I’ve had a lot of fun and done some cool things working at companies that lose more money than they make, but I’m not going to sit here and tell you that it’s the healthiest environment. It is — by definition — an inherently untenable situation, which creates both urgency and nagging sense of existential dread. Maybe you find that motivating (I do, sometimes!), but more often than not I’ve found it eventually lead to paranoia and panic.

Even weirder, success in this world is often more distorting than failure, because it’s so tied to fundraising and valuations. That might seem reasonable enough, until you consider that the first thing is just “someone giving you money with no oversight or rules”, and the second thing is using the first thing as proof that you’re making progress.

I’ve been doing this for a long time now, but I’ve never quite seen an environment like this, where two companies operating entirely inside this sort of business mirror dimension are just throwing billion-dollar-losing haymakers at each other in the hopes of being… declared the winner, I guess?

As of this post in March of 2026, it seems clear to me that Anthropic is clearly winning the perception war. Maybe that’s because they’re inherently less shady (although possibly more fundamentally deluded) than OpenAI, or maybe it’s because they were smart enough to focus on selling to non-users (business people) instead of today’s broke-ass consumers. Or maybe it’s that OpenAI has been around longer, burning money longer, and is simply closer to reaching the logical, obvious end state of a company like this where it starts flailing around and trying to monetize things people only like because they’re free.

Either way, Anthropic is “winning”, and that means OpenAI is “losing”. Are they both losing unsustainable amounts of money? Yes! Are they both relying on fundamental changes to society that don’t appear to be happening yet (mass AI adoption and huge productivity improvements across white-collar work), while ignoring fundamental changes to society that do appear to be happening right in front of us (the internet it needs to function/improve turning into a cesspool of AI spam)? Most certainly, yes!

But… Anthropic is winning, you see. They’re WINNING! Claude is COOL, man! It’s got momentum! Have you made your crappy single page custom notes app, yet?

(Oh, I have.)

Look, a lot of this is fine. Startups need to spend money, take big swings, and figure it out later. I myself have advocated for this many times, in fact. But this whole era is taking the concept beyond even my wild desires for the ambitions of venture backed companies, largely because I never envisioned the entire economy placing one large combined bet on, essentially, one technology spread out among maybe five companies, two of which have never been in the black for one second and have no clear path to ever getting there and seemingly feel no obligation to even consider the issue.

The “winning the narrative” thing is like “winning free agency” in sports. I get where it comes from, and I get why people get excited, and I get the relevance of the challenge on the actual results of the real games that occur several months later. But we give free agency the level of primacy it gets because we’re bored and there are no games at the time. We don’t just replace the season with it. There are actual games to be played that matter way more!

There’s a lot of hand-waving going on with the AI industry, and tech in general right now, for sure. But even when Amazon was sinking money for years and years, they could very clearly and cogently explain that choice to you. The upsides, the downsides, and how if push came to shove they could pivot to making money in a matter of weeks or months.

That’s just really different than where we are now. I kinda think the people in charge know that, but the longer this goes on, the less sure I am about it, and the less confident I am in any kind of graceful landing here.