Tech Billionaires Spend $140M Against Prop. 40 as Squarespace Cuts 19%

Technology wealth and artificial intelligence infrastructure dominated economic news on Monday evening as Silicon Valley billionaires poured $140 million into defeating California Proposition 40, web-hosting platform Squarespace cut 19% of its workforce to accelerate AI product development, and voters across the country prepared to decide local ballot measures governing AI data centers.

Silicon Valley Billionaires Pour $140M Into Campaign Against Proposition 40's 5% Wealth Tax

As reported by San José Spotlight, the opposition committee Building a Better California has raised $140 million—more than 4 times the $32 million raised by the union-backed Yes on Proposition 40 campaign—ahead of Tuesday's statewide vote:

• Sergey Brin's $103M Contribution & Tech Donor Roster: Proposition 40, sponsored by SEIU-United Healthcare Workers West (SEIU-UHW) and supported by Sen. Bernie Sanders and Rep. Ro Khanna, would levy a 1-time 5% tax on the net worth of approximately 200 California residents holding fortunes above $1 billion (and 2.5% above $1 billion for certain trusts) to raise an estimated $100 billion over 5 years, with 90% dedicated to Medi-Cal and healthcare programs and 10% to K-14 public schools and food assistance. Google co-founder Sergey Brin contributed $103 million to the opposition committee, joined by $20 million from Charles Schwab, $5 million each from former Google CEO Eric Schmidt and Sequoia Capital partner Douglas Leone, $3 million from Jayshree Ullal, $2 million from Henry Samueli, and $1 million from LinkedIn co-founder Reid Hoffman.
• Debate Over Retroactive January 1, 2026 Residency Date: Because Proposition 40 applies retroactively to billionaires residing in California as of January 1, 2026, opponents—cited by Santa Clara University political science professor Matt Harrigan and UC Law San Francisco tax professor Darien Shanske—have warned that billionaire departures by Larry Page, Peter Thiel, and David Sacks could erode state income tax collections, while SEIU-UHW chief of staff Suzanne Jimenez argued that the measure protects California hospitals from federal Medicaid cuts.

Squarespace Cuts 19% of Staff (~300 Workers) in AI Pivot; Voters Weigh Data Center Ballots

Two companion reports examined how AI adoption is reshaping both tech payrolls and municipal ballot measures:

• Squarespace Cuts ~300 Employees Across All Departments: According to TechCrunch, website builder Squarespace—taken private by private equity firm Permira in a $7.2 billion buyout in 2024—laid off 19% of its roughly 1,700-person workforce (approximately 300 employees) across every department on Monday. In a company blog post, founder and CEO Anthony Casalena wrote that Squarespace is restructuring around AI-native workflows, including its Blueprint AI website generator and Forma, an AI business assistant launched last month.
• Data Centers Become a National Election Day Ballot Issue: Meanwhile, on KCBS Radio, anchor Margie Shafer interviewed Bloomberg reporter Miquela Thornton on how the rapid expansion of energy-intensive data centers—driven by artificial intelligence training and cloud computing—has sparked local ballot measures and zoning referendums across the country on Tuesday's Election Day ballot.