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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.

All Cross-BorderUS TaxCanadian TaxSmall Business & BookkeepingCFO & AdvisoryTax Planning

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Small Business & Bookkeeping

Stock Options and Restricted Stock Awards: Tax Treatment of Equity Compensation for Business Owners and Employees

Equity compensation is one of the most complex areas of individual and business taxation because the tax consequences depend on the type of award.

Sep 5, 2026
Small Business & Bookkeeping

Tax Implications of Taking on a Business Partner: What Changes and What to Plan For

Adding a partner to a sole proprietorship changes the tax structure from Schedule C to Form 1065 (partnership return). What changes when you add a partner.

Sep 5, 2026
Small Business & Bookkeeping

Tax Treatment of Business Litigation: Settlements, Attorney Fees, and Damages

The tax treatment of business litigation proceeds depends on the origin of the claim. Tax treatment of damages received (recipient's perspective): |.

Sep 5, 2026
Small Business & Bookkeeping

C-Corp vs. S-Corp: Complete Entity Selection Guide for Business Owners

A C-Corp pays 21% with double taxation on distributions. An S-Corp passes income through to the owner's personal return with no entity-level tax.

Sep 5, 2026
Small Business & Bookkeeping

Tax Planning for Family Businesses: Hiring Children, Income Shifting, and Family Employment Strategies

Hiring family members is one of the most underutilized tax strategies for small business owners because it accomplishes multiple objectives.

Sep 5, 2026
Small Business & Bookkeeping

Year-End Bonus Tax Planning: Timing, Deductibility, and Payroll Tax Strategies

Bonuses are deductible when properly accrued and paid within 2.5 months of year-end (the IRC 267/404(a)(5) rule for related parties).

Sep 5, 2026
Small Business & Bookkeeping

Tax Planning for Real Estate Developers: Dealer vs. Investor Classification, Ordinary Income vs. Capital Gains, and Entity Structuring

Real estate developers face one of the most consequential tax classifications in the code: dealer vs. investor. Dealer vs.

Sep 5, 2026
Small Business & Bookkeeping

Real Estate Professional Status: How to Qualify, Material Participation Tests, and Passive Activity Loss Rules

Real estate professional status (REPS) under IRC 469(c)(7) is one of the most valuable tax classifications a taxpayer can achieve because it allows rental.

Sep 5, 2026
Small Business & Bookkeeping

Tax Planning for Rental Property Owners: Depreciation, Cost Segregation, 1031 Exchanges, and Loss Deductions

Rental real estate is the most tax-advantaged asset class in the U.S. Depreciation, 1031 exchanges, and cost segregation can defer or eliminate the tax.

Sep 5, 2026
Small Business & Bookkeeping

Tax Planning for Rental Property Investors: Depreciation, Passive Loss Rules, and Building a Tax-Efficient Portfolio

Rental property investing offers unique tax advantages that no other investment class can match. Tax benefits of rental property.

Sep 5, 2026
Small Business & Bookkeeping

Business Tax Recordkeeping: What to Keep, How Long, and What the IRS Requires

The IRS requires businesses to keep records that support the income and deductions reported on tax returns for the applicable statute of limitations.

Sep 5, 2026
Small Business & Bookkeeping

Tax Treatment of Intellectual Property: Patents, Copyrights, Trademarks, and Royalty Income

Intellectual property (IP) has unique tax treatment depending on how it is created, acquired, and monetized. IP classification and tax treatment: | IP.

Sep 5, 2026
Small Business & Bookkeeping

Prepaid Expenses and the 12-Month Rule: How Cash-Method Businesses Accelerate Deductions

Cash-method businesses can accelerate deductions by prepaying certain expenses before year-end. Under the 12-month rule (Reg.

Sep 5, 2026
Small Business & Bookkeeping

Business Travel Deduction Rules: The Overnight Test, Per Diems, and What You Can Write Off

Business travel expenses are deductible under IRC 162 when the trip requires an overnight stay away from the taxpayer's tax home.

Sep 5, 2026
Small Business & Bookkeeping

Business Travel Tax Deductions: Rules, Per Diem, and Documentation Requirements

Business travel is deductible when the trip is primarily for business, requires overnight stay. Business travel deductions are among the most valuable.

Sep 5, 2026
Small Business & Bookkeeping

Trust Fund Recovery Penalty (IRC 6672): When the IRS Comes After You Personally for Payroll Taxes

Under IRC 6672, a responsible person who willfully fails to pay over payroll taxes withheld is personally liable for 100% of the unpaid trust fund tax.

Sep 5, 2026
Small Business & Bookkeeping

Trust Fund Recovery Penalty (IRC 6672): Personal Liability for Unpaid Payroll Taxes

The trust fund recovery penalty under IRC 6672 holds 'responsible persons' personally liable for the employee portion of payroll taxes (federal income tax.

Sep 5, 2026
Small Business & Bookkeeping

Vacation Rental Tax Rules: The 14-Day Rule, Mixed-Use Allocation, and IRC 280A

IRC 280A establishes the tax rules for properties that serve dual purposes as both personal residences and rental properties.

Sep 5, 2026
Small Business & Bookkeeping

Vacation Rental Tax Rules: The 14-Day Rule and IRC 280A

Renting your home for 14 days or fewer per year makes the income completely tax-free (the 'Masters exemption'). Above 14 days, the personal use vs.

Sep 5, 2026
Small Business & Bookkeeping

Business Vehicle Deduction: Standard Mileage vs Actual Expenses, SUV Loophole, and Documentation

Business owners choose between standard mileage rate (70 cents/mile in 2025) and actual expenses for vehicle deductions.

Sep 5, 2026
Small Business & Bookkeeping

Business Vehicle Deductions: Standard Mileage vs. Actual Expenses for Self-Employed Owners

Self-employed business owners who use a personal vehicle for business can deduct either the standard mileage rate or actual vehicle expenses.

Sep 5, 2026
Small Business & Bookkeeping

Business Vehicle Deductions: Standard Mileage vs. Actual Expenses, Section 179, and the 6,000 lb Rule

Business vehicle deductions come in two methods: standard mileage (70 cents/mile in 2025, simpler) or actual expenses (gas, insurance, repairs.

Sep 5, 2026
Small Business & Bookkeeping

Business Vehicle Deductions: Section 179, Bonus Depreciation, and the 6,000 lb Rule

Vehicles over 6,000 lbs GVWR qualify for full Section 179 or bonus depreciation (no IRC 280F luxury auto limits). Includes IRS rules, documentation.

Sep 5, 2026
Small Business & Bookkeeping

Business Vehicle: Buy vs. Lease Tax Comparison

Buy vs. lease on a business vehicle turns on weight. Under 6,000 lbs GVWR, luxury limits cap depreciation; heavier trucks and vans can be expensed in year one.

Sep 5, 2026