Series B’s first confirmed reader from a tent on the Appalachian Trail
When you quit your San Francisco tech job to hike the 2,200 mile Appalachian Trail for six months, you have lots of newfound free time.
Often, though, you don’t have service.
“I did read a bunch of Series B stuff in my tent,” said Phillip Masters, Buffalo expat turned hiker turned repat. “Because it's interesting to me. But also because if you don't have service, Gmail will load the body of the e-mail and that’s one thing I was subscribed to.”
Masters was born and raised in Tonawanda and studied sociology at SUNY Geneseo. An interest in education and equality took him to Chicago, where he spent two years in a service corps program teaching math to high schoolers.
"It was long enough for me to realize that I didn't want to be a teacher," he said.
He pivoted, first into a brief stint at Deloitte and then into strategy consulting with an ad agency. When the pandemic sent everyone remote, Masters moved to San Francisco. He landed a gig as the second US hire for a Japanese chatbot startup, ZEALS, that later pivoted into voice AI agents for e-commerce.
But, like many, he started to feel the burnout. He was serving East Coast customers in the morning and a product team in Tokyo at night. His brother had a baby. His cousins were in Buffalo. Most of the friends who had left Buffalo were now back.
And, he had a piece of mom’s advice replaying in his ear: “Always leave the party while you're having fun.”
So, he decided he was ready to move back home. But not before an adventure while he still had the chance.
"This is probably my only chance before retirement to just bail on life for a while," he said. He was single, with no car and no mortgage. "I might as well do the big one."
He gave notice in December, left the job in January and was back in Buffalo in February. On March 1 he started walking north from Springer Mountain in Georgia for 2,200 miles to Mount Katahdin in central Maine.
He slept mostly in his tent, sometimes in a three-walled shelter, or even splurging on a motel room when really in need. His main luxury item was a Kindle, reading books to pass the time. He started a blog, Potential Credentials. He met recent college students, retirees, and backcountry savants who knew which mushrooms to eat.
"For every 60-year-old that was on the trail, there's probably 10 more that for some reason or another weren't able to make it out there," Masters said. "The fact that I could just bail on everything and go be in the woods for six months, that's extremely fortunate."
2,200 miles later, he reached Mount Katahdin in central Maine on September 6. A few days later, he was back in Buffalo, ready for his next chapter.
Today, Masters rents a desk on the 43North floor, doing fractional lead generation for a few remote clients. He spends much of his time getting reacquainted with the tech and entrepreneurial scene locally. The reception has been immediately more welcoming.
“You don’t see that in San Fran,” he said. “People are a lot more closed. They've got really cool stuff going on there, but Buffalo is a lot more my speed."
He also deeply believes in the potential of Buffalo. He sees an ascending ecosystem, with strengths in talent, and the defense and advanced manufacturing industries.
Masters envisions himself going full time at a Buffalo company in the not so distant future. But for now, some part-time gigs and the exploration of the ecosystem suits him. He’s found the time for cousin soccer games and visiting with old friends.
"What I think is great about being in Buffalo right now, besides the food and my friends, is just being able to show up in person for the people I care about," Masters said. "This is why I'm back here. The people are just that important to me."
