Matthew “Matty” Gregg ’00 was six years old when he first dreamed of being a transcontinental runner. The idea was sparked after he watched a biopic on Terry Fox, a Canadian amputee, who ran coast to coast in 1980 to raise money and awareness for cancer research.
Gregg let the idea simmer until Nov. 6, 2018, when, at the age of 40, he set out from Cupertino, California, on a nine-month, 5,425-mile epic adventure. His journey crossed 24 states, ending in Concord, New Hampshire, and included unexpected twists such as being mistaken for a highway bomber by Louisiana police, running through snowstorms and heatwaves, and adopting a stray kitten that followed him through a desolate town in Georgia.
Gregg was a manager and engineer at Apple for 13 years, leading the Apple Pay global team and developing internal and external training tools that are still in use at Apple retail stores. He decided to plot his run — and give his 18-month notice — in 2017 after surgery to repair a neck injury. “If I didn’t do it soon, I wouldn’t be healthy enough to do it at all,” he says, explaining that years of undertaking ultramarathons (50-mile and 100-mile races) and ultra-distance obstacle course racing had taken their toll.