The 33-Hour WordPress Coup: $8 Million, Two Executives, and One Very Confused Pirate

I've been trashing WordPress for years. Security vulnerabilities, plugin nightmares, architectural nonsense. The whole platform is a hot mess.

In fact, on September 16, I published an article titled PSA: Get Your Business Off WordPress. As it turns out, that was the exact same day TechCrunch published a story about two Automattic executives who had apparently managed to turn a 33-hour corporate coup into a potential $8.15 million payday.

And folks, I have to admit something. For the first time in years, WordPress has produced something I genuinely enjoyed. Let me explain.

On September 9, the board of Automattic, the company behind WordPress.com, voted to put founder and CEO Matt Mullenweg on a paid leave of absence.

They installed CFO Mark Davies as interim CEO. Matt was out. Corporate coup. Mission accomplished.

Except for one tiny detail.

Matt reportedly controlled 84% of the shareholder voting power. Which meant the board had essentially staged a revolution against a guy who owned the revolution.

Whoops.

Thirty-three hours and twenty minutes later, Matt was back. The board was out. The executives involved were out. And somewhere in that brief window of corporate musical chairs, things got spectacularly entertaining.

According to TechCrunch, Davies and chief legal officer Andy Missan had signed severance agreements for each other. Not ordinary severance agreements, either. A year's salary. Accelerated equity vesting. Additional health coverage. Combined potential value: $8.15 million.

These guys essentially took control of the company for lunch, signed each other's golden parachutes, and got fired before the weekend. That's not a corporate takeover. That's a Groupon for executive compensation.

Now, to be fair, whether those agreements are ultimately enforceable is another question. Automattic was reportedly examining its legal options. But the sheer comedic engineering involved is magnificent.

And Matt?

Matt returned to the company Slack announcing he was a pirate now, started swearing after decades of apparently avoiding profanity, and when reporters asked him to explain what had happened, he published a blog post about buying a houseboat. A houseboat.

I couldn't make this stuff up if I tried.

Look, my position on WordPress hasn't changed. I still wouldn't recommend building critical business infrastructure on it. Between its security baggage, dependency headaches, and increasingly bizarre governance, there are better options. But I also believe in giving credit where credit is due. And somehow, the company that spent years making me miserable with software updates has finally delivered an update I can enthusiastically endorse.

A 33-hour coup. An $8 million potential parachute. A pirate CEO shopping for a houseboat.

Thank you, WordPress.

I still wouldn't use your platform. But I would absolutely watch your sitcom.

Sources: TechCrunch's investigation into the severance agreements and reporting on Mullenweg's return.

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Rich Washburn is a technologist, strategist, and Founder & Chief AI Architect of ARIA AI Labs, working at the intersection of AI, infrastructure, communications, and capital. He also serves as Managing Partner and Chief AI Officer at Eliakim Capital.