I imagine the answers would be,
wp.org needed to be a charitable foundation, and the code separate, for it to have gotten the wide spread adoption that it saw and for hosting companies to be so willing to offer up one click instal and larger publisher adoption ect. They would of seen a direct relationship to a for profit as a threat
or
we haphazardly juggled trademarks and constantly had to have a team to seek funding for the foundation, with a properly crafted mission statement to hold us accountable that might of been preferable
I did find him on bluesky although looks like he hasn’t been on in a week so probably making an ass of my self by speculating here