Ryan DeWald grew up in Reading, Pennsylvania, the son of a steelworker in a blue-collar town where outcomes were rarely accidental. Many of his childhood peers did not find a way forward. He did – on two wheels.
In the mid-1990s, a small bicycle shop in Lebanon, Pennsylvania – Gretna Bikes – provided critical early support under the ownership of Bill Gentile. By 1996-1997, DeWald was the single winningest junior mountain biker in the United States on NORBA (National Off-Road Bicycle Association) points. He advanced to the Trek JBL Mountain Bike Team, competing on the full NORBA circuit. Those formative years were defined by long road trips, shared hotel rooms, modest budgets, and uncompromising ambition.
In the early 2000s, DeWald earned selection to the U.S. National Team in Belgium and secured his first continental contract in 2003 – the same year he founded Skyline Bicycle in Reading, Pennsylvania. As owner since its inception, he built the shop alongside his father, establishing both a business and a foundation for international competition. Over the next decade, he competed against some of the top riders in the world across North America and Europe.
In 2013, he founded Team Skyline while continuing to compete at the elite level. In 2014, DeWald was diagnosed with Type 1 diabetes. Rather than retreat from competition, he adapted. That decision led to the founding of Winning The Race With Diabetes, a 501(c)(3) nonprofit dedicated to advocacy, education, and access to affordable insulin and medical technology.
By 2019, Team Skyline earned a UCI Continental license. At nearly 40 years old, DeWald returned to Europe to compete in UCI 1.1 events while managing a professional racing program and navigating a chronic condition that requires constant precision.
Between 2019 and 2025, he led sponsorship acquisition, financial guarantees, operational logistics, and athlete development, while also serving as a facilitator for congressional meetings in Washington, D.C., advocating for insulin affordability and medial device access.
Now entering 2026 at age 47, DeWald resides in Montreal with his wife and children. He continues to compete at the front of elite Masters racing while expanding his foundation’s reach, including plans for Canadian nonprofit development.