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Guides · Tax Planning

Tax Planning guides

167 plain-English guides on tax planning, each one ending in what to do next.

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

Page 5 of 7, newest first.

Tax Planning

Tax-Loss Harvesting for Business Owners: Capital Gains Strategies and Wash Sale Rules

Tax-loss harvesting offsets capital gains with realized losses, reducing your current-year tax bill. The wash sale rule under IRC 1091 limits repurchases.

Sep 5, 2026
Tax Planning

Tax-Loss Harvesting for Small Business Owners with Investment Portfolios

Tax-loss harvesting involves selling losing investments to offset capital gains, reducing tax by up to $3,000/year even without gains.

Sep 5, 2026
Tax Planning

Tax-Loss Harvesting for Business Owners: How to Turn Investment Losses Into Tax Savings

Tax-loss harvesting is the practice of selling investments at a loss to offset capital gains and, within limits, ordinary income.

Sep 5, 2026
Tax Planning

Year-End Tax Loss Harvesting for Small Business Owners

Tax loss harvesting basics: How it works: 1. Identify investments in your taxable brokerage account that have declined in value (unrealized losses) 2.

Sep 5, 2026
Tax Planning

Tax Planning for Accounting Firms and CPA Practices: SSTB Classification, Partner Buy-In, and Practice Valuation

Accounting firms and CPA practices are explicitly classified as specified service trades or businesses (SSTBs) under IRC 199A.

Sep 5, 2026
Tax Planning

Tax Planning for Agricultural and Farm Businesses: Income Averaging, Crop Insurance Deferral, and Farm Equipment Depreciation

Agricultural businesses operate under a unique set of tax rules that recognize the inherent volatility of farm income. Farm-specific tax provisions: |.

Sep 5, 2026
Tax Planning

Tax Planning for Farms and Agriculture: Cash Method, Farm Income Averaging, Soil Conservation Deductions, and Commodity Sales

Farmers and agricultural businesses receive more favorable tax treatment than almost any other industry in the Internal Revenue Code.

Sep 5, 2026
Tax Planning

Tax Planning for Amazon FBA Sellers: Inventory Accounting, Multi-State Nexus, Sales Tax, and Cost of Goods Sold

Amazon FBA (Fulfillment by Amazon) sellers face a unique multi-state tax exposure because Amazon stores inventory in warehouses across the country.

Sep 5, 2026
Tax Planning

Tax Planning for Architecture and Engineering Firms: SSTB Classification, Project Accounting, and Entity Structure

Architecture and engineering firms aren't SSTBs under IRC 199A(d)(2), so principals above the income threshold can keep the QBI deduction, subject to W-2 wage and property limits.

Sep 5, 2026
Tax Planning

Tax Planning for Auto Dealerships: Floor Plan Interest, LIFO Reserve, Demo Vehicles, and Inventory Accounting

Auto dealerships operate under a specialized tax framework that differs significantly from most retail businesses because of three unique features.

Sep 5, 2026
Tax Planning

Tax Planning for Beauty Salons, Barbershops, and Booth Renters: Tip Income, Booth Rental vs. Employment, and Product Sales

Beauty salons and barbershops choose between W-2 stylists, where the salon can claim the IRC 45B FICA tip credit, and booth renters who pay their own SE tax.

Sep 5, 2026
Tax Planning

Tax Planning for Breweries, Wineries, and Distilleries: Excise Tax Credits, COGS, and Taproom Revenue

Craft beverage producers (breweries, wineries, and distilleries) face a unique two-layer tax structure. CBMA excise tax rates (permanent).

Sep 5, 2026
Tax Planning

Cannabis Business Tax Rules: How IRC 280E Eliminates Most Deductions and What Operators Can Do About It

Cannabis businesses face a unique and punitive federal tax rule that no other legal industry confronts: IRC 280E. IRC 280E impact on cannabis.

Sep 5, 2026
Tax Planning

Tax Planning for Cannabis Businesses: IRC 280E, COGS Deductions, and Entity Structure Under Federal-State Conflict

Cannabis businesses operate under the most punitive tax regime of any legal industry in the United States because of IRC 280E.

Sep 5, 2026
Tax Planning

Tax Planning for Construction Companies: Completed Contract, Percentage of Completion, and Contractor-Specific Rules

Construction companies face unique tax rules that differ significantly from other industries. Revenue recognition methods for construction contracts: |.

Sep 5, 2026
Tax Planning

Tax Planning for Consultants, Freelancers, and Independent Professionals: Entity Structure, Deductions, and Self-Employment Tax

Consultants, freelancers, and independent professionals face a unique tax landscape where self-employment tax (15.3% on the first $176,100 of net.

Sep 5, 2026
Tax Planning

Tax Planning for Daycare and Childcare Centers: Dependent Care Credits, Food Program Reimbursements, and Home-Based Deductions

Daycare and childcare center operators face a unique tax profile because the business is labor-intensive (70-80% of revenue goes to staff wages.

Sep 5, 2026
Tax Planning

Tax Planning for Dental Practices: SSTB Classification, Equipment Depreciation, Associate Compensation, and Practice Sales

Dental practices are classified as specified service trades or businesses (SSTBs) under IRC 199A, falling within the 'health care' category of Treas. Reg.

Sep 5, 2026
Tax Planning

Tax Planning for Dental Practices: Equipment Depreciation, Retirement Plans, SSTB Considerations, and Entity Structure

Dental practices face a tax planning environment that closely mirrors medical practices but with several key differences.

Sep 5, 2026
Tax Planning

Tax Planning for E-Commerce Businesses: Amazon FBA, Multi-State Sales Tax Nexus, and Inventory Accounting

E-commerce businesses face a tax compliance landscape that is more complex than traditional brick-and-mortar retail because online sellers create sales.

Sep 5, 2026
Tax Planning

Tax Planning for E-Commerce and Amazon FBA Sellers: Inventory, Nexus, and Multi-State Sales Tax

E-commerce businesses face a unique combination of tax challenges that brick-and-mortar retailers do not encounter. E-commerce tax obligations: |.

Sep 5, 2026
Tax Planning

Tax Planning for E-Learning, Online Education, and Course Creators: Revenue Recognition, Platform Fees, and SSTB Classification

Online education businesses (course creators, membership sites, coaching programs. E-learning business SSTB classification.

Sep 5, 2026
Tax Planning

Tax Planning for Gym Owners, Fitness Studios, and Personal Trainers: Equipment Depreciation, SSTB Rules, and Entity Optimization

The fitness industry presents specific tax planning opportunities and challenges that differ from typical service businesses.

Sep 5, 2026
Tax Planning

Tax Planning for Fitness Centers, Gyms, and Personal Trainers: Membership Revenue, Equipment Depreciation, and SSTB Classification

Fitness businesses span a wide range of models (from solo personal trainers to multi-location gym chains). Fitness business SSTB classification: |.

Sep 5, 2026