Dave Ramsey Screams as Larry Kicks Oracle’s Cash-Flow Can to the 2030s With a YUGE $50B AI IOU

Dave Ramsey: Let me get this right. Your stock is down 50% from its all time highs… you and your son have embarrassed your family name with your never ending pursuit of Warner Bros… and now your company’s projected AI cloud profits, whatever that is, are getting pushback as just a bunch of smoke and mirrors?

Caller: Yes, that’s right Dave.

Dave Ramsey: And you think the best decision right now is to put $50B on a credit card to build even more infrastructure even though you’re cash flow is already negative likely through 2030?

Caller: Yes, that’s right Dave…

Oracle’s stock is up 5% today after Larry Ellison announced plans to raise $45-$50 billion next year to keep feeding the AI data-center beast. Which is a normal sentence in 2026 and not at all something that would’ve gotten you escorted out of a boardroom ten years ago.

Let me translate for you what actually happened. Oracle looked at its balance sheet, looked at the AI arms race, looked at its free cash flow falling into a deep, dark hole… and said: run it.

More specifically, the money is earmarked for building out more cloud and data-center capacity to meet already-contracted demand from customers who are very serious about AI and very impatient about waiting for servers (read: Nvidia, Meta, OpenAI, AMD, TikTok, xAI).

These aren’t moonshot guesses. These are contracts that are signed and inked. “Please don’t make us wait six more months” types of deals. Oracle isn’t building castles in the metaverse… it’s pouring concrete because the tenants are already pacing outside.

(Source: Marketwatch)

And yes, half of this raise is expected to come from equity. Dilution. The thing investors usually hiss at like vampires seeing sunlight. But in this case, Wall Street actually liked it. Why? Because issuing stock sends a very specific message: we care about our credit rating and don’t want to lever ourselves into oblivion chasing GPUs.

The other half comes from debt… because of course it does. Oracle already sold $18B in bonds recently, and this next round is shaping up to be one of the biggest corporate bond offerings in years. Banks are lined up. Fees will be collected. Spreads will be debated. Everyone will pretend this is totally fine.

That said, here’s the catch… Oracle’s free cash flow is negative and expected to stay that way for years. Its stock is still down roughly 50% from its peak, and the company has become a weird proxy for whether the AI spending boom turns into a gold mine… or the most expensive overbuild since telecom fiber in the early 2000s.

(Source: Inc. Magazine)

Add in the small detail that one of Oracle’s biggest customers (OpenAI) is not profitable, and suddenly the phrase “contracted demand” comes with an asterisk and a raised eyebrow. 

Also, let’s not play dumb here. Dropping a massive capital plan on a Sunday afternoon isn’t typical behavior for a mature company unless management is trying to stop the narrative from getting worse before Monday’s open. In my opinion, this move looks like an attempt to give investors something (anything) to cling to other than the cold hard reality.

For now, it worked. The stock popped, sentiment stabilized, and Oracle bought itself a little breathing room.

But none of this answers the big question. It just delays it.

At the time of publishing this article, Stocks.News holds positions in Meta as mentioned in the article.