I would’ve thought that this could be quite simple.
A few flights in a private jet, or long-term purchasing for the whole month to take you wherever you want.
Several $250k-500k cars in each location to take you wherever you want
A private show from a famous band can set you back a few million. Do this each day.
Go to Vegas and get in a pissing content with some rich cunt where you send expensive drinks to each others table, until one folds. That’ll be a few million each night.
Trump spent a ton on sex, so high class hookers?
A few ads across multiple providers to promote something
Prize fights can be set up quickly, and have the best in combat sports ready in 30 days. Offer $1m per division for the winner, and do it across maybe 4-5 sports, pay for TV and streaming, set up a venue, and you’ll probably blow through it all.