In this episode we speak to Graham Watson, perhaps the world's most prolific cycling photographer. Over five decades, Graham didn't just witness cycling history - he documented it. Some might say the pioneers had it easy, but as you'll hear, Graham's path was anything but. He made his own luck, opening doors through persistence and talent. And whoever said "nice guys finish last" never met Graham.

Today's episode runs longer than usual because there's no way to do justice to Graham's remarkable 40-year career in an hour. Buckle up for a ride with the man who captured cycling's most historic moments.

In 1999, Joe Friel was drowning in faxes. The legendary cycling coach, later author of The Cyclist’s Training Bible, had 72 clients sending training data every Monday. His desk was buried under paper. His son Dirk, then racing in Belgium, figured there had to be a better way.

Over beers at The George in Vail, Dirk convinced his best man—and the only web developer he knew—Gear Fisher, to build a solution. Dirk paid him $3,000. That handshake deal became TrainingPeaks, now the go-to platform for endurance athletes, from amateurs to Tour de France winners.

If you’ve worked with a coach or followed a structured plan, you’ve likely used TrainingPeaks. What stood out to me while researching this story is that TrainingPeaks wasn’t built primarily for athletes. Their real customers are coaches. That focus, counterintuitive at the time, turned a simple web tool into a 300-person company that now stretches beyond endurance sports into areas like virtual cycling and even music education software.

This story is personal for me. Friel’s Cyclist’s Training Bible changed my life three decades ago. Back then, I’d wait by my inbox for his UltraFit newsletter, one of the few reliable training resources for everyday cyclists.

In this episode, you’ll hear the founding story of TrainingPeaks directly from Joe and Dirk Friel, along with co-founder Gear Fisher, who ran the company for 20 years. It’s about solving your own problem, knowing your real customer, and how three guys with no business plan built a cornerstone of modern endurance sports.

If you enjoyed this and want to hear more, please become a member of Escape Collective by joining here: https://escapecollective.com/join

Charlie Stewart, Rupert Hartley, and Jack Howker started the British apparel brand Albion nearly a decade ago. It began not in a boardroom, but in the wild weather of Wales.

I first met founders Charlie and Rupert by chance on the roads of Mallorca, before they’d launched a single product. Years later, Albion has grown into a respected name in the ultra-distance and adventure cycling scene. This episode traces their journey from pre-dawn London rides to post-work email threads, through the hurdles of product development and the pivotal hires, like legendary designer Graeme Raeburn, that helped transform them from three friends with an idea into a serious brand.

It’s a story about staying small when everything tells you to scale fast. About designing for three seasons in a day. And about why authenticity, patience, and humility still matter in building a business—especially one worth believing in.