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This article first appeared in the Wall Street Journal.

Ben Horowitz, a 58-year-old as responsible as anyone for creating the modern internet, was raised a son of radical Berkeley. His grandfather’s tombstone featured a Marx quote: “Life is struggle.” His father was a famous New Left activist who published Che Guevara’s writings and helped build the Black Panthers. 

Horowitz would choose a different path, making a name for himself in a job with the word “capitalist” right in its title. (We all rebel in our own way.) As he rose in Silicon Valley, first as a dot-com era pioneer and now as one-half of a leading venture-capital firm, he left politics to the older generations. It was easy to do: Everyone in the Valley was a Democrat anyway. 

That changed this summer, when Horowitz and his business partner, Marc Andreessen, joined the growing fraternity of tech executives backing Donald Trump. President Biden, “the worst president in my lifetime on tech policy,” Horowitz said, had to go.  

The endorsement threw into cognitive dissonance what was widely known about Horowitz—a man who had written movingly about his trans son, who spent part of his fortune supporting forgotten hip-hop stars, who had a Black wife who’d grown up in Compton.  

Battle lines were drawn on Sand Hill Road. A “V.C.s for Harris” group accumulated hundreds of members who pledged to prove that “not all V.C.s have turned MAGA.” Employees groused. Acquaintances blasted him on social media. Oprah Winfrey asked mutual friends what was up with their buddy Ben. His mom was mad. 

In other words, it was Horowitz family history repeating itself. 

‘They Won’t Let You Get Away With Anything’

Forty years ago, a different controversial Republican was running for re-election, and a different Horowitz alienated the community he’d known when he announced his shocking support. That was David Horowitz, Ben’s father, who in 1985 went from being a hero of the New Left to a conservative flamethrower after he declared himself a “Leftie for Reagan” in a 4,000-word essay published in the Washington Post.

The endorsement shook the political world and would come to symbolize a generation’s disillusionment with the 1960s. Ben Horowitz, who enrolled at Columbia just ahead of his father’s declaration, watched as his dad’s friends accused him of treason, calling him a crypto-fascist and steadily abandoning their friendship.

Horowitz’s own political pivot, born out of concern over the Biden administration’s tech policies, lacked his father’s ideological fireworks.

He and Andreessen announced their support for Trump in July in their in-house podcast. Trump, they said, was the better choice on their primary concern: the “little tech agenda.” That included the growth of cryptocurrency and the need to develop artificial intelligence so that the new technology isn’t dominated by China.

It was not a screed against wokeness or based on vibes. It was almost certainly the first political endorsement in history to include a primer on “floating-point operations per second” as a measure of computing capability. Family ties have complicated Ben Horowitz’s life since Vice President Kamala Harris replaced Biden at the top of the Democratic ticket. Harris has known Horowitz for years; she and his wife, Felicia Horowitz, had been members of Glide Memorial Church in San Francisco around the same time. Felicia agrees with her husband’s view on Biden’s tech policy and had been stewing over other Democratic policies herself, but she wanted to support her friend Kamala, too.

Doctrinaire liberals today, she said in a recent interview, reminded her of the religion she grew up practicing, and “saying anything bad about the Democrats is like urinating on a painting of Jesus for them.”

“I must say that this whole experience with Ben getting into politics has proven me right,” she added.

Horowitz donated $2.5 million to “Right for America,” a PAC supporting Trump, as a disclosure statement revealed this week. Earlier this month, Horowitz sent a note to staff saying that the couple, who still believe that Trump has the better tech policy, would also be contributing a “significant” amount to groups supporting the Harris campaign. It’s not clear yet how much he has given to Harris. 

The shifts in Horowitz’s political support over just three months neatly encapsulate the position of an industry caught between the halcyon days of 2008 (“Facebook got Obama elected!”) and the present moment, when significant elements in both parties are critical of Big Tech. To the surprise of many who know him and even to himself, Horowitz has followed in his father’s footsteps, once again turning the family name into shorthand for a broader political realignment shaping the nation.  

He recalled recently an observation that the neoconservative Norman Podhoretz had shared with his father after his ideological turn in the 1980s: “When you were on the left, you got away with everything. Now that you’re on the right, you’d better be careful, because they won’t let you get away with anything.” 

For years, Horowitz challenged his father on the point. After the past several months, he’s not so sure. 

“The fact that he was right about that really scares me,” he said.

In Silicon Valley, few things can change an entrepreneur’s life more than the right email from Ben Horowitz. As part of the Andreessen Horowitz venture-capital firm, he has bet on startups that have transformed the web, from Twitter to Airbnb to Stripe. Fifteen years after opening with a $300 million capitalization, the firm now has more than $43 billion in committed capital.  

Horowitz, bald and a bit reserved, fits the mold of the modern tech leader: part coder, part guru. Andreessen has been the more recognizable of the two since he was proclaimed by Time magazine at 24 years old to be one of the dot-com era’s “Golden Geeks.”  

While Andreessen is prone to Delphic pronouncements (“software is eating the world”), Horowitz is the one to whom entrepreneurs gravitate for advice on organizational structure or personnel decisions. He pairs business-casual sweaters with a thin gold chain around his neck, and his office in Menlo Park combines the sleek comfort of a California C-suite, in varying shades of beige and tan, with a Nas poster on the wall. His books on business advice and startup culture feature a healthy dose of hip-hop lyrics. 

“He’s rapping songs from ‘86 word for word,” said the writer and activist Shaka Senghor, one of several friends who bonded with Horowitz over their love of the music. 

Horowitz met Senghor after hearing his story from Winfrey, who described how he had spent 19 years in prison—seven in solitary confinement—for killing a man when he was a teenager. When Horowitz told his wife of Senghor’s story, she friended him on Facebook and invited him to dinner. The two men became fast friends, and Horowitz drew lessons from Senghor for his business advice books: “Senghor had been the CEO of a prison gang,” he wrote.  

On the 10th anniversary of Senghor’s release, Horowitz treated him to a weekend of Golden State Warriors basketball, Las Vegas Raiders football and a boxing match.  

“Just two bros having a bro weekend,” said Senghor.  

Horowitz has worked in tech since receiving his master’s degree in computer science at UCLA in 1990. He helped build the pipes that would host the fun stuff, earning a fortune and a reputation for workplace credos like the Law of Crappy People, which holds that the least impressive person hired at any level becomes the standard for that level. 

After completing several Valley benchmarks as entrepreneurs—rise, fall, IPO, $1 billion-plus payout—Horowitz and Andreessen formed their venture-capital firm in 2009, meeting with startup founders from behind a foldout table in an industry still quivering from the 2008 financial crisis.

Rather than build companies, they placed bets on startups that they believed stood a chance of becoming the next “unicorn”(a privately held enterprise worth at least $1 billion). Within a few years, the Andreessen Horowitz imprimatur became the clearest sign in the Valley that what may have sounded like a harebrained idea could actually be the next Facebook, Google or Oracle.  

Radicalized by Biden 

Few in Silicon Valley were of the generation or the milieu to know that Ben’s father was David Horowitz, the author of “The 101 Most Dangerous Academics in America,” a fan of Steve Bannon and an intellectual influence on members of the Trump administration. When David spoke on college campuses, his son paid for a bodyguard. 

David Horowitz has spent much of the past four years publishing booklets like “Beijing Biden,” which alleges that the president is in the thrall of the Chinese Communist Party. Ben had little enthusiasm for Trump or Biden in 2020—he wrote in Kanye West’s name on his ballot—but he did not expect the current administration to radicalize him. 

In his view, the Biden administration has targeted crypto and entangled tech startups in red tape and litigation. Regulation of cryptocurrency has a direct impact on the bottom line of Andreessen Horowitz, which has raised more than $7.6 billion to invest in crypto companies. The firm’s investments stand to gain if the government eases its scrutiny.

Trump has embraced crypto as a campaign issue, speaking at conferences for its enthusiasts and touting his own “TrumpCoin.” Horowitz fears that Biden’s agencies have thrown such obstacles in front of crypto entrepreneurs that would-be founders are opting to start their companies in other countries, or not at all.  

Andreessen Horowitz has also raised billions of dollars to invest in AI tech firms. Horowitz believes that the Biden administration is hamstringing the sector by setting thresholds for AI computing power and calling for a “pause” on development—an idea supported by many lawmakers and even some in the tech industry.  

As Horowitz and others like to point out, China isn’t stepping back from the new technology to take a breath, and the future of geopolitical influence may depend on who takes the lead in this new arms race. “The country that’s dominant in technology, or winning in technology,” he said, “is very likely to be winning in culture, winning militarily, winning economically.”

The Tiger Woods of Communism 

Horowitz came of age in a family where the idea of America winning was the problem, not the solution.  

His grandfather, Phil Horowitz, was an English teacher and aspiring writer who embraced Communism in the 1920s and traveled to the U.S.S.R. in 1932. Phil’s activism once took him to Palo Alto, where he organized teachers against a loyalty oath movement that demanded they pledge allegiance to the U.S. Constitution. He told his wife he found the area had “the usual repellance that all swanky places have.” The couple raised their family in New York, where “The Little Lenin Library” was kept on a shelf hidden away in the basement.  

David Horowitz went into the family business, reared from an early age to be, in his son’s words, the “Tiger Woods of Communism.” As a young radical in the Bay Area, David coedited Ramparts, a New Left magazine founded in 1962 out of an office space in Menlo Park. One iconic cover of the magazine showed four Vietnam draft cards held aloft in flames. 

Ramparts published glamorizing pieces on the Black Panthers, and David Horowitz grew close to the group’s leaders. He raised money for the Panthers and helped establish its community center in Oakland while raising his own young family. He also recommended that the Panthers hire a bookkeeper at Ramparts named Betty Van Patter. 

“It was a time when the apocalypse struggling to be born seemed to need only the slightest assist from the radical midwife,” Horowitz would later write. Every concern was refracted through the Vietnam War: “Fantasizing the death of local cops seemed warranted by the role they played as an occupying army in America’s black ghettos, those mini-Vietnams we yearned to see explode in domestic wars of liberation.” 

But in late 1974, Van Patter went missing, and then her body was found in the bay. The murder has never been solved, but Horowitz believed the Panthers were behind it.  

“Everything I had believed in and worked for, every effort to ally myself with what was virtuous and right, had ultimately led to my involvement with the Panthers, and the invitation to Betty to take the job that killed her,” he wrote in his 1997 memoir “Radical Son.”   

While Ben Horowitz was a teenager obsessed with hip-hop in the 1980s, his father was growing disenchanted with radical politics. His former comrades refused to accept what he saw as their complicity in the fall of Saigon and the horrors that followed. Those on the left, in his view, were so reflexively critical of America that they did not see the ongoing threat of Communism and the danger it posed to the United States. By 1984, Horowitz and other like-minded refugees from the New Left found themselves doing the impossible: voting to re-elect Ronald Reagan.

David Horowitz had become a full-blown culture warrior by the time his son opened Andreessen Horowitz on Sand Hill Road in Menlo Park, three miles from where Ramparts magazine had started.  

‘I Could Not Hail a Cab Before Uber’ 

Just before Ben Horowitz helped to start building the early internet, he met Felicia Wiley on a blind date in L.A. He was a student with a day job, and Felicia recalled, “I was cool dating a very nice person who loved rap music and bartended for a living. We had a very simple life.” 

The two married in 1989 and made a decidedly modern California pair. Felicia Horowitz was a former Miss Congeniality in the Sugar Ray Robinson Youth Contest, the daughter of an oil pipeline worker who had grown up in some of L.A.’s roughest neighborhoods. The family had moved to California after her grandfather was murdered in Texas—rumor had it, by the Ku Klux Klan.  

When Felicia’s parents met David Horowitz for the first time, the in-laws were delighted to find they had something in common: They all thought their kids were too liberal.  

Felicia, whose family still lives in “the ‘hood,” as she put it, has a different perspective on the tech ecosystem her husband works in. She sees its liberating potential, especially for people with a background like hers.  

“I could not hail a cab before Uber. Crypto/blockchain doesn’t look at your race when issuing loans,” she wrote. “When I was a kid, we had very few books in the house, but I have access to every book on my iPhone.”     

As their fortune grew, the Horowitzes became a familiar sight at fundraising galas for organizations like Glide, which helps homeless people priced out of San Francisco by the city’s new wealthy class. 

For years, Felicia volunteered at a church in San Francisco feeding meals to the homeless. Then a new pastor came in whose approach seemed further evidence of “how race has burrowed into a religion that I love,” she said. One day, she and the new pastor, who was also Black, walked out of the church as he spoke of white privilege. 

Felicia pointed to a homeless white man nearby, she remembered. “What privilege does he have that you don’t?” she asked. 

“He won’t get arbitrarily pulled over by the police,” the pastor responded. 

“He doesn’t even have a car,” said Felicia.  

Growing up in California, she said she had seen racism and crime decline. Today she holds the state’s Democratic lawmakers responsible for reversing that progress.  

“The new policies—defund the police, don’t prosecute crime—are destroying the communities where I grew up. If you want to genocide black people, the California policies are a great blueprint,” she said.  

Her 88-year-old mother lives in a home with bars on its windows and doors, she said, “a prisoner of these horrible policies.”  

In 2021, Horowitz and his family moved to Las Vegas. Felicia has tried to move her mother out, too, but she wants to stay close to her church. 

Ben and Felicia’s son Jules is pursuing the state’s other trademark career: entertainment. He’s a stand-up comedian who leans on his family’s unorthodox background for jokes. During a recent set at Flappers Comedy Club in Burbank, he told the audience that his skin tone can confuse people. 

“I am Black and Jewish,” he said, gesturing toward his face, “which, somehow, equals Mexican.” In Florida, people think he’s Cuban. “In New York, I’m Puerto Rican,” he said. “And in Texas, I’m deported.” 

Not a Contest Over ‘Proximity to Blackness’ 

At a divisive moment in America, the Horowitzes have maintained an unusual constellation of friends. This summer, about a week before Horowitz released his Trump podcast, Ivanka Trump and her daughter stopped by their home in Las Vegas, where they took in a David Copperfield show and an Adele concert with Felicia.  

Also joining the festivities was the Horowitzes’ close friend Alice Marie Johnson, a 69-year-old criminal justice reform advocate who received a life sentence for a cocaine trafficking conviction in 1996. Her case was taken up by several supporters, including Kim Kardashian, who successfully urged President Trump to commute Johnson’s sentence in 2018. She met Felicia soon after.  

Johnson and Trump’s daughter both had birthdays during the Vegas trip, so Ben arranged cake for the whole group. Johnson calls Ben and Felicia her “brother” and “sister,” and they’re so close that they plan to spend Christmas together this year. 

But she hadn’t known about Ben’s plan to go public with his endorsement of Trump. A few months after the Ivanka Trump visit, Johnson was back at the Horowitz house, this time for a discussion on tech policy with members of the Congressional Black Caucus. It went on for so long, she said, that Felicia had to stand at the door with the guests’ coats so they would leave. 

After announcing his support of Trump, Horowitz saw his marriage and his friendship with people like Johnson come under scrutiny. Shaka Senghor was visiting with Oprah Winfrey at a bookstore opening in Montecito, Calif., when she asked him why their mutual friend was backing Trump.  

Senghor recalls telling Winfrey that he wanted to put friendship above politics. He’d been irritated by the assumptions people had drawn about Horowitz based on relationships he had with people like Senghor.  

“He’s not trying to win some identity contest because of his proximity to Blackness,” he said. 

Felicia, for her part, said, “It’s deeply offensive to me to infer my political beliefs based on my race.” She added, “To not be seen as a person but as a puppet to their agenda feels exceptionally hurtful and racist to me. It’s ironic, isn’t it?”  

Ben Horowitz is entering the political maelstrom just as his father has retreated from it. At a recent luncheon thrown by the David Horowitz Freedom Center, the organization’s namesake, now 85, was invoked like a phantom godfather. Unable to attend, he passed along his gratitude that the group of die-hard Trump supporters was gathering in liberal Los Angeles.  

The Freedom Center distributes literature on “Islamist political machines” and hosts a “Restoration Weekend” in Naples, Fla., with former lawmakers and Fox News commentators. The Los Angeles luncheon was held the day after the Harris-Trump debate, in which the former president gave a rambling performance that included false accusations that Haitian immigrants in Ohio were eating pets. 

“Don’t worry, cat’s not on the menu,” a Freedom Center organizer joked to the crowd before salads were served.  

Several hundred miles north, Ben Horowitz was making the business case for a candidate whom this room followed with a religious fervor, father and son embodying the strange bedfellows that Trump has somehow brought under one political tent.  

Growing up with a dad who had swung so dramatically from one political orientation to the other, Horowitz said, had left him with a reluctance to wholly embrace any side. 

“I kinda grew up hearing both arguments,” he said. “Loudly.”