Ando Caulfield Captures the ‘#RealSF’

By Julissa James

Ando Caulfield’s #RealSF photography project is a deeply personal endeavor into the heart of San Francisco’s homeless crisis. (Ando Caulfield)

It was 2014, and Ando Caulfield was back home in San Francisco recovering from a severe arm injury he suffered while photographing skate-board culture around the world.

One day, frustrated and unable to work, he made the two-hour trek from his house in the Richmond District to the Embarcadero with a small camera in his hand. Along the way, he met and photographed dozens of fellow San Franciscans — most of them, the ones whose portraits he found most powerful, were homeless.

He vowed to walk around the City and photograph people every day like that until his arm healed, and over a year of long nights spent roaming later, he had a photography book on his hands that he called #RealSF, which documents 100 people in San Francisco’s homeless community. Caulfield wasn’t out to profit from the project, so he only released a handful of copies for close friends and family. He didn’t think about it again until this summer, when George Floyd’s killing inspired a groundswell of fundraising efforts for vulnerable communities worldwide. It motivated Caulfield to release more copies of #RealSF and donate all sales proceeds to San Francisco organizations serving the homeless community in a tangible way.


Gazette readers know him as part of Drew Altizer’s trusty crew of gala photographers — a job he left in February to focus on other creative projects before the pandemic took hold — but Caulfield’s portfolio extends far beyond parties. Along with photographing the skateboarding scene since the early aughts, his specialty is capturing people in a moment: Method Man commanding the stage. Maya Rudolph with a mic in her hand. Jimmie Fails standing tall in the Richmond District.

The Cause.

Caulfield learned from his time making the book that, for as many programs as the City has to assist the homeless, people living on the streets still feel like hands-on help is lacking. Caulfield is quick to point out that Larkin Street Youth Services is an effective anomaly. His goal with re-releasing #RealSF is to raise money for Larkin Street, which helps homeless people on the ground.


Caulfield is moved by documenting acts of resistance. In the spring, he was one of the many photographers capturing swarms of people protesting racism and police brutality. He made prints of some of his images and sold hundreds of them, raising more than $20,000 for Black Lives Matter causes. While the subjects and struggles captured in #RealSF are different, his goal was the same: Documenting people fighting for something important, then giving back to the communities he photographed. Caulfield recognizes parallels in his projects, noting: “The prejudices that people have against homeless people are equal to racial prejudices.”

The images — at once humanizing and moving — are premised on Caulfield’s ability to build trust and connection with his subjects before the shutter snaps. (Ando Caulfield)


For #RealSF, Caulfield’s ice-breaker was to hand out socks to people on the street and smoke a cigarette with them. He’d strike up conversation and eventually form a bond, only later requesting to take their photograph. “I wouldn’t just walk up and take a photo,” he says. Caulfield spent so much time connecting with people that folks on the street actually thought he was homeless. “I was disgusted by street photographers taking photos of people where their pants are down, and they’re passed out,” he says. He decided to do it in a different way, taking portraits with consent and dignity. “[In] every single photo in the book, people are looking into the camera. I want people to know I engage with these people.”


The project sheds light on the fact that many individuals are only an injury, eviction or bad break away from a life on the street. Caulfield wants to instill that reality while celebrating the people captured on its pages: “I really just want people to see the human side of what’s happening here.”

Get involved.

Caulfield is donating proceeds to Larkin Street Youth Services. #RealSF is available at andonesia.bigcartel.com.

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