The S-corp health insurance deduction is one of the easiest deductions to lose without realizing it — and if you employ family, you may be losing it right now. Do you have a spouse, kids, or other family members who work in your S corp? Do you cover their health insurance? If you do, there's […]
The AI tax deduction most business owners don't know about could cover the bulk of what they're spending to bring AI into their company this year. Excited about AI. Overwhelmed by AI. That's where most business owners sit right now — at the halfway point. They just don't know where to start, who to trust, […]
An S-corp accountable plan is the one-page document standing between you and hundreds or thousands of dollars in lost deductions every year. If you elected S-corp status to save on self-employment tax — smart move — there's a catch most owners never hear about: you quietly lost your home office deduction, and maybe more. The […]
The grind gets me like any other business owner. And then I get a swift kick in the pants that reminds me why I do what I do. A Name Spoken at the Airport This weekend, I mentioned to the gate agent at the airport that I was passing through Carlsbad CA, and she stopped […]
AI tax advice risks for business owners are not theoretical anymore. Back in April, I warned you about people using AI to do their taxes. Well, here’s a cautionary tale for you. In Clinco v. Commissioner, T.C. Memo. 2026-16, a lawyer was in Tax Court defending a client against a nearly $2.3 million IRS notice […]
Build something valuable with your own two hands, a patent, a copyright, a piece of software, and you would expect the profit on a sale to land at the lower long-term capital gains rate. For a specific set of intangibles, the tax code says no. The gain comes out as ordinary income, taxed at your […]
You can, in the right circumstances, and in 2026 it may be the difference between a real tax break and almost none at all. Here is the short answer for a business owner who supports a church, a school, or another 501(c)(3): if the payment is directly tied to your business and you make it […]
A 401k alternative for employees may be coming through TrumpIRA.gov — giving your team a better path to retirement savings, and it costs you nothing. If you're a business owner who's been meaning to set up a retirement plan for your team but keeps putting it off…I know why. You know you should. You've probably […]
A hire your child tax strategy is usually discussed one way: hire your kids, put them on payroll, and deduct the wages. That can work when the facts fit. But a hire your child tax strategy is not limited to regular payroll. In some cases, your business may be able to pay a child or […]