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Recently disclosed regulatory filings have drawn market attention to a series of “contrarian trades” involving tech giants. The hedge fund of Palantir co-founder and billionaire investor Peter Thiel established new positions in Apple (AAPL) and Microsoft (MSFT) during the third quarter of 2025.
Interestingly, during the same period, Berkshire Hathaway continued to reduce its Apple holdings, while the Bill & Melinda Gates Foundation Trust sold a significant portion of its Microsoft stake. This divergence in operations among these top investors reflects differing judgments on the valuation and prospects of tech stocks.
Thiel’s fund executed notable portfolio adjustments that quarter, liquidating its entire Nvidia position, substantially reducing Tesla, and reallocating capital to Apple and Microsoft. In contrast, Berkshire sold 15% of its remaining Apple stake (having cut its position by nearly 75% since late 2023), and the Gates Foundation disposed of nearly two-thirds of its Microsoft shares.
However, a closer look reveals that a fundamental consensus is not entirely broken: Apple remains Berkshire’s largest equity holding by market value, and Microsoft still accounts for nearly 12% of the Gates Foundation’s portfolio weight. This indicates the divergence lies more in “position sizing” rather than “whether to hold.” Thiel’s contrarian purchases are not a simple rejection of Buffett’s and Gates’s judgments but rather an active allocation based on his own deep research into industry trends in the AI era.
As an investor deeply involved in founding tech companies like PayPal, Meta, and Palantir, Thiel’s decision-making core lies in identifying and betting on the “core infrastructure” that will define or dominate the next technology cycle. His purchases of Apple and Microsoft embody this thinking.
Microsoft: The Absolute Leader in AI Cloud Services and Enterprise Software
Thiel’s optimism toward Microsoft hinges on its establishment of a formidable AI service advantage through its strategic investment in OpenAI. Microsoft not only holds a 27% equity stake in OpenAI but has also secured commercial licenses for all OpenAI models through 2032 and $250 billion in Azure commitments. This has enabled its Azure cloud business, already a $75 billion annual revenue operation, to maintain a growth rate of nearly 40% year-over-year. Simultaneously, deeply integrating generative AI (like Copilot) into enterprise software such as Microsoft 365 has directly driven product price increases and revenue growth. In Thiel’s view, Microsoft has successfully transformed AI into a solid growth engine and a wider moat.
Apple: Ecosystem Stability and the Potential Catalyst of AI Upgrades
Compared to Microsoft, Apple has appeared more cautious in adopting generative AI. However, Thiel’s investment is likely based on two points: First, its unparalleled ecosystem profitability and financial health. In 2025, Apple saw growth across all its major hardware lines, with high-margin services revenue surpassing the $10 billion mark for the first time and generating a massive $99 billion in free cash flow, consistently returned to shareholders via buybacks. Second, the impending AI feature upgrade cycle. The market anticipates the long-promised Siri overhaul, incorporating more advanced AI capabilities, to launch in 2026. This could act as a catalyst for a large-scale iPhone replacement wave. Investing in Apple, within Thiel’s framework, is a bet on the immense monetization potential of its vast user base in the AI era.
The apparent opposition in trades reflects differing investment philosophies and time horizons. Buffett’s reduction may stem from valuation discipline (Apple’s forward P/E is around 31) and partial profit-taking. The Gates Foundation’s sales could be related to funding needs for its philanthropic work. Thiel’s additions, however, represent a growth-investing perspective based on the evolution of tech trends—he believes that regardless of short-term valuation fluctuations, Microsoft and Apple, leveraging their existing ecosystem advantages and clear AI strategies, will continue to capture the immense value created by the AI revolution in the long run.
Therefore, the lesson for ordinary investors from this “divergence” might be this: For tech giants like Apple and Microsoft, the market holds multiple pricing logics. Thiel’s contrarian move does not point to an either-or answer but reinforces one viewpoint: Amid the AI wave, holding leading companies with both deep moats and clear AI transition paths remains a crucial long-term investment option.
