I spend a good part of my time advising athletes, talent and celebrities on endorsement deals with brands companies of all sizes and stages of their life cycle, and across many different industries. Over the last few years we've seen various trends come and go very quickly, such as virtual reality (VR), gambling/gaming, cannabis, initial coin offerings (ICO's), non-fungible tokens (NFT's) and crypto, leaving in their wake a number of now-defunct companies, along with tainted reputations for those involved. Many new companies have offered incredible above-market deal terms to lock celebrities in ambassador and endorsement deals — including significant ownership stakes in these companies — in which the endorsers do not fully undertake a deep analysis of the underlying company or the uncertainty of the legal landscape they may stepping in to. 

As this article notes, many celebrities do not properly vet their brand partners, and when it comes to being associated with something like FTX or a situation like the Fyre Festival, the reputational damage is not easy to mitigate. 

Less publicly, we've seen many equity deals structured in tax-inefficient manners that resulted in significant adverse tax results for celebrities, because legal and tax advisors were not consulted.

So, in short, as Taylor Swift does, never leave home without your trusted counsel.