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1990s Business man private jet
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US corporate spending on private flights for executives has ballooned in recent years

The median expense spent by America’s largest companies on air travel jumped 66% from 2020 to 2024.

Max Knoblauch

In 2025, Corporate America’s top executives aren’t trying to get their carry-ons gate checked. And as far as perks go, they expect a bit more than free coffee and granola bars.

Hence the steady rise of spending on private and chartered flights by the US’s 500 largest companies (by revenue). According to data provided to Sherwood News by executive intelligence firm Equilar, companies’ median spending on private flights for execs jumped 19% from 2021 to 2024. When factoring the change from 2020, when travel was depressed because of the pandemic, the jump is 66%.

(The Wall Street Journal had analyzed Equilar data to first report that spending on private flights for execs had, collectively, jumped nearly 77% from 2020 to 2024.)

Last year, Meta CEO Mark Zuckerberg was paid a salary of $1, the same pay he’s collected going back to 2013. But in proxy statements, Meta reported that it spent $1.5 million chartering business travel flights for Zuckerberg and $2.6 million on private jets for his personal use. Tyson paid $2.98 million last year for the use of corporate jets for Chairman John H. Tyson’s personal travel, and Tootsie Roll doled out about $1.8 million for CEO Ellen Gordon to fly on its company aircraft for both business and personal uses.

But these aren’t the only execs kicking back in PJs on company dime. Per Equilar, the median private flight expense has increased in nearly all industries across Corporate America.

And, as WSJ notes, at the same time that execs’ private flight perks have surged, much of Corporate America has slashed costs and laid off workers.

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OpenAI is reportedly working with Pentagon to hash out guardrails amid Anthropic standoff over AI safety

OpenAI CEO Sam Altman said the company is working with the Pentagon to negotiate safety guardrails for AI models used in the battlefield, which comes as one of its top competitors, Anthropic, is at a standoff with the government.

According to a memo obtained by several media outlets, Altman told staff OpenAI believes “that AI should not be used for mass surveillance or autonomous lethal weapons, and that humans should remain in the loop for high-stakes automated decisions. These are our main red lines.”

Anthropic, the company behind the AI chatbot Claude, was one of several firms that received a $200 million contract from the Department of Defense for “agentic workflows.”

Since then, tensions between Anthropic and the Pentagon have reportedly risen as the startup insists on surveillance restrictions. The government’s attack on Venezuela last month that led to the capture of President Nicolás Maduro reportedly involved the use of Anthropic’s Claude AI models for planning, which caused the startup to push back on the alleged violation of its terms of use.

Anthropic has until 5:01 p.m. ET on Friday to reach a deal with the Pentagon, which has threatened consequences against the company if it doesn’t allow the government unrestricted use.

Altman’s comments come as the Financial Times reports that executives at Amazon, Google, and Microsoft are being pushed by workers to support Anthropic in its dispute with the Pentagon and adopt similar guardrails as the Claude company in any work they undertake with the US military.

According to a memo obtained by several media outlets, Altman told staff OpenAI believes “that AI should not be used for mass surveillance or autonomous lethal weapons, and that humans should remain in the loop for high-stakes automated decisions. These are our main red lines.”

Anthropic, the company behind the AI chatbot Claude, was one of several firms that received a $200 million contract from the Department of Defense for “agentic workflows.”

Since then, tensions between Anthropic and the Pentagon have reportedly risen as the startup insists on surveillance restrictions. The government’s attack on Venezuela last month that led to the capture of President Nicolás Maduro reportedly involved the use of Anthropic’s Claude AI models for planning, which caused the startup to push back on the alleged violation of its terms of use.

Anthropic has until 5:01 p.m. ET on Friday to reach a deal with the Pentagon, which has threatened consequences against the company if it doesn’t allow the government unrestricted use.

Altman’s comments come as the Financial Times reports that executives at Amazon, Google, and Microsoft are being pushed by workers to support Anthropic in its dispute with the Pentagon and adopt similar guardrails as the Claude company in any work they undertake with the US military.

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Jon Keegan

Report: Anthropic CEO Amodei meeting with Hegseth at the Pentagon as tensions mount

Anthropic CEO Dario Amodei has been summoned to meet with Defense Secretary Pete Hegseth at the Pentagon on Tuesday, according to a report from Axios. Tensions are running high between the Trump administration and Anthropic, as the startup’s surveillance restrictions on the use of its AI are reportedly causing outrage within the Pentagon.

Last month’s attack on Venezuela that led to the capture of Maduro reportedly involved the use of Anthropic’s Claude AI models for planning, which caused the startup to push back on the alleged violation of its terms of use.

Per the report, the Pentagon is considering effectively blacklisting Anthropic’s AI from government work if it doesn’t capitulate to the administration’s terms.

Antagonizing the Trump administration could cause Anthropic to face potential regulatory hurdles as it races toward an IPO this year. The company recently hired former Microsoft CFO Chris Liddel to its board, who formerly served as deputy White House chief of staff in the first Trump administration.

Last month’s attack on Venezuela that led to the capture of Maduro reportedly involved the use of Anthropic’s Claude AI models for planning, which caused the startup to push back on the alleged violation of its terms of use.

Per the report, the Pentagon is considering effectively blacklisting Anthropic’s AI from government work if it doesn’t capitulate to the administration’s terms.

Antagonizing the Trump administration could cause Anthropic to face potential regulatory hurdles as it races toward an IPO this year. The company recently hired former Microsoft CFO Chris Liddel to its board, who formerly served as deputy White House chief of staff in the first Trump administration.

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Jon Keegan

Anthropic donates $20 million to pro-AI regulation PAC

The war to build a better AI model may be mostly happening in Silicon Valley, but now another important front has opened: Washington, DC.

Anthropic announced a $20 million donation to Public First Action, a new super PAC that advocates for AI policies and regulations that prioritize public safety. The PAC describes itself as “a counterforce that will defend the public interest against those who aim to buy their way out of sensible rule-making.”

The move is seen as a counter to OpenAI’s growing investments in PACs that argue for less AI regulation.

OpenAI recently donated to Leading the Future PAC, which has received over $50 million from the family of OpenAI president and cofounder Greg Brockman, and the VC firm Andreessen Horowitz. The PAC says it is focused on “identifying, maintaining, and growing pro-AI candidates in order to support an AI innovation policy agenda at the state and federal level.”

OpenAI’s Brockman and his wife, Anna, recently donated a total of $25 million to the pro-Trump MAGA, INC. PAC.

OpenAI recently donated to Leading the Future PAC, which has received over $50 million from the family of OpenAI president and cofounder Greg Brockman, and the VC firm Andreessen Horowitz. The PAC says it is focused on “identifying, maintaining, and growing pro-AI candidates in order to support an AI innovation policy agenda at the state and federal level.”

OpenAI’s Brockman and his wife, Anna, recently donated a total of $25 million to the pro-Trump MAGA, INC. PAC.

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