Taxes & Tax Prep

If you’ve ever been hit with an IRS underpayment penalty, you already know how annoying it is. It is one of the most avoidable penalties in the tax code, yet people get tagged with it every year because they misunderstand one basic point: the U.S. tax system is pay-as-you-go. The IRS does not just care […]

If you’re selling investments at a loss and buying them back too quickly, you can accidentally trigger one of the IRS’s most misunderstood rules: the wash sale rule. The stakes are real. A single mistimed trade can wipe out a legitimate tax deduction, push that loss into the future, and create reporting issues that are […]

If you invest in real estate and feel trapped by taxes, you’re not imagining it. Most investors are boxed into passive loss limits, forced to carry forward deductions for years, and often exposed to the 3.8% Net Investment Income Tax (NIIT) on top of everything else. Real Estate Professional Status (REPS) is one of the […]

If you’ve heard “hire your kids and it’s all tax-free,” you’ve heard the version that gets people in trouble. The real version is simpler and more boring: you can deduct wages paid to your child for legitimate work and, in the right unincorporated setup, those wages can also be exempt from FICA (under 18) and FUTA (under 21). Separately, the […]

The Augusta Rule (IRC §280A(g)) is one of the most powerful – and most misunderstood – tax strategies available to S-Corp and LLC owners. When used correctly, you can rent your home to your business for up to 14 days per year, deduct the expense on your business return, and pay zero income tax on […]

2026 and all of its tax deadlines are here. Below is a quick reference guide to the most important dates to keep in mind this calendar year. January 15th: due date to pay 4th quarter estimated taxes. February 2nd: Due date to send out 1099s and W-2s to recipients. Due date to file 1099-NECs and […]

Q: How can S-Corp owners maximize their QBI deduction? A: By strategically adjusting W-2 wages. For high-income S-Corp owners, the QBI deduction is limited by wage thresholds. Paying too little in salary can eliminate the deduction entirely – while a properly optimized salary can unlock tens of thousands in tax savings. But the salary must […]

Q: What are the biggest tax changes in the One Big Beautiful Bill Act compared to an expiring TCJA? A: OBBBA locks several TCJA breaks in place and softens others. QBI stays permanent, the child credit rises to $2,200, the standard deduction is permanently increased, SALT gets a four‑year $40k cap, Pease is repealed, and […]

Q: Which business entity saves the most tax – sole proprietor, LLC, S-Corp, or C-Corp? A: For owner-operated businesses above roughly $50k profit, an S-Corp usually wins: it slashes self-employment tax on distributions without double taxation. Single-member LLCs add liability protection but no tax break, partnerships keep the full 15.3% SE hit, and C-Corps look […]

Q: Does the $10 million/$15 million QSBS exclusion make a C-Corp the best structure for most small-business owners? A: Rarely. QSBS can erase capital-gains tax, but only when you: (1) run a domestic C-Corp, (2) meet every §1202 rule for all required years (3) find a buyer willing to do a stock sale, and (4) […]

Q: Can the 10.5% Net CFC Tested Income (NCTI) regime really beat an S-Corp for a small-business owner? A: Only in very specific circumstances. Under the Net CFC Tested Income (NCTI – formerly GILTI), the structure can win if you’re a high-earning US expat who (1) routes profits through a US C-Corp that owns a bona fide foreign subsidiary, (2) […]

Q: Is electing a state Pass-Through Entity Tax (PTET) always a smart SALT-cap workaround? A: Almost always – but not universally. PTET converts state tax into a deductible business expense, cutting federal tax. It can backfire only in edge cases, mainly when (1) you already get the full SALT benefit on Schedule A or (2) […]