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. […]
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 […]
Safe harbor 401(k) for business owners is not just a retirement topic. It is a plan design question that can affect how much you can contribute, how much your business can deduct, and how often your retirement strategy gets constrained by rules you are not actively thinking about. When did you last look at how […]
The ACA subsidy repayment 2026 rules are harsher than many taxpayers realize. If you buy coverage through the Marketplace and your income comes in higher than expected, the old repayment caps are no longer there. For business owners, early retirees, and anyone managing MAGI carefully, that changes the planning math in a big way. For […]
The qualified bicycle commuting reimbursement eliminated after 2025 is now the rule under the One Big Beautiful Bill Act (OBBBA). If you reimburse employees for bicycle commuting costs in 2026 or later, those payments are taxable wages to the employee—and the employer deduction is no longer allowed. Before this final change, the Tax Cuts and […]
If you received a CP53E notice (or you got your refund by paper check in the last filing season), this is the update you don’t want to learn the hard way. In past years, if your direct deposit failed—or if you didn’t want direct deposit—you could often default to a paper refund check and move […]