Microsoft emails revealed skepticism about OpenAI in 2018

Court documents from the lawsuit between Elon Musk and Sam Altman revealed letters from Microsoft executives: in 2018, they were skeptical about OpenAI, but simultaneously feared losing the company to Amazon.

What the Letters Revealed

Microsoft's letters from 2018 reveal an ambivalent attitude toward OpenAI. The company's top executives openly expressed doubts about Altman's strategy and the potential of language models. However, in the same correspondence, there is visible a risk that concerned them even more: if Microsoft withdrew from cooperation, Amazon could seize the growing project and become the main beneficiary of the AI revolution. This dilemma—between skepticism and fear of loss—determined the company's subsequent tactics. The letters reveal the internal contradictions of a major tech giant facing uncertainty.

The 2018 Context: Why the Doubts

At that time, OpenAI did not appear to be such an obvious bet. The company had existed for only three years, with no clear commercial products. Sam Altman had led the organization for less than four years, and his vision of the AI future did not inspire enthusiasm across all corners of the tech industry. Mass interest in language models would only emerge with the release of ChatGPT in 2022.

By 2018, the competitive landscape looked quite different:

• Amazon had already established itself in cloud and AI through AWS
• Google was actively developing TensorFlow and its AI researchers
• Facebook was investing in its own neural network projects
• Microsoft held a timid position in the AI race, despite investments in Cortana
• The success of new technologies was difficult to predict in advance

In this context, Microsoft's doubts sound logical: a startup without a proven business model, high operating costs, market not ready. But the letters show that managers who didn't believe in OpenAI feared something even more—that a competitor would create a monopoly.

From Skepticism to Investments

Paradox: despite written doubts, Microsoft did not abandon its work with OpenAI. Instead, the company gradually increased its presence. In 2019, an investment of $1 billion followed, then a series of new rounds. In 2023, Microsoft announced investments of over $10 billion in developing its partnership with OpenAI. The strategy worked brilliantly. Today, Copilot is embedded across Microsoft's entire office ecosystem, Azure OpenAI Service has become a powerful competitive advantage, and Altman and his team have reconceived the possibilities of large language models. What looked risky in 2018 became the most successful AI bet in history.

What This Means

The Microsoft and OpenAI story is a lesson about the difference between rationality and intuition. Internal skepticism was reasonable: the vast majority of startups fail. But the strategy of "invest to avoid losing" proved wiser. For other companies, the simple takeaway: sometimes you need to act against internal doubts if the risk of loss outweighs the conviction of failure.