Ask a contractor when taxes are due and most will say "April 15." That's the deadline that gets all the attention — and it's only one of them. For business owners, the IRS wants its money four times a year, and the penalties for missing those dates compound quietly in the background. September 15 is

A contractor with a CPA, doing everything "right," still overpaid by more than $22,000. How? His entity structure had never been revisited. His equipment timing was never planned. Family payroll was never set up. Estimated payments were on autopilot. His CPA wasn't bad. His CPA was a historian — and he'd hired a historian to

When your business buys something that lasts more than a year — a truck, an excavator, a trailer — the tax code generally won't let you deduct the whole cost at once. Instead, you spread the deduction over the asset's useful life. That spreading is called depreciation. But Congress created accelerators. And for contractors —

They had kids — and weren't paying them through the business. We set it up correctly: real work, reasonable pay, proper payroll. Income shifted to the kids' lower brackets, the business got the deduction, and the family kept more. Everybody won. This is the family payroll strategy in real life. Not theory, not a loophole