Scenario: You have won the Mega Millions, leaving you with a lump sum of $100 million after taxes. (The original jackpot would have been around $400 million.) What do you do?
I know exactly what I'd do.
For one thing, Invicta Studios would become a real thing. We would do the radio show for real, as a podcast, with professional production. Plus we'd film videos and short films for upload to our website, YouTube channel, etc. It would be AWESOME. Basically just like you'd imagine I'd make Invicta if I could simply will it to exist in real life. Nas, KB, Thrash, Phate, and whoever else wanted to come work for me would be welcome. Just be aware that would mean moving to Massachusetts. Because we'll be doing it here. In this house, in fact. I plan to work from home. 
There's a pool:
Which will naturally be clothing-free. Note I did not say clothing optional. You wanna swim, you get nekkid.
I figure we turn this into the recording studio:
I would do other stuff, too. I'd set up a charitable foundation, the Stafford Foundation, which would focus on issues of education and opportunity. I'd make sure my friends and family were taken care of, which in most cases would mean paying off people's houses, paying for their kids' educations, etc. Much of mine and the Foundations' money would be invested in socially-responsible portfolios; I have a very close friend whose brother-in-law specializes in just such matters. Likely I would have some kind of vacation property in addition to the house above, but probably not right away. I'd do a lot of traveling.
Invicta would be a vanity project, essentially, but fuck it; at $100 million I could afford it. Let's say I spend $1 million for a kick-ass recording studio/production setup, which is a shit-ton. We could have an amazing setup for a quarter of that. But let's say I spend a million on it, just go all out. A studio of that quality could probably attract professional clientele and generate revenue, but that's beside the point. I wouldn't want to rent it out.
So we've got a million-dollar studio for Invicta Radio, or whatever we decided to call it. Hell, maybe we just stick with Jorost & Friends. Now let's say I take on enough staff to have around $300-500 grand a year in staffing (say six of you at $50 grand apiece plus associated benefits, etc.). I could still afford it. Even in a bad year, the money I'd have invested would be bringing in something on the order of $3-4 million, all taxed at the virtually nonexistent capital gains rate. In a good year it would be a lot more. Plus a lot of the money Invicta "lost" me could probably be written off in taxes. So fuck it, what do I care? And frankly with that kind of equipment and manpower we could generate some seriously good stuff. I bet we could even make money on it. Maybe even get a real-life show.
So, bottom line, if Jorost wins the lottery, EVERYBODY wins.