When Billionaire Diverge: Peter Thiel's PLTR-Backed Bets Against Warren Buffett and Bill Gates' Strategic Exits

The Tale of Two Investment Philosophies

Billionaire investors rarely find themselves on opposite sides of the same trade. Yet that’s precisely what’s happening in the market right now. Peter Thiel, the visionary behind Palantir Technologies (NASDAQ: PLTR), has recently taken fresh positions in Microsoft (NASDAQ: MSFT) and Apple (NASDAQ: AAPL) — the exact same stocks that Warren Buffett’s Berkshire Hathaway and Bill Gates’ charitable foundation have been trimming.

This divergence raises a critical question for investors: Are these tech giants worth accumulating, or should portfolio managers be lightening exposure?

The Exits vs. The Entries

The picture becomes clearer when examining the specifics. In Q3, Warren Buffett reduced his Berkshire Hathaway stake in Apple by roughly 15%, continuing a broader retreat that has slashed the holding by nearly three-quarters since late 2023. Bill Gates, through his charitable foundation, liquidated approximately two-thirds of its Microsoft position during the same period.

Simultaneously, Thiel’s macro hedge fund — which maintains a lean, selective portfolio focused on macroeconomic trends — added Microsoft back to its holdings and established a new Apple position. To fund these moves, Thiel completely exited his Nvidia stake and significantly downsized his Tesla exposure.

Yet here’s what complicates the narrative: Neither Buffett nor Gates has fully abandoned these positions. Apple remains Berkshire Hathaway’s largest single equity holding by a substantial margin. Microsoft still comprises nearly 12% of the Gates Foundation’s portfolio, with Gates personally holding additional shares earmarked for future donation.

The conclusion? All three billionaires may believe in these stocks’ long-term merit — they’re simply operating on different timelines and thresholds.

Why These Two Tech Powerhouses Command Attention

Microsoft’s transformation into an artificial intelligence powerhouse stems from its strategic relationship with OpenAI. The company secured exclusive cloud computing rights through Azure, a deal that has since evolved into a 27% equity stake in OpenAI, $250 billion in committed Azure services, and perpetual commercial licenses for all OpenAI models through 2032.

The results speak volumes. Azure revenue surged 39% last quarter — remarkable for a division already generating $75 billion annually as of fiscal 2025’s conclusion. The cloud division still can’t keep pace with demand for AI services. Simultaneously, integrating generative AI into Microsoft 365 pushed commercial revenue up 15% and consumer revenue up 25%, demonstrating how AI monetization extends across the enterprise ecosystem.

Apple, conversely, has moved more deliberately on artificial intelligence adoption. Its anticipated Siri redesign — featuring enhanced AI capabilities — arrives this year and could trigger a meaningful iPhone upgrade cycle. Yet the iPhone ecosystem’s competitive moat proved itself throughout 2025: revenue grew across all three main product categories, and the high-margin services business exceeded $100 billion for the first time, climbing 14% year-over-year.

Capital efficiency matters here. Apple spends modestly on AI infrastructure relative to competitors, maintaining its status as a free cash flow generating machine. Last year’s $99 billion in free cash flow largely funded share repurchases, driving earnings per share growth of 23%.

The Valuation Tension

Trading at forward P/E ratios of 29 and 31 for Microsoft and Apple respectively, neither stock qualifies as bargain-basement pricing. Valuation anxiety partly explains why Buffett has methodically reduced his Apple exposure.

But premium prices don’t necessarily equal poor investments. Apple possesses an unmatched ecosystem moat spanning brand, technology, and hardware. Microsoft commands the enterprise productivity software landscape and is building formidable competitive advantages in AI-driven cloud infrastructure. Analyst consensus projects double-digit earnings per share expansion for both companies, with meaningful upside catalysts embedded in their AI product roadmaps.

That’s precisely why Thiel sees opportunity — and why Buffett and Bill Gates haven’t completely retreated. In tech investing, positioning adjustments don’t always signal disagreement about an asset’s worth.