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1. Introduction

• Purpose of the guide
• Who it’s for (small business owners, freelancers, entrepreneurs)
• How taxes impact cash flow, growth, and compliance

2. Business Structure and Tax Implications

• Sole proprietorship
• Partnership
• Limited Liability Company (LLC)
• S Corporation
• C Corporation
• Key tax differences and filing requirements for each
• Choosing the right structure for tax efficiency

3. Business Registration and Employer Identification Number

• Federal Employer Identification Number (EIN)
• State tax registration
• Local business licenses
• How registration affects taxation and deductions

4. Federal Income Taxes

• Overview of federal income tax for businesses
• Reporting income
• Deductible business expenses
• Tax brackets and rates for different structures
• Filing deadlines and forms (Schedule C, 1065, 1120S, 1120)

5. Self-Employment Taxes

• What self-employment tax covers (Social Security, Medicare)
• How to calculate self-employment tax
• Paying estimated taxes quarterly
• Examples for sole proprietors and partners

6. Employment Taxes

• Payroll taxes for employees
• Social Security and Medicare contributions
• Federal Unemployment Tax (FUTA)
• Withholding requirements
• Reporting and filing forms (941, 940, W-2, W-3)

7. Sales and Use Taxes

• When businesses must collect sales tax
• Nexus rules (state and local)
• Collecting and remitting sales tax
• Use tax for purchases without sales tax
• Filing requirements and deadlines

8. Business Expense Deductions

• Ordinary and necessary expenses
• Home office deduction
• Vehicle expenses and mileage
• Travel, meals, and entertainment rules
• Office supplies, software, and equipment
• Health insurance deductions for self-employed

9. Depreciation and Section 179

• Depreciation basics
• Section 179 deduction for equipment and assets
• Bonus depreciation
• Examples of tangible and intangible assets

10. Retirement Contributions and Tax Benefits

• SEP IRA, SIMPLE IRA, and solo 401(k) options
• Contribution limits
• Deductible contributions and tax impact
• Planning for owner and employee retirement benefits

11. Tax Credits

• Common federal business tax credits (R&D, Work Opportunity, Energy)
• State-specific tax credits
• How credits differ from deductions
• Claiming credits properly

12. Estimated Taxes

• Who needs to pay estimated taxes
• Calculating estimated payments
• Quarterly deadlines
• Penalties for underpayment

13. Recordkeeping and Documentation

• Importance of accurate records
• Digital vs. paper records
• Retention periods for tax purposes
• Tools and software for bookkeeping

14. State and Local Taxes

• Income tax obligations by state
• Sales and use tax
• Property tax considerations
• Franchise taxes or excise taxes
• Understanding multistate taxation

15. Tax Planning Strategies

• Timing income and expenses
• Choosing accounting methods (cash vs. accrual)
• Retirement planning and deferrals
• Hiring family members and related tax benefits
• Managing estimated tax payments

16. Audit Preparedness and Compliance

• How audits work
• Common audit triggers
• Documentation to keep handy
• Working with accountants or tax professionals

17. Filing Your Taxes

• Choosing the right forms for your business structure
• Step-by-step guidance for filing federal taxes
• Filing state and local taxes
• Using e-file vs. paper filing

18. Special Topics

• Pass-through entity rules (S Corp and LLC)
• Qualified Business Income Deduction (Section 199A)
• Tax implications of business loans and PPP forgiveness
• International considerations for small businesses

19. Common Mistakes to Avoid

• Missing deadlines
• Incorrect deductions
• Not paying estimated taxes
• Poor recordkeeping

20. Resources

• IRS resources and publications
• State-specific resources
• Recommended software and tools
• Professional advisors (CPAs, enrolled agents, tax attorneys)