Josaiah “Cloud” Naylor has been selling Street Roots on and off for 15 years.
“It’s my favorite newspaper, of course,” Cloud said. “I recently submitted my first two poems. I was encouraged by other vendors.”
When he’s not selling newspapers, artistic pursuits occupy much of Cloud’s time. His grandmother was a puppeteer, and his mother is a painter and musician. It’s a passion that runs in his family.
“I’m a singer and dancer,” Cloud said. “I’m also a circus performer. I’ve even used props to be theatrical when I’m selling newspapers.”
Cloud has lived in Portland for more than 30 years and has been homeless since he was 15. He cites the long-term community that comes with selling papers as a highlight of his life.
“I run into people I’ve met in the past,” Cloud said. “Being out there in the open helps me meet friends and acquaintances I’ve lost touch.”
A longtime resident of Southeast Portland, Cloud sells Street Roots outside Powell’s Books on Southeast Hawthorne Boulevard.
“It’s my go-to spot,” Cloud said. “I love it, of course, or I’d go somewhere else. The vast majority of my time on and off the street has been in that neighborhood.”
Although Cloud has used his performance skills in the past to sell newspapers, he has other approaches to engaging with the community as well, like meditating in public.
Spirituality and wellness are important values for Cloud. One of his proudest achievements is becoming a certified yoga instructor. He is also a self-taught masseuse.
“I’ve never worked in a studio, but I’ve made a little money teaching privately,” Cloud said. “That’s been very rewarding.”
Cloud, who frequently visits churches throughout the city, enjoys customer interactions, but he also treasures relationships with fellow vendors.
“The camaraderie is mutually beneficial,” Cloud said. “The ability to reach the community on a very special plane is a huge factor in how I can continue to do something that doesn’t earn a lot of money but pays me with other energies.”
Cloud is also employed part-time with a moving company and said he finds the work fulfilling.
“It’s an intimate experience seeing all these different walks of life,” Cloud said. “I’m going to keep doing this for as long as I can because the rewards I get are worth so much more than money.”
Family is an important part of Cloud’s life. He’s proud of his two children, who recently graduated from the same high school where he was unable to finish decades earlier. Cloud has siblings living throughout Oregon, and he said his mom lives in her van, traveling around and visiting each of them.
Cloud said he’s also lost a lot of friends in the past year, along with his father. This has motivated him to be more responsive to his own health. He said he doesn’t think about the future too much and prefers to live in the present. This helps him to practice love for others.
“Any time you can help somebody, do it,” Cloud said. “I do it every day. Don’t be afraid to be an enabler. That word is supposed to be a positive thing.”
Cloud is normally outside Powell's on Southeast Hawthorne Boulevard. You can support Cloud through the @StreetRoots Venmo by entering his name and badge number (852) in the payment notes.
Street Roots is an award-winning weekly investigative publication covering economic, environmental and social inequity. The newspaper is sold in Portland, Oregon, by people experiencing homelessness and/or extreme poverty as means of earning an income with dignity. Street Roots newspaper operates independently of Street Roots advocacy and is a part of the Street Roots organization. Learn more about Street Roots. Support your community newspaper by making a one-time or recurring gift today.
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