The Biggest Check Ever Written

Last week we talked about Anthropic. So it’s only fair that this week we turn to OpenAI, which (like most weeks over the past year) has been back in the headlines.

But even by their standards, this was a big week.

OpenAI just closed the largest private funding round in history. $122 billion at a post-money valuation of $852 billion (…that's almost a trillion dollars). 

The round was co-led by SoftBank, Andreessen Horowitz, and D.E. Shaw Ventures. Amazon committed up to $50 billion. Nvidia threw in $30 billion. SoftBank another $30 billion. Microsoft participated too, on top of the $13+ billion they've already put in. And for the first time, OpenAI opened the round to individual investors through banks, raising about $3 billion from retail.

On the demand side, the numbers are pretty staggering. ChatGPT now has over 900 million weekly active users, more than 50 million paying subscribers, with revenue running at $2 billion per month, and they did $13.1 billion in revenue in 2025.

But despite all this, they're still not profitable.

Right before this mega-round, OpenAI shut down Sora, the AI video generation app that let users upload their faces into AI-generated scenes. Remember when that was everywhere? (We know we have some readers who will be devastated about this one… you know who you are.)

Sora was a flop. Usage peaked around 1 million users, then dropped below 500,000. Meanwhile, Sora was burning roughly $1 million per day in compute. Every playful video was eating up AI chips that OpenAI needed for products that actually make money. And while OpenAI was burning cash on video clips, competitors like Anthropic were winning over software engineers and enterprise customers. Sora was a money pit and a distraction.

This is where things get interesting for people who actually use these tools (i.e., you).

OpenAI is going all-in on what they're calling the "SuperApp." The idea is to merge ChatGPT, Codex, and their agent-based tools into a single system; one interface that understands what you're trying to do and executes work across your entire workflow.

Here’s what this means practically: right now, you might use ChatGPT for writing, a separate coding tool, and a separate agent for tasks. OpenAI wants all of that living in one place. Regardless of whether you’re a consumer or an enterprise, you ask it to do something, and it figures out which tool to use under the hood.

If OpenAI can pull it off, the lock-in is massive. Higher revenue per user, deeper data-network effects, and a switching cost that makes it hard to leave. That's the pitch to investors that justifies their $852 billion valuation.

There is obviously massive execution risk. Building a SuperApp is one of the hardest things in tech. And there's a real question about whether regulators will let one company consolidate that much AI capability into a single product.

In the same week, OpenAI also bought a talk show. (We told you it was a big week.) 

TBPN (Technology Business Programming Network) is a daily three-hour live tech show hosted by founders John Coogan and Jordi Hays. Think of it as SportsCenter for tech. They've had Zuckerberg, Nadella, Benioff, and Altman himself on the show. It's on track to do over $30 million in revenue this year.

This is OpenAI’s first media acquisition.

Here’s their official PR party line: TBPN has great "comms and marketing instincts" and will help OpenAI explain AI to the public. The show keeps its brand, keeps its editorial independence, keeps choosing its own guests.

Here’s a twist… TBPN will sit under OpenAI's strategy team, reporting to Chris Lehane, who is a political operative known for aggressive message management. This is happening right as OpenAI faces growing backlash over defense contracts, political influence, and the QuitGPT movement.

So a soon-to-IPO AI lab (valued at $852 billion) is acquiring the tech show that covers it and its competitors, and placing it under its political strategy arm… a bit “sus,” as they say.

Sam Altman says he doesn't expect easier treatment. He joked he'll "help enable" their criticism with his "occasional stupid decisions."  But the optics are hard to ignore.

Let’s zoom out for a minute. Here's what OpenAI did this week:

That's a company clearing the decks.

The question is whether the SuperApp vision is real or whether it's the kind of thing that sounds great in a pitch deck and falls apart when actual users need it to work across ten different tools on a Tuesday morning.

We'll find out. But one thing's clear, OpenAI is building a machine around AI: the capital, the narrative, the distribution, the lock-in.

Whether that machine runs or stalls is the trillion-dollar question.

Stay curious,

Julia & Russell