Peter Thiel is one of the most successful entrepreneurs and tech investors in the world.

Thiel was a co-founder of PayPal and used the money from its sale to eBay to start a hedge fund. He acquired a 10% stake in Meta Platforms (then Facebook) as its first outside investor. He holds substantial stakes in Stripe and SpaceX, which are worth billions on their own.

Thiel’s biggest source of wealth, however, comes from his stake in Palantir Technologies (PLTR +0.36%), which he co-founded after selling PayPal. His shares of the AI stock are worth about $12.7 billion, as of this writing.

Image source: Getty Images.

All this is to say it’s worth paying attention to any investments Thiel makes. Luckily, we get some insight into his buy-and-sell decisions from required SEC disclosures, including the 13F filings for his macro hedge fund, which focuses on major economic trends.

But it can be somewhat confusing when Thiel’s on one side of a trade and two other well-known billionaires are on the other side. Such is the case recently, when Thiel bought two stocks that Warren Buffett’s Berkshire Hathaway (BRK.A 0.30%) (BRK.B +0.00%) and Bill Gates’ charitable foundation just sold.

Here, details matter. And that can give investors a better idea of who’s worth siding with when it comes to their own investments.

Two new stock purchases for Thiel’s Macro fund

Thiel’s hedge fund holds only a handful of marketable equity positions at a time. In the third quarter, he made some significant changes to the portfolio, selling its entire Nvidia position and substantially paring back his Tesla position. With some of the proceeds, he re-added Microsoft (MSFT +0.30%) to the portfolio and established a stake in Apple (AAPL +0.19%).

By comparison, the Gates Foundation Trust sold nearly two-thirds of its stake in Microsoft, the company Gates founded, during the third quarter. Likewise, Warren Buffett sold 15% of Berkshire Hathaway’s remaining stake in Apple, which he’s slashed by nearly three-quarters since late 2023.

Importantly, though, neither has completely divested from the two stocks that Thiel has been buying for his hedge fund. Apple, notably, remains Berkshire Hathaway’s largest marketable equity position by a fairly wide margin. Microsoft accounts for nearly 12% of the Gates Foundation’s portfolio, and Gates holds a substantial number of shares in his personal portfolio that he plans to donate.

So, while the billionaires may be on opposite sides of the trade, they may all agree that the stocks are worth owning to at least some degree. So, when asking “Who’s right?” the answer can be “all of them.”

The case for owning these two tech giants

Microsoft has emerged as a leader in artificial intelligence services thanks to a smart strategic investment in OpenAI. Originally, it had the exclusive rights to serve OpenAI’s cloud computing needs with its Azure platform, but as OpenAI has grown, its deal has evolved. The current contract includes a 27% equity stake in OpenAI, $250 billion of Azure commitments, and commercial licenses for all OpenAI models through 2032.

Microsoft has made the most of its relationship with OpenAI. Not only has it made Azure the premier destination for developers seeking to utilize OpenAI’s foundation models, but it has also successfully integrated generative AI into its premier enterprise software suite, Microsoft 365.

Today’s Change

(0.30%) $1.42

Current Price

$479.53

Key Data Points

Market Cap

$3.6T

Day’s Range

$472.21 – $479.82

52wk Range

$344.79 – $555.45

Volume

804K

Avg Vol

23M

Gross Margin

68.76%

Dividend Yield

0.71%

Azure’s growth has been phenomenal, with revenue up 39% in the most recent quarter, despite already being a $75 billion business as of the end of fiscal 2025. Management continues to note that demand for its AI services outstrips supply growth. Meanwhile, the addition of AI services to its enterprise software has pushed commercial revenue 15% higher and consumer revenue 25% higher for Microsoft 365.

Apple, by comparison, has been slow to adopt and implement new generative AI features. Its long-promised Siri revamp, which will include more advanced AI capabilities, is slated to debut this year, however, and it could cause a flurry of iPhone upgrades.

That said, the competitive strength of Apple’s iPhone and overall ecosystem remained on full display in 2025. The company experienced revenue growth across all three main product lines — iPhone, Mac, and iPad — last year. Importantly, its high-margin services revenue surpassed $100 million for the first time, climbing 14% year over year.

Today’s Change

(0.19%) $0.49

Current Price

$259.53

Key Data Points

Market Cap

$3.8T

Day’s Range

$256.22 – $260.20

52wk Range

$169.21 – $288.62

Volume

1.9M

Avg Vol

46M

Gross Margin

46.91%

Dividend Yield

0.40%

With limited capital expenditures on AI infrastructure, Apple remains a free cash flow machine. It generated $99 billion in free cash flow last year, most of which went toward share repurchases. As a result, earnings per share soared 23% last year.

Both stocks command premium prices, with forward P/Es of 29 and 31 for Microsoft and Apple, respectively. Valuation concerns are a big reason Buffett pared back on Berkshire’s Apple position. But there’s no denying the wide moat of Apple’s brand, technology, and products. Likewise, Microsoft has a stranglehold on enterprise productivity software, and it’s carving out a significant share of AI-focused cloud computing.

With analysts expecting double-digit earnings per share growth from both companies going forward, and with upside potential from AI products and services for both, they don’t look too expensive to own. That’s why Thiel added them to his hedge fund’s portfolio, and they still remain significant positions for both Berkshire Hathaway and the Gates Foundation.