I read a book by Bob Weir which stated that the Grateful Dead didn’t begin paying taxes until the 1990’s ,, they pooled all the income , distributed it and since there was nothing left there was nothing to pay taxes on!!!
In the 60s, at least, the Dead owed Warner Brothers Records enormous amounts of money.
They pooled income and distributed it all? To whom? The members of the group? In that case each individual member of the Grateful Dead would pay taxes on their share of income, even if the Grateful Dead as a business entity didn’t have any income to be taxed.
That’s really not that uncommon in the music biz, especially back in the day. Record companies pay the bills and put it on the tab, along with studio and touring costs, and give a cash stipend. The band is selling millions of records but they owe millions to the record company. On paper they’re broke and losing money. If they leave they’ll be bankrupt.