For months, I'd been planning to record this podcast with Joe Montgomery, the founder of Cannondale, alongside his son Scott Montgomery. Sadly, Joe passed away peacefully on January 2, 2026, at the age of 86 and I never got to sit down with him.
However, I was fortunate to speak with Scott for a few hours, who lived and breathed Cannondale for most of his career. He packed Bugger trailers (Cannondale's first bike product) on the factory floor as a 10 year-old. He launched Cannondale Europe from a rented office in the Netherlands at 27 with no real business plan and a CFO back in Connecticut telling him the numbers sucked. He started Cannondale Japan after befriending a Mormon missionary named Michael Jackson at a Tokyo bike show. He signed the iconic Saeco road team deal for a million dollars without telling his father. And he came back from retirement to help pull the company out of bankruptcy in 90 days.
In this conversation, Scott doesn't feed us a sanitised corporate history. Instead, he is candid about the hard years: the low margins, the layoffs, the night Joe realized that hundreds of thousands of frames in the wild were going to crack and they might have to recall them all. Their solution was to put a sticker on every bike that read:
Competitors mocked them. Even though they earned the undesirable nickname 'Crack'n'Fail', sales continued to grow. Customers wore it as a badge of honour.
Scott is upfront about how much he thinks of business as luck and timing, and how dangerous it gets when you start believing your own luck. The European expansion worked because German buyers were willing to pay 40% more than Americans for the same bike. The Saeco pro team deal worked because an Italian coffee magnate got fed up with his fellow sponsors lowballing him. And then the luck ran the other way.
Joe bet big on motocross motorcycles, trying to compete with Honda on a fraction of the budget. Cannondale burned through $100 million and pushed the company into bankruptcy in 2003. Joe lost the business he'd spent 32 years building. Scott describes it as the biggest heartbreak of his father's life.
Below, you'll find a visual timeline of Cannondale's major milestones and the full podcast with Scott embedded above. [AI design tools were used to create the timeline visuals. -Ed.]
If you care about how this iconic bike company was built and the history behind it, this one is worth your time. I hope you enjoy it.
Timeline
Cannondale began as a cycling accessory company before moving into aluminum bicycles in the early 1980s. The brand gained recognition through racing and engineering innovation before a failed motorcycle project nearly destroyed the company. It was later rebuilt under new ownership.
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