Overnight Success

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.

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/

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.

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 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

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.

The Pro's Closet represents a quintessential modern startup journey, evolving from a professional mountain biker's eBay side hustle into America's largest certified pre-owned bicycle marketplace. The company's trajectory mirrors both the opportunities and challenges of the pandemic era, riding high on $90 million in funding before facing the harsh realities of market volatility.The Pro's Closet experienced a meteoric rise during the pandemic cycling boom. However, the company soon encountered the perfect storm of challenges that defined the era: cheap capital driving unsustainable growth, miscalculating the cycling boom's longevity, and the whiplash effect that rattled the entire bike industry.

Welcome to this special episode where we dive deep into one of cycling's oldest, most fascinating, and perhaps largely unknown stories - how a single French family, best known as their business entity the Amaury Sporting Organisation or ASO, came to control the Tour de France, the world's most famous bicycle race. Because, if you recall, they didn’t invent the TdF. A little french newspaper called L’Auto did. Today we're exploring this remarkable story detailed in Alex Duff's book "Le Fric" (which is slang in french for The Money) and we’ll be speaking with Alex himself about this incredible saga of family, power, and money. Alex is a UK born sports journalist and author of 3 books who has spent much of his career covering the intersection of business, money, and sports. To understand the ASO and the grip they have on the crown jewel of professional cycling, you need to understand the history of the Tour de France and how the Amaury family acquired it. History, national pride, politics and legacy mean so much more than money to this family, and is why the Tour de France will likely never have a price tag put on it.

You could argue that Bonnie Tu is the most powerful woman in cycling, although she wouldn’t think of describing herself that way. She’s best known for being the face of the Liv brand she created back in 2008, but more than that she’s chairperson of the largest bike brand in the world: the Giant Bicycle Group. What does that mean? Quite simply, she runs the entire company.Giant Bicycles is a US$2.1 billion-per-annum publicly traded company that produces millions of bikes per year, while also serving as manufacturer for some of the largest and most reputable bike brands.Giant was founded in 1972. That’s 48 years ago, and Bonnie was one of the founding shareholders. As you’ll hear, she has been very influential in many of the company’s foundations and its pathway up until now.This is the growth story of Bonnie Tu and not necessarily the story of Giant Bicycles or Liv. But they’re so intertwined that it’s hard not to tell one without the other.

Indoor training has been around for longer than I can remember, but when Zwift came along in 2014 it changed the market forever. The company came into the world with bold ambitions, reimagined the space and what it could become, and has grown the market to a size that nobody could have imagined.Some of the earliest pioneers in the indoor virtual world space were the likes of Computrainer and Tacx back in the late 90s, early 2000s. But they never really delivered on the promise of making indoor training much more enjoyable. They can’t be blamed for lack of vision or not trying – the technology wasn’t even there at the time. Social networks didn’t exist, multi player online games weren’t around, broadband speeds were slow and wireless protocols such as ANT+ and BTLE hadn’t been invented yet. But, in 2010 when a gaming software developer in Southern California named Jon Mayfield began tinkering with his kinetic trainer and finding ways for it to communicate with a virtual world he built, he had no idea how big this would become.Escape Collective is entirely member-funded. If you like this podcast please consider supporting us by becoming a member: https://escapecollective.com/member/

Many would argue that Cervélo is one of the most innovative bike brands in the cycling industry. Back in the 1990s when they first started, almost everyone else was focusing on lightweight bikes. Cervélo, meanwhile, was busy pioneering bicycle aerodynamics. I’ve ask engineers at various bike companies which brand impresses them most with regards to engineering and innovation, and overwhelmingly I hear them say Cervélo.The genesis of Cervélo started in 1995 when two young engineering students named Phil White and Gerard Vroomen met in the composites lab at McGill University in Canada. Over a span of 15 years they went from building a crazy aerodynamic time trial bike as a university project to creating one of the most disruptive and loved bike brands in the world. But what many people don’t know is that as wildly successful Cervélo was up until 2011, it was a pressure cooker of constant financial challenges which ultimately led to Gerard and Phil selling the business to Dutch holding company, PON. 2008-2011 had been the perfect storm for Cervélo with the global financial crisis, setting up a professional team that was far more successful than anticipated, and a private lender which led to the company’s turn of events.Escape Collective is entirely member-funded. If you like this podcast please consider supporting us by becoming a member: https://escapecollective.com/member/

It’s been said that Kona is 'The Smallest Biggest Bike Company in the World'. They’re best known as the quintessential North Shore bike brand, yet their global head office is just down over the border in Ferndale, Washington.The quirky company stood out with outrageous bike model names such as the Stinky Dee-Lux, Sex One, Sex Too, and, Jackshit, which placed them well and truly as the "alternative" bicycle company.The business was founded by Dan Gerhard, Jacob Heilbron in Vancouver, BC along with mtb hall of famer Joe Murray as their designer.With a rich history of iconic bikes and factory race teams, it was all overshadowed by the recent events of their former owners, Kent Outdoors, who were responsible for running Kona into the ground (my words, not theirs) before the original founders bought the company back last month. Only a few weeks after Dan and Jake bought the company back, I spoke to Jake about Kona’s founding story that dates back to 36yrs ago in 1988, the sale of the business to a private equity-backed company, and what happened that led them to buying Kona back. If you like this podcast and want to hear more, please support our work by becoming a member: https://escapecollective.com/member/