Did OpenAI really “raise” that much? The startup world is not my area of expertise but I remember reading language in the announcements that implied those dollar amounts where more of a conditional promise of money in the future instead of a check today.

Yeah if they sold 1/800th of the company for a billion dollars then they are valued at 800b even if they only have a billion dollars. It’s advantageous for investors to both buy in as cheaply as possible but also have future investors to buy in as expensive as possible to prop up a, perhaps inaccurate, valuation.

It's a valuation, not the amount they raised.

It's raised in the sense that some people made a pinky promise to give them cash. But those people also don't have the money and have to raise it from other places. It's largely SoftBank, Oracle, Microsoft and Nvidia, all of whom don't have big piggybanks full of hundreds of billions. They ask for loans based on the promise of making cash to pay for it, and that cash is based on people wanting to use OpenAI. So it's kind of a big financial circle jerk. (Debt, SPVs, loans from Nvidia (at high interest rates), etc)