They raised $588m across rounds in 2019 and 2021. For a company founded in 2005. They’ve started doing something that’s burning A LOT of cash and I didn’t find public product direction that explains it (in only 20 minutes of googling tbf).

Dwindling runway as a theory to explain squeezing WPE and Matt’s public communications is getting harder to ignore.

Matt has stated in a recent Slack conversation that Automattic is doing great financially.

Has anybody credible made that claim though?

The only rational reason to lay off 159 employees and demand millions of dollars from your competitors, ruining your reputation in the process and losing all your customers, is if not doing that results in an even worse outcome.

You begged the question of whether this is rational and I think it’s worth considering that it isn’t. It would not be out of character with other middle-aged guys making bad decisions because there’s something else going on in their life which they don’t control and so they’re going to flex their power where they can – Musk appears to have flushed tens of billions of dollars on Twitter in no small part because his daughter isn’t a robot he can control – but an even simpler explanation I’ve heard is that MM simply hadn’t had anyone tell him no about his business in decades and has gotten used to it. That’s not uncommon for CEO-types in unregulated industries and can be particularly bad if paired with an unwillingness to recognize that you’re making a mistake.

I think we're far past rational behavior

I mean, that's the question.

Is this Matt being a mercurial, megalomaniacal jerk, or is there some darker motivation that makes his behavior here borderline-rational?

It kinda doesn't matter, but it would be interesting to know. OTOH, I'm well past being surprised when some super wealthy tech bro shows his ass, so...

They most certainly did not do a lay-off. Private companies in financial trouble don't do voluntary buy-outs. The "demand for millions of dollars" also explicitly stated "or equivalent investment in WP".

I guess you shouldn't let facts get in the way when you're pushing a narrative...

If they were strapped for cash, they would’ve made the severance amount much lower.

Unless the lack of cash is expected to manifest 6 months in to a very costly and lengthy lawsuit.

All of Matt's discourse suggests that there will be no settlement because he sincerely believes (in the face of all released evidence) he's in the right, so this very well could be them preparing for the long haul.