Bill Ackman is reshuffling his concentrated portfolio as the AI race moves deeper into cloud computing, software and digital advertising. The billionaire investor sold roughly a quarter of his Amazon stake during the second quarter while adding to Microsoft and Meta Platforms. His moves suggest he still sees value across Big Tech, but currently sees stronger AI opportunities in enterprise software and consumer platforms.
Microsoft gains favor
Microsoft became one of Ackman’s bigger AI bets as its cloud and enterprise software businesses continued growing. Azure remains a major part of that story, while Microsoft also holds a 27% ownership stake in OpenAI and benefits from large cloud commitments tied to the AI company.
Copilot is strengthening the software side of the business by bringing AI tools into products already widely used by enterprises. Strong fiscal fourth-quarter results pushed Microsoft shares sharply higher in late July, although the stock has changed little over the past year or since the start of 2026.
Amazon was reduced rather than abandoned and remains one of Ackman’s largest holdings. AWS continues investing heavily in AI infrastructure, while Amazon also benefits from e-commerce, robotics and a fast-growing advertising operation.
Meta builds AI flywheel
Meta Platforms was another position Ackman increased during the second quarter. Artificial intelligence is already helping the company improve content recommendations, keep users engaged longer and deliver more targeted advertising. Second-quarter results showed ad impressions rising 14%, while average ad prices increased 12%. Those gains illustrate how Meta can turn AI improvements directly into advertising revenue.
Another opportunity comes from Meta’s new Muse AI agent, which is designed to help users write emails, plan trips, shop and handle other tasks. Free and paid plans are part of the model, but affiliate and transaction fees could eventually become a larger revenue source. Ackman’s portfolio changes therefore look less like a rejection of Amazon and more like a shift toward AI businesses with clearer near-term monetization opportunities.
