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 […]
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. […]