Personally purchasing buildings to rent out to the We company definitely crosses some lines. Same with purchasing the “We” brand which he generously licensed to WeWork for some $5 million.
That was known and the board allowed it. I am on the fence about this because this kind of fraud is team effort. The board and the investors avert their eyes for things that are unethical or even illegal because the "founder" is the golden goose that can do no wrong. They also seem to like being lied to.
"Due diligence" is a dirty phrase in that world. They are geniuses, man. Movers and shakers!
I see no reason to assume what someone was or was not thinking in this case. Both parties had sufficient resources to do due diligence, and both parties engaged completely voluntarily under zero duress.
Only if you view rules as pointless adversaries to be beaten. But often rules exist for good reasons to keep people safe and keep interactions fair and trustworthy.
Bending rules isn't something that you should take inherent pride in, and personally, it always lowers my opinion of such people.
Self dealing is very much breaking the rules. Sure, maybe the powers that be let it slide, but it is not playing fair.
Edit: in fact, when the musical chairs stopped and the IPO failed, there were lawsuits about the self dealing. So long as people were making money the board were willing to look the other way.