OpenAI, the company behind ChatGPT, is apparently thinking big. Really big. According to Reuters, citing The Information, the AI startup has been holding early conversations with investors about raising as much as $100 billion at a valuation of roughly $750 billion.

From $500 Billion to $750 Billion in Months

If this funding round actually happens, it would represent a sharp leap from where OpenAI stood just a few months ago. Back in October, the company was valued at $500 billion when current and former employees sold approximately $6.6 billion worth of shares to investors. That deal included backing from SoftBank Group (SFTBF), Thrive Capital, Dragoneer Investment Group, Abu Dhabi-backed MGX, and T. Rowe Price.

That earlier valuation already made OpenAI the world's most valuable private startup, surpassing even Elon Musk's SpaceX. Now the company is looking to push even higher.

A Trillion-Dollar IPO on the Horizon?

But wait, there's more. While OpenAI pursues this private funding round, it's simultaneously laying the groundwork for what could be one of the largest initial public offerings in history. Microsoft Corp. (MSFT), a major backer of OpenAI, is watching closely as the company reportedly prepares to file with U.S. securities regulators as early as the second half of 2026.

The potential IPO valuation? A cool $1 trillion. That would put OpenAI in rarefied air, competing with the market capitalizations of tech giants that took decades to build.

Amazon Enters the Picture

As if a $100 billion fundraise and a potential trillion-dollar IPO weren't enough to digest, OpenAI is also reportedly in discussions with Amazon.com Inc. (AMZN) about a possible investment exceeding $10 billion. These talks apparently include more than just a capital infusion. The two companies are exploring the possibility of OpenAI using Amazon's artificial intelligence chips, adding a strategic technology partnership to the financial arrangement.

OpenAI did not immediately respond to requests for comment on any of these discussions.

For context on the broader tech landscape, Microsoft currently shows a positive long-term outlook despite some near-term headwinds, reflecting the mixed sentiment surrounding AI investments and their eventual payoff.