Concerning is not just the things he's said, but what he has done that go along with this. Self-dealing? Improper tax accounting?
If there is insider inurement, the IRS fine is directed to the Board of Directors (each one of them, however many) for 25% of the value of the benefit. If they do not pay in a timely manner, the bill is 200% of the inurement. Matt is the ultimate insider, "giving" the valuable trademarks to the foundation and then getting to use them for free, while leaning on other companies to pay millions. So the insider inurement is in the millions of dollars, per year, for years. Those two unknown board members of the WordPress Foundation? I hope they have great tax lawyers!
[1] https://www.mercadien.com/resource/steep-penalties-for-exces...