Tax Strategy Blog for Business Owners

Walter is 54. His self-directed IRA holds a rental property that pays him steadily every month, and for a few years he has been moving pieces of that account into the Roth version, a little at a time, whenever the numbers worked. His thinking was simple: get it into the Roth, let it grow, take […]

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 […]

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 […]

$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 […]

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 […]

New to crypto tax terms? Explore our quick-reference Crypto Tax Glossary for Business Owners to understand key concepts before diving in. 2025 has been a big year for cryptocurrency. If you’ve held Bitcoin or other digital assets through new highs, your portfolio might look great on paper—but that also means a bigger potential tax bill. […]

The clock is ticking on 2025. Your retirement is one year closer, and you still have time before December 31 to lock in powerful 2025 year-end retirement deductions. With a few intentional moves, you can: Below are five opportunities to review before December 31. The limits and thresholds here reflect the IRS’s 2025 inflation adjustments. […]