Friedenbach says one of the officers was angry with her, suspecting she put Makayln up to it, but she explained it was her son's idea.
"The other police officer was actually really embarrassed by it and felt bad about the whole situation, and could see from a 10-year-old's perspective how wrong it was. This boy clearly had nowhere to go and was homeless."
Friedenbach says her two sons have learned to "just treat people as people," and have joined her on weekend demonstrations, like one that was recently organized to protest a crackdown on homeless people sleeping at BART stations.
"You know, from a kid's perspective, they don't understand why," says Friedenbach. "They see someone who's homeless and they're like, 'Mom, why don't you talk to them and give them a house?' "
"That’s a perspective," she adds, "that is shared by all children unless there’s some reason for them to have fear."
Friedenbach is a familiar face at City Hall, where she has been on the front lines of policy battles over homelessness for nearly two decades. The problem, she says, has actually gotten worse in some ways.
"We've accomplished a lot but as we're fighting and get all these accomplishments, we end up losing ground," says Friedenbach, pointing to the current housing crisis that has displaced many San Franciscans.
Despite programs aimed at reducing homelessness, San Francisco's homeless population has remained steady over the past decade. Last year's count put the number of homeless people at 6,436, with an additional 914 in a supplemental youth count. However, according to the San Francisco Unified School District, 2,357 public school students are homeless.
"When you talk about who's homeless [to public school kids] they say, 'My uncle, me.' They talk about this stuff," says Friedenbach. "Whereas if I'm doing a speaking engagement somewhere else and I ask that question, people will say, 'Drug addicts, mentally ill people.' "
Makayln, who attends the Harvey Milk Civil Rights Academy, says he likes to engage his classmates about homelessness. He's very proud of the work his mom does, and Friedenbach is proud of him.
"It’s a very different perspective and I think it’s really beautiful," says Friedenbach, which is why in her line of work she often asks herself: "What would my kids do?"