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Automattic were an early investor in WPEngine, but they exited the investment around 2018.

Thanks.

2018 would tie in with about when I first got the impression he was not a fan of WP Engine. I'm sure there was fuss once before (about them not being on the "recommended hosting" page?)

That's when they were bought by private equity. So there was a big fuss about that.

Automattic made an investment in WP Engine in 2011:

https://wptavern.com/automattic-makes-second-investment-wpen...

Automattic invested in WP Engine ~13 years ago. I don't know if they still own the shares though.

https://techcrunch.com/2011/11/15/silverton-automattic-put-1...