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HOME/NEWCOMER NEWSLETTER/Big Tech Defied Tradition With a…
NEWS
// NEWSLETTER ISSUE
NEWCOMER NEWSLETTER

Big Tech Defied Tradition With a Risky Bet on Trump. It’s Not Looking Like a Winner.

DATE October 30, 2026SOURCE NEWCOMER NEWSLETTERPARTICIPANTS ERIC NEWCOMER
In this episode
// SUMMARY

1. Key Themes

Theme 1: Tech's unprecedented, concentrated bet on electoral politics, and the risk it carries

Tech money now outspends traditional GOP megadonors

The scale of tech political spending has no historical precedent, and it extends well beyond Musk.

"Elon Musk, of course, has made by far the biggest play, spending almost half-a-billion dollars supporting Republicans in the midterms thus far, according to the latest campaign finance reports. Almost $200 million of that has gone to Ken Paxton..."

"Ben Horowitz and Marc Andreessen have kicked in $92 million to GOP super PACs, Jeff Yass of Susquehanna $110 million, and Greg Brockman of OpenAI $50 million. (On the Democratic side, George Soros gave $102 million and Michael Bloomberg $84 million, with no other donors exceeding the $40 million mark.)"

The break from the "play both sides" tradition

"It's no mystery why business leaders typically try to play both sides of the aisle: politicians and party dominance can come and go, but corporations are forever."

"But there's no precedent for Musk putting such a massive pile of chips on red, or for the overall scale of tech spending on politics."

Political headwinds are building, including AI backlash

"On top of Trump's disastrous policies and dismal approval ratings, opposition to AI has suddenly emerged as a major campaign issue and the GOP is on the wrong side of it."

"Talarico and Hinojosa have both leaned into anti-billionaire rhetoric while Abbott plays defense on data centers."

Retribution risk if Democrats win

"If team blue wins the Senate, and especially if they win the Texas Senate race and/ or the governorship, Musk's investment is likely to look very foolish. Democrats are already salivating about how they might take their revenge, floating ideas like new laws that apply only to people with a net worth of more than $500 billion. The nationalization of parts of SpaceX could even be on the table."

"Tech firms are already scrambling to hire lawyers and lobbyists as they brace for inquiries from a Democratic House and possibly the Senate."

Theme 2: A wealth-tax fight is mobilizing tech billionaires

California's billionaire tax draws a massive counter-campaign

"In California, tech figures led by Sergey Brin are also investing huge sums to beat back a proposed one-time 5% wealth tax on billionaires. The campaign against it has spent an astonishing $330 million so far, with Brin contributing more than $100 million on his own and Silicon Valley heavyweights including Eric Schmidt, John Doerr, and Patrick Collison accounting for most of the rest."

"...around 70 current and former billionaire residents to spend $612 million in statewide races so far, per Politico, with around half of that in direct opposition to the initiative. The latest polls show support for the tax falling but the outcome is far from predictable."

Tax fights are spreading to other states

"The legislature passed a 9.9% tax on household income exceeding $1 million per year this March, scheduled to go into effect in 2028. Opponents rallied to get Ballot Initiative 645, which would repeal the tax, in front of voters."

Theme 3: 2026 as a historic year for venture returns, alongside a mega-IPO debate

A "most epic year in the history of venture capital"

"Odds are looking pretty good that 2026 will go down as the most epic year in the history of venture capital, with Anthropic, SpaceX, and a few others (Cerebras, OpenRouter, Hugging Face, Cursor) all delivering legacy-making returns for numerous investors."

Anthropic's S-1 sparks valuation and wealth-creation debate

"NYU Stern professor Aswath Damodaran broke through on Wednesday with his case that Anthropic should be valued at $1.475 trillion, not in its $1.5- $2 trillion current standing."

"if you had 2 cofounders, raised from top teir vc, exited for a few billion dollars, you still wouldnt make as much as employee #400 at Anthropic will from the IPO."

Capital is flowing to hardware and prediction markets

"Prediction markets platform Kalshi reaches a $40 billion valuation. Plus, hardware startups have VCs shelling out for manufacturing, robotics, and compute..."

Theme 4: Deglobalization is eroding the market for global-impact coverage

Why Rest of World is likely to close

"Now, though, in the era of deglobalization and Trumpian hostility to journalism, idealistic non-profits, and anything that smacks of 'rest of world,' there just isn't the same interest in those kinds of stories."

"cratering traffic and lack of a viable growth path will ultimately do in a non-profit just as they would a business."

"Yet the expected demise of the publication... is about much more than AI's impact on Google search and the ever-present challenges of new media business models."

2. Contrarian Perspectives

Tech's Trump bet may be a losing position, not a power play. The prevailing narrative in some circles is that tech's alignment with Republicans buys durable influence. Newcomer argues the opposite: the downside is being underpriced.

"Elon Musk, Marc Andreessen, and many other tech leaders are long on Trump and that's not a good position."

"Investors who want to bet on politics would be better off sticking with Kalshi."

Supporting facts: Paxton is "in danger of becoming the first Republican to lose a statewide race there in decades," and AI opposition is emerging as a campaign issue that cuts against the GOP.

Musk's race to merge Tesla and SpaceX is read as a defensive, unhealthy move. Rather than a bold strategic play, it is framed as locking in federal money before political winds shift.

"Musk appears to be in a race to merge Tesla and SpaceX and lock in as much federal money as he can while he still has a friend in the White House. That dynamic is in itself… unhealthy!"

Hedging may be the rational endgame, and Democrats may take the money. The piece suggests that even after a loss, the retribution risk may be softened by political pragmatism.

"It's also possible that in the event of defeat, he'll simply switch his massive underwriting to Democrats, many of whom would be sorely tempted to take the money rather than go to war with the world's richest man. A16z likely made this sort of calculation, having shown a willingness to hedge its bets when Horowitz said he'd also donate to Kamala Harris shortly after the firm endorsed Trump."

Skeptical views on the Anthropic IPO (the bear case). Against the euphoria, Roger McNamee calls the offering dangerous for investors.

"Roger McNamee calls the IPO 'a very dangerous thing for investors,' and regards the S-1 as 'speculative fiction.'"

"In many use cases, the cost of the infrastructure of AI is still rising – those are not formulas for high returns for equity investors from here."

3. Companies Identified

Anthropic

  • Description: AI lab that has filed for the largest IPO in history.
  • Why mentioned: Central subject of the week's "chatter" and a driver of record venture returns in 2026.
  • Quotes: "Anthropic S-1 brings plenty of takes and a searing critique from Roger McNamee." / "The largest IPO in history is bringing out a lot of emotions" (Ed Elson, quoted via tweet).

SpaceX

  • Description: Musk's space company, cited as a major 2026 venture return.
  • Why mentioned: Both a source of venture gains and a potential political target.
  • Quotes: "The nationalization of parts of SpaceX could even be on the table."

Tesla

  • Description: Musk's electric-vehicle company.
  • Why mentioned: Part of Musk's reported push to merge with SpaceX.
  • Quotes: "Musk appears to be in a race to merge Tesla and SpaceX and lock in as much federal money as he can..."

Kalshi

  • Description: Prediction markets platform.
  • Why mentioned: Raised a large round at a $40B valuation, and held up as the better way to bet on politics.
  • Quotes: "Kalshi raised a billion." / "Prediction markets platform Kalshi reaches a $40 billion valuation."

Andreessen Horowitz (a16z)

  • Description: Venture capital firm.
  • Why mentioned: Endorsed Trump but hedged by also supporting Democrats.
  • Quotes: "A16z likely made this sort of calculation, having shown a willingness to hedge its bets when Horowitz said he'd also donate to Kamala Harris shortly after the firm endorsed Trump."

Rest of World

  • Description: Non-profit publication covering technology's global impact, founded 2020.
  • Why mentioned: Case study in the limits of philanthropy-funded journalism amid deglobalization.
  • Quotes: "Schmidt said it will close in January absent a white knight." / "...a richly funded international reporting operation like Rest of World, doing ambitious work on major global stories, just couldn't find a way."

Thrive Holdings / ADT

  • Description: Thrive acquired the home-security business ADT (referred to in the intro as "ADP").
  • Why mentioned: Notable deal in the weekly roundup.
  • Quotes: "Thrive bought ADP, the venerable home-security business." / "Seven Notable Deals: Kalshi, Thrive Holdings + ADT, Re:Build, Bedrock Robotics, Serval, General Compute, Disruptive."

Fairshake

  • Description: Crypto industry PAC.
  • Why mentioned: Spending heavily to defeat a longtime industry critic in Ohio.
  • Quotes: "The crypto industry PAC Fairshake has poured over $55 million into the race in an effort for defeat Democratic challenger and former Senator Sherrod Brown."

Cerebras, OpenRouter, Hugging Face, Cursor

  • Description: AI companies delivering outsized returns.
  • Why mentioned: Cited as part of 2026's exceptional venture year.
  • Quotes: "Anthropic, SpaceX, and a few others (Cerebras, OpenRouter, Hugging Face, Cursor) all delivering legacy-making returns for numerous investors."

Jio

  • Description: Indian phone operator.
  • Why mentioned: Celebrating India's biggest-ever IPO.
  • Quotes: "Phone operator Jio celebrates India's biggest-ever IPO."

Revolut

  • Description: Fintech company.
  • Why mentioned: Founder has critical views on VC (details paywalled).
  • Quotes: "Revolut founder Nik Storonsky has choice words for VC."

Google, Amazon, Microsoft

  • Description: Big tech incumbents.
  • Why mentioned: Mixed earnings reactions.
  • Quotes: "Big tech earnings paint a mixed picture as Google and Amazon shares plummet while Microsoft jumps."

4. People Identified

Elon Musk

  • Description: Tesla/SpaceX CEO and the largest tech political donor in this cycle.
  • Why mentioned: Biggest single political bet and most exposed to retribution.
  • Quotes: "spending almost half-a-billion dollars supporting Republicans in the midterms thus far." / "He's put in an additional $5 million into the Governor's race and nearly $168 million into the Senate race."

Marc Andreessen and Ben Horowitz

  • Description: a16z co-founders.
  • Why mentioned: Major GOP super PAC donors who also hedged.
  • Quotes: "have kicked in $92 million to GOP super PACs."

Sergey Brin

  • Description: Google co-founder.
  • Why mentioned: Leading the opposition to California's billionaire tax.
  • Quotes: "Brin contributing more than $100 million on his own."

Eric Schmidt, John Doerr, Patrick Collison

  • Description: Prominent tech figures.
  • Why mentioned: Co-funders of the anti-wealth-tax campaign.
  • Quotes: "Silicon Valley heavyweights including Eric Schmidt, John Doerr, and Patrick Collison accounting for most of the rest."

Jeff Yass

  • Description: Susquehanna co-founder.
  • Why mentioned: $110M to GOP super PACs.
  • Quotes: "Jeff Yass of Susquehanna $110 million."

Greg Brockman

  • Description: OpenAI executive.
  • Why mentioned: $50M to GOP super PACs.
  • Quotes: "Greg Brockman of OpenAI $50 million."

Jeff Bezos, Tim Cook, Jensen Huang, Mark Zuckerberg, Marc Benioff

  • Description: Tech CEOs.
  • Why mentioned: Courted the President through White House appearances, praise, and funding the ballroom.
  • Quotes: "appearing at the White House and showering the President in gifts and praise, and kicking in for the infamous ballroom, as Jeff Bezos, Tim Cook, Jensen Huang, Mark Zuckerberg, and even Marc Benioff have all done."

Ken Paxton

  • Description: Texas attorney general and Senate candidate.
  • Why mentioned: Recipient of Musk's largest single contribution.
  • Quotes: "the noxious Texas attorney general who's in danger of becoming the first Republican to lose a statewide race there in decades."

Aswath Damodaran

  • Description: NYU Stern valuation professor.
  • Why mentioned: Published a $1.475T valuation of Anthropic.
  • Quotes: "I value it's equity at about $1.475 trillion, which will inform my decision on whether to buy or sell its shares."

Roger McNamee

  • Description: Elevation Partners co-founder.
  • Why mentioned: Leading bear voice on the Anthropic IPO.
  • Quotes: "a very dangerous thing for investors."

Matt Levine, Ed Elson

  • Description: Finance commentators.
  • Why mentioned: Analyzed the S-1's risk factors and language.
  • Quotes: "Matt Levine delivered a sharp observation on the S-1's blend of AI doomerism and banker verbiage." / "Ed Elson did a breakdown on which risks on the S-1 actually matter."

Sophie Schmidt

  • Description: Founder of Rest of World.
  • Why mentioned: Funded the publication personally, a case study in philanthropy's limits.
  • Quotes: "personally committed up to $60 million over a decade for what she called her 'life's project.'"

Reid Hoffman

  • Description: Investor and Democratic donor.
  • Why mentioned: Quoted on the Democratic side of the money-in-politics debate.
  • Quotes: "While others spend outrageous amounts to keep authoritarian clowns in power, those of us who believe in the ideals of America cannot yield."

Matthew Yglesias

  • Description: Commentator.
  • Why mentioned: Argued progressives should embrace large Democratic donors.
  • Quotes: "I think people who donate large sums of money to Democrats are good and progressives should rethink their strategy of treating them like the enemy."

Gina Hinojosa, James Talarico, Greg Abbott

  • Description: Texas candidates.
  • Why mentioned: Key figures in the high-stakes Texas races.
  • Quotes: "Governor Greg Abbott fending off a strong challenge from Gina Hinojosa and Ken Paxton in a dead heat with James Talarico."

Sherrod Brown, Jon Husted

  • Description: Ohio Senate candidates.
  • Why mentioned: Crypto-industry target and data-center attack line.
  • Quotes: "Brown has been attacking his opponent, incumbent Senator Jon Husted, for being too supportive of data center construction."

Byron Donalds, David Jolly

  • Description: Florida governor's race candidates.
  • Why mentioned: Data centers as a campaign flashpoint.
  • Quotes: "Byron Donalds has been running possibly the most pro-data center campaign in the country as Americans broadly sour on their construction... David Jolly, has branded him 'Data Center Donalds.'"

Nik Storonsky

  • Description: Revolut founder.
  • Why mentioned: Teased as having critical views on VC (content paywalled).
  • Quotes: "Revolut founder Nik Storonsky has choice words for VC."

David Packard

  • Description: HP co-founder, former deputy secretary of defense.
  • Why mentioned: Historical precedent for tech-government ties.
  • Quotes: "Going back to David Packard, who served as deputy secretary of defense under President Richard Nixon, tech executives have certainly had their partisan loyalties at times."

5. Operating Insights

Hedge political exposure; don't tie company fortunes to one party. The historical norm exists for a reason, and firms that deviated are now scrambling.

"It's no mystery why business leaders typically try to play both sides of the aisle: politicians and party dominance can come and go, but corporations are forever."

Prepare for regulatory and congressional scrutiny before the political shift, not after.

"Tech firms are already scrambling to hire lawyers and lobbyists as they brace for inquiries from a Democratic House and possibly the Senate."

A mission-driven business needs a defined audience and monetization path; philanthropy alone won't sustain it. The lesson from Rest of World applies to any founder-subsidized venture.

"an expensive exercise in high-quality journalism about important topics that lacked a well-defined target audience or monetization strategy... But philanthropy is rarely enough by itself."

6. Overlooked Insights

Data centers are becoming a toxic campaign issue across party lines and regions. Candidates in Texas, Ohio, and Florida are using data centers as a political cudgel, suggesting local resistance could become a real constraint on AI infrastructure buildout.

"Abbott plays defense on data centers." / "Americans broadly sour on their construction."

AI wealth concentration is generating a political backlash target. The sheer scale of individual wealth creation from the Anthropic IPO (even for employee #400) reinforces the anti-billionaire sentiment fueling wealth-tax campaigns and populist rhetoric.

"if you had 2 cofounders, raised from top teir vc, exited for a few billion dollars, you still wouldnt make as much as employee #400 at Anthropic will from the IPO."