He’s stood his ground against Gov. Gavin Newsom (D-CA) on the homelessness crisis, advocated tough-on-crime measures that have ticked off members of his own party, and instituted what is believed to be one of the first performance models that ties pay raises for senior staff and council members to measurable results.

In a wide-ranging interview with the Washington Examiner from his 18th-floor office in downtown San Jose, Mahan broke down his plans for the city, including its goals, obstacles, and successes. Some of his proposals have been slam dunks, while others, such as arresting unsheltered homeless people if they refuse help three times in 18 months and remain on the streets, have been met with criticism. Mahan has refused to back down, maintaining that making difficult decisions is necessary to steer San Jose in the right direction.

“I think government is the way we solve complicated societal problems at scale,” Mahan said. “But, that requires you to actually, if you want to be a problem solver, be willing to set aside ideology and party and partisanship and all of this very narrow parochial thinking and actually be willing to look at data from first principles and experiment.”

Mahan, who was part of two Silicon Valley startups, said it’s a view not widely embraced in the government.

“Typically, we punish people for making mistakes. If one city, though, is going to figure out how to be more experimental and iterative, it’s going to be San Jose here in Silicon Valley,” he said. “It’s a startup culture. I don’t mind taking a lot of hits publicly in the press and from other elected officials and from what I consider to be essentially a political establishment in California.” 

Depending on who you ask, Mahan is seen as either a hard-working, no-nonsense mayor who is acutely aware and tackling the city’s problems head-on or the devil. 

Arresting the homeless

David Dickens, a homeless man who lives in a broken-down RV with a blue tarp over it in Columbus Park, views Mahan as the devil. 

“I hate that guy,” he told the Washington Examiner.

Dickens is one of approximately 50 people who call the park home and think Mahan’s solutions for the city are out of touch. 

“The mayor’s like [President Donald] Trump,” Dickens said. “He don’t get the struggle. He’s a rich white guy trying to arrest everyone out here.”

Mahan, a Democrat, has ruffled more than a few feathers for saying homeless people should be arrested if they are living on the streets and have refused shelter three times. It’s a rare approach for an elected official in a liberal Bay Area city, but one that has gained support. 

“Mayor Mahan’s governance style and approach adopts a more independent streak from the status quo in California politics,” Jeff Le, managing principal at 100 Mile Strategies and former deputy Cabinet secretary to former Democratic Gov. Jerry Brown, told the Washington Examiner.

Rising rates of homelessness in Silicon Valley, one of the wealthiest areas in the nation, have frustrated residents and left them open to proposals that would have once seemed too right-leaning in the dark blue metropolis. 

Years ago, the approximately 200 homeless residents of Columbus Park would park their RVs and trailers on the streets, fields, and basketball courts. They slowly turned a community area into a public safety hazard. The Federal Aviation Administration threatened to withhold millions of dollars in funding if the encampment wasn’t cleared because it sits under the flight path of San Jose Mineta International Airport. The city cleared it in 2022, but since then, many have returned. 

Not only is the park an eyesore, but when the Washington Examiner visited it earlier this month, there were sounds and sights of human misery everywhere. There was feces on the sidewalks, open-air drug use, and people walking around like zombies. There was a man riding a toddler’s big wheel with a 40-ounce malt liquor bottle in one hand, and a woman wearing just a torn T-shirt was cursing up a storm.

Dickens, who is originally from Los Angeles, admitted “no one should live like this” but added, “Where we gunna go?”

Mahan has insisted he’s not trying to punish people for being homeless. He wants to enforce trespassing laws when interim housing has been repeatedly offered and refused by someone living on the streets. 

Not another tech bro

Mahan was born in San Francisco and raised by working-class parents. His mother was a Catholic school teacher, and his father was a letter carrier. His parents, whom he described as “young and poor at the time,” eventually moved to the small farming town of Watsonville. 

His interest in politics was piqued at an early age when he saw the challenges of crime, unemployment, and poor education in his hometown. When it was time for high school, Mahan was offered a full work-study scholarship for low-income students at Bellarmine College Prep in San Jose. He had a four-hour daily commute, joined the wrestling team, and worked on the grounds crew in the summers to help pay for his education. 

Mahan was accepted to Harvard University, where he was an honors student and president of the student body. After graduating, he spent a year in Bolivia building irrigation systems for farmers. He eventually returned to San Jose to teach English and history to middle school children. 

Mahan then joined Causes, a startup and early Facebook app. He worked his way up from director of business development to CEO. Causes, which allowed people to raise awareness and funds for nonprofit organizations, grew to 190 million users in more than 150 countries. He also co-founded Brigade, the world’s first voter network platform that allowed people to discuss matters and advocate their elected officials. 

Since then, Mahan has been on a government kick. He has served on neighborhood and civic boards and ran for City Council in 2020, focusing his campaign on improving the quality of life by holding City Hall accountable. He cleared his calendar and spent nine months on the campaign trail, knocking on more than 10,000 doors.

Learning curve

When Mahan stepped into the new world of local politics, he was “flabbergasted” and “incredibly disillusioned” by how little was getting done. 

“My first six months on Council were pretty miserable,” he said. “I felt lonely, and I just felt like, ‘Am I having an impact?’”

Mahan said the disconnect was the most striking. 

“There is plenty of wealth here,” he said. “We should have the resources to make meaningful progress. But then I get to City Hall, and people are literally giving 20-minute speeches on the dais. Political speeches. They don’t even offer solutions. They’re often demonizing people and coming up with these random boogeymen like it’s the fault of tech or developers or it’s the media.”

It was then that Mahan found himself at a crossroads. 

“I thought, there’s two options here. I can either double down and try to fundamentally change this system and make us far more focused and accountable and really push through, or I can wrap up this term and go back to the public sector,” he said.

Mahan decided to stay and run for mayor. He won his first term in 2022 with 51.3% of the vote after residents pushed to move the mayoral election to align with the presidential one to increase voter turnout. Two years later, Mahan won a four-year term, securing 87% of the vote. 

Needling Newsom

Since he was elected, Mahan has needled Newsom multiple times. It began when Mahan threw his support behind Proposition 36, a ballot measure that strengthened penalties for people who have repeatedly been convicted of shoplifting or caught using and dealing hard drugs such as fentanyl. Newsom, an early front-runner for the 2028 Democratic presidential nomination, did not support Proposition 36.

Instead of falling in line with other mayors to support the governor, Mahan spoke out, calling the state’s response to addiction, mental illness, and repeat low-level criminal activity “fairly lax and almost avoidant.”  

SAN FRANCISCO MAYOR TO REMOVE REQUIREMENTS FOR HOMELESS SHELTERS IN EVERY DISTRICT

Mahan is currently tangled in an escalating war of words with Santa Clara County officials over homelessness and has refused to back down. During his time in office, Mahan has also whittled down a list of San Jose’s 41 “priorities” to four: homeless, crime, blight, and housing affordability. 

“It will take a revolution of common sense to make sure our government is working as hard as we do,” he said.