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Post: : Match.com founder Gary Kremen has pivoted to local politics, and lit a fire in Silicon Valley assessor’s race

The man who fought a notorious decade-long legal battle for the rights to the Sex.com domain is engaged in a new fight that is becoming just as offbeat: The right to decide how much the Apple Inc. campus is worth.

Former tech executive Gary Kremen has waged an aggressive campaign for assessor of Santa Clara County — at the heart of California’s Silicon Valley — and is questioning the technical qualifications of long-time incumbent Larry Stone, who, in turn, has accused the founder of Match.com of “hijacking” his personal email list of 1,300 contacts.

“He [Stone] lives in a horse-and-buggy world vs. cars; mainframe computers vs. PCs; Sears vs. Amazon,” Kremen said. “He hasn’t adapted to the digital economy, and that hurts homeowners and renters.” To drive home his point, one of Kremen’s campaign tag lines is, “Getting us out of the Stone age.”

“People don’t understand why he [Kremen] is running. He has no qualifications for this job at all. It’s kind of humorous,” Stone, who has been county assessor for 27 years and is seeking his eighth term, told MarketWatch. “He seems to look at this job as a stepping stone, perhaps to become California governor.”

It gets weirder.

Stone is ready to play hardball to make his point. He is letting the electorate know about Kremen’s colorful background as the onetime owner of the domain Sex.com, who engaged in a decade-long battle for its rights with notorious internet businessman Stephen Michael Cohen. “This guy was engaged in pornography, and voters frown about that,” Stone said. Kremen brushes off Stone’s assertion as classic hit-piece politics for a business chapter in his career that occurred some two decades ago.

Just another slice of Silicon Valley life.

The unlikely race is happening because Kremen — a trained engineer who received an MBA from nearby Stanford University and founded online dating site Match.com in 1994 (he left the company two years later, and received just $50,000 after the site was later sold) — has in recent years pivoted to public service. To that end, he has invested in various projects for residential solar financing, brought credit to the underbanked, and helped oversee mentorship programs. Along the way, he has served on the Purissima (Calif.) Hills Water District, and was elected to the Santa Clara Valley Water District board of directors in 2014.

In the months leading to the June 7 election, both candidates have established battle lines that illustrate the decades-long divide between the high-tech industry and local politicians — a gap that extends to the current national debate over antitrust legislation to rein in Big Tech. Neither side seems to understand, or respect, one another.

“Why can’t more tech people give back?” Kremen told MarketWatch. “I started at the bottom, the absolute lowest level, in a town’s [Los Altos Hills, Calif.] landscaping committee, then moved on to the local water district there… People in tech are spending money but doing nothing on the local level.”

Quixotic journeys are nothing new for Kremen; in fact, it’s familiar ground. For the better part of a decade, he engaged in an odyssey over Sex.com. In the early years of the World Wide Web, Kremen registered a number of available domain names, Sex.com among them. In 1998, Kremen sued Stephen Michael Cohen for allegedly stealing the rights to Sex.com, accusing him of cheating Kremen out of millions of dollars in e-commerce sales. Thus began a series of suits and countersuits that read like a Jackie Collins potboiler. Kremen eventually won a $65 million judgement, but did not a collect a penny from Cohen, who has served multiple stints in jail and is now operating an online drug company.

Cohen, who has maintained a low profile for years, could not be reached for comment.

Stone, who as mayor and a city councilmember in Sunnyvale, Calif., in the 1970s and ’80s helped mold the town into a Silicon Valley hot spot, is gobsmacked by Kremen’s candidacy.

One of the assessors office’s functions is to estimate county property values, which jumped almost 5% to a record $577 billion last year. “I highly doubt [Kremen] can assess the value of the Apple

spaceship or Levi’s Stadium,” home of the San Francisco 49ers, said Stone, who has more than 50 years of real-estate experience. “These are complicated decisions. I am stunned by how little he knows about the job.”

The animus runs deep, leading Stone to accuse Kremen of “hacking” his personal email list of some 1,300 friends, family, business associates and elected officials. Kremen said a county official whom he declined to name shared Stone’s list with him after Stone copied it in an email. “He [Stone] doesn’t understand the difference between CC and BCC,” Kremen said, laughing.

Kremen later chortled at the accusation he is angling for a run at California governor. “That is laughable!” he said. “I never thought of it. So funny.”

“I hope to think of this as a story of technology giving back,” Kremen said. “That is my only intent.”

Kremen, who maintains Stone is a luddite hopelessly behind the times in technology use, calls the opposition research “salacious shit” and why most people — particularly tech executives — stay away from public service.

“People in tech are spending money but nothing more, doing nothing, with the exception of [venture capitalist] Peter Thiel,” said Kremen, in reference to the co-founder PayPal Holdings Inc.

and Palantir Technologies Inc.

who recently stepped down from the board of Facebook owner Meta Platforms Inc.

to campaign on behalf of conservative candidates during the 2022 midterm elections. “How many are doing anything at the local level? Very few.”

Tech executives have a star-crossed track record running for public office in California. In 2010, former eBay Inc.

Chief Executive Meg Whitman lost the gubernatorial race to Democrat Jerry Brown despite spending $140 million of her fortune, while then-Hewlett-Packard Co.

CEO Carly Fiorina, came up short against then-U.S. Sen. Barbara Boxer. (Whitman was nominated by President Joe Biden to serve as U.S. ambassador to Kenya in December 2021.)

A decades-long schism on full display

The hardball tactics pitting Kremen against Stone vividly crystallizes the decades-long friction between Silicon Valley and local government. Where tech executives flout their expertise as a means to bring antiquated systems into the digital age, long-serving public officials scoff at the arrogance of overhauling complex government systems so easily.

“We see this dynamic play out in areas of government in California: Someone with a little technical know-how vows to make sweeping changes,” Garrick Percival, chair of the political science department at San Jose State University, told MarketWatch. “The problem is that government processes don’t present easy solutions. These are built in for a reason. Change isn’t so easy.”

While Kremen has expressed a desire to apply his engineering skills to improve efficiencies at the assessor’s office, Stone contends the Santa Clara Valley Water District has the “reputation of being the most mismanaged government agency in the county” — an accusation Kremen dismissively laughs off.

As much as anything, Stone is trying to make Kremen the focus of the race. Internal polling, based on an online survey of 2,400 people, shows a “very negative reaction” to Kremen, according to Stone. County assessor is “just the wrong job for him,” Stone said. “He should run for the board of supervisors, which is political. He is portraying me as being here too long. That is an asset, not a liability. You want experience and integrity for this job.”

Still, campaign-finance documents show Stone has spent around $275,000 on his campaign vs. $170,000 for Kremen. Stone has received about $55,000 in donations, compared with $71,000 for Kremen. Each has produced a long list of endorsements.

For Kremen, who dueled with Cohen for years in court and in the press, the back-and-forth is all just par for the course.

Indeed, it is Kremen’s eclectic — some might argue, perplexing — career path that make him a compelling, if not divisive, character.

“The thing about Gary that makes him so interesting is he is someone who iterates — with varying degrees of success. For people, it can be bewildering for him to go into seemingly disparate areas,” said David Kushner, author of “The Players Ball: A Genius, a Con Man, and the Secret History of the Internet’s Rise,” which chronicled Kremen’s fight with Cohen over the Sex.com domain.

“He sees around corners, and has the guts to place bets on himself,” Kushner told MarketWatch. As an engineer, Kremen has a hacker mindset in how systems work, and coming up with solutions, he added.

“Gary owns who he is; he always has,” Kushner said.

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