01
Your biggest deal is not taxed like your game checks
Dana signed a two-year, $520,000 endorsement contract, the biggest of her rookie year, with a $60,000 signing payment the week she inked. Her lawyer reviewed the image-rights clauses. Nobody reviewed the payment terms. The agreement named Dana personally, not her S corp, so every payment ran through her SSN as sole proprietor income: full self-employment tax, no salary and distribution split. The following April she owed an extra $61,000 she had not budgeted.
Do this today: Before your next deal lands, check whose name and TIN are on the payment terms, the W-9, and the first payment. All three must be the entity.
Dana's endorsement deal, as the IRS saw it


