaks, which is an app where you track something that you do every single day. So if you say, I want to walk at least 30 minutes a day, you just tap that and it tells you how many days in a row you've done something. So on the personal work side, I try to fix at least one bug a day. On the personal side, I'm trying to, you know, did you have any bad sugars today? Like, okay, it's a negative one. You know, try to go as many days without, you know, maybe have some that are like, okay, don't drink today. You know, just make sure to see how long you can get with. Well, you know, maybe you can have one. It's no big, you know, it's kind of like one.

Personal accountability. Personal.

Yeah. And you see how many days in a row you can do something and then you try and. Because the idea that you see that you've done something positive a number of days in a row, you don't want to cheat and then not do it because then you ruin your streak. And on the professional side, a lot of those are like, write a piece of documentation, which is a thing you have to do as the company gets bigger.

Yeah. And that personal accountability and self discipline is really important. As founders, your days can get away from you and your week can get away from you. And especially when you're faced with adversity and challenges, it becomes difficult to have, I guess the proper balance in your life. And so I definitely see how those type of apps are valuable if you are able to put yourself in a mindset where you want to be self disciplined and hold yourself accountable for what you should be doing.

It's also important for people like me at our stage to maintain some connection to our customers. So one of mine is actually post something on social media because I can get in my own head down workspace. I forget that ultimately it's a social media management company and I do have some idea of what social media looks like. Another one that I have is answering a customer support ticket every day. That is just something, you know, you really. We have so many support people but one thing we do at later is everyone has to do a customer support shift at least once a month. I try and do at least one ticket once a day just to have that connection to our customer and realize that there's real people using our software for their jobs.

Yeah, that's truly invaluable because there's certain things that will just get buried or not surface to you through the staff because they don't think it's important or they don't want to burden you. But at the end of the day you really want to want to know those type of things because that's how you mold and shape what the future of the company will look like.

Yeah, ultimately you have to solve your customers problems if there's one big kind of takeaway.

Awesome. Ian, you've been really generous with your time with us today and hopefully our audience appreciates it. I want to close out with a call to action. What's your call to action? What can our audience do for you?

We are hiring for a whole bunch of roles. You can go to later.com careers. Of course if you're an entrepreneur go and create your company but if you're not, go look@later.com careers. We are hiring constantly.

Well, even as an entrepreneur learning from a startup that's on fire is really valuable and getting in there and seeing how things are really done and it's a great lesson learned like get in there and work for startups that are on fire and hopefully you can learn what you can apply back to your own business. So yeah, really appreciate you taking the time today and the insight, especially from a technical co founder is something that we really value and hopefully our audience found it valuable as well. Thanks Ian.

All right, thanks for having me. Ray.

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