TheOneWithTheHair

Roll20 appears to be a privately held LLC.

https://help.roll20.net/hc/en-us/articles/360037254274-About-Roll20-LLC

Source: https://blog.roll20.net/posts/roll20-has-acquired-demiplane/?_hsmi=310100938

"We’re excited to announce that Roll20 has acquired Demiplane, the best-in-class character-building solution for tabletop roleplaying games! Demiplane joins a growing suite of TTRPG (tabletop roleplaying game) offerings from Roll20 that include Roll20 Tabletop, DriveThruRPG, and Dungeon Scrawl."

I suppose "hand over fist" is a subjective term, but you don't acquire companies for free.

DriveThruRPG (which merged with Roll20 in 2022) according to https://www.wargamer.com/dnd/roll20-buys-demiplane

Roll20's making some cash to keep their payroll* and purchase other companies.

*the business running

It has merchandised in the past with some success.

Back when TSR was sold out from under Gygax's clutch, Lorraine Williams tried some similar marketing, there was a beach towel with Dungeons and Dragons' red dragon in this design:

Only as I recall it, the lettering and dragon were pink. I have never seen it posted online, and I didn't buy one*. I don't know that many sold.

*Of course there was this whole Satanic Panic back then, and why would anyone want to advertise they played D&D at a pool where likely everyone would have given you a bunch of crap for playing "the Devil's game"?

After seeing Forbes write about D&D on multiple occasions, years of RPGs in video games, 50 years of RPGs being in society, a successful movie, and absurdity of the 80s situation gone, it could work now.