By Titik Puspa 
Boston, MA | June 9, 2026
The landscape of venture capital, once defined by strict allegiances and the unspoken pact between investors and the companies they back, is undergoing a seismic shift. As artificial intelligence powerhouses OpenAI and Anthropic are poised to finalize staggering funding rounds – OpenAI reportedly on the cusp of an $100 billion deal and Anthropic recently closing its own monumental $30 billion Series G – the traditional notion of investor "loyalty" is rapidly dissolving, hanging precariously by a thread. This phenomenon is vividly illustrated by the growing number of direct investors simultaneously backing both OpenAI and Anthropic, two of the most formidable competitors in the generative AI race.
Anthropic’s recent $30 billion funding announcement, which valued the company at $380 billion post-money, revealed a striking list of its backers. At least a dozen entities that are also prominent investors in OpenAI were publicly declared as supporters of Anthropic. This includes venerable venture capital firms such as Founders Fund, Iconiq, Insight Partners, and Sequoia Capital. This widespread participation in both camps raises fundamental questions about the future of investor commitment and the ethical considerations that arise when firms fund direct rivals.
While some overlapping investments might be more readily understood within the context of large hedge funds or asset management firms like D1, Fidelity, and TPG, whose primary focus often remains on public market investments, even these represent a departure from established norms. These entities, by their nature, often manage diversified portfolios that can span across entire industries, making simultaneous investments in competing public companies a more common, albeit still scrutinized, practice. However, the situation becomes far more complex when venture capital firms, traditionally more hands-on and strategically aligned with their portfolio companies, begin to straddle the lines so starkly.
One particularly eyebrow-raising development within Anthropic’s funding round was the participation of affiliated funds of BlackRock. This is especially noteworthy given that Adebayo Ogunlesi, a senior managing director and board member at BlackRock, also holds a seat on OpenAI’s board of directors. In the intricate world of institutional investment, it is acknowledged that BlackRock, managing a vast array of funds including mutual funds, closed-end funds, and ETFs, will likely seize opportunities to invest in a high-growth asset like OpenAI stock. This pragmatic approach often prioritizes financial returns for their diverse investor base, sometimes superseding the personal associations or strategic implications of individual board memberships.
The entanglement of BlackRock’s investment arms in both OpenAI and Anthropic underscores a broader trend of strategic hedging by major players. The well-documented, and at times strained, relationship between OpenAI and Microsoft serves as a prime example of this. Microsoft, a significant investor in OpenAI, is also reportedly exploring deeper ties and investments in other AI ventures, including Anthropic, to mitigate risks and ensure access to leading AI technologies. Similarly, Nvidia, a crucial hardware provider for AI development, is navigating a complex web of relationships, investing in multiple AI labs to secure its position in the ecosystem.
However, the traditional operational model for venture capital funds has historically differed significantly from that of broad-based asset managers. Venture capital firms typically market themselves as deeply committed partners to the startups they invest in, emphasizing their role as "founder-friendly" and "helpful." This ethos is built on the premise that by taking an equity stake, VCs will actively contribute to a startup’s success, offering strategic guidance, operational support, and crucial network access. A core tenet of this relationship is the implicit understanding that VCs will champion their portfolio companies, particularly in their competitive battles. When a venture capital firm holds significant stakes in both OpenAI and Anthropic, the fundamental question arises: to whom does their ultimate loyalty belong, beyond their own limited partners?
The unique nature of private company investments exacerbates this dilemma. Startups, by definition, are private entities that share sensitive, non-public information regarding their business status, strategic roadmap, and technological advancements with their direct investors. This confidential data, often crucial for competitive strategy, is not publicly disclosed in the same manner as information from public companies. Furthermore, venture capitalists frequently take board seats in their portfolio companies. This position carries a significant fiduciary responsibility, a legal and ethical obligation to act in the best interests of the company and its shareholders. Investing in direct competitors while holding board positions creates an inherent conflict of interest, potentially compromising the integrity of decision-making and the confidential information shared.
The current scenario is made even more compelling by the background of Sam Altman, OpenAI’s CEO. Altman himself hails from the venture capital world, having served as the president of Y Combinator, one of Silicon Valley’s most prestigious accelerators. He is intimately familiar with the dynamics of the VC ecosystem and the expectations of founder-investor relationships. In 2024, reports emerged that Altman had provided his investors with a list of OpenAI’s perceived rivals, explicitly advising them against investing in these companies. This list reportedly included ventures launched by individuals who had departed OpenAI, such as Anthropic, xAI, and Safe Superintelligence.
While Altman later denied that he had issued an outright ban on investors backing his list of rivals, threatening exclusion from future OpenAI funding rounds, his statements did acknowledge a nuanced position. According to documents surfaced during the lawsuit between Elon Musk and OpenAI, and reported by Business Insider, Altman admitted that if investors made "non-passive investments" in OpenAI’s competitors, they would forfeit access to OpenAI’s confidential business information. This revelation, though framed as a data access issue rather than a direct investment prohibition, highlights Altman’s awareness of the delicate balance and the potential for conflicts.
The sheer scale of the current AI boom is undoubtedly a significant contributing factor to this erosion of traditional VC norms. The record-breaking sums being raised by leading AI labs are a testament to the unprecedented growth and the immense data center infrastructure required to power these advanced models. When faced with opportunities that promise astronomical returns and address such colossal market needs, the pressure to participate becomes immense. For many investors, the potential upside of being involved in the next frontier of technological innovation may outweigh the traditional concerns about backing competitors.
However, it is important to note that not all venture investors have fully embraced this new paradigm. Some prominent firms are still adhering to more traditional investment strategies. For instance, Andreessen Horowitz, a major backer of OpenAI, has not, to date, publicly announced an investment in Anthropic. Conversely, Menlo Ventures is a known investor in Anthropic but has not been reported as a direct investor in OpenAI. This selective approach suggests that while the trend of dual investing is growing, it is not yet universal, and many VCs are still navigating the ethical and strategic complexities with caution.
In an admittedly not exhaustive review, the current landscape reveals approximately a dozen investors who appear to have made direct investments in either OpenAI or Anthropic, but not both. This includes firms like Bessemer Venture Partners, General Catalyst, and Greenoaks. It is worth noting the difficulty in compiling such a definitive list. For instance, initial attempts to have an AI model like Claude identify these dual investors yielded a list with a significant number of inaccuracies, underscoring the evolving and sometimes opaque nature of these investment strategies, and perhaps the current limitations of AI in fully grasping the nuances of complex financial and ethical relationships.
Nevertheless, the fact that established and respected firms within the venture capital community, such as Sequoia Capital, have chosen to invest in Anthropic, despite its direct competition with OpenAI, is a significant development. As previously reported, this move by Sequoia has been described as breaking a long-standing taboo in venture capital. When queried about the implications, one investor, who preferred to remain anonymous, simply remarked that as long as the firm in question does not hold a board seat in both competing companies, the perceived harm is minimal. This perspective suggests a shift towards defining conflict of interest more narrowly, focusing primarily on direct control and access to proprietary information through board representation.
Despite this evolving perspective, the implications for founders are substantial. The traditional investor playbook is being rewritten in real-time. Founders embarking on fundraising journeys must now add conflict-of-interest policies to their list of due diligence items when evaluating potential investors. Understanding who else an investor backs, particularly in competitive markets, is no longer a peripheral concern but a critical factor in ensuring strategic alignment and safeguarding proprietary interests. The era of unquestioned investor loyalty is over, replaced by a more pragmatic, and perhaps more challenging, landscape where strategic diversification and return maximization often take precedence. The race for AI dominance is not only a technological and capital-intensive battle but also a profound test of the established norms within the venture capital industry.