When Vince Masiello headed out for Portland in the summer of 2017, he had money in his pocket. He had a used Prius he’d purchased with a buyout from a tech business he’d helped start. He thought he might find work in the “Silicon Forest” of Portland.
He drove from New York City to the Idaho border and into Ontario, Ore., where he joined thousands of people to watch the solar eclipse. Then he drove straight to Portland. There, he became immersed in the homeless population and a world far from the one he’d known.
Vince was raised in a big Italian family in a poor neighborhood about 30 miles from Manhattan. He was an excellent student in high school, he said, and earned a full scholarship to The American University in Washington, D.C. There, he studied philosophy and psychology, earned a bachelor’s degree, and went right on to a master’s program.
And then he dropped out.
“I looked around me, and I was so disheartened. I was going into this master’s program, starting to take on loans. And I started talking to adjunct professors, asking, ‘What’s the future like?’ And they were like, ‘Not great. You want to be an adjunct in North Dakota?’”
He spent a couple of years in Maryland developing apps and websites, but eventually Vince spiraled into depression.
“I couldn’t get out of it. I was just spinning. The real low where you ask yourself, ‘Is it worth it to be alive?’ There were a lot of questions, a lot of loneliness, because I wasn’t sure that what I was doing was right. I think the mid-20s, for men especially, are tough. You’re in this old-school belief where you’ve gotta be a man. Whether it’s subliminal or direct, the message is you get good feelings from being financially successful.
“I just realized I had to move, had to get away from everything.”
He dropped his first name, Robert (also his dad’s name), and began to go by his middle name, Vince. And he made a clean break.
From there, a combination of unforeseen circumstances – and some intention, as well – led to homelessness.
He had a room in a house for a few months, but he was never there. He found himself out every day, exploring Portland, “feeling the vibes,” sleeping in his car because it was more comfortable. Then, on a road trip to visit his dad in Texas, the battery in his Prius died. Repair costs were out of his reach. So he bought a bus ticket back to Portland. His bags were stolen at the bus station.
“In a way, I wanted to commit to a new path,” he said. “What I really wanted, I wanted to go down to nothing.”
Vince is inspired by his position to help.
“I can go to these meetings, pitch an idea. I’ve already got my ticket for the Doers and Contributors conference here in Portland April 24. They all want to hear from somebody who’s homeless. But they don’t expect Italian, and they don’t expect New York City. I can ‘yell logic.’
“It’s like Socrates; he called himself the gadfly for the state. When a gadfly bites you, it’s a jolt. It’s not going to topple the system. But to be a constant reminder that community and family are just as important on the streets as they are to people with money, with resources, with a day job,” he said.
“And I have my Spider-Man initiative. If I’m on my bike at night and I see someone just screaming or just yelling ‘why?’ I try to help. I come up peacefully. I usually flash my Street Roots badge. Maybe they just want someone to talk to. Maybe I pick a flower and say, ‘Hey, I found this for you.’”
Sometimes he can trigger the wrong memory, he said, “but most of the time, at least I can get them to move from the spot they’re in.”
Vince said he appreciates Street Roots as a way make money and as a social network.
“It’s a place where people can come in the morning; they’re talking about this interaction with sweepers, that interaction the night before,” he said. “They’re talking about life. You need that. You need to vent so you’re not talking about it at midnight at the Willamette River.”
Vince sells Street Roots near Sisters of the Road Café on the corner of Northwest Sixth Avenue and Davis Street.