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Guides · Small Business & Bookkeeping

Small Business & Bookkeeping guides

491 plain-English guides on small business & bookkeeping, each one ending in what to do next.

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Page 7 of 21, newest first.

Small Business & Bookkeeping

Employee Retention Credit (ERC) Status for Small Businesses in 2025

The ERC program ended for new claims as of January 31, 2024. Businesses that already filed ERC claims should check their status through the IRS processing.

Sep 5, 2026
Small Business & Bookkeeping

Tax-Advantaged Employee Benefits for Small Businesses

Small businesses can offer tax-deductible benefits that cost less than equivalent salary increases: health insurance (100% deductible).

Sep 5, 2026
Small Business & Bookkeeping

Employee Stock Options: ISO vs. NSO Tax Treatment and Exercise Strategies

ISOs and NSOs have different tax timing and rates. NSOs are taxed as ordinary income at exercise; ISOs get capital gains treatment if holding periods.

Sep 5, 2026
Small Business & Bookkeeping

Employee vs. Independent Contractor: The Complete Classification Guide for Small Business Owners

Misclassifying workers as contractors costs businesses back payroll taxes, penalties, and interest. The IRS three-category test and safe harbor rules.

Sep 5, 2026
Small Business & Bookkeeping

Employing Family Members: Tax Benefits, FICA Exemptions, and IRS Compliance for Family Businesses

Employing family members gives sole proprietors FICA exemptions for children under 18 and income-splitting benefits for spouses. The work must be real.

Sep 5, 2026
Small Business & Bookkeeping

Hiring Your Spouse or Children: FICA Exemptions and Family Employment Tax Benefits

Hiring your children or spouse can save thousands in FICA taxes each year. Children under 18 working for an unincorporated parent pay zero FICA.

Sep 5, 2026
Small Business & Bookkeeping

Employment Tax Deposits: 941 Filing Schedule, Deposit Deadlines, and Penalty Avoidance

Employers must deposit federal employment taxes (income tax withholding, Social Security. Deposit schedule determination.

Sep 5, 2026
Small Business & Bookkeeping

Employment Tax Penalties: The Most Expensive Mistakes Small Businesses Make

Employment tax penalties are among the harshest in the tax code. Late payroll deposits trigger 2-15% penalties. Employment tax penalty tiers: Late deposit.

Sep 5, 2026
Small Business & Bookkeeping

Energy Efficiency Tax Credits for Small Business: Commercial Buildings, Vehicles, and Equipment

Small businesses can claim tax credits for energy-efficient improvements under several provisions: the Clean Vehicle Credit (IRC 30D.

Sep 5, 2026
Small Business & Bookkeeping

Employee Retention Credit (ERC) Status in 2025: Moratorium, Audits, and Voluntary Disclosure

ERC status as of 2025: 1. Moratorium on new claims. The IRS stopped processing new ERC claims filed after September 14, 2023.

Sep 5, 2026
Small Business & Bookkeeping

Employee Retention Credit (ERC) Status: Where Claims Stand and What Business Owners Need to Know

The IRS has paused processing of most new ERC claims and is auditing previously paid claims. The Employee Retention Credit (ERC) was a pandemic-era.

Sep 5, 2026
Small Business & Bookkeeping

Estimated Taxes for New LLCs: First-Year Safe Harbors, Set-Aside Strategy, and Common Mistakes

New 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.

Sep 5, 2026
Small Business & Bookkeeping

Avoiding Estimated Tax Penalties: Safe Harbor Methods, Annualized Income, and Year-End Fixes

The IRS assesses estimated tax underpayment penalties when quarterly payments fall short. The estimated tax penalty (IRC 6654 for individuals, IRC.

Sep 5, 2026
Small Business & Bookkeeping

How to Avoid Estimated Tax Penalties in Your First Year of Business

First-year business owners have no prior-year tax liability, making the prior-year safe harbor the easiest penalty-free strategy.

Sep 5, 2026
Small Business & Bookkeeping

Avoiding the Estimated Tax Penalty: Three Safe Harbor Methods and When to Use Each

The 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).

Sep 5, 2026
Small Business & Bookkeeping

Estimated Tax Penalty Calculation: How the IRS Computes Underpayment Penalties

The IRS charges an estimated tax penalty on Form 2210 when quarterly payments fall short. How the penalty is calculated and the safe harbor exceptions.

Sep 5, 2026
Small Business & Bookkeeping

How to Calculate the Estimated Tax Penalty: Form 2210 and the Underpayment Math

The estimated tax underpayment penalty is calculated on Form 2210. It applies quarter-by-quarter based on the IRS's short-term interest rate.

Sep 5, 2026
Small Business & Bookkeeping

How to Avoid the IRS Estimated Tax Underpayment Penalty

The estimated tax underpayment penalty is approximately 8% annualized (2024-2025). It applies per quarter, not per year.

Sep 5, 2026
Small Business & Bookkeeping

Estimated Tax Safe Harbor Strategies: How to Avoid Underpayment Penalties Every Time

The IRS imposes penalties for underpaying estimated taxes, but two safe harbors provide complete protection. The two safe harbors: Safe Harbor 1:.

Sep 5, 2026
Small Business & Bookkeeping

Estimated Tax Safe Harbor: How to Avoid the Underpayment Penalty Every Year

The 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.

Sep 5, 2026
Small Business & Bookkeeping

Estimated Tax Safe Harbors: The 110% Rule, Annualized Income Method, and Penalty Avoidance

Self-employed business owners must pay quarterly estimated taxes or face penalties. The 110% prior-year safe harbor eliminates penalties even if income.

Sep 5, 2026
Small Business & Bookkeeping

Using W-2 Withholding to Cover Side Business Taxes: The Backdoor Estimated Tax Strategy

Business owners with a W-2 job (or S-Corp owners paying themselves a salary) can increase W-2 withholding to cover self-employment taxes.

Sep 5, 2026
Small Business & Bookkeeping

Excess Business Loss Limitation: IRC 461(l) Cap on Business Losses

IRC 461(l) limits the amount of business losses that can offset non-business income to $305,000 (single) or $610,000 (MFJ) per year.

Sep 5, 2026
Small Business & Bookkeeping

Excess Business Loss Limitation: IRC 461(l) Rules for Non-Corporate Taxpayers

Non-corporate taxpayers cannot deduct business losses exceeding $305,000 (single) or $610,000 (MFJ) for 2024 against non-business income.

Sep 5, 2026