What Do You Actually Do? Episode 59: Toby Cannon, Running a startup

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Interested in startups or working for yourself? That’s what this episode is all about. Toby Cannon graduated from York in 2019 with a degree in Computer Science. He now runs Myles, a startup that began as an app allowing people to complete virtual challenges by tracking their fitness activity. He explains what his day looks like, what it takes to work in a startup and what students can do to follow in his footsteps.

Toby’s bio:

After graduating in 2019 Toby joined Capital One as a Software Development Engineer, working on a range of products which are used by millions of people. At the start of the pandemic, he launched Myles initially as a tool to keep himself and his family motivated with their fitness goals. The company has grown since then and he’s now full time on the business and is part of a team of four, with clients including Dell, Brewin Dolphin and Capital One.

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Related podcast episodes (freelance and self-employed):

Related podcast episodes (working in tech):

Transcript:

Kate 

Hello and welcome to this episode of what do you actually do? My name is Kate Morris and I’ll be your host today. In today’s episode, we’ll be talking about working in tech, sports and entrepreneurship. Today we’re joined by Toby Cannon, who’s an entrepreneur and founder of Myles Challenges. So Toby, what do you actually do? 

Toby 

Hey Kate, thanks so much for having me looking forward to it, looking forward to this chat, so yeah, as you mentioned, I’m the founder of Myles Challenges and we started a couple of years ago and my role as founder is essentially it started off as a as a one person team, just myself, so it’s kind of wearing all the hats and we’re now a four person team so it’s not quite not all the hats, but essentially my role is to set the direction for the company and to fill in all the gaps that aren’t being done and ensure that that we continue growing. 

Kate 

So you’ve got that oversight of everything. 

Toby 

That’s correct, yeah. So it’s gradually getting more zoomed out. So my background is actually in software engineering, so I’m still kind of working in the business, so bashing the keyboard, writing, writing lots of code, as well as looking at that oversight and making sure we’re moving in one unified direction. 

Kate 

What is Myles Challenges then? Because I kind of my colleague actually uses it, so it looks to me like it’s a app that helps you kind of set your own personal fitness goals, and it looks like you can kind of pretend you’re running up Mount Kilimanjaro or something, but looking at your description of it, it’s also something that you’ve been sort of pitching to businesses and other organisations to help them with team building and stuff is that, is that right? 

Toby 

Exactly that I’m super pleased to hear that your colleague is using it and hopefully they’re enjoying it, and but I can zoom out a little bit and maybe give more context on how it came about and that it kind of came to be a thing really. So just before the pandemic around January time, I never was a runner. Never run before, but I thought you know what, let’s let’s set a big goal and try and run a marathon. So I booked in for the Manchester Marathon, which was in maybe April early April time, April 3rd. So this was 2020. And lots of gruelling training runs, I remember waking up at like 4 in the morning to do big runs before work, carrying on and then two weeks before the marathon, the pandemic hit, so the marathon was postponed. So to keep my motivation levels high, being a software developer, I thought I’d tinker around and create a little app that would essentially let my family collectively run from Land’s End to John O’Groats. So me and my dad cycled it the year before in person and I thought this would be a good way for for the kind of the four of us that were running to keep motivation levels high. And we just found this hybrid of competition and collaboration, we’re all working together, but there was still a leaderboard to see who contributed the most, it did wonders for motivation. So initially it was built for my family and then we launched it properly to the public in August 2020 and you’re quite right, so we provide gamification to really encourage people and empower people to go out and take ownership of their physical wellbeing. Like what interests me with fitness is the psychology point that I’m sure we’ve all thought like do I want to go for a run or eat this donut? And in our head we all know the answer is go for run, but we still eat this donut. We all have this value action gap in our hand right, so we’re here to try and try and help people with that gap. Trying to encourage more, more healthy habits, and doing that through gamification so applying concepts from games such as leaderboards, group chats, levelling up, that sort of thing. And also really quite powerful social dynamics, so those leaderboards, you kind of want to beat each other at the same time you’re working together, and those really quite human feelings that we all have that have been building up for thousands of years, how can we harness those in order to get people moving and get people active? 

Kate 

So you kind of built the technology side of it, but now that’s kind of up and running what are you, what does a day look like for you then? If you’re if you said earlier, you’ve got the oversight of the rest of your team, what sort of things are you doing? 

Toby 

Yeah, so we built the first product, which as you mentioned was these virtual challenges. And that was fantastic. So we grew that to worry about 20,000 users and you mentioned the different companies, kind of the business angles, we’ve worked with some great names such as Capital One, Dell, Brewin Dolphin, doing one off events. So let’s say University of York wanted staff to walk from York to Paris and that sort of thing. So we can use one off events. With the tech side where we’re at now, one off events are great but we want to try and encourage year round well-being rather than well-being for one month in the yea. So we’re actually at the midpoint of a really exciting project building out a whole new platform, so we’re rebuilding stuff from the ground up, and which really provides that year round well-being so rather than one off challenges, there’s these ongoing leaderboards and different kinds of incentives, and also ways that we can compare data across different activities so let’s say you’re a cyclist and I’m a runner and our friend does yoga and someone else does kickboxing, like building a platform we can all contribute to that. So most of my day at the minute is spent like two thirds building this new platform and third like looking at more of the strategy, direction and all of that side of it. So hopefully by mid summer this new platform should be available so it’s really exciting times for us. 

Kate 

Yeah, really exciting and that’s interesting to sort of. The mission there to kind of look at well-being and health as well as do something fun. And you know, team building and that kind of stuff. And you mentioned that you worked as a software developer, so you did a grad scheme for the first couple of years after you graduated. I’m just wondering how that experience impacted on your career. 

Toby 

After my second year or during the summer, I did an internship for three months as a software developer at a company called Capital One who are a finance company based in Nottingham and that was in their mobile app teams for a lot of kind of coding to build their mobile app. I was lucky enough and fortunate enough to get an offer to come back there as a grad, so when I finished at York went straight into their grand scheme which is a rotational grand scheme which is really really good. So essentially I got to see lots of different teams see their ways of working and that had two massive impacts. Well, lots, but two that I can kind of come straight up top of my mind really. The first was the technical learning because it’s, you go through different teams, you get this really broad experience really. For a startup that’s that helps massively where you’re having to to do lots of different roles and develop lots of different tech bits. Having that breadth was so, so valuable and then also from more of a like a team ways of working point, rotating around those teams. It helped me kind of pull out OK in all these teams which were all absolutely fantastic teams, pulling out the best bits from them. So when I started this startup trying to have a real focus on how, how can we as well as build great tech, how can we build a great team? I think the great team is way more important than having the great tech. 

Kate 

Yeah, that’s really interesting actually that it’s not really the technical skills that was the key takeaway from there, it was the experience of having to integrate yourself with different departments quickly learn what they’re doing as you say, wear a lot of different hats, undertake a lot of different tasks at once. Those are the things that it sounds like a really helped you to then build your own business. 

Toby 

Definitely and you used the word like quickly learn and that’s definitely a kind of a key phrase there cause you’re rotating around you almost learn to learn different stuff if that makes sense which is so helpful with startup there’s so much ambiguity, and so much learning going on and having that experience where you are put into these kind of unknown environments and having to figure things out. And yeah, I think really helped me. Learning to figure things out I guess is the main thing. 

Kate 

I appreciate you said you know you would develop the app for your family it was a way to sort, not waste all that amazing training that you’ve done for the marathon. But I’m wondering, kind of, that’s one thing, giving up your cushty graduate scheme to then start up your own business is another thing. So where was your sort of starting point for deciding to be an entrepreneur and set your own kind of startup come from? 

Toby 

Yeah, and that was that was really, really hard really hard because I genuinely loved being at Capital One like would recommend the grand scheme and the internships to people and so that made it made a lot harder. It was a few months where I genuinely wished that I hated my job, so It made that transition lot easier, but it was, it was really hard. so I started Myles in the kind of March in the first pandemic, so or the start of the pandemic sorry, and it kind of it grew and it grew and it was started out as a bit of a side project like you mentioned for my for my family and we then started to take it more seriously. We’re getting quite quite good clients on board and all of our clients like these companies in early these were all coming inbound to us, so we weren’t going out saying, hey, do you wanna work For us, they’re all coming through our website, which is nothing fancy, but they would say, hey, this looks great. We really need this sort of thing, so that was kind of proof for us that there was there was some real demand there and and then had a bit of a choice Really. do we, do we just keep this as a bit of a side project and I say we because at this point there was there was two of us, so I started Myles and after a few months, a friend who I actually met at uni in York called Mike McCready joined, so he’s been there since kind of after four months of me starting it as well since the very early days. Yeah, we had a choice. We thought we can carry on like this in on the side or we could actually go off this try and try and make it work and try and raise some investment and really really grow this thing. And I thought there’s a few different scenarios really. The first is I mean I never try it. Another scenario is I try it and it goes horribly wrong, in which case I’d probably learn a tonne of stuff and then can try again with something else or try and find something else. And the other one is try it and it goes right. And I think the only one that I’d massively regret is if I if I never scratched the itch and never tried it. And that’s what kind of got me in the right mindset was, even if I tried it and it went horribly wrong I would still learn tonne of stuff and not regret trying it. So that was that was what convinced me to say, OK, let’s hand the notice in and then really really go at it and see what happens. 

Kate 

So what kind of personal strengths or qualities would you say you need to have to have to be successful and happy as an entrepreneur? Because that risk, like the way you describe, that it’s actually very logical reasoning. But for many of us that would feel like a huge massive risk, so this sort of the not trying it in it not working out is like Oh well I’ve lost my really good graduate job, we’re in the middle of a pandemic, I might not be able to find another graduate job, will it look weird or my CV, will I feel like a failure, you know? This, uh, for some people there’d be a lot of kind of barriers to actually going for it. So what would you say? What kind of skills or personality do you need to have if you if you are going to actually enjoy this type of work? 

Toby 

Yeah, it’s I think you need to be happy with ambiguity, and that’s something that I’m still still learning on. If you’re at any kind of grad scheme or structured job, there’s a fair, here’s a structure to it, there’s some kind of structure there’s, there’s someone else to go to you to ask for answers. And there’s a bit more routine there. You know what your role is and something that I’m still getting used to is the amount of ambiguity. And so in order to do well I think you need to be not not good at handling all the ambiguity, but happy to handle it and learn how to handle that and work through that like there’s so many different things that that you could go after during the startup. I think learning to prioritise tasks is something that I’m learning and I’m getting better at. I think that’s another skill also, handling ambiguity and as a subset of that being able to to prioritise tasks and really make those calls. And what else? I think you use the word successful, but when you look at lots of stats out there, you could startup values. On average, you’ll learn less as as startup founder then you will as a like a normal salary job and this sort of thing, but I think you have to. You have to want to do it for the mission not just for the money really like do something that really, really aligns with you. This, like for me, was fantastic, so I’m fascinated by technology, so my background in tech and sports and also psychology. I’m no psychologist or sports psychologist but I’m fascinated by where those three worlds intersect, that bit in the middle of the Venn diagram really excites me. So doing something that aligns with you if you’re doing it to chase some money I think in a startup you’ll quickly burnout in my opinion, if you don’t actually align with what you’re going after. 

Kate 

That’s interesting, so the work feels very much authentic to you, it’s something that you genuinely believe in and I think as a careers consultant, I see a lot of students and graduates who that is something they really want from a job, so it’s not just about, oh, I want to earn X amount of money, they want to do something they find meaning in in some way, so that’s sounds amazing that you kind of get to do this thing that really aligns with what you’re interested in. What’s the worst aspect of being self-employed then is it that ambiguity or is there anything else that’s kind of like this is the thing that I put up with because the other stuff is so good. 

Toby 

Probably trying to explain to people like your grandparents why you quit your fantastic job to go and try this thing and earn no money for it, that’s it. That’s always a hard one. 

Kate 

So it’s not you justifying the risk to yourself, it’s you, you’re prepared to take that, but it’s kind of justifying that to other people. 

Toby 

Yeah, a little bit. I gotta say about that with tongue in cheek but it’s and it is hard as well like it’s. You almost are questioning things in your head and it’s, you need to enjoy doing it because it’s it’s not something you can just switch off from almost it’s not just going in that nine to five and then it’s it’s really easy to turn your brain off and it’s it’s not easy in in most jobs anyway. it’s really hard, it’s even harder when you are the kind of the founder of the business and you’re trying to drive it forwards. So that’s that’s one of the hard things like being able to to fully switch off. I don’t think in a startup you’re ever able to fully switch off, which is, yeah, one of the hard things. But also if you enjoy doing it, it’s it’s one of the pros because it keeps you. It keeps you going and it keeps you excited. 

Kate 

Yeah I guess it’s just a very different model of work, isn’t it? There isn’t that those same clear boundaries between your personal life and your work life. 

Toby 

That’s it, definitely. And it’s lots of, it’s a very dangerous, dangerous area, right when you think about burnout. If you look at all the pandemic burnout because those boundaries were blurred too much and but if you enjoy doing it and then that allows you almost to be OK, I’m totally at home and I’m also the same Toby when I’m working on Myles and it it’s kind of almost less mentally straining if you are fully behind it. And on that mission, but it’s very it’s very dangerous, very very dangerous. 

Kate 

Just thinking ahead to the future, then what do you think the key challenges will be for tech startups over the next few years for any sort of students or recent grads who are thinking about this and thinking they might want to get into it. Is there anything that they sort of should have a heads up about? Or perhaps research a bit more or start to anticipate? 

Toby 

I think there’s a lot more people doing startups now like myself, so that’s a challenge in itself, the kind of startup market is more saturated, but at the same time there’s lots more problems to be solved out there, so it’s by no means there’s is going to be a massive challenge, but that’s one of them. But again, flipped as positive that more people doing startups the more normal it becomes the more support there is, the more guidance there is and all this sort of stuff there, so it’s almost a benefit. And another challenge, I think not just startups but around other industries too is talent. How do you, how do you attract and hire the right kind of people? And especially if you’re a startup if you’re fully remote, which I think a lot of startups are going now. It’s you need to have 100% trust in that team in their attitude to the work, their abilities, their skills. And when there are more startups for them to choose from, how do you stand out in order to get people to join you really, how do you get people on board your mission. But I think there is a, there is a big shift with employees globally that more more people want to work for an employer that they’re aligned with from the mission. Whether that’s because they really care about fitness or education, or because that employer is carbon neutral or something there which I think has a massive benefit for startups, because normally startup through an a mission. And they have quite a clear mission, whereas sometimes a big corporate, they’re on a mission but if you have less impact as individual because there’s it’s such a big a big corporate. So I think there’s a benefit there that could attract more people to startups. So yeah, a con that is there, it’s hard to find talent, but it’s also a benefit that maybe that’ll make it easier for startups. 

Kate 

Yeah, that’s really interesting, I haven’t thought about it in that way before because ideally you do want to grow the business and ideally you want to then take on people to help you do that, and as you say, it’s quite a different thing a if you’re young and you maybe haven’t had a lot of work related experience and employed people before, and you know how to select candidates and stuff. But b if, as you say, you’re doing that fully remote it must take some leaps of faith, but yeah, that’s interesting as well as you say, to sort of, you’re competing with other graduate recruiters, but could potentially offer something much more attractive and interesting, and particularly with the remote working if that sort of does appeal to a lot of people. I’ve just wondered if you got any other bits of advice for students thinking about setting up their own company. Is there any kind of work experience that would give them an insight into whether they might enjoy or appreciate it? You did work experience with an actual graduate company, so that helped you understand that sector bit more work. What would you suggest students do if they’re thinking they might want to go down this path? 

Toby 

Yeah, I think the first thing is the kind of the misconception of, you can, you can do it all alone. I definitely couldn’t have done this without going to the grand scheme first and doing all this stuff. It’s definitely. It’s definitely possible. But you still need some kind of support network, so a bit of advice to start with I guess if you asked uni, I know York have a fantastic enterprise department, so get in touch with Chris and the people the Enterprise Department is definitely worth it because it’s not a path taken by the majority, and so if you can can speak to people that are already doing it, that’s so valuable. Just set up set up calls. Most people that work in startups are more than happy to talk about what they do because they’re genuinely excited by it. So if you can get in touch with most started people you say, hey, I’m thinking about starting this thing. I’ve no idea if it’s going to be for me. Like I’d love to hear about your journey for the past few years, you get a really high yes rate to a quick zoom call. And if you’re thinking about kind of joining a startup rather than an like starting one maybe there’s loads of roles there. There’s different startups job boards available to you. Just search startup jobs. There’s job boards specifically for startups. And from an experience point, I think startups want someone who is happy to learn, is curious and happy to grow, and I think most of them value that over, oh I’ve had all this experience doing this or whatever just for the sake of experience. The experience complements that nicely. But you can, you can teach skills. You can’t teach someone not to be, or teach someone to be proactive and curious so it doesn’t really matter where, doesn’t matter as much I should say, where your experience it, but just get really curious about something. Go and learn something, whether that’s a really a niche sport or an instrument or some work experience that’s something which you genuinely love. I think startups, you just need to learn to get curious about things I guess. 

Kate 

That’s really useful, especially this sort of searching specifically for startup jobs to sort of learn you know from someone else who’s perhaps already done a startup. Is that the place that you would identify people to contact then as well, to have these chats about, oh, how did you do it and that kind of thing is, is there something through that startups jobs website where they can network? Or do you just identify brands and then look them up, the people up on LinkedIn? How would you go about doing that? 

Toby 

Yeah, I’d definitely use linkedin, use linkedin as your friend to find these people connect with them, kind of interact with them in a bit and you can always just ping your message and you’ll be surprised how it’ll be a breath of fresh air for them, for it not to be a sales pitch coming through on LinkedIn. So I definitely ping them and say, hey, I love what you’re doing and I’m a student thinking about founding a startup. Do you have 15 minutes for a zoom chat? I think the pandemic has really helped all those just quick coffee zoom chats that were a bit, they were still happening before, but it wasn’t as common to hop on a zoom call with someone for 15 minutes. Now everyone knows how they all work, knows the format, it’s way easier just to kind of have a 15 minute chat and I’m sure that if if they respond to you and they want to chat like they’ll enjoy it just as much as you enjoy chatting to them, so there’s lots of people out there that are willing to help, and have a trawl on LinkedIn have a look what they’re doing and just yeah, have some chats and learn some stuff. 

Kate 

Wow, that’s brilliant. Well for more information about the careers we’ve mentioned today and the resources that we talked about, I’m going to add some relevant links to the episode description and a link to the full transcript of today’s show, but Toby thank you so much for that that was really interesting to hear about your experiences and all your advice like thank you. I’m sure a lot of students and graduates will find that really, really helpful. 

Toby 

Thank you so much for having me. I really hope they do and if anyone wants to chat about startups or anything in between like you can definitely find me on LinkedIn and I’m one of those people who’s more than up for a zoom chat at any point with anyone, so yeah definitely.