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Fortune
Fortune
Paolo Confino

A post about Kamala Harris pushed a long-simmering feud between tech execs into the open

Venture capitalist David Sacks speaking at a podium

A dispute born out of Silicon Valley’s growing political divide became personal on Thursday when conservative venture capitalist David Sacks, well-known startup guru Paul Graham, and Rippling CEO Parker Conrad traded barbs on X

The back-and-forth started when Sacks, who was a longtime executive and venture capitalist before becoming known for his outspoken support of former President Donald Trump, posted on X that he disagreed with the Democratic party’s decision to back Vice President Kamala Harris after President Joe Biden announced he wouldn’t seek reelection. Sacks wrote in a post that during the storming of the Capitol on Jan. 6, 2021, Biden was in “no danger of being deposed” but was “actually deposed,” when he stepped down as the party’s presumptive nominee this Sunday, calling the move a "coup."

The mention of a coup prompted Conrad to reply. “Let me tell you, coups are this man’s speciality,” Conrad posted, recalling the acrimonious falling out the men had nearly a decade ago while at a software startup.

The background to the brief sparring session is the two worked together at Zenefits, a startup founded by Conrad where he was CEO. Sacks was an investor in the company and served as COO. In 2016, Conrad and Zenefits encountered compliance issues that ultimately resulted in an SEC settlement and his departure from the company. 

While the argument on X this week quickly turned personal, with Sacks and Conrad reliving their years-old feud, it started because of a post that’s emblematic of an industrywide rift that is distinctly contemporary. The November election between Trump and Harris has divided Silicon Valley in ways previous elections haven’t. A growing contingent of high-profile industry leaders—Sacks, Elon Musk, and venture capitalist pairing Marc Andreesen and Ben Horowitz— have thrown their support behind Trump. That, in and of itself, is a surprising development for the tech industry, which is centered in the traditionally liberal Bay Area and has historically backed Democrats. Harris, a Bay Area politician herself, is familiar to many tech executives, whom she has both regulated and courted for donations. 

Sacks did not respond to a request for comment from Fortune. Conrad, through a spokesperson for his current company, Rippling, declined to comment for this article. 

Zenefits was an HR software company that also acted as a health insurance brokerage firm. However, the company ran into trouble when Buzzfeed alleged that Conrad wrote a computer script that made it appear as though some brokers had completed a legally required training course when they hadn’t. Ultimately, in 2017 the SEC settled with Zenefits and Conrad for a combined $1 million for “materially false and misleading statements and omissions.” (Conrad and the company neither admitted nor denied wrongdoing as part of the settlement.)  

On X, Sacks brushed off Conrad’s mention of their shared history. “You were sanctioned by the SEC,” Sacks wrote on X with a screenshot of Conrad’s reply. “Nobody else, only you. But you’ve spent the last decade trying to shift the blame onto others for your own poor ethics.”

That’s when Paul Graham chimed in on X to offer his two cents. (Graham, a veteran tech investor, is best known for starting the wildly successful startup incubator Y Combinator.) 

“Do you really want the full story of what you did to Parker to be told publicly?” Graham replied to Sacks. “Because it's the worst case of an investor maltreating a founder that I've ever heard, and I've heard practically all of them.” Graham did not respond to a request for comment from Fortune.

While at Y Combinator, Graham funded hundreds of startups, as spots in the incubator became increasingly competitive and coveted. Over his career he’s worked with the likes of Airbnb founder Brian Chesky, Dropbox founders Drew Houston and Arash Ferdowsi, and the Collison brothers, who founded Stripe

Sacks dismissed Graham, saying the two had never met or worked together, and accused Conrad of “publicly fuming and smearing me.” Others leapt to Conrad’s defense, with former journalist and tech watcher Eric Newcomer accusing Sacks of unfairly blaming Conrad for company problems.

Conrad maintains he was unfairly forced out of the company he started. In a 2022 interview, Conrad said that, after he agreed to step down from Zenefits to be replaced by Sacks, the duo, in conjunction with the board, drafted a “friendly” press release announcing his departure. Conrad said he was blindsided when, a few hours after he signed the paperwork to resign, Sacks issued a press release blaming him for Zenefits’ problems. 

On Thursday, Sacks seemed ready to move on from the issue. “Personally I think it’s a huge waste of time to still be talking about this a decade later,” he wrote on X.

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