The most expensive 33 hours in WordPress history...

Overview

The video reports a dramatic, rapid leadership coup at Automatic (the company behind WordPress.com, Tumblr, and WooCommerce), framed as “the most expensive 33 hours in WordPress history.”

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What happened (timeline and mechanism)

• Earlier in September 2026, Automatic’s board sought to remove founder/CEO Matt Mullenweg via a board vote.
• On the day the vote was set to occur, Matt was away (the video references Burning Man) and returned to find the board intended to proceed within minutes.
• Matt asked for time for his lawyer to review the proposal; the board denied the request.
• The move to oust Matt was carried out by:
  • CFO Mark Davies
  • Board members Sue Decker
  • Board member Anne Dunwy (described in the video as a retired four-star general)
  • Tony Schneider (described as Automatic’s first CEO, and as someone Matt previously praised as a “business soulmate”)

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Why the board move was controversial

The video claims Matt believed the board action was connected to his ongoing legal war with WP Engine, including accusations by WP Engine of evidence destruction.

It also suggests Matt thought WP Engine’s backers (notably Silver Lake, as stated in the video script) may have influenced the board effort.

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Matt’s counter-move: “a pirate” return to control

While away, Matt made pointed communications, including:

• Posting that he would not attend leadership meetings due to an alleged board conspiracy.
• Referencing himself as a “pirate,” including Slack messages about being a pirate after “42 years” without cursing.
• Using Reddit/Slack hints that he could replace board seats because of his controlling stake.

The video asserts Matt effectively could overturn the board decision because he held 84% of Automatic’s voting power.

• After about 33 hours, he returned and announced the board was back in agreement and that he was again in control.

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Aftermath: major financial fallout

The video claims:

• Automatic confirmed Matt was CEO again, but that the entire existing board was gone.
• Matt fired Mark Davies and chief legal officer Andy Massan.
• It alleges Davies and Massan had preemptively negotiated severance deals that included:
  • one year salary
  • one year of health insurance
  • immediate stock vesting
• As a result, Automatic allegedly owes them over $8 million.

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Employee reaction and unanswered questions

• Employees reportedly told TechCrunch they were initially excited when Davies was positioned as CEO.
• The video notes employees still don’t have clear explanations for why the leadership challenge occurred.
• It also describes the public-facing response during the turmoil as confusing—for example, employees waiting for a message and instead receiving unrelated blog content.

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Sponsor/editorial framing

A sponsor segment promotes an AI code-review tool, unrelated to the corporate coup, and is used as a transition before the video concludes the story.

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Presenters / contributors (as mentioned in the subtitles)

• Matt Mullenweg (Automatic founder/CEO)
• Mark Davies (CFO; CEO attempt during Matt’s absence)
• Andy Massan (chief legal officer)
• Sue Decker (board member)
• Anne Dunwy (board member; retired four-star general)
• Tony Schneider (board member; first CEO of Automatic)
• Matt (referred to as founder; also the narrator’s subject of the story)
• TechCrunch (credited source for employee/press comments in the narrative)
• Reptile (sponsor)
• GPile / Gpiles / G (as named in the ad segment; the tool/brand being promoted)
• Axios (mentioned in the sponsor segment)
• T-Rex (feature name in the sponsor segment)
• Slack, Reddit (platforms mentioned in the storyline; cited sources of Matt’s statements, not “contributors”)