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.

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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.

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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.

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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.

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.

Rapha recently celebrated its 20-year anniversary and for the majority of that time it was the darling brand of cycling. Everything Rapha touched turned to gold. Founder Simon Mottram saw cycling apparel differently than anyone else and created an entirely new market for people who connected with his vision.

In 2017, RZC, the Walton brothers’ investment arm, bought a majority stake in Rapha. Things began to change, and not in a way their customers and community hoped. In 2021, Mottram stepped down as CEO and the business has gone through two (or three, depending on how you count) CEOs since. Not only have they had to deal with the lasting effects of COVID, but many customers will say that the brand is not what it used to be.

Last year, in August 2024, Fran Millar stepped into the role of CEO. She has a wide array of experience that has prepared her for this unique challenge, most recently turning around the struggling British heritage brand, Belstaff. Earlier, she was instrumental in starting and running Team Sky, organising Eliud Kipchoge’s sub-two-hour marathon project, and many other career achievements.

In this wide-ranging interview with Millar, we talk about what she intends on fixing at Rapha, how she’s going to go about that, and what her long-term vision is for the business.