Building Cannondale

In this episode, we are going deep inside the founding story of Cannondale, which has arguably been one of the most innovative bike companies in the world to this day.The founder who is the main character in this story is Joe Montgomery. But he wasn’t a hardcore cyclist as you might expect. He was an entrepreneur who liked building things, hired his customer, and figuring it out as he went. Sadly, Joe passed away peacefully on January 2, 2026. Telling Cannondale's origin story in this episode is Joe's son, Scott Montgomery. Scott lived and breathed Cannondale for most of his career, is synonymous with leadership of his father, and is more than able to do the story justice. If you like this podcast and want to hear more, please support our work by becoming a member: https://escapecollective.com/join/

This episode's guest is Rachel Burnside, who is the creator and force behind Uplift, a mentoring and networking program she built from scratch to support women working in the cycling industry.Uplift started simply: connect women early in their careers with senior women who'd already navigated the road ahead. But it's grown into something much bigger - a global community with over a thousand women in the bike industry, and  live events at Sea Otter, Eurobike, the Tour de France Femmes and many other smaller ones. All of it built in Rachel's spare time, powered by goodwill, and kept free for everyone involved.We talk about how Uplift works, what she's learned across five rounds of mentoring, the role of male allies, and what it'll take to keep more women in cycling for the long haul. Find out more at www.shiftactivemedia.com/uplift/ and you can get in touch directly by emailing [email protected] you like this podcast and want to hear more, please support our work by becoming a member: https://escapecollective.com/join/

In this episode replay, I speak to Phil Liggett about how he got his start in commentating, how he met Paul Sherwen, how he’s been doing since Paul’s untimely passing, about his relationship with Lance Armstrong, and the cut-throat nature of his position at the top of his profession.Liggett is undeniably the most recognisable voice in cycling and his dulcet tones have brought the sport we all love into the mainstream through his ‘Liggetisms’, through his descriptions of châteaux, and through his partnership with co-commentator Paul Sherwen.Many enthusiasts say that Phil is long past his prime and should retire. There’s no denying that the media landscape is a very different place now than it was when Phil started commenting — before many of us were even born. But Phil has witnessed and called so many of cycling’s most significant and historic moments; moments that made us all jump out of our chairs with excitement. You have to thank Phil for being part of those memories. Personally, I bookmark my years by who won the TdF in that particular July, and Phil and Paul’s voices are part of that.Phil is now 76 years old and has been commentating since the late 70s. Think about that. His impact on the sport and his pioneering role have been tremendous. These days, while he might get some details wrong while calling a race in front of millions of people, I call tell you first-hand through many interactions with him that he’s still sharp as a tack. And as much as you don’t want to hear it, his commentary isn’t really for you or me, the hardcore cycling fans – it’s for the people who immerse themselves in the Tour de France once a year, and who still love him.From aspiring pro bike racer, to journalist, to commentating with Paul Sherwen for 33 years, Phil is now in the twilight of his career. I sat down with him to hear how he got started, and to learn about some of his struggles along the way.

Mikel Delagrange is the reluctant face of Team AMANI. While he prefers the title of 'Head Cheerleader,' he was left to carry the torch after the project's founder, Sule Kangangi, tragically died in a high-speed crash in Vermont. Now leading the mission to dismantle the barriers facing African cyclists, Mikel oversees a unique ecosystem: From building a high-altitude training center in Kenya to the Migration Gravel Race. With a moonshot goal of fielding an all-African team at the Tour de France, Team AMANI is fighting to ensure the next generation can bridge the gap to the sport's highest levels.

Last month, I traveled to the Great Karoo in South Africa for the inaugural Nedbank Gravel Burn. It is the latest brainchild of Kevin Vermaak, the man who built the legendary Cape Epic.I cannot overstate how spectacular the experience was for me. While the riding was incredibly challenging, the event's culture was the true standout. It was a rare leveling of the playing field: World Tour pros like Tom Pidcock. Ashleigh Moolman-Pasio, and Alison Jackson,  Ivan Glasenberg’s cohort of Glencore billionaires, all telling the same war stories from the road around the campfire and and dinner tables as us weekend warriors. Pretentiousness was left at the gate. For a week in the Great Karoo, we shared the same tents, the same food, and the same challenges.Typically, on this show, I wait for a business to mature for at least ten years before we profile it, afterall, an overnight success takes about a decade to buid. but given Kevin’s track record and the instant impact of this event, I’m breaking my own rule. I have no doubt Gravel Burn will quickly become a fixture on every cyclist’s bucket list.In this episode, we aren’t just talking about the ride; we’re dissecting the business model of an event like this, the critical choices made, and where it goes from here.Here is my conversation with Kevin Vermaak.If you like this show and want to support it so we can continue, please head to www.escapecollective.com/join and become a member.

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. 

Over the weekend The Service Course announced its closure. This is a re-play of the episode we previously did that talks about its origin story. We will aim to do a follow-up when the time is right.---If you follow professional cycling and are attracted to specialty coffee, beautiful custom bikes, and boutique travel, then you’ve surely come across Christian and Amber Meier’s businesses. The couple from Canada, of all places, embarked on a professional cycling career for Christian and settled in the once sleepy Catalan town of Girona. The two of them are the founders of La Fabrica, Espresso Mafia, and The Service Course which have now become Girona institutions that people actively seek out.Now, The Service Course boasts four European locations and includes some of cycling’s biggest stars as both investors and employees. Michael Woods, Kasia Niewiadoma and Edvald Boasson Hagen are all investors, and Simon Gerrans is CEO. It’s a remarkable story that isn’t even close to being finished yet, so grab a coffee, strap in, and hear where Christian and Amber’s story started so you can follow where it’s going.

In this episode of Overnight Success we hear the story of cycling commentator Matthew Keenan.