Matty Gregg, a 40-year-old former Apple engineer, needed a change in his life. So, he decided he would run across the country.
“A complete change,” Gregg told Runner’s World. “Beyond the running portion of this, I’m selling my condo, bought my childhood home in New Hampshire, and am running toward that. I quit my job at Apple as well.”
Gregg said he wants to run for office in 2022 in New Hampshire and hopes to get in touch with the “real America” by running 5,075 miles across the country before he does so. He is also trying to raise $1 million for Firefighter Cancer Support Network.
“It’s a great conversation starter with complete strangers,” Gregg said. “I think we can raise $1 million, and I also think our firefighters are worth it, especially in light of what’s happening now in California.”
Gregg started his run on November 6 and has planned stops almost everywhere. So far, he has been averaging about 25 miles a day and has made stops in Santa Cruz and Salinas, California. His route will take him down the coast of California to Los Angeles, over to Arizona and New Mexico, all the way to Georgia and up the East Coast. His planned end date is August 7, 2019. He will finish at the state house in Concord, New Hampshire.
“I’ve had this goal for a very long time, ever since the Terry Fox Story. That movie inspired me to start running as a kid, and running across the country I always felt would be something that would change my life,” Gregg said. “Lo and behold, it did.”
Running ultras and obstacle course races has prepared Gregg for this journey. He has participated in six World’s Toughest Mudders (which are 24-hour races), Obstacle Course Racing World Championships (OCRWC), and ultramarathons that range in distance from 50Ks to 100 milers. Last year, he won the Humanitarian of the Year Award from OCRWC.
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Gregg will have company on his journey. On November 11, he ran with two fire houses and even got a fire engine escort. “While I was really embarrassed that was happening, it was pretty awesome that they ran with me for a bit,” Gregg said.
He also has friends who are ultrarunners and are joining in. Amelia Boone—an obstacle course racer, World’s Toughest Mudder Champion, and attorney at Apple— plans to run with him through Mississippi. RaceSLO—a team responsible for sporting events in San Luis Obispo County, California—is taking on the responsibilities of Central California. Gregg said he has friends all throughout Texas and people on the East Coast as well.
“My family loves it. We’re all a little ambitious. My coworkers mostly think I'm insane. My friends love that I’m taking a different path to my life knowing that I was very comfortable at Apple,” Gregg said. “But I see real places in this world where I can make a larger impact, and I need to get out there and learn more before I can help.”
Gregg recently purchased his childhood home on his 40th birthday—the house had been off the market for 20 years. “The idea that I’m running back to it keeps me motivated every day. My father passed away when I was young, and he built that house,” Gregg said. “I’ve only spent two days in it (I haven’t slept in it yet), and I can’t tell you how excited I am to go back to it to explore.”
Before this run, Gregg spent the last 13 years working in various roles at Apple.
“I loved my 13 years there. I was there pre-iPhone and almost pre-iPod. Many of my team members there did a lap with me to see me off,” he said. “It is amazing how many things came together at the very end to make this run special.”

Jordan Smith is a freelance writer, editor, and author with 10 years of experience reporting on health and fitness news and trends. She's also an ISSA certified running coach, and is passionate about making fitness accessible to all. You can find her work in publications including Runner's World, SELF, Prose, Vital Proteins, and more. The Philadelphia-based writer has yet to meet a workout class she doesn't like and can be found exploring the robust Philly food scene, hiking with her three dogs, and chronicling her attempt at tackling her endless TBR.