Even by the standards of WorldTour racing, Dennis van Winden’s career has seen a lot of highs and lows. Starting out on the legendary Rabobank development team as a teenager, he landed a spot on the WorldTour team and was starting to distinguish himself as a promising new talent when a catastrophic health incident changed his trajectory. He returned to Rabobank (then LottoNL–Jumbo) through 2016, but eventually stepped away from road racing and began focusing on the U.S. gravel scene. Now, he coaches a long roster of American talents through Orange Seal Academy, including Cole Paton and World Cup rider Savilia Blunk.  Payson sat down with Dennis in Girona this week to talk about his 13 years in the pro peloton and his transition into coaching. Dennis discusses the mistakes he made as an overly-disciplined young racer, the surgery he had in his early 20s that was meant to improve his cycling career but nearly ended it, and how his “Dutch directness” ultimately led to his current role at Orange Seal Academy. He also reflects candidly on what it was like to enter road racing on the tail-end of the doping era, and how he’s coaching young cyclists to approach their training in exactly the opposite way that he did. Instagram: @theadventurestache YouTube: Payson McElveen