The case: B, a self-employed, serviced the entertainment business. He reported income and expenses on one Sched. C. The IRS denied many of his deductions for lack of proof.

Held: For the IRS. The taxpayer admitted his recordkeeping was scanty. He produced PayPal receipts to support deductions for advertising, depreciation, legal and professional expenses, and many "other expenses"—no supportive invoices, receipts or similar records.

The PayPal receipts substantiated only the amounts, vendors paid and dates of payment—not that the expenses were ordinary and necessary for operating the business.

Crucial missing details: exactly what was purchased and how it was used in one of the businesses. The court found the records insufficient, even for estimating the amount of allowable expenses. The deductions were denied and accuracy-related penalties were imposed.

[Bridges v. Commissioner, T.C. Summ. Op. 2021-16]