When he first ran for president in 2016, Donald Trump infamously enjoyed the support of PayPal co-founder Peter Thiel. But for the most part, Silicon Valley avoided Trump and funded his opponent. However, the weeklong Republican National Convention in Milwaukee, where Trump will give his first speech tonight after surviving Saturday’s would-be assassination, has made it clear that a significant number of Silicon Valley bigwigs have hopped on the Trump train.

Look no further than David Sacks, the venture capitalist and co-host of the popular “All-In” podcast, who in recent years has become a representative of the increasingly reactionary wing of the tech elite.

After Trump summoned a mob to the U.S. Capitol on Jan. 6, 2021, Sacks said Trump had “disqualified himself from being a candidate at the national level again.” But last month, Sacks and fellow “All-In” co-host Chamath Palihapitiya hosted a high-dollar fundraiser for Trump in San Francisco — $50,000 per VIP ticket and $300,000 to join the hosting committee — shortly before “All-In” hosted him for a chummy interview. In a speech Monday at the convention, Sacks sounded like he’d picked up some Trumpian rhetorical ticks.

“We still don’t know which puppet Democrat party bosses will install as their nominee, but we know what their agenda will be: four more years of chaos and failure both at home and abroad,” Sacks said. He later called for voters to replace the “Biden-Harris cabal with a president who is strong and smart, rather than sleepy and senile, or in her case, clueless and embarrassing.”

That echoed Thiel’s case for Trump in 2016. The co-founder of Palantir and Silicon Valley’s arch right-winger — who once wrote, “I no longer think that freedom and democracy are compatible” — also spoke at the RNC that year.

But Trump’s tech crowd is growing now that the former president is polling favorably to retake the White House in November. Some tech billionaires are even making their support public and betting big on MAGA. The world’s richest man, Elon Musk, endorsed Trump on Saturday and plans to give $45 million a month to America PAC, a new super PAC led in part by Palantir co-founder Joe Lonsdale and supported by the Winklevoss twins, billionaire venture capitalist Doug Leone and tech founder John Hering, The New York Times reported Monday.

Musk has long embraced far-right conspiracy theories and has occasionally expressed support for Republican politicians. But he has also claimed to have voted for Joe Biden in 2020 and Barack Obama and Hillary Clinton before that. For this year’s election, he said as recently as March, “I am not donating money to either candidate for US President.” (Donation records for America PAC so far don’t show any money from Musk through June, but he indicated he planned to start giving this month, The Wall Street Journal reported, citing an unnamed person familiar with the matter. Trump is also reportedly considering some sort of advisory role for Musk should Trump win in November.)

The list goes on. In late May, Sequoia Capital partner Shaun Maguire announced a $300,000 donation to Trump, falsely claiming that there was widespread interference in the 2020 election — despite plainly acknowledging that “there’s not public evidence” to support the claim.

And Marc Andreessen and Ben Horowitz, two of the most prominent tech investors in the country, also reportedly plan to back Trump with significant political donations. Andreessen voiced his support for Clinton over Trump in 2016 after saying he was deciding between a candidate, Trump, who “doesn’t believe in science,” and another, Clinton, who “doesn’t believe in economics.” In an episode of his and Horowitz’s “Ben & Marc Show” podcast released Tuesday, Andreessen narrated a long personal history of supporting Democratic politicians before eventually hammering the Biden administration on several regulatory stances. The “final straw,” he said, was Biden’s support for an unrealized capital gains tax on the super rich. (A partner at Andreessen Horowitz, Elizabeth Gunn, referred HuffPost to the pair’s podcast but declined to comment further on their political spending.)

Even if Silicon Valley is still mostly blue — and as Vox noted, it is — a few high-profile, deep-pocketed defections can add up quickly. On Tuesday, Sacks posted a list on social media that appeared to show tech investors who are backing Trump. “Come on in, the water’s warm,” he wrote.

“It’s tempting to paint this with a broad brush and say all of Silicon Valley is getting behind the former president, but what’s actually happening is that Silicon Valley’s right wing has been activated and persuaded to open their pockets,” Max Chafkin, author of “The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power,” told NPR on Wednesday.

‘They Need Electricity’

It’s no surprise that tech oligarchs — or those willing to admit it — like Trump. He gave rich people the biggest tax break in American history in his first term, and he has said he wants to slash corporate taxes even more if elected again. He’s likely to change course from Biden’s historic antitrust push. He offers a friendlier ear to cryptocurrency investors. And he supports slashing regulations, particularly around fossil fuel production, which would be an immense benefit to Silicon Valley investors who’ve bought into the artificial intelligence boom that sucks up energy at an astounding pace.

“When we were at David’s house and talking to a lot of geniuses from Silicon Valley and other places, [I realized] they need electricity at levels that nobody’s ever experienced before,” Trump said on the “All-In” podcast in June. “To be successful, to be a leader in AI, the amount of electricity they need is like double what we have right now and even triple what we have right now. It’s incredible how much they need to be the leader, and we’re going to have to be able to do that. And a windmill turning, with its blade knocking out the birds and everything else, is not going to be able to make us competitive.”

Some have pet causes, such as Tyler Winklevoss, who announced a $1 million-equivalent donation to Trump in bitcoin and his own endorsement last month because Trump is the “pro-bitcoin, pro-crypto and pro-business choice.”

Mark Cuban, a Biden supporter, similarly argued that Trump support among Silicon Valley types is “a bitcoin play,” though in Cuban’s thinking, bitcoin investors are betting on Trump’s protectionist tariff policy and tax cuts driving up inflation, weakening the dollar and driving up bitcoin value.

Sacks, for his part, worries that America’s support for Ukraine will lead to a world war. He got Trump to say on “All-In” that he would not send American troops to directly fight in the conflict.

And some may simply embrace Trump’s so-called “anti-woke” stance — that is, defying societal norms on racism, sexism, nativism and science. Vivek Ramaswamy, the investor-turned-presidential candidate who also now owns a portion of BuzzFeed, HuffPost’s parent company, lamented in his own RNC speech embracing Trump on Tuesday that “faith, patriotism, hard work and family have disappeared only to be replaced by race, gender, sexuality and climate.”

Lobbying For JD Vance

If some conservative and right-leaning tech investors were leaning Trump because of their bottom lines and favorable Trump polling, his pick of JD Vance as a vice presidential contender likely helped the calculus quite a bit.

Vance, who shot to fame with his book “Hillbilly Elegy,” is by now as much a son of the venture capitalist scene as he is of Ohio.

After service in the Marines and a stint as a lawyer, Vance moved to San Francisco and became a Thiel protege; the pair first met more than a decade ago when Vance was a student at Yale Law School. Vance later benefited from tens of millions in seed money from Thiel, Google’s Eric Schmidt and others when he co-founded his own venture capital firm in 2020 — it’s still Vance’s listed job on LinkedIn — which held stakes in space security, biotech and even Rumble, the right-wing YouTube alternative. Thiel later donated $15 million to a super PAC that backed Vance’s 2022 Ohio Senate bid.

Vance was in attendance at Sacks’ fundraiser for Trump last month, where Sacks and Palihapitiya expressed their support for Vance as Trump’s vice presidential pick, the Times recently reported. (Sacks was, in a sense, returning a favor: Vance had introduced him to Donald Trump Jr. a few months prior, the Times reported in a separate story last month.)

The recent Times report detailed Vance’s deep connections in Silicon Valley, particularly with Thiel, who helped advance Vance’s career through several iterations and blurbed his book. Thiel “placed calls to encourage Mr. Trump to choose Mr. Vance,” the outlet reported, and Musk encouraged Trump directly to pick Vance.

And on top of all that, Vance has self-reported on his federal financial disclosure that he owns between $100,000 and $250,000 in bitcoin, according to NPR.

Lucy And The Football

The surge in powerful tech investors backing Trump comes with an open question: He’s winning their support, but are they winning his?

Trump knows how to work a crowd, whether at a rally full of party-line voters or a closed-door meeting of wealthy big shots. But history has shown that his sweet talk only lasts as long as it’s politically expedient. Then, without warning, he can give you the cold shoulder.

For tech investors, there’s no clearer example than a recent Trump flip-flop on visas for skilled foreign workers.

Trump sharply limited these skilled worker visas, known as H-1Bs, during his first term. And on “All-In,” co-host Jason Calacanis pressed Trump on expanding businesses’ ability to recruit employees throughout the world.

“Please promise us you will give us more ability to import the best and brightest from around the world to America,” Calacanis said.

Trump gushed in support.

“I do promise, but I happen to agree, that’s why I promise, otherwise, I wouldn’t promise,” Trump said, pledging support for “automatically” rewarding green cards to college graduates who aren’t American citizens and lamenting high-skilled workers who “become multibillionaires” in India or China after being educated in the United States.

Trump suddenly sounded like the New York Democrat he was a decade ago. He also happened to be stealing an idea from Hillary Clinton, who supported “stapling” green cards onto the back of advanced degrees. “We all wholeheartedly agree with that,” Sacks told Trump, without mentioning that Trump had aped Clinton’s homework. After Trump signed off on the podcast, the co-hosts celebrated his “new” visa policy, with Palihapitiya saying Trump’s promise was “very positive for our community, meaning the tech industry.”

But Trump’s promise didn’t last a day. Quickly, Trump’s campaign said that, actually, the promise of green cards for all college graduates would exclude “communists, radical Islamists, Hamas supporters, America haters and public charges.”

“He believes, only after such vetting has taken place, we ought to keep the most skilled graduates who can make significant contributions to America,” Trump spokeswoman Karoline Leavitt said. “This would only apply to the most thoroughly vetted college graduates who would never undercut American wages or workers.”

Needless to say, the policy isn’t included in the Trump-aligned Republican Party platform. Instead, it trumpets the “Largest Deportation Program in American History” while only vaguely mentioning “Merit-based immigration” without any mention of college graduates or skilled visas.

“Trump has a Lucy with a football quality — every time it looks like he might change, that he might pivot to the middle and do something more measured, he disappoints,” tech journalist Eric Newcomer wrote Wednesday, reflecting on increasing Silicon Valley support for Trump.

“Now with Vance at his side and with Silicon Valley titans whispering in his ear, some of Silicon Valley elites seem to believe he’ll rise to the occasion.”

Calling the case for Trump “totally misguided and unprincipled,” Newcomer had a warning for Trump’s wealthy new supporters: “We shouldn’t sacrifice our principles and our country just because a bully says he wants to be our friend.”