Monday, June 1, 2026Vol. III · No. 152Subscribe
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Technology · Analysis

The Billion-Dollar Squeeze

Anthropic just overtook OpenAI at a $965 billion valuation—but the real story isn't who's winning. It's what's breaking: the economics of AI itself, as companies burn through annual budgets in weeks and CFOs face a choice between tokens and people.

The Billion-Dollar Squeeze
PhotographAnthropic just overtook OpenAI at a $965 billion valuation—but the real story isn't who's winning. It's what's breaking: the economics of AI itself, as companies burn through annual budgets in weeks and CFOs face a choice between tokens and people.

Anthropic raised $65 billion last week and leapfrogged OpenAI to become the most valuable AI startup on the planet, worth $965 billion. OpenAI sits at $852 billion after its March mega-round. Between them, the two San Francisco labs have pulled in more than $250 billion in funding since ChatGPT launched in late 2022, according to CNBC. That capital didn't disappear. It moved—violently—away from nearly everything else.

More than 220 companies that once held billion-dollar valuations have now fallen below that threshold, according to PitchBook.

Startups that last raised in 2021 are worth 68% less on average, while those that last raised in 2022 saw a 52% decline. The sharpest pain is concentrated in enterprise software: 75 SaaS companies appear on PitchBook's fallen unicorn list—double the number of fintech firms. Calendly, Glossier, and The Farmer's Dog are among the names now trading below their peak marks. One former DoorDash executive told CNBC his thesis bluntly: "All workflow-driven enterprise SaaS companies will be either disrupted or dead in the next decade."

Can Pre-ChatGPT Companies Survive the Funding Drought?

AI companies captured 80% of Q1 2026 venture funding at roughly $242 billion, and AI deals made up 81% of all funding during the quarter. That leaves roughly 20% of venture capital for everyone else—every fintech, every SaaS platform, every marketplace, every crypto project, every healthtech company. Venture investors who might have written follow-on checks to a SaaS company growing at 40% year on year are now deploying that same capital into AI-native firms growing at 200%.

The logic is straightforward, if brutal. If a startup was built on assumptions that predate large language models, its entire value proposition might be one API call away from irrelevance. One venture investor told CNBC that companies invested in post-ChatGPT "were already making more money than most of the companies we invested in before ChatGPT" by 2023. AI-native companies like Cognition are raising at $26 billion valuations while shipping products built almost entirely by their own AI.

Meanwhile, Anthropic raised $65 billion in a Series H financing at a $965 billion valuation—nearly tripling its $380 billion valuation from February. The round was led by Altimeter Capital, Dragoneer, Greenoaks, and Sequoia Capital. Anthropic's run-rate revenue crossed $47 billion earlier this month, driven largely by Claude Code, its AI coding assistant. OpenAI, for its part, is expected to hit $20 billion in annualized revenue this year, up from $3.7 billion the year before—a 5x increase in twelve months, according to Foundation Capital research.

Both companies are preparing for IPOs later this year. Reuters reports OpenAI is laying groundwork for a listing that could value it at $1 trillion.

Why Are Companies Burning Through AI Budgets in Weeks?

The funding frenzy masks a deeper problem: AI is turning out to be far more expensive than anyone expected. CFOs at major U.S. companies are now facing a brutal new trade-off: tokens or humans, according to two enterprise AI CEOs who spoke to CNBC this week.

"Companies are telling us that their AI budgets are getting exhausted in one month or two months, and these are annual budgets," Arvind Jain, CEO of enterprise AI firm Glean, told the network.

Each new model release from the frontier labs is roughly twice as expensive per token as the one it replaced, and Jain called the trajectory "unsustainable." "This is the first time ever that I can remember that technology costs the same as people," he said. That growing AI budget is increasingly coming in lieu of future headcount growth.

Uber's CTO told The Information in April that the firm had already burnt through its entire 2026 AI coding tools budget in just four months—after the company had actively incentivized adoption through internal leaderboards ranking teams by AI tool usage. Microsoft has reportedly scaled back internal AI use for similar reasons, according to Fortune.

The root cause is inefficiency. Roughly 95% of enterprise AI usage is still running on the most expensive frontier models, even for tasks that could be handled by cheaper alternatives, Jain said. Companies moved through three phases in roughly a year: boards demanding CEOs "do something" about AI, then "tokenmaxxing"—using AI by any means necessary regardless of cost—and now a reassessment phase where leadership teams ask whether they really need Opus-level intelligence for every single task.

Dell, meanwhile, is riding the infrastructure wave. The company's revenue rose 88% to $43.84 billion in its first fiscal quarter, handily beating analysts' estimates, with adjusted EPS of $4.86 topping estimates of $2.94.

Dell booked $24.4 billion in AI orders and recognized $16.1 billion of AI server revenue—a 757% increase year over year.

The company now expects AI server revenue of roughly $60 billion for fiscal 2027, up from its prior expectations of $50 billion. Dell shares jumped 39% in extended trading after the results.

What Does SoftBank's $87 Billion Bet Tell Us?

SoftBank CEO Masayoshi Son told CNBC on Monday that the AI revolution is "probably 50x bigger" than the dot-com boom, a day after the company announced it's investing 75 billion euros ($87 billion) to build AI infrastructure in France, including 5 GW of AI data center capacity.

"This is the biggest revolution of technology and realization that mankind ever experienced," Son said.

Son acknowledged that market corrections are inevitable but argued they create attractive buying opportunities, drawing a parallel to the 1929 crash. "There may be some correction, but that will be the best investment opportunity to me," he said. Despite SoftBank's significant investment in OpenAI, Son dismissed concerns of overexposure, stating that the AI startup comprises just over 20% of the group's net asset value, and expressed optimism about OpenAI's potential IPO.

The French investment—SoftBank's largest AI infrastructure commitment in Europe—will involve constructing 3.1 GW of AI data centers in the northern Hauts-de-France region by 2031, in partnership with Schneider Electric and state-backed utility EDF. The company said the investment will largely be financed through project financing rather than direct funding from SoftBank's balance sheet.

What Changed This Week

Anthropic overtook OpenAI as the world's most valuable AI startup at $965 billion, nearly tripling its valuation in three months. The funding concentration is historic: AI captured 80% of Q1 venture capital while making up just 18% of funded companies. Meanwhile, the cost crisis is forcing a reckoning—CFOs are exhausting annual AI budgets in weeks, and companies are choosing between tokens and future headcount. Dell's 88% revenue surge shows infrastructure providers are the clear winners, at least for now.

What to Watch

Both Anthropic and OpenAI are preparing for IPOs later this year, with OpenAI reportedly targeting a Q4 listing that could value it near $1 trillion. Watch for Anthropic's Wilson Sonsini-led IPO preparations and whether either company can demonstrate a path to profitability at scale. SoftBank's 75-billion-euro French data center buildout is expected to deliver its first phase by 2031—track whether project financing materializes and whether hyperscaler customers sign long-term agreements. Finally, monitor whether enterprise AI spending patterns shift from frontier models to cheaper alternatives as CFOs impose stricter governance on token consumption.

Coverage aggregated and synthesized from leading energy-sector publications. See linked sources within the article.

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