.The Watsonville Roots of San Jose Mayoral Candidate Matt Mahan

On the surface, San Jose mayoral candidate Matt Mahan’s image coincides with the trappings of wealth and influence. He went to elite schools—San Jose’s Bellarmine College Preparatory and Harvard University—and has ties to technology industry luminaries like Mark Zuckerberg and Sean Parker, as well as the support of San Jose Mayor, Sam Liccardo. His political adversaries have tried to frame him as a Republican out of step with progressive San Jose.

His origins, however, don’t suggest a silver spoon upbringing or conservative roots. 

The mayoral candidate grew up on the outskirts of Watsonville, just off Amesti Road near Pinto Lake, in the 1980s and ’90s. His mother taught at a Catholic school in Salinas, and his father was a letter carrier in Pebble Beach.

“I remember waking up at the crack of dawn, and farm workers were already out there working,” Mahan says. “That always left an impression on me.”

Mahan, a first-term San Jose City Councilmember elected in 2020, is facing off against Cindy Chavez, a longtime Santa Clara County politician who has previously served on the San Jose City Council and as the city’s vice-mayor, as well as a county supervisor, a position she has held since 2013.

Mahan’s campaign released a poll this week showing that while Chavez enjoys much higher name recognition and a 1-point lead among likely voters, 25% of the electorate is still undecided and shares Mahan’s view that San Jose is not headed in the right direction.

“You can see that in terms of sprawling homeless encampments, concerns about public safety, blight and trash, lack of affordability, high cost of living particularly due to housing—the list goes on and on,” Mahan told me in the leadup to the June primary, saying that San Jose politicians’ “culture of complacency” is the biggest issue the state’s tech hub faces.

Even though he’s declared himself a pro-choice Democrat, mailers by the labor-aligned independent PACs suggested he might not be a reliable ally on reproductive rights. Mahan called the accusation a “distraction” to draw attention away from the political establishment’s failed policies on homelessness and public safety. 

Mahan, who held prominent roles in tech startups before delving into politics, has been cast as the political outsider heading into November. It’s a role that he’s very much accustomed to.

South County Kid

“What I love about Watsonville is that it has that small-town feel where everybody knows everybody, and it has incredible access to nature,” Mahan says. “Where we lived on the outskirts of the town, we had access to a creek on the hillside and I spent much of my childhood outside. I have a great love for nature.”

Despite the beauty of the surrounding area, life in Watsonville had its challenges.

“It is a small town, with a strong sense of community, primarily agriculture—people work hard. It has that small-town culture,” he says. “On the other hand, it struggled quite a bit. We had a high unemployment rate, high crime rate, a lot of gang activity and a lot of violence. It ended up being that two people in my neighborhood were drug dealers.”

Mahan stops to reaffirm his fondness for Watsonville. His mom still lives there, and he regularly visits; as a teenager, however, he felt some growing pains.

“When you turn 13 or 14, you start to wonder about your place in the world, and it felt kinda restraining at the time,” he says. “I don’t mean anything negative—it is just the nature of a small agricultural town.”

His parents encouraged Mahan to take the entrance exam to Bellarmine College Prep, an all-boys Jesuit school that most South County natives will know as Watsonville High School’s bitter rival in soccer.

“I will never forget, my dad took me over and we got lost in East San Jose and barely made it in time for the test,” he says. “I was late, and everyone had already gotten started. I remember walking in and sitting down. They were all San Jose residents and knew each other. I was one kid from Watsonville that came in late to take the test.”

After a grueling examination, Mahan was accepted into Bellarmine, but faced the realization that the entrance exam was just the first test. The next hurdle was figuring out how his family could afford the private-school tuition. Luckily, the answer came in the form of a 200-hour work-study scholarship in which he spent the summers before each school year working with the maintenance crews watering plants, landscaping and joking with the permanent crew members.

“When I showed up on day one, the only people I knew were the grounds crew,” he says.

Now able to attend Bellarmine without worrying about tuition, he still faced a four-hour round trip bus ride on Highway 17 each day of the school week.

“My dad would get me up in the dark at 4:45 in the morning and I would be so tired he would pick me up off the bed and put me on the cold floor just to wake me up,” he says.

Despite being a self-described awkward kid—and, for all purposes, an outsider—Mahan found himself not only welcomed at Bellarmine, but also able to attain a leadership position as the student body president. The position was not always about shaking hands and being a pep leader. Sometimes it was talking about uncomfortable topics or standing up for others.

“Being in an all-boys Catholic high school at that time, talking about homophobia wasn’t the most comfortable thing, but it was important to me. Two of my best friends there were not fully accepted by many of my classmates,” says Mahan.

He used the platform to disclaim bigotry through speeches in front of classmates and faculty, and in a column for the school newspaper.

“That was where I became interested in social justice,” he says. “I ended up getting involved in student government. I pushed the campus to move away from sweatshop labor for its apparel.”

Crafting His Future

Mahan says that on most mornings, the first thing he would see when waking up from the cold floor his father placed him on was a photo of Georgetown University.

“I had a picture of Georgetown on the ceiling, because my dream for years was to get into a great university,” he says. “Because I wanted greater opportunities. I didn’t want to live paycheck to paycheck like my parents did.”

But after visiting both Georgetown and Harvard while on a trip to the East Coast with a friend visiting family, he “fell in love with Cambridge and Harvard.” 

“It is a place driven by ideas and people interested in thinking about what’s right, should be, and what the future is like,” he says. “I saw a lot of my core views challenged in a really productive way. I kinda see myself as a centrist or a moderate who tries to take what is most true of the progressive and conservative traditions in our country—because Harvard and my interactions with fellow students and professors made me realize that no ideology has a monopoly on the truth.”

Harvard at this time turned out to be a powder keg of innovation mixed with opportunity. Mahan succeeded in his economics program and became student body president once again. While later graduating magna cum laude (and also meeting his future wife), he also rubbed some influential elbows. 

Mahan arrived at Harvard precisely at the same time as Mark Zuckerberg. 

“He and Mark [Zuckerberg] lived in the same dorm,” says longtime friend Katie O’Keefe. “I think some of the reasons he got into tech later was because he was offered the opportunity to help with the original Facebook. He turned it down because he wanted to do the class president thing. He was constantly volunteering, working on political campaigns, and then it [Facebook] took off. 

A 2005 article in the Harvard Crimson noted Mahan’s disillusionment with Harvard’s career track system. “They’ll, you know, live in a beautiful suburb where they never have to confront homelessness and poverty, and all end up in the same retirement home where they’ll play golf until they die,” he was quoted as saying about his classmates.

The article also noted his volunteer work with Democratic nominee John Kerry’s 2004 presidential campaign, and his activism with the campus’ Black Men’s Forum president to create a fund to protest Harvard’s investment in a Chinese state energy corporation linked to the Sudanese genocide.

Political Shift

Two years after graduating from Harvard, he volunteered for two weeks as an early supporter of Barack Obama’s nascent presidential campaign.

“I was in Iowa in 2007 before the caucuses and spent two weeks knocking on doors and getting people out in the snow. It was freezing cold,” he says. “I’ll never forget how cold it was.”

Mahan became a public school teacher at Joseph George Middle School on San Jose’s East Side while working for nonprofit Teach for America, and being a “card-carrying member” of the teacher’s union.

He made his shift to the tech industry in 2008 when he joined Causes, a social platform for users to share fundraisers and raise awareness for nonprofits that was co-founded by Sean Parker and Joe Green. The app aligned with what O’Keefe describes as Mahan’s “North Star” of social justice. Mahan eventually became the company’s COO and then its CEO. The experiences Mahan picked up at Causes allowed him to extend his business ventures with his old dorm mates into Brigade, a successor social advocacy platform that was later sold to Pinterest.

This incursion into tech eventually did come to an end, and Mahan turned his eyes back to his ultimate goal: becoming mayor of San Jose. 

“I always thought it would be the best job in the world. I am more into action and getting things done. You get to champion initiatives and push the bureaucracy to deliver results. I like the idea of trying to organize people around solving problems,” says Mahan.

“The city [San Jose] has given me incredible opportunities. I just fell in love with it when I came here. Maybe it is a little bit of nostalgia from my youth, but I came here in the ’90s and it just felt like a city on the rise.”

Only time and the voters will tell if he will reach that North Star.

“Matt has always wanted to be mayor of San Jose. It wasn’t a stepping stone; it was specifically for San Jose,” says O’Keefe. “I think growing up in Watsonville, San Jose was the big city, and he wanted to be part of it.”