Andy Weiner was quoted in a Bloomberg Tax article titled “Bees and Bonus Depreciation: How to Get Creative With Your Taxes.”
The article explores unusual tax strategies that can come with unusual businesses and side hustles, such as beekeeping, and the unorthodox bets taking place on alternative sports betting platforms. Passage of the One Big Beautiful Bill Act (OBBB) in 2025 has given rise to lots of unconventional tax planning strategies.
While these exotic tax strategies may sound appealing, Andy stresses the importance of keeping accurate records that help prove your intent, transaction history, and more.
"Anyone undertaking an unusual strategy should keep good records and ensure they can substantiate asset valuations, business use, and costs," Andy said.
The article warns that traditional tax strategies, such as bonus depreciation of assets, tax implications of gambling winnings or losses, and even agricultural land classifications, are being used in novel ways that may draw more scrutiny from the IRS.
For example, most alternative betting gains and losses don't get the same tax treatment as gambling winnings. Gambling winnings are taxed at the ordinary rate and gambling losses can only be deducted up to 90%. Alternative wagers and prediction market activity may qualify for long-term capital gains rates and preferential capital loss treatment worth up to $3,000 per year without requiring the taxpayer to itemize. However, the IRS may still clarify how alternative betting activity must be classified and reported. The article advises taxpayers to retain all documentation from their activities on these platforms, including transaction histories.
Although these unusual tax strategies gained a boost under OBBB, Andy stresses caution because the IRS will not be under-resourced forever. “As quickly as things change from a year and half ago, that can swing the other way,” Andy said.
Read the complete article at Bloomberg Tax here.
About Andy
Andy focuses his practice on tax controversies, both civil and criminal, at all stages of the administrative and judicial process. A former U.S. Department of Justice attorney, he has argued approximately 50 tax cases in the U.S. courts of appeals. He is a frequent writer and speaker on tax issues and a regent of the American College of Tax Counsel for the D.C. Circuit.
