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Family Offices Adjust Investment Strategy: Fewer Deals, Bigger Stakes In AI Innovation

A recent review of family office investment activity reveals a marked shift in strategy. Although senior investors have scaled back the number of transactions, their underlying commitment to transformative sectors—particularly artificial intelligence—remains robust.

Declining Transaction Volume With Persistent High-Value Plays

Data from private wealth platform Fintrx indicates that family offices executed just 51 direct investments in October, representing a 63% year-over-year decline. Despite this reduction in deal count, the focus has pivoted to high-stakes investments that drive significant value. The trend highlights a cautious yet opportunistic approach, where fewer, but weightier, transactions are favored over a higher volume of smaller deals.

High-Profile Investments In The Fast-Growing AI Sector

Family offices are increasingly leaning into the artificial intelligence arena. Notably, Gemini co-founders Tyler and Cameron Winklevoss recently participated in a $1.4 billion Series E funding round for Crusoe, a data center development firm now valued at $10 billion. Similarly, Hillspire—the family office of former Google CEO Eric Schmidt—joined a $2 billion Series B round for Reflection, an open-source AI laboratory valued at $8 billion. These landmark rounds underscore the growing reliance on supersized investments to bolster emerging technologies.

Consistency In Large-Scale Investments

Further evidence of this investment philosophy comes from participation in other headline-making rounds. Investors from Hillspire, alongside Laurene Powell Jobs’ Emerson Collective and Stanley Druckenmiller’s Duquesne Family Office, contributed to Commonwealth Fusion’s $863 million Series B2 fundraising effort. PwC’s recent report supports this narrative, noting that while the number of deals has contracted by 23% in the first half of 2025, the overall investment value dipped only 18%. Moreover, the proportion of deals exceeding $100 million remains steadfast, with a significant share of transactions now surpassing the $500 million threshold.

Strategic Shift: Fewer But Bigger Deals

Family offices are evidently prioritizing larger investments and aiming for outsized returns. As PwC points out, the proportion of investments below $25 million has decreased appreciably over the past decade, while the share of deals between $25 million and $100 million has increased. This evolution in deal structure reflects rising ambitions among family offices as they assert themselves as pivotal players in the global investment landscape.

Ultimately, while the pace of deal-making may appear to have slowed, family offices are not shying away from high-value opportunities—especially in sectors with transformative potential like artificial intelligence.

Copyright Law Struggles To Keep Up With AI Training

Courts Are Still Applying Old Copyright Rules To AI

AI companies train models on enormous amounts of published material, including books, articles and academic research. Whether using that content without authors’ permission violates copyright law remains unresolved.

Much of the debate centres on fair use, which allows copyrighted material to be used without permission in certain circumstances. Courts consider factors such as the purpose of the use, how much material was involved and its impact on the original market.

Anthropic Case Sets An Important Precedent

A major case involving Anthropic and a group of authors provided one of the clearest rulings so far. Judge William Alsup found that using copyrighted books to train AI models was lawful, comparing the process to people reading and studying literature before creating something new.

Anthropic was nevertheless ordered to pay $1.5 billion in a settlement. The penalty concerned books the company had obtained from illegal online libraries rather than the AI training itself.

For AI companies, that distinction could prove significant because it separates studying copyrighted material from directly copying it.

Competition Could Be The Key Issue

A case involving Thomson Reuters and Ross Intelligence offers a different perspective. A court ruled that Ross could not claim fair use after using Reuters’ copyrighted material to develop a competing AI-powered legal research platform.

The decision suggests courts may be less willing to consider AI training fair use when copyrighted content is used to build a product that directly competes with the original.

For authors, an unresolved question is whether AI-generated content should be considered competition for the works used to train these models.

The Law Has Yet To Catch Up

US copyright law predates generative AI by decades, leaving courts to apply old principles to new technology. Questions also remain over copyright protection for AI-generated works. In Thaler v. Perlmutter, a court ruled that material created entirely by AI cannot receive copyright protection.

Major AI companies remain involved in copyright litigation, and different courts could reach different conclusions. For now, there is no universal rule: the legality of AI training will depend on the circumstances of each case and how courts ultimately interpret copyright and fair use.

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