When this thread was started, he was 100% self-funded and just grifted his audience for pennies at a time. He'd get $10, try to make it last, lose it in minutes.
At some point (I take credit for this) he started blowing up and then e-casinos started giving him play money. He does sometimes take out money. He may spend a couple hundred dollars a month on vanity items, like sneaks, or a bong, or some streaming equipment. Just a couple times a month, tops. He's also bought PMs a few times.
However, the main reason he will take money out is to pay back loans from juicers he knows. And these loans he takes out are almost always informal liens against his income from streaming. He does genuinely have thousands of subs giving him thousands of dollars a month. If he just took the Twitch/Kick sub money and gave that to his dad, his family income would probably double - it's seriously between $5 and $15 thousand a month. Instead, he takes cash advances and pays them back.
So even though Boss does sometimes cash out, the fact is he still generates actual income from his audience, and almost all of that goes into the casinos too. They can give him thousands of dollars a day and they still are making all that back, then some.
It's really a marvel.