Sam Altman

Money Moves

Leading OpenAI through confidential IPO process; S-1 filed May 22, targeting Q4 2026 listing at up to $1 trillion

On May 28, Anthropic closed a $65 billion Series H at a $965 billion valuation, passing OpenAI to become the world's most valuable private AI company. The round disclosed annualized revenue at $47 billion, up from $44 billion three weeks earlier. Anthropic is targeting an IPO this autumn.

Updated 3 hours ago

Money Moves

Released GPT-5.5 (April 23) while managing CFO revenue concerns; OpenAI annualized run rate ~$24-25B as rival Anthropic reportedly surpassed $30B ARR; $250B Azure contract disclosed by Microsoft deepens cloud dependency

The four largest cloud providers—Microsoft, Meta, Alphabet, and Amazon—are tracking toward over $720 billion in combined AI infrastructure spending for 2026, up sharply from $410 billion in 2025. All four reported first-quarter results on April 29, 2026. Microsoft delivered the clearest signal: $77.7 billion in revenue (up 18% year-over-year), Azure cloud growth of 40% (above its 37% guidance), and earnings per share of $4.13 versus analyst estimates of $3.67.

Updated 3 days ago

Money Moves

Leading the company into its public-market debut

OpenAI filed a confidential draft registration with the Securities and Exchange Commission (SEC) on Friday, May 22, 2026. The filing is the first formal step toward a public listing that could value the ChatGPT maker above $1 trillion.

Updated 7 days ago

Money Moves

Publicly endorsing ads after years of resisting them

OpenAI ran ChatGPT as a paid and API-only product for three years. On May 21, the company opened a self-serve ad platform that lets any business buy placements inside the chatbot, with no minimum spend.

Updated May 21

New Capabilities

Leading Stargate infrastructure buildout

The White House mobilized America's 17 national laboratories and major tech companies—OpenAI, Anthropic, Google, Microsoft, NVIDIA. The Genesis Mission aims to double US research productivity in a decade by connecting supercomputers, quantum systems, and AI into one discovery platform. Energy Secretary Chris Wright announced 24 corporate partners at a January 11 summit.

Updated May 20

New Capabilities

Leading OpenAI through intense competition and infrastructure challenges

OpenAI's GPT-5 dropped August 7, 2025, completing AI's shift from chatbots that string words together to systems that think through problems step-by-step. Google DeepMind's models won the International Math Olympiad by solving problems only five humans cracked, as Anthropic's Claude, Meta's Llama, and every major AI lab raced to build reasoning models.

Updated May 19

Money Moves

Pushing for Q4 2026 IPO at up to $1 trillion valuation; testified in Musk trial May 12; under congressional scrutiny over personal investment conflicts

After the $122 billion round closed in April, OpenAI ended its Azure cloud exclusivity and capped Microsoft's revenue share at $38 billion through 2030. On May 18, a jury dismissed Elon Musk's suit seeking $134 billion and the reversal of OpenAI's for-profit structure.

Updated May 18

New Capabilities

Competing directly as Google pushes Gemini into Search and developer defaults.

The rollout didn't stop at "Flash is the default." In the days after launch, Google filled in the missing contract with developers. Gemini 3 Flash Preview is now explicitly priced in the Gemini API, with context caching rates, batch pricing, and a note that Gemini 3-era Search grounding will begin billing on January 5, 2026.

Updated May 15

New Capabilities

Running OpenAI, which fell to 32.3 percent enterprise share in April 2026 — the second consecutive monthly decline — as Anthropic extended its lead

Ramp's May 2026 AI Index shows 50.6 percent of US businesses now pay for AI tools, up from 50.4 percent in March. Anthropic holds 34.4 percent of those paying customers against OpenAI's 32.3 percent — the second consecutive month Anthropic has led.

Updated May 15

Money Moves

Driving OpenAI to lock in premium IP and consumer use cases as Sora scales.

Mickey Mouse just shook hands with the algorithm Hollywood spent two years trying to tame. Disney is investing $1 billion in OpenAI, letting Sora and ChatGPT Images legally generate short videos and images of more than 200 Disney, Pixar, Marvel, and Star Wars characters — not the actors who play them.

Updated May 11

Money Moves

Pushing for a Q4 2026 OpenAI IPO despite CFO concerns and missed revenue targets

SoftBank Group cut its target for a margin loan backed by OpenAI shares from $10 billion to as low as $6 billion after lenders pushed back, Bloomberg reported May 8. The reduction came days after the Wall Street Journal reported that OpenAI had missed internal revenue and user-growth targets in early 2026. Anthropic had gained share in coding and enterprise markets. Lenders said the difficulty of pricing a private company with slowing growth made them unwilling to commit at the original size.

Updated May 8

New Capabilities

Leading OpenAI's accelerated model-iteration strategy

ChatGPT receives roughly a billion visits a month, and on May 5 those visitors began talking to a different model by default. OpenAI replaced GPT-5.3 Instant—the everyday workhorse it shipped earlier this year—with GPT-5.5 Instant, a faster system the company says produces 52.5% fewer hallucinated claims on medical, legal, and financial questions. The new model can also pull context from a user's past chats, uploaded files, and Gmail to personalize answers, and it appears in OpenAI's developer interface as 'chat-latest.'

Updated May 5

Money Moves

Leading the enterprise pivot ahead of a planned public listing

OpenAI previewed Sora as a glimpse of cinema's AI future in February 2024. Twenty-six months later, on April 26, 2026, the company switched off the Sora consumer app for good. The underlying programming interface (the API that lets other developers tap the model) keeps running until September 24, but the standalone product, the iOS social feed, and the Disney character partnership all end now. When Sam Altman personally called new Disney CEO Josh D'Amaro to break the news, he said he felt 'terrible' — and D'Amaro replied, 'I get it.'

Updated Apr 27

Money Moves

Preparing OpenAI for its own IPO, targeted for late 2026

Anthropic offered employees up to $6 billion in liquidity through a tender offer at a $350 billion valuation — the same price as its February fundraising round. Employees mostly said no. The sale completed in early April well below its target because staff chose to hold their shares, betting that the company's planned initial public offering (IPO) later in 2026 will deliver a higher price.

Updated Apr 10

Rule Changes

Named personally in multiple wrongful death lawsuits

Florida's attorney general announced a formal investigation into OpenAI on April 9, 2026, alleging that ChatGPT played a role in the April 2025 mass shooting at Florida State University that killed two people and injured five. Court records show the accused shooter entered more than 270 prompts into ChatGPT in the hours before the attack, including questions about how the country would react to a campus shooting, what time the student union is busiest, and how to operate his firearms. The investigation marks the first time a state attorney general has targeted an artificial intelligence company over an alleged connection to a violent crime.

Updated Apr 9

Money Moves

Leading IPO preparations while managing infrastructure pivot

Four months ago, Sam Altman told the world OpenAI had $1.4 trillion in data center commitments. Now the company is telling investors the real number is $600 billion — and that it would rather rent computing power than build its own facilities. The retreat, disclosed to investors in February 2026 and detailed publicly on March 22, marks the sharpest pivot in the short history of the artificial intelligence spending boom.

Updated Mar 22

New Capabilities

Leading OpenAI's expansion into security and enterprise markets

For decades, finding security flaws in software has required either expensive human experts or pattern-matching tools that miss complex bugs. In the span of five months, all three frontier artificial intelligence labs — OpenAI, Anthropic, and Google — have released autonomous agents that read code like a human researcher, discover vulnerabilities traditional scanners miss, and generate patches. On March 6, 2026, OpenAI launched Codex Security in research preview, an agent that scanned 1.2 million code commits in its first month of beta testing and discovered 14 previously unknown vulnerabilities serious enough to receive formal identifiers in projects including OpenSSH, Chromium, and PHP.

Updated Mar 6

Rule Changes

Managing fallout from Pentagon deal backlash

For decades, the United States military chose its weapons contractors and the contractors complied. Artificial intelligence changed that equation. On March 3, OpenAI and the Department of Defense amended a freshly signed AI contract to explicitly ban the use of the technology for domestic surveillance of American citizens—a concession the Pentagon had refused to grant Anthropic just days earlier, triggering that company's blacklisting from all federal agencies.

Updated Mar 3