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Fred, 48 is in his favorite barber’s chair, getting a fresh fade and puffing a cigarette.
“You mess up people’s hair, you get your ass whipped!” he chuckles, sitting under a knockoff Louis Vuitton hair cutting cape.
Desmond Cannady, standing behind him holding a trimmer in one hand and a brush in the other, agrees. For a long time, he only cut his own hair — the idea of touching anybody else’s was daunting. “I was nervous to fuck somebody up. It took me a minute.”
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Fred and Desmond aren’t in a salon. They’re on the sidewalk outside the Kelly Cullen Community building on Leavenworth Street, a popular gathering area for Tenderloin residents during the day that on most days hosts an outdoor barbershop. Beneath the cape, Fred sits on a wooden diner chair. Others nearby chat or doze on overturned milk crates, wheelchairs, or the steps into the building, when they’re not gated off to prevent loitering.
Clumps of Fred’s hair fall to the ground and mix with loose trash scattered on the sidewalk.
Cannady, 24, grew up in Stockton helping around a barbershop where his uncles worked, but picked up cutting hair on his own when he was 12 or 13, after his parents stopped paying for his weekly haircuts.
“My parents, they wanted me to learn how to hustle,” he said. “So I’m like, you know what? Let me just learn how to cut hair. I asked my grandma that Christmas for some clippers.”
Cannady started doing his own hair and, as he got better, people started asking him to do theirs. It became his side hustle during high school in San Jose, but he remembers being a “bad kid” — stealing clothes at the mall and going to juvenile hall for robbery.
Desmond Cannady cuts his customer Fred’s hair on Oct. 28, 2025. Photo by Eleni Balakrishnan.
It wasn’t until he was out of school that he recognized his passion for cutting hair and began pursuing it as a calling. As he got started, people would let him cut hair in their shops under the table, or he’d offer cuts out of his apartment or car. A few years ago, his family friend living in the Tenderloin recommended he start working on Leavenworth Street.
Today, he’s juggling barber college, working at a barber shop in Berkeley and, whenever he has time, swinging by the Tenderloin and cutting hair on the sidewalks for $20 a pop. Once a month, he sets up in the area and offers free haircuts to whoever needs them.
On Tuesday afternoon, Cannady, sporting a fuzzy trucker hat that says “Excuse my devilish ways,” is laser-focused for nearly an hour on Fred’s head. But beyond a solid haircut, Cannady hopes to offer wisdom and a listening ear for the people who sit in his chair.
“A lot of people have no hope out here. They feel like they can’t go nowhere or do anything with their life, feel like their life is over,” Cannady said. “I always try to preach life to people, you know what I’m saying? You never know, one conversation could really change somebody’s life.”
He remembers asking a man high on crystal meth, screaming in the middle of the street, how he was doing. Cannady sat down and had a genuine conversation with the man, asking questions he’s learned from observing therapists and other professionals who work with addiction and mental health issues.
“No one ever talked with him,” Cannady said. “Sometimes that’s all people need.”
For Cannady, cutting hair has offered him a way out when he’s needed to “refocus” his own life away from “distractions.”
Just two weeks ago he finished serving about a month in jail, got his backpack full of trimmers and supplies, and began reconnecting with his clients. It was too expensive to get his cart out of impound, so now he rides the train, the bus, and an electric scooter to show up wherever he needs to be.
On Thursday afternoon, Cannady is trimming another customer’s hair down the block by the TL Tobacco and Market, where he’s got his phone charging inside. People pause to say hello, chat, or admire his work.
“I really thank God for this,” Cannady said. “God gave me a talent and and really, before he blessed me with talent, I feel like he blessed me with my voice.”
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