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Fortune 500 Digest with Alyson Shontell
Saturday, August 22, 2026
Foreword
Alyson Shontell
Editor-in-Chief

In the AI era, the lifespan of a startup has never been more precarious.

Companies that looked poised to become the next billion-dollar hits can find themselves transformed overnight into the equivalent of a VCR or fax machine business, made obsolete by the latest update from Anthropic, Google, or OpenAI.

If you’re a venture capitalist whose job it is to invest in startups, that’s a scary thought. Anything in your portfolio that pre-dates ChatGPT’s November 2022 launch is an investment made in a different world—and a lot of those investments were made at unicorn valuations. That means that any VC worth their salt should be hyper focused on reevaluating all the startups in their orbit on an almost weekly basis to see who has a moat, who is toast, and who they need to help pivot or land softly.

Fortune’s Allie Garfinkle spoke to a number of VCs about how they’re doing this triage exercise. Those that spoke to her on record seemed to couch the situation, with one citing that only 10% to 20% of their portfolio was at risk.

That ratio feels off to me, given the amount of money that’s been pumped into the startup ecosystem over the past decade and the types of businesses that were hot in the pre-AI days. I would expect it to be the inverse, with only 10% to 20% of the startups being secure in this unprecedented moment.

When I tweeted my skepticism, one honest VC, Bullish’s Mike Duda, agreed. Duda has been one of New York’s most successful angel investors over the past decade, putting early money into companies like Warby Parker, Casper, and Peloton.

“Yes, it’s higher,” he replied.

It’s hard to blame the VC industry for clamming up about the issue. There’s little upside to publicizing the predicament. And the road ahead—particularly for startup accelerators like Y Combinator, which produce classes of hundreds of startups every year—is particularly challenging. What do you say to the founders whose businesses are now irrelevant? And, perhaps more importantly, how do you vet new founders on viable ideas in this uncertain moment?

As any parent trying to advise their kids on choosing a college major or career today can attest, it’s not easy. The transition to an AI economy is still very much a work in progress, and knowing what to hold on to and what to say goodbye to can feel overwhelming.

Check out Garfinkle’s take on the mad dash of startup investors to reevaluate their portfolios for the AI era.

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

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Fortune 500 C-suite Power Moves
GE HealthCare Technologies (No. 217) appointed William K. Grogan CFO, effective Sept. 14. Andrea van der Berg will succeed Grogan as CFO of Xylem (No. 443), effective Sept. 1. Centene (No. 19) announced that CFO Drew Asher is stepping down from the role at the end of the year, but will remain with the company through the end of 2027.

Read more: CFO turnover at America’s largest companies is on pace to hit 18.3%—the highest since the pandemic

And more in this week's Fortune 500 Power Moves.
Deals & Developments
  • Amazon (No. 1) plans to expand drone delivery to nearly 500 U.S. cities and towns by the end of the year, a sixfold increase from its current footprint. The push comes as Uber Technologies (No. 92) partners with Zipline to bring drone deliveries to Uber Eats later this year, targeting up to 1 million daily deliveries by the end of 2029.
  • Apple (No. 4) once again changed its EU App Store policies, replacing its unpopular per-install Core Technology Fee with a 5% commission on electronic transactions in apps distributed outside the App Store and lowering some App Store commissions (effective Oct. 1). It also expanded eligibility for developers to operate alternative app stores and distribute apps on the web, amid growing antitrust pressure in Europe, the U.S., and elsewhere.
  • Google, owned by Alphabet (No. 5) secured the right to buy up to $12.2 billion of Marvell Technology (No. 476) shares as part of a deal for Marvell to develop chips for Google’s AI systems. Broadcom (No. 70), Google’s existing AI chip partner, fell 4.6% on Wednesday as investors worried Marvell could take some of its Google business.
  • Nvidia (No. 16) capped its guaranteed investment in OpenAI’s planned Ohio data center campus at $105 billion, far below the $250 billion initially reported. That reduces Nvidia’s immediate financial exposure, but it still sparks concerns about AI companies financing the same data centers that will eventually buy their chips.
Overheard
“The board is basically saying, ‘We’re good.’And the management team is saying, ‘Whoa, whoa, whoa.’”
—Brad Jayne, a principal at Pearl Meyer and co-author of its Q2 2026 Market Intelligence Survey. Read more: Companies are spending trillions on AI. The C-suite doesn’t know who is in charge of it
On earnings calls:
  • Walmart (No. 2) beat expectations with $187.94 billion in quarterly revenue, as well as nearly $3 billion in tariff refunds that the retailer says will be used to invest in lower prices “because customers need us to,” per CFO John David Rainey.
  • Home Depot (No. 25)