2,121 plain-English guides on cross-border moves, US and Canadian returns, and small-business money. Each one ends in what to do next, and says when a written Diagnostic is the smarter first step.
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The federal estate tax exemption is $13.61 million per person (2024) but is scheduled to drop to approximately $7 million in 2026.
CFO & AdvisoryEstate tax planning is critical for business owners because a closely held business is often the largest asset in the owner's estate.
Small Business & BookkeepingNew LLC owners have no prior-year tax liability, which means the usual 100% safe harbor is $0. First-year estimated tax for new LLCs: 1.
Small Business & BookkeepingThe IRS assesses estimated tax underpayment penalties when quarterly payments fall short. The estimated tax penalty (IRC 6654 for individuals, IRC.
Small Business & BookkeepingFirst-year business owners have no prior-year tax liability, making the prior-year safe harbor the easiest penalty-free strategy.
Small Business & BookkeepingThe estimated tax penalty (7-8% annualized in 2025) is fully avoidable using one of three safe harbors: prior-year (100%/110% of last year's tax).
Small Business & BookkeepingThe IRS charges an estimated tax penalty on Form 2210 when quarterly payments fall short. How the penalty is calculated and the safe harbor exceptions.
Small Business & BookkeepingThe estimated tax underpayment penalty is calculated on Form 2210. It applies quarter-by-quarter based on the IRS's short-term interest rate.
Small Business & BookkeepingThe estimated tax underpayment penalty is approximately 8% annualized (2024-2025). It applies per quarter, not per year.
Small Business & BookkeepingThe IRS imposes penalties for underpaying estimated taxes, but two safe harbors provide complete protection. The two safe harbors: Safe Harbor 1:.
Small Business & BookkeepingThe IRS imposes an estimated tax penalty when a taxpayer owes more than $1,000 at filing time and did not meet one of two safe harbors.
Small Business & BookkeepingSelf-employed business owners must pay quarterly estimated taxes or face penalties. The 110% prior-year safe harbor eliminates penalties even if income.
Small Business & BookkeepingBusiness owners with a W-2 job (or S-Corp owners paying themselves a salary) can increase W-2 withholding to cover self-employment taxes.
Small Business & BookkeepingIRC 461(l) limits the amount of business losses that can offset non-business income to $305,000 (single) or $610,000 (MFJ) per year.
Small Business & BookkeepingNon-corporate taxpayers cannot deduct business losses exceeding $305,000 (single) or $610,000 (MFJ) for 2024 against non-business income.
CFO & AdvisorySelling a business triggers different tax consequences depending on whether it is structured as an asset sale or a stock/membership interest sale.
Small Business & BookkeepingHiring your spouse, children, or parents in your business creates legitimate tax savings. Family employee tax rules: Children under 18 (working for a sole.
Small Business & BookkeepingA sole proprietor can hire their child under 18 and the wages are exempt from FICA and FUTA. The tax math: - The business deducts the wages on Schedule C.
Tax PlanningHiring family members in a legitimate business is one of the most effective tax planning strategies for small business owners.
Small Business & BookkeepingEvery federal tax deadline for small businesses in 2025, organized by month. 2025 tax calendar (federal deadlines, calendar-year businesses): January: |.
Small Business & BookkeepingFirst-year business owners with no prior-year tax liability have no safe harbor and must estimate current-year taxes accurately.
Small Business & BookkeepingA 15-item checklist for new business owners: EIN, entity selection, accounting method, estimated taxes, record-keeping, and first-year deductions.
Small Business & BookkeepingWhen a foreign person or entity owns a US business or invests in US real property, the US tax rules are significantly more complex than domestic taxation.
Small Business & BookkeepingBusinesses must file 1099-NEC for contractors paid $2,000+ in 2026 ($600+ for 2025 payments), 1099-MISC for rent and royalties, and 1099-INT for interest paid.