- OpenAI is preparing a second venture fund, reportedly far bigger than its first.
- Its $175M debut fund has already turned into stakes in Cursor maker Anysphere and $11B-valued Harvey.
- The move deepens OpenAI’s control over which AI startups win, and raises real conflict questions
OpenAI is preparing a second $400 million venture fund, far larger than its original $175 million vehicle, according to The Wall Street Journal, which reports that the company is seeking an experienced venture capitalist to run it.
What’s not in question is what OpenAI does with money like this once it has it.
The first fund already picked some winners
The original Startup Fund launched in 2021 with $175 million from outside backers, Microsoft included, with Sam Altman holding legal control of it rather than OpenAI itself.
Since then, it’s raised a string of special-purpose vehicles on top of that, including a $44.3 million SPV that Tech Funding News covered in 2024, its largest at the time.
The portfolio built with that money spans nearly every corner of the application layer: 1X Technologies, Anysphere, Descript, Figure AI, Speak, Physical Intelligence, Harvey, Thrive AI Health. TFN tracked the full list last year.
Two names show how fast a small early cheque can compound. Anysphere, the company behind Cursor, took an $8 million seed round led by the fund in 2023, years before Cursor became a default tool in developers’ workflows.
Harvey moved even faster: $5 billion in 2025, $8 billion by December, then $11 billion in March 2026 off a $200 million round co-led by GIC and Sequoia. TFN has tracked this closely, including Khosla Ventures’ early conviction in AI legal tech before it was obvious.
More recently, OpenAI backed Isara, a nine-month-old startup run by two 23-year-olds, one of whom is a former OpenAI safety researcher, with no shipped product. It still landed a $650 million valuation on a $94 million round, with Stanley Druckenmiller and Michael Ovitz investing alongside OpenAI.
Why size matters more than it sounds like it should
The logic is simple, even if OpenAI never says it out loud: a startup that takes OpenAI’s money is more likely to become an OpenAI customer, an OpenAI distribution partner, or eventually an OpenAI acquisition.
Money goes out, loyalty and API revenue come back. It’s the same loop Google Ventures has run for Alphabet, and Amazon’s Industrial Innovation Fund has run for Amazon, just newer and hungrier.
What’s changed is the stakes. OpenAI, Anthropic and Google are converging fast on what their base models can do, so the real fight has moved up a layer, to who owns the workflow, the data, the customer relationship. A bigger fund lets OpenAI plant more flags there before the map is settled.
It also raises a question nobody involved seems eager to answer: can a venture fund controlled by a foundation-model company back startups without nudging them toward that company’s own stack, and away from whoever’s competing with it?
Harvey and Cursor both took OpenAI money early and grew into category leaders regardless, but that’s two data points, not a pattern, and OpenAI is about to place a lot more deals.
