By Alex Sirois
Publication Date: 2026-10-02 13:45:00
Microsoft holds a stake in OpenAI that no public market has ever priced, and one investor argues that gap between the stock and the business is exactly where the opportunity lives.
This post may contain links from our sponsors and affiliates, and Flywheel Publishing may receive compensation for actions taken through them.
I keep buying Microsoft (NASDAQ:MSFT | MSFT Price Prediction), and every quarter gives me another reason to add more. The reason I bring up most at dinner is OpenAI. Microsoft owns roughly 27% of the company behind ChatGPT. That stake was valued at approximately $135 billion when the partnership was restructured. One day the stake will get a public price, and I want my shares in place before then.
Paper Value Wall Street Still Can’t Price
OpenAI is reportedly aiming a valuation of about $1.2 trillion, and its listing now points toward 2027. If OpenAI lists near that figure, a 27% stake would be worth about $324 billion on paper before dilution. That equals…

