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.