DealBook: Mark Cuban vs. California’s wealth tax
Also, behind the scrutiny of Mark Walter.
DealBook
August 17, 2026

Good morning. Andrew here. The president of OpenAI, Greg Brockman, is expected to publish an essay today about the increasing cybersecurity threats that artificial intelligence presents, describing a tipping point that may be underappreciated.

He says that OpenAI is improving its cyberdefenses as models get smarter and more dangerous, and he offers advice to others: “Over the coming months, every organization will need to begin significantly automating its security program to stay secure.”

Keep an eye out for it later this morning. More below. (Was this newsletter forwarded to you? Sign up here.)

Mark Cuban, the investor and entrepreneur, is seen in profile.
Mark Cuban, the investor and entrepreneur, has expressed his concerns that California’s wealth tax proposal could chill the state’s start-up culture. Julia Demaree Nikhinson/Associated Press

Cuban vs. Khanna on the wealth tax

California’s wealth tax proposal has become an expensive and closely watched political fight, as the issue of economic disparity looks set to dominate midterm elections in November and beyond.

Now, more tech heavyweights have weighed in amid concern that Proposition 40 — which would impose a one-time 5 percent tax on California billionaires — could upend the state’s start-up ecosystem.

The latest: On Saturday, Representative Ro Khanna, a Democrat who represents parts of Silicon Valley, posted on X that the measure was gaining traction.

“California voters want a Democratic Party that will stand up for the working class over the billionaire class,” Khanna said, adding that the proposal has the backing of Senator Bernie Sanders, independent of Vermont, and California labor groups.

The backlash was swift. Mark Cuban, the prominent entrepreneur and investor, warned Khanna that the California proposal would sock entrepreneurs who raise billions for their start-ups.

Cuban wrote on X:

How are you going to tax them ? Make them borrow money against their shares, if they can? They just raised money to grow their company and a bank will come along and loan them money ? A company that has been in business maybe less than a year ?

“IMO, if this passes, only idiot startup founders stay in Cali,” Cuban added.

The debate continued. Khanna responded that state assistance would let founders pledge shares with a loan (of perhaps 10 years) from the government to pay tax, paid back in cash or in equity.

Palmer Luckey, a founder of the start-up Anduril and a supporter of President Trump, responded on X:

Great, so founders would have 10 years to speedrun their way to a giant pile or cash and forced to surrender their company to the government if they can’t do it fast enough.

The fight over Prop 40 is drawing more money. Building a Better California, a coalition backed by Sergey Brin, a Google founder, donated $5 million to oppose the measure.

Other California billionaires have donated nearly $40 million to the campaign to defeat the measure as well, according to The Financial Times, including John Doerr of Kleiner Perkins, a venture capital firm; Chris Larsen of Ripple; and Neil Mehta of Greenoaks Capital.

HERE’S WHAT’S HAPPENING

Stripe reportedly reaches a deal for OpenRouter. Stripe, the big payment processor, agreed to pay more than $7 billion for OpenRouter, which runs a marketplace for artificial intelligence models, Bloomberg reports, citing unnamed sources. The acquisition would give Stripe a bigger presence in A.I. and reflects interest in helping companies limit their spending on the technology.

The Trump family’s crypto business moves closer to the banking world. The company, World Liberty Financial, said on Friday that the Office of the Comptroller of the Currency had granted a subsidiary, World Liberty Trust, preliminary conditional approval to operate as a chartered national trust bank. The effort underscores the Trump family’s ties to the cryptocurrency industry, which have weighed on national legislation to regulate the sector.

The Fed and retailers’ earnings are in focus this week. The health of the consumer will be a big discussion point in earnings reports, including from Home Depot tomorrow; TJX, Lowe’s and Target on Wednesday; and Walmart on Thursday. Investors will also closely scrutinize the minutes from the last policy meeting, which are set for release on Wednesday.

Mark Walter, the owner of the Los Angeles Dodgers, is seen walking on the field, wearing a team jacket.
Mark Walter, the financier and owner of the L.A. Dodgers, in March. Jayne Kamin-Oncea/Imagn Images, via Imagn Images Via Reuters Connect

The spotlight on Mark Walter’s businesses grows

The sports world is still reeling over the $12.5 billion that Josh Kushner, the venture capitalist, and Bob Iger, the former Disney C.E.O., agreed to pay to buy the L.A. Lakers.

But Wall Street is increasingly taking note of the seller: Mark Walter, the financier who bought control of the N.B.A. franchise just over a year ago.

Federal prosecutors are reportedly examining several Walter-linked businesses, according to The Wall Street Journal, which cited unnamed sources. They include Bradford Allen, a real-estate broker, and Hudson Trading, a Chicago financial firm.

The authorities are investigating whether Walter or his companies committed fraud by failing to disclose connections between insurers that the financier controlled and other businesses of his. Proceeds from the loans passed through the entities that prosecutors are examining, The Journal added.

The inquiry could have wider repercussions, particularly for the trillion-dollar private credit industry, which has largely copied Walter’s strategy of using insurers’ cash hoards to bet on alternative assets, according to The Financial Times:

The private capital industry is worried that a scandal engulfing Walter’s insurers could fuel doubts about how trillions of dollars of US retirement funds are being managed by private capital groups, spoiling the party.

While the issues at Walter’s insurers could unfold over many months, one top insurance adviser said their new disclosures pose longer-term risks over their capital position.

Separately, the sports industry is still unpacking the repercussions of the Lakers sale, and the increasingly escalating valuations of sports teams.

  • “I am absolutely convinced that we have not reached anything close to a ceiling,” Irwin Kishner, a chair of the sports law division at the law firm Herrick, told The Times.
  • Mark Cuban, who previously owned the Dallas Mavericks, added that soon, “One individual writing a check for a team will be rare.”

Meet OpenAI’s new revenue chief

The departure of Denise Dresser as OpenAI’s chief revenue officer after just eight months on the job added to the flurry of executive exits at the artificial intelligence giant.

But it’s worth paying attention to her replacement, Dali Rajic, whose experience and technical expertise could be key as OpenAI prepares to go public as soon as next year, Sri Muppidi reports.

Who is Rajic? He was most recently the president and chief operating officer of Wiz, the cybersecurity company that Google bought in a $32 billion acquisition that closed this year.

Before Wiz, Dali was a top executive at Zscaler, a publicly traded cloud security company. He was also the chief customer and revenue officer at AppDynamics, a software analytics company that Cisco bought for $3.7 billion in 2017.

Rajic is methodical about go-to-market planning, say people who have worked with him. He tracks in-depth data about sales to ensure that a company hits its quarterly goals.

That could help OpenAI demonstrate a predictable revenue stream to prospective I.P.O. investors.

He brings a similar technical approach to hiring salespeople. “Dali was able to recruit like a scientist,” Shardul Shah, a partner at Index Ventures who led the firm’s investment in Wiz, told DealBook.

Rajic’s also an expert in selling to business customers, a key focus of OpenAI as it seeks to catch up with Anthropic on enterprise sales.

  • OpenAI has now topped $40 billion in annualized revenue, according to Bloomberg. The company’s C.F.O., Sarah Friar, told investors on Friday that most of its sales now come from business customers, according to a person with knowledge of the matter, who was not authorized to discuss it publicly. At the start of 2026, a majority of OpenAI’s revenue came from its consumer business.
  • Anthropic said in May that its annualized revenue surpassed $47 billion. It generated more than $11.5 billion in revenue in its second quarter, up from $787 million a year prior, Bloomberg reported.

Rajic’s hire comes as Greg Brockman assumes a bigger role at OpenAI, DealBook has learned. Brockman, the company’s president, has taken charge of commercial functions — including sales, partnerships and advertising — since Fidji Simo stepped down as a full-time executive.

Brockman has been hiring executives like Rajic who are aligned with his metrics-driven approach.

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THE SPEED READ

Deals

  • Higgsfield, an artificial intelligence start-up, has raised $400 million at a $5.4 billion valuation in a round led by DST Global. A Goldman Sachs fund and Intel’s venture capital fund also participated. (Higgsfield)
  • The trading firm Jane Street reportedly lost about $15 billion last month amid market volatility and its exposure to Situational Awareness, the A.I.-focused hedge fund founded by Leopold Aschenbrenner. (WSJ)

Politics, policy and regulation

  • President Trump has gutted much of the Biden administration’s clean energy agenda, except for reportedly a roughly $600 billion chunk of it. (Politico)
  • Jamie Dimon of JPMorgan Chase reportedly warned John Healey, Britain’s new chancellor of the Exchequer, that higher taxes on banks risked job losses in the sector. (FT)

Best of the rest

  • Alex Cooper, the star podcaster, is reportedly switching talent agencies to C.A.A. from United Talent Agency amid a shake-up in her business empire. (Bloomberg)
  • How Ralph Lauren won the work wear wars as America returned to the office” (FT)
  • Tommy John, who notched 288 wins as a pitcher but is better known for the surgery that saved careers, has died. He was 83. (NYT)

Thanks for reading! We’ll see you tomorrow.

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Andrew Ross Sorkin, Founder/Editor-at-Large, New York @andrewrsorkin
Brian O'Keefe, Managing Editor, New York