Who is the biggest asshole in Silicon Valley? For obvious reasons, this is a difficult question to answer. The tech industry and the venture capital business that finances it are notably riddled with sociopaths and walking personality disorders. Lately, however, denizens of both of those communities have been pointing fingers at one another, trying to suss out who is the biggest douchebag.
This unique discourse, which is weirdly existential for a group of people who spend most of their time thinking about money and software, evolved out of a long-simmering personal feud that was triggered, appropriately by a tweet. That tweet came from David Sacks, a rightwing tech billionaire and unabashed Trump supporter, who, on Tuesday, posted criticism of the Democratic Party over its decision to run Kamala Harris as President instead of Joe Biden. “This wasn’t a voluntary abdication; it was a political hit, with Nancy Pelosi as the button. That’s a coup in my book,” Sacks said, sharing his political analysis.
What followed was a blast from Sacks’ past. Parker Conrad, who, years ago, worked with Sacks at a company called Zenefits (and who lost a job at the company that eventually went to Sacks) quote-tweeted the “coup” post with a little commentary of his own.
“Let me tell you, coups are this man’s specialty,” Conrad tweeted.
Let me tell you, coups are this man’s specialty. https://t.co/qGSGorBa9B
— Parker Conrad (@parkerconrad) July 24, 2024
Outside of the tech industry, this is a bit of a deep cut. The context is this: in the mid-2010s, Conrad was the co-founder and CEO of Zenefits, an HR and payroll company. The company hit a rough spot in 2016, involving licensing violations and compliance issues. Not long afterward, Conrad resigned from the company. Sacks, who was an investor in Zenefits and worked as its COO at the time, subsequently took Conrad’s job. According to Conrad, Sacks effectively helped tarnish his reputation on the way out, spinning the media narrative to push a majority of the blame on him. In subsequent interviews, Conrad has said that “something like 70 percent of the licensing violations were actually on” the “team that reported directly to David and happened while he was running it.”
On Thursday, Sacks responded to Conrad’s tweet with his own fiery response: “You were sanctioned by the SEC. Nobody else, only you. But you’ve spent the last decade trying to shift the blame onto others for your own poor ethics.” Sacks ended the post with a clown emoji.
On the topic of “poor ethics,” however, there seem to be more than a few people in Silicon Valley that view Sacks as the paragon of them. Most notably, wealthy tech entrepreneur Paul Graham swooped in to castigate Sacks for his comments against Parker: “Do you really want the full story of what you did to Parker to be told publicly? 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 tweeted.
In a now-deleted tweet, Graham went on: “I was talking recently to another investor about whether you’re most evil person in Silicon Valley. He thought about it for a few seconds, and agreed that he couldn’t think of anyone worse.” Screenshots of this tweet have circulated widely on X.
Others joined in. Cloudflare CEO Matthew Prince, himself a billionaire and self-described “rich asshole,” chimed in to claim that Sacks stood out in a crowded field of ethically dubious corporate hacks: “I know this story. It’s very bad,” Prince tweeted, referencing Zenefits. “Don’t know if David is most evil person in SV. Lots of competition. But can say: we overlapped a year in law school and even way back then he had a reputation for being a complete asshole. And that was at @UChicagoLaw, which is full of assholes.”
George Fraser, the CEO of the data company Fivetran, seemed to agree with Graham’s interpretation: “10 years ago David Sacks participated in one of the ugliest founder-coups ever, replacing Parker Conrad as CEO of Zenefits,” Fraser tweeted. “I was close to the Zenefits team at the time, so I’m not a neutral observer, but I can describe how events were perceived at the time.”
Siri Srinivas, a partner at prominent venture capital fund Gradient Ventures, quote tweeted one of Graham’s earlier comments about Sacks, adding: “This is turning into the Netflix roast of David Sacks.” She later quipped: “I really really hate bullying and pile-ons except when it’s well-deserved.”
Ilhar Mahaniok, a managing partner at VC firm Geek Ventures, tweeted merely: “I’m glad that finally David Sacks is getting the treatment he deserves.”
“Clearly some of the vitriol is related to my politics,” Sacks later offered, seeming to imply that it was his love for Donald Trump, a former reality TV star who ran the country poorly for four years but who gave people like Sacks giant tax cuts, that was compelling people to diss him.
Others online discussed the trend of venture capitalists bickering with one another and emphasized the fact that it made the whole industry look bad. Eric Bahn, co-founder and general partner at Hustlefund, tweeted: “VC has a serious brand problem. All the bickering, finger pointing, name calling, ad hominem attacks within the industry are being noticed by founders. There are good VC humans on this side of the table, but this clowniness makes us all look bad.”
TechCrunch has pointed out that this is really only the latest open, public spat between high-level tech executives, with C-Suite folks showing an increasing propensity for highly transparent blow-ups.
Gizmodo reached out to Sacks for comment on why so many people seem to hate him and will update this story if he responds.
