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AMA: Toby Cannon, founder of Myles Challenges

AMA: Toby Cannon, founder of Myles Challenges

Table of Contents

In 2020, many of the world's largest running events couldn't go ahead due to the pandemic. But that didn't stop Toby Cannon in his tracks for long.

Toby is the Senior Associate Software Engineer at Capital One and the founder of Myles Challenges, an app that fitness fanatics can use to challenge and motivate each other.


Hi Toby, tell us a bit about your company.

At Myles Challenges, we make fitness fun by providing engaging, motivational and accessible virtual fitness challenges. Launching less than a year ago we have organically attracted tens of thousands of users in over 120 countries.

We’ve also created bespoke challenges for a range of organisations across the UK including large companies, charities and the military.

Challengers can join as an individual or part of a group and can run, cycle or walk any of our challenges. Virtual location tracking, group leaderboards, our Challenge Dashboard and JustGiving integration make it ideal for fundraising.

How did the idea for Myles Challenges come about?

In 2020, due to the pandemic, my co-founder (Michael McCreadie) and I had marathons cancelled. Not wanting months of training runs to go to waste, we wanted to create something to continue training and stay motivated.

We created an initial version of Myles before launching it for iOS and Android in July 2020.

How do you keep your team aligned?

We currently have a small team of passionate individuals, so this has never been a problem for us. We make sure to listen and make all information as transparent as possible.


Small yet mighty! What does company culture mean to you?

Our culture reflects the Myles app; fun, motivational and always celebrating progress.

Love that. Can you share any practical tips or processes to help people work remotely?

In a remote world, everything has to be deliberate. You can’t just ‘soak’ up all of that side of desk context by hanging around the coffee machine. One thing I try to do at Myles is visible, be transparent and over-communicate.

Oversharing is caring. Did you ever experience a business disappointment that led to something better?

Every sales call that doesn’t go our way leads to something better. We’re a young company growing fast and we have a number of different sales calls every week with various organisations.


For some potential customers, Myles isn’t quite right for them. This is initially disappointing, but usually, the feedback they give us is more important than the revenue we would have generated from the sale.

We’re constantly listening, learning and adapting.

Give us an interesting fact about yourself that the business community doesn’t know.

I cycled 1,000 miles from Lands End to John o’Groats in 2019. It was only right that this was the first route on Myles!

Wow! Thanks so much for your time Myles. It's been great.

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