The inherent optimism of entrepreneurs makes thinking about things that mitigate the effect of failure not that unpleasant. In a career in accounting, you are likely to see many deals that don’t work out, so it’s best to remember anything that will lessen the pain. Section 1244 is such a provision. Section 1244 allows what would otherwise be a capital loss to be treated as ordinary. Its significance has been somewhat diminished, but every little bit helps.

Lessons Learned from the Tax Court: An Olive Branch in Tax Court
“Everything is deductible until the audit” is an adage frequently repeated in the tax preparation industry. Generally, it’s mentioned tongue-in-cheek, but today’s taxpayer (and her tax pro boyfriend) may have taken it a bit too literally. Additionally, cutting corners may seem like a time-saving strategy in the moment, but the potential to backfire can’t be ignored. In this case, the taxpayer is about to learn things the hard way.


