According to Jermaine Dupri, he was the one really living that life and not Jay when they recorded Money Ain't a Thang.
In the year 1998 I'm sure JD had way more money than jay-z. But jay still wasn't broke though, especially not in 98, see unlike other rappers he owned part of the label his 3 albums released on, not that fake ownership.
Jay came into the game with money (which his peers have all vouched for) that's what made shyt like dead presidents and imaginary player even funnier.
"You got show dough, little to no dough,
Sell a bunch of record and you still owe dough"
"I got bail money, XXL money
You got flash now but time will reveal money"