Overnight Success

Industry Special Part 2, Episode 1: The False Dawn

In our last Industry Special series, we asked how the bike industry got itself into such deep trouble. What we found was a supply chain riddled with problems, a leadership culture built on false optimism, and an industry that mistook a pandemic bump for a permanent new normal. They called it the bike gold rush. Sadly it came to an abrupt end. Since that time, businesses have gone bankrupt. Shops have closed. Thousands of employees have been laid off. So the question has changed. We know how the industry got into trouble. Now we're asking something harder: why can't it get out?Over the past few months, my colleague Suvi Loponen and I have spoken to leaders and employees across the industry to find out if this is something far more systemic than COVID ever was.The following 4 episodes after this one will be exclusive for our members. If you want become a member, go to www.escapecollective.com/overnightsuccess to sign up for a limited time offer.

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Checking in with Rapha's Fran Millar: 18 months in, the hard part is just beginning

2w ago00:59:56Tap to summarize

In January 2025, I sat down with Rapha's newly appointed CEO, Fran Millar, after she'd been in the job for about three months. Founder and previous CEO Simon Mottram stepped away from the business in 2021 and hired William Kim as his successor. Kim was brought in as an outsider with impressive experience in luxury fashion and retail – Burberry, Gucci, Abercrombie & Fitch. Unfortunately he lasted less than a year, and after Kim stepped away in 2022, Rapha internally promoted François Convercey and Daniel Blumire as co-CEOs. Blumire left the business shortly after, and the sole leadership position was left to Convercey until Fran Millar was appointed in August 2024.In that period of multiple leadership changes, Rapha faced increased competition, a pandemic, and what many would say was a loss of focus while trying to expand and appeal to a larger market – all while being newly owned by the Walton Brothers' investment fund RZC.It's been roughly a year and a half since I first spoke with Fran about her vision for Rapha's future. In this interview, we check in on what she's been able to do, what's been more challenging than she anticipated, and where her focus lays now.

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Building Rose Bikes

Mar 2800:58:08Tap to summarize

In this episode we take a deep dive into Rose Bikes - a 120 year old bicycle brand that many of you may not have heard of, and that's about to change. Rose Bikes is a German company that sells direct to consumer, similar to Canyon. Founded in 1907 as a small family workshop, it evolved into one of Europe’s early adopters of the D2C model. Thank you to my colleague Suvi Loponen for doing this interview. You'll be hearing more from Suvi on this channel much more in the future, so stay tuned! If you like this podcast and want to hear more, please support our work by becoming a member: https://escapecollective.com/join/

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Building Cannondale

Mar 901:30:15Tap to summarize

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/

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Uplift - The Woman Lifting Women in the Bike Industry

Mar 400:44:30Tap to summarize

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 uplift@shiftactivemedia.com.If you like this podcast and want to hear more, please support our work by becoming a member: https://escapecollective.com/join/

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The remarkable life of Phil Liggett (replay)

Jan 2800:56:33Tap to summarize

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.

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Building Team AMANI

Dec 1001:34:51Tap to summarize

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.

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Building Gravel Burn

Nov 3001:10:15Tap to summarize

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.

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The life and story of cycling photographer, Graham Watson (replay)

Nov 1801:45:42Tap to summarize

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.

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Building TrainingPeaks

Aug 2001:45:58Tap to summarize

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

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All episodes

Industry Special Part 2, Episode 1: The False Dawn

Checking in with Rapha's Fran Millar: 18 months in, the hard part is just beginning

Building Rose Bikes

Building Cannondale

Uplift - The Woman Lifting Women in the Bike Industry

The remarkable life of Phil Liggett (replay)

Building Team AMANI

Building Gravel Burn

The life and story of cycling photographer, Graham Watson (replay)

Building TrainingPeaks