Billionaire Stanley Druckenmiller Sold Shares of Palantir and Tesla in Favor of Another Artificial Intelligence (AI) Stock With a $50 Billion Addressable Opportunity

Key Points

• Form 13Fs (filed quarterly) allow investors to analyze which stocks Wall Street's brightest money managers are buying and selling.

• Duquesne's billionaire chief was a big-time seller of Palantir and Tesla stock during the March-ended quarter -- and this selling may have to do with more than just profit-taking.

• Meanwhile, Druckenmiller's fund opened a nearly 1.1-million-share position in a cloud-based software provider that's leaning heavily into artificial intelligence (AI).

• 10 stocks we like better than Docusign ›

For the better part of the last three years, no trend has captivated the attention and capital of investors more than artificial intelligence (AI). Giving software and systems the capacity to make split-second decisions without human oversight is a game-changer for most industries around the globe. It's also the reason analysts at PwC foresee AI boosting worldwide gross domestic product by $15.7 trillion come 2030.

While most Wall Street analysts have lofty expectations for the AI revolution, billionaire money managers have been more tempered with their optimism.

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For example, Duquesne Family Office's billionaire investor Stanley Druckenmiller was an active seller of a number of brand-name AI stocks during the March-ended quarter. We know this, because institutional investors with at least $100 million in assets under management are required to file Form 13F no later than 45 calendar days following the end to a quarter. A 13F provides a concise snapshot of which stocks the smartest fund managers have been buying and selling.

While Druckenmiller was sending shares of AI-data mining specialist Palantir Technologies (NASDAQ: PLTR) and North American electric-vehicle (EV) leader Tesla (NASDAQ: TSLA) to the chopping block, he was also piling into an AI-driven business with an estimated addressable market of $50 billion.

Popular AI stocks get the heave-ho from billionaire Stanley Druckenmiller

Between Dec. 31, 2024, and March 31, 2025, Duquesne's billionaire chief was a busy bee. The total number of securities overseen by Druckenmiller dropped from 78 to 52 in just three months. Two of the more prominent stocks that were pared down or jettisoned include Tesla, which was reduced by 50% (18,837 shares sold), and Palantir, where all 41,710 shares were sold.

There's no denying that both companies have enjoyed clearly defined competitive advantages. Palantir's government-focused Gotham platform has no one-for-one replacement, while its enterprise-driven Foundry service lacks large-scale competition. As for Tesla, it became the first automaker in more than a half-century to successfully build itself from the ground up to mass-production.

However, these first-mover and scaling advantages didn't protect either stock from being reduced or removed.

Considering that the stocks overseen by Druckenmiller have an average hold time of less than nine months, it's quite possible this selling activity represents nothing more than profit-taking.

Shares of Palantir and Tesla both surged following Donald Trump's November victory. Palantir is a logical winner of a unified Republican government that (likely) favors strong defense spending. Meanwhile, Tesla CEO Elon Musk temporarily joining the Department of Government Efficiency (DOGE) as a special employee was viewed as a positive for Tesla.

The worry is there may be more to this story than just benign profit-taking. While this is merely speculation, Stanley Druckenmiller may have been turned off by Palantir's and Tesla's respective nosebleed valuations.

Tesla's EVs, which heavily incorporate AI, have endured more than a half-dozen sweeping price cuts as competition picked up and inventory levels rose. This has pummeled Tesla's vehicle margin and reduced its earnings per share (EPS). Paying close to 130 times forward-year earnings for a company whose growth engine has stalled, and whose margins are floundering, may not be appealing to Duquesne's billionaire chief.

Likewise, Palantir Technologies is valued at a price-to-sales (P/S) ratio of more than 140! To offer some context, companies that are leading next-big-thing trends have historically topped out with P/S ratios in the range of 30 to 40. No megacap company has ever been able to maintain such an absurd premium as that of Palantir. Seeing this may have coerced Druckenmiller to take his chips completely off the table.

Image source: Getty Images.

Duquesne's billionaire chief is piling into this up-and-coming artificial intelligence stock

On other end of the spectrum, billionaire Stanley Druckenmiller oversaw the addition of one dozen new stocks to his fund's portfolio during the March-ended quarter. None of these new stocks was purchased more prominently than digital-signatures specialist DocuSign (NASDAQ: DOCU).

During the first three months of 2025, Duquesne Family Office purchased 1,074,655 shares of DocuSign, which had a market value of approximately $87.5 million. In other words, it became a top-10 holding for Druckenmiller.

DocuSign became a Wall Street darling during the height of the COVID-19 pandemic. With people encouraged to stay in their homes to prevent a worsening of the pandemic, DocuSign's e-signature services became a staple in a host of industries. Though life has returned to normal in the wake of the pandemic, DocuSign has managed to hang onto the bulk of digital-signature market share. According to Datanyze, it currently holds a 71% share.

But e-signatures make up just around half of DocuSign's total addressable market. While the digital-signature market is estimated to be worth $26 billion, DocuSign has a fast-growing, high-margin opportunity in contract lifecycle management (CLM) that makes up another $24 billion in addressable opportunity.

The company's cloud-based CLM operations includes the relatively new Intelligent Agreement Management (IAM) platform, which leans on AI insights to analyze, tailor, and automate the entirety of the agreement lifecycle for businesses. DocuSign's IAM platform can also reduce errors associated with agreements and be integrated with other core systems, such as customer relationship management software, to improve efficiency.

Although competition is picking up in the e-signature arena, and DocuSign's annual growth rate has slowed considerably from the height of the COVID-19 pandemic, the company's balance sheet and valuation may be added lures for Druckenmiller.

When DocuSign's fiscal first quarter came to a close on April 30, it had nearly $1.11 billion in cash, cash equivalents, and restricted cash and investments on its balance sheet, along with no debt. A pristine balance sheet has allowed for a steady diet of share repurchases, which tend to have a positive impact on EPS over time.

In terms of valuation, DocuSign is trading at 19 times forecast EPS for fiscal 2027. Even accounting for a slower annual growth rate, this represents a 37% discount to its average forward price-to-earnings ratio over the last half-decade.

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Sean Williams has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Docusign, Palantir Technologies, and Tesla. The Motley Fool has a disclosure policy.