2 Artificial Intelligence (AI) Stocks Billionaire Bill Ackman of Pershing Square Absolutely Wants to Own in 2026

Pershing Square’s latest 13F shows Bill Ackman concentrated large stakes in two AI-anchored platform companies—30.27 million shares of Uber (making it his largest holding) and 5.82 million shares of Amazon (about $1.3 billion as of Sept. 30)—within an 11-position portfolio valued at roughly $14.6 billion. Ackman’s bullish case: Uber’s dominant U.S. ride-share position and diversification into Eats, freight and AI-driven matching/autonomy (including a deal to deploy at least 20,000 Lucid robotaxis) position it to capture a ride-sharing market Stratis Research pegs at ~$918 billion by 2033; Amazon’s AWS, which accounted for 18.5% of net sales but 60.3% of operating income through nine months of 2025, is being infused with generative-AI capabilities that could accelerate its ~20% revenue growth and cash-flow expansion. Valuation looks supportive to Ackman—Amazon traded around 10x forecast 2026 cash flow in Q2 and ~12x on Dec. 9—so his moves signal a strategic bet that AI-driven monetization and scale at both companies will drive disproportionate earnings and share-price upside.

Analysis

Pershing Square's most recent 13F shows Bill Ackman concentrating large stakes in two AI-anchored platform companies: 30,270,518 shares of Uber purchased during the first quarter (making it Pershing's largest holding) and 5,823,316 Amazon shares bought in the June-ended quarter (worth roughly $1.3 billion as of Sept. 30) inside an 11-position portfolio valued at approximately $14.6 billion. Ackman's commentary and buying pattern mark both names as high-conviction positions he intends to hold into 2026.

Uber's case rests on durable U.S. share (68%–76% between Sept. 2017 and Mar. 2024, peak 76% in Mar. 2024), a transition to cash-generation under CEO Dara Khosrowshahi, and a strategic AI/autonomy roadmap that includes matching, demand forecasting and a July agreement to deploy at least 20,000 Lucid Gravity robotaxis over six years; Stratis Research projects the global ride-share market could reach ~$918 billion by 2033. The company's diversification into Eats and freight provides multiple revenue levers but preserves cyclicality tied to the U.S. economy.

Amazon's investment thesis centers on AWS, which accounted for 18.5% of net sales but 60.3% of operating income through the first nine months of 2025 and is growing ~20% year-over-year; embedding generative-AI and LLM services is the primary lever to accelerate revenue and cash-flow growth. Valuation appears supportive to Ackman — roughly 10x forecast 2026 cash flow in Q2 and ~12x as of Dec. 9 — but key risks are AI monetization execution and timing of autonomous mobility deployments, which warrant close monitoring.

Key Decisions for Investors

• Consider initiating or increasing a measured exposure to Amazon as a core AI/cloud compounder given AWS's outsized operating-income contribution and the historically cheap ~10–12x forecast cash-flow multiple, while dollar-cost averaging to avoid near-term timing risk
• Consider a tactical, modest position in Uber to capture AI-driven matching and autonomous upside plus Eats/freight diversification, but cap position size because mobility and freight revenues remain cyclical and robotaxi deployment execution is uncertain
• Track concrete catalysts — AWS AI product adoption metrics and quarter-to-quarter operating-income contribution, U.S. ride-share share trends, and robotaxi deployment milestones with Lucid/Nuro — and use missed or delayed milestones as triggers to reassess or hedge exposure
• Avoid mirroring Pershing's full position sizes given its concentrated, activist posture; employ staged entries, position limits, or protective hedges to manage concentration and execution risk