Tax strategy after Tax Day for business owners starts now — not next March, not when your CPA asks for documents, and definitely not after another painful April surprise. If Tax Day kicked you in the cojones this year, you are probably asking the same question a lot of owners ask once the return is […]
AI tax prep risks for business owners are getting harder to ignore. About 25% of Americans say they plan to use AI to help file their taxes this year, which sounds efficient until you remember how quickly things break when a return involves K-1s, 1099s, multiple entities, state issues, or recent law changes. AI tax […]
OBBBA tax changes for business owners are available right now, but a lot of owners still are not feeling the benefit yet. And honestly, that should not surprise anyone. The latest U.S. Chamber Small Business Index shows softer confidence, lower hiring and investment expectations, and inflation still sitting near the top of the worry list. […]
Tax compliance vs tax strategy is the difference between reporting what you owe and changing what you owe — legally — before the year is over. A business owner made $1.2 million last year. His CPA filed everything correctly. Every form. Every deadline. Every dollar reported. He still owed six figures he never saw coming. […]
HSA after death rules are very different from IRA and 401(k) rules. If your spouse is the beneficiary, the account can continue as that spouse’s HSA. If the beneficiary is someone else, the account generally stops being an HSA on the date of death, and the tax result can be much harsher. That matters because […]
A tax strategy for profitable business owners starts with a hard question: if your business did $1 million, $3 million, or $5 million last year, where did that money actually go? After payroll, overhead, and taxes, how much did you actually keep? And of what you kept, how much is working for you right now […]
If you're thinking about selling a property, you probably know capital gains tax may be coming. But depreciation recapture on a rental property sale is the second bill that catches a lot of sellers off guard. Most people are planning for one tax hit. Then they find out the federal tax math is doing something […]
$400,000. Same money. Wrong strategy. This Roth conversion strategy for business owners is not really about how much you save. It is about where that money ends up by the time you need it. Last week on my webinar, I shared my personal financial north star with attendees: by age 70, I want the wealth […]
Goodwill clothing donation deduction rules are stricter than most taxpayers realize. In Besaw v. Commissioner, the Tax Court disallowed a $6,760 noncash charitable contribution deduction even though the court appeared to accept that the donations were real. The problem was substantiation. John Besaw claimed the deduction on his 2019 return and attached Form 8283. But […]