Plus: Why it might be time to dump Magnificent 7 stocks.
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Fortune 500 Digest with Alyson Shontell
Saturday, March 21, 2026
Foreword
Alyson Shontell
Editor-in-Chief

If it feels like the AI frenzy has hit a fever pitch lately, that’s because it has.

But while 2025 was a year of excessive AI investment and hype, 2026 could be the year we find out which companies emerge victorious—and which will be left in the dust in both the public and private sectors.

Winners are starting to emerge. Over the past year, Anthropic appears to have surged past OpenAI as the LLM-maker of choice for Big Business, even as it faces headwinds from the Trump administration and the Pentagon. It’s attracting so many enterprise clients and first-time AI spenders that OpenAI is reportedly shifting some of its focus away from consumers to start reclaiming ground.

In the private markets, AI threatens to make the lifespans of startups shorter than ever. Traditionally, venture capitalists have had to wait seven to 10 years to see investments pan out. Today, that feels closer to seven months or even seven weeks. Even the most promising companies can be threatened by the ripple effects of a minor Anthropic or Gemini product update.

On that front, Fortune’s Allie Garfinkle brings us a riveting case study: Cursor, an AI coding company whose valuation soared from $2.5 billion to almost $30 billion last year. Along the way, Cursor was one of the fastest startups in history to reach $1 billion in annualized revenue. That figure has since doubled to $2 billion, with help from the biggest American companies: Cursor estimates that 67% of the Fortune 500 are using its tools.

Yet the company and its 25-year-old CEO and cofounder, Michael Truell, now face an existential crisis, trying to prove what they’re building is a durable business rather than a nice-to-have feature that Anthropic or OpenAI can easily replicate.

Truell spoke with Allie for the story and acknowledged the scramble to adapt to new demands. VCs and Cursor customers did too.

“I’ve been building some form of software for 27 years now,” Aaron Levie, Box CEO and Cursor customer, told Allie. “The sheer rate of change is unlike anything we’ve ever seen.” Read her story here.

Follow Alyson on X, LinkedIn, TikTok, Instagram, and the Titans and Disruptors vodcast.

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Deals & Developments
  • Microsoft (No. 14) is considering suing Amazon and OpenAI over their $50 billion partnership, according to the Financial Times. The dispute centers on whether OpenAI can offer its Frontier enterprise platform through Amazon Web Services without violating its exclusivity agreement with Microsoft, which requires OpenAI’s models to be accessed through Azure.
  • Meta (No. 22) agreed to a five-year, $27 billion AI infrastructure deal with AI cloud company Nebius.
  • Uber Technologies (No. 101) plans to acquire 10,000 robotaxis from EV maker Rivian, with an option for up to 50,000 more, alongside a $300 million investment and an additional $950 million if Rivian hits certain performance milestones. The autonomous vehicles are set to launch first in San Francisco and Miami in 2028. Read more: Uber will operate its own robotaxis again—this time with Rivian’s not‑yet‑built EVs
  • IBM (No. 68) has closed its $11 billion acquisition of data streaming company Confluent. The deal, originally announced in December, is designed to supply IBM’s clients with the data their AI agents need for training and deployment.
  • U.K. regulators are investigating Adobe (No. 201) over its early cancellation fees, which require customers on “annual billed monthly” plans to pay 50% of their remaining yearly cost if they cancel more than two weeks after signing up. Customers then lose access to Adobe’s products at the end of the monthly billing period when they cancel. Antitrust officials say the terms may be unfair to consumers.
Overheard
“More and more, you’re seeing CEOs like Blackstone’s, McDonald’s, and others jump on social channels to try and be some version of, well, me.”
—Jack Schlossberg, grandson of President John F. Kennedy and a Democratic congressional candidate running in Manhattan’s 12th District, in a commentary piece for Fortune published this week. Schlossberg also spoke in conversation with Fortune’s Diane Brady at the Fortune CEO Initiative dinner in New York City Wednesday evening.
On earnings calls:
  • FedEx (No. 49) beat estimates with $24 billion in quarterly revenue and raised its fiscal 2026 revenue growth outlook from a range of 5% to 6% to a range of 6% to 6.5%. CEO Raj Subramaniam told analysts he expects demand to hold steady despite rising energy costs tied to the conflict in the Middle East.
  • Dollar Tree (No. 139) met Wall Street expectations with $5.45 billion in quarterly revenue, up 9% year-over-year, and reported $506.1 million in profit, a sharp turnaround from a $3.7 billion loss in the same quarter last year. CEO Michael Creedon acknowledged a dip in store traffic for the quarter, which the company expected, but said customers are responding positively to improvements in the company’s product assortment and value offerings.
  • Micron Technology (No. 170) beat earnings estimates with $23.86 billion in quarterly revenue, nearly triple its year-ago figure, as demand for its AI chips surges. Despite the strong results, the company’s stock fell after the earnings call, reflecting concerns over soaring capex to meet demand.
  • Macy’s (No. 193) beat expectations with $7.6 billion in quarterly revenue. CEO Tony Spring remarked that “our customers have remained resilient,” but the company is taking a “prudent” approach to its 2026 guidance as “there are many macroeconomic and geopolitical factors that could influence discretionary spend.”
  • Lululemon athletica (No. 401) beat expectations with $3.64 billion in quarterly revenue but issued a cautious outlook for the current quarter and fiscal year, citing higher costs including tariffs and an ongoing