When three of the most influential investors of the past half‑century make opposite moves on the same stocks, it’s hard not to pay attention. That’s exactly what happened recently when Peter Thiel—the billionaire co‑founder of PayPal and Palantir—added Microsoft and Apple to his hedge fund’s portfolio at the same time Warren Buffett and Bill Gates were trimming their positions.
At first glance, it looks like a clash of titans. But a closer look shows a more nuanced story—one that says as much about each investor’s strategy as it does about the companies themselves.
Thiel's Macro Fund Makes Two Big Additions
Thiel’s hedge fund is known for its concentrated, macro‑driven approach. It typically holds only a handful of public equities, making any new position meaningful. In the third quarter, the fund made two notable moves:
- Re‑added Microsoft (MSFT)
- Initiated a new stake in Apple (AAPL)
These buys came after Thiel exited Nvidia entirely and sharply reduced his Tesla holdings—moves that suggest a shift toward large‑cap tech with durable cash flows and long‑term AI leverage.
Thiel’s track record makes these decisions hard to ignore. He was Facebook’s first outside investor, holds major stakes in Stripe and SpaceX, and built a multibillion‑dollar fortune through Palantir. When he rotates into something, it’s rarely casual.
Meanwhile, Buffett and Gates Are Trimming—Not Abandoning
The headlines about Buffett and Gates "selling" Microsoft and Apple can be misleading. Yes, both reduced their stakes, but neither walked away.
Buffett’s Apple Trim
- Berkshire Hathaway sold 15% of its remaining Apple stake
- Apple is still Berkshire’s largest equity position by far
- Buffett has reduced his Apple exposure since 2023 largely due to valuation concerns, not a loss of conviction
Gates Foundation’s Microsoft Sale
- The foundation sold nearly two‑thirds of its Microsoft shares
- Microsoft still makes up about 12% of the foundation’s portfolio
- Gates personally holds additional shares he plans to donate over time
In other words, Buffett and Gates are managing portfolio concentration and valuation risk—not making a statement that Microsoft or Apple are past their prime.
This is why the question of "Who’s right?" doesn’t have a simple answer. All three billionaires may be acting rationally based on their mandates, time horizons, and risk tolerance.
Why Thiel Likes Microsoft Right Now
Microsoft has become one of the most strategically important companies in the AI era, thanks largely to its early and aggressive partnership with OpenAI.
A Transformational AI Partnership
Microsoft’s current agreement with OpenAI includes:
- A 27% equity stake
- $250 billion in Azure cloud commitments
- Commercial licensing rights to all OpenAI models through 2032
- This deal has turned Azure into the default cloud platform for developers building on OpenAI’s models.
Azure’s Growth Is Surging
In the most recent quarter:
- Azure revenue grew 39%
- Microsoft 365 commercial revenue rose 15%
- Consumer revenue climbed 25%
Demand for AI services continues to exceed Microsoft’s ability to expand capacity—a rare problem for a company already generating $75 billion annually from Azure.
Enterprise AI Integration Is Paying Off
Microsoft has successfully embedded generative AI into:
- Office applications
- Teams
- Dynamics
- Security products
This has strengthened its enterprise moat and created new pricing power.
For a macro‑focused investor like Thiel, Microsoft offers a combination of AI leverage, recurring revenue, and global scale that’s hard to replicate.
Why Thiel Is Buying Apple Too
Apple’s AI rollout has been slower and more cautious than Microsoft’s, but the company’s fundamentals remain exceptionally strong.
A Massive Installed Base and Loyal Ecosystem
In 2025, Apple posted revenue growth across:
- iPhone
- Mac
- iPad
Its services business—high‑margin and recurring—surpassed $100 billion for the first time, growing 14% year over year.
A Free Cash Flow Machine
Apple generated $99 billion in free cash flow last year. Most of it went toward buybacks, which helped earnings per share jump 23%.
AI Upgrades Could Spark an Upgrade Cycle
Apple’s long‑awaited Siri overhaul, powered by more advanced generative AI, is expected to debut this year. Analysts believe it could trigger a wave of iPhone upgrades similar to the 5G cycle.
For Thiel, Apple represents a stable, cash‑rich platform with optionality around AI—an attractive combination in a volatile macro environment.
Why Buffett and Gates Are Selling—But Not Leaving
Buffett’s Perspective
Buffett has repeatedly said he loves Apple’s business but must manage concentration risk. At one point, Apple made up more than half of Berkshire’s equity portfolio. Trimming that exposure—especially at premium valuations—fits his long‑standing discipline.
Gates’s Perspective
The Gates Foundation regularly rebalances its holdings to fund philanthropic commitments. Selling Microsoft shares doesn’t reflect a negative view of the company; it reflects the foundation’s liquidity needs and diversification goals.
Both investors still hold large positions in the companies Thiel is buying. Their actions are not contradictory—they simply reflect different mandates.
So Who's Right?
In this rare case, the answer may genuinely be all of them.
- Thiel is positioning for long‑term AI dominance and sees Microsoft and Apple as foundational winners.
- Buffett is managing valuation risk and portfolio concentration while still keeping Apple as his largest holding.
- Gates is rebalancing for philanthropic purposes while maintaining meaningful exposure to Microsoft.
The divergence isn’t about conviction—it’s about strategy.
The Bigger Picture for Investors
Microsoft and Apple remain two of the strongest companies in global markets:
- Both have wide moats
- Both generate enormous cash flow
- Both are deeply embedded in enterprise and consumer ecosystems
- Both are positioned to benefit from AI, albeit in different ways
Their forward P/E ratios—29 for Microsoft and 31 for Apple—reflect premium pricing, which explains why some investors trim while others accumulate.
But the fact that three of the world’s most successful investors all continue to hold these stocks in size says something important: these companies remain core long‑term holdings, even if the timing of buys and sells differs.