
Welcome to the Enterprise AI Hangover
It feels like we're having an Enterprise AI hangover — just as Anthropic and OpenAI climb toward IPO territory.
Expert perspectives on venture capital, private markets, and the future of investment.

It feels like we're having an Enterprise AI hangover — just as Anthropic and OpenAI climb toward IPO territory.

What is it that investors want: exposure to Anthropic, or exposure to something exceptional — something they can't easily own?

Analysts say 40% of agent projects will fail. Nvidia, Google, and Amazon just bet hundreds of billions otherwise. Who's right?

Two mega-rounds last week. Six of the top 25 fit the old framework. The other nineteen don't.

While all eyes are on compute partnerships, things are moving fast on the agentic commerce side — and it looks very much ready.

Last week's Anthropic announcements signal a bigger ambition: going somewhere software could never reach. The financial services agents.

Last week's Q1 earnings from Amazon and Google left investors with a problem they couldn't quite name. By every observable signal, the hyperscalers are winning.

SpaceX claims a $26.5 trillion AI TAM and lines up a $60 billion Cursor acquisition it plans to pay for with IPO stock.

Half of 2026's planned data centers won't be built. States are banning them. Two of the winners just filed to go public.

Anthropic overtook OpenAI on ARR, Sam Altman got a brutal New Yorker profile, and both labs are racing toward IPO

Ramp just launched Ramp AI Spend Intelligence, a tool to help companies track their AI costs across model subscriptions, API spend, and tool sprawl.
Databricks introduced Omnigent, a meta-harness designed to combine, control, and share AI agents, expanding its agentic AI capabilities for enterprise workflows.
Source: Databricks
Ripple CEO Brad Garlinghouse has revealed a goal of reaching $1 billion in revenue by end of 2026, with the target excluding XRP-related income, highlighting the company's push to grow its core business lines.
Source: U.Today
Databricks introduced Omnigent, a meta-harness designed to combine, control, and share AI agents, expanding its agentic AI capabilities for enterprise workflows.
Source: Databricks
Anthropic has taken its latest AI models, Fable 5 and Mythos 5, offline to comply with new US government export controls that bar the company from giving foreign users access to these models.
Source: AP News
Anduril is calling for a reset of U.S. arms export controls, signaling the defense tech startup's push to reshape regulatory frameworks that govern international weapons sales.
Source: Financial Times
A coalition of state attorneys general has launched an investigation into OpenAI, requesting information from the company on a wide range of topics.
Source: bloomberg-tech
Executives from Anthropic, OpenAI, and Google are scheduled to attend the G7 summit in France, signaling growing engagement between AI industry leaders and world governments.
Source: bloomberg-tech
Mistral AI is reportedly in funding talks at a valuation near €20 billion, signaling continued investor interest in the European AI company.
Source: TipRanks
AI startup Sierra is moving into software solutions for utility companies, marking a new vertical expansion for the company.
Source: Axios
Sacra estimates that Supabase hit $170M in ARR in May 2026, up from ~$101M at the end of 2025.
Source: Sacra
Axiom Space, which is developing what it hopes will be the world’s first commercial space station, is also aiming to IPO within the next year.
Source: TheInformation
OpenAI will acquire Ona(opens in a new window), bringing its secure cloud execution and orchestration technology into our rapidly expanding Codex ecosystem.More than 5 million people use Codex each week to research, analyze, build, and automate their work—up 400% from earlier this year. Codex began as a tool for software developers and now helps a wider range of people do complex work from an initial request through to a finished result.
Source: OpenAI
Waymo is readying its first national advertising push as competition in the autonomous vehicle space intensifies and critics of the technology grow more vocal.
Source: WSJ
Prometheus, one of Jeff Bezos’ newest ventures, announced a $12 billion funding round on Thursday that values the company at $41 billion.
Source: CNBC
OpenAI is reportedly considering significant price cuts to its products as it anticipates intensifying competition with Anthropic for users, according to a WSJ report. The move signals a potential pricing war in the consumer and enterprise AI market.
Source: WSJ
Sierra Space is reportedly plotting an IPO alongside Axiom Space as SpaceX's success fuels investor frenzy in the commercial space sector.
Source: The Information
Mastercard has launched an AI agent payments capability in collaboration with major crypto firms including Coinbase and Ripple, expanding its crypto-integrated payment infrastructure into the agentic AI space.
Source: Decrypt
Kalshi is rolling out new security measures including a workplace disclosure rule aimed at combating insider trading on its platform, following scrutiny over suspicious trading activity by public figures.
Sacra estimates that ClickHouse hit $250M in annualized revenue in May 2026, up from $160M in 2025.
Source: Sacra
Regulators are moving to permit most sports betting on prediction platforms like Kalshi and Polymarket while barring wagers on war casualties and similar sensitive topics, marking a significant regulatory development for the industry.
Source: New York Post
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