Tax Strategy Blog for Business Owners

"Information is the resolution of uncertainty."
Claude Shannon

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November 3, 2026
Putting Your Kids on Payroll: The 2026 Playbook

You were going to give your kids money anyway. For the car. Or college. Or whatever they're asking for this week. When you hand it over as a gift, it comes out of after-tax dollars. When you pay it as a wage for real work in your business, your business deducts it, and your child […]

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October 14, 2026
Long-Term Care Insurance Tax Deduction: How Your Business Can Pay the Premium

If you write the check for your long-term care insurance from your personal account, the same way you pay for car insurance or a gym membership, you may be paying for it the hard way. There is a side door most business owners walk right past. Here is the short answer. The IRS treats long-term […]

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September 17, 2026
The Roth Conversion 5-Year Rule: Why an Old Roth IRA Can Still Cost You a 10% Penalty

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 […]

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September 11, 2026
Missed Depreciation on Rental Property: How to Catch It Up in One Year, Without Amending

If you own a rental, there is a good chance you are sitting on a deduction you never claimed. Not a gray-area deduction. Depreciation you were entitled to, and never took. Missed depreciation on rental property can be caught up in a single adjustment on this year's return. The tax code calls the mechanism a […]

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September 8, 2026
Short-Term Rental Cost Segregation: How to Make the Deduction Bigger

Qualifying your short-term rental was step one. Most owners stop there, take the deduction the default way, and leave the biggest part of it sitting on a schedule that runs for decades. A short-term rental cost segregation study is the second decision, and it controls how big the deduction gets. The study breaks the property […]

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September 3, 2026
QBI Aggregation: Why Owning Multiple Companies Can Cost You the Deduction

This is Part 5 of our series on Section 199A, the qualified business income deduction, or "QBI." We've been running a series for business owners on the 199A deduction — most people know it as the QBI deduction. If you missed any of them, here is what we covered: We were getting some replies from […]

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August 18, 2026
SSTB and the QBI Deduction: Why One Owner Keeps $100K and the Other Gets Zero

This is Part 4 of a four-part series on Section 199A, the qualified business income deduction, or "QBI." Catch up on Part 1, Part 2, and Part 3 first. Is the business having a good year? Great. Here is what decides whether you keep the 20% deduction on it. Two things determine this: how much […]

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August 13, 2026
The S-Corp Salary Sweet Spot for the QBI Deduction

This is Part 3 of a four-part series on the qualified business income deduction. Missed the first two? Read Part 1 and Part 2 — they're here. Still on paychecks this week. Last week I told you which side of the line you're probably on. If you're over it, this is the post that matters […]

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August 13, 2026
The QBI Wage Limitation: How $600K in Profit Became a $45K Deduction

This is Part 2 of a four-part series on the qualified business income deduction. Read Part 1 here. Last week I told you about a line on your tax return — $403,500 if you are married, half of that if you are single. Cross it, and the 20% deduction most business owners count on stops […]

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