All Articles

102 long-form guides on entities, structuring, and tax basics, grouped by topic.

Choosing a Business Entity

• C-Corporations for Small Businesses: When the Extra Layer of Tax Is Worth It
• Changing Your Entity Type: Converting an LLC, Sole Proprietorship, or Corporation
• LLC vs S-Corp vs C-Corp: How to Choose for Your Small Business
• Multi-Member LLC Taxes: Partnership Returns, K-1s, and Guaranteed Payments
• How a Single-Member LLC Is Taxed: Schedule C, Self-Employment Tax, and Payroll
• Sole Proprietorship vs LLC: What Actually Changes
• When Does It Make Sense to Elect S-Corp Status?

S-Corporations: Election, Salary, and Basis

• S-Corp Distributions Explained: Rules, Timing, and Tax Treatment
• How to Elect S-Corp Status: Form 2553 Step by Step
• S-Corp Eligibility Rules: Shareholders, Stock, and Entities That Can Elect
• Health Insurance for S-Corp Owners: The 2-Percent Shareholder Rules
• Ten S-Corp Mistakes That Create Tax Problems (and How to Prevent Them)
• S-Corp Payroll for Owner-Employees: Setup, Withholding, and Filings
• S-Corp Reasonable Compensation: What the IRS Expects Owners to Pay Themselves
• S-Corp Shareholder Basis: Stock Basis, Debt Basis, and Why It Matters
• Form 1120-S Guide: How the S-Corp Tax Return Works
• How to Set Your Owner Salary in an S-Corp: A Practical Method

Holding Companies, Series LLCs, and Multi-Entity Structures

• Holding Company Structures for Small Business Owners: What They Do and When They Help
• Intercompany Charges and Agreements: Leases, Loans, and Services Between Your Entities
• What an LLC Does and Does Not Protect: Understanding the Limits of the Liability Shield
• Management Company Structures: Charging Fees Between Related Businesses
• One LLC or Separate LLCs for Multiple Businesses? A Decision Framework
• Parent and Subsidiary LLCs: How to Set Up and Operate a Two-Tier Structure
• Piercing the Corporate Veil: How Owners Lose Their Liability Protection
• Series LLCs Explained: Cells, Liability, Taxes, and the Risks Owners Overlook

Formation, Operating Agreements, and State Notes

• LLC and Corporation Annual Reports and Franchise Taxes: Staying in Good Standing
• Beneficial Ownership Information Reporting: Where the Rules Stand for Small Businesses
• Corporate Formalities for Small Companies: Minutes, Consents, and Records That Matter
• DBAs and Trade Names: When You Need One and What It Does Not Do
• Foreign Qualification: When Your LLC or Corporation Must Register in Another State
• Delaware, Wyoming, Nevada, or Your Home State? How to Pick Where to Form
• Getting an EIN: Who Needs One, How to Apply Free, and Common Pitfalls
• How to Form an LLC: A Step-by-Step Checklist From Name to Bank Account
• Multi-Member Operating Agreement Clauses That Prevent Owner Disputes
• The LLC Operating Agreement: What It Is, What It Covers, and Why You Need One
• Registered Agent Guide: What They Do, Who Can Serve, and How to Choose
• Operating Agreement for a Single-Member LLC: Essential Provisions
• California LLC and Corporation Notes: Franchise Tax, LLC Fee, and What Owners Overlook
• Delaware, Wyoming, and Nevada Entity Notes: Fees, Reports, and Who Really Benefits
• Florida Entity Notes: Annual Report Deadline, Corporate Income Tax, and Sales Tax
• New York LLC Notes: Publication Requirement, Biennial Statement, and Filing Fees
• Texas Entity Notes: No Personal Income Tax, the Franchise Tax, and Reports

Bookkeeping, Banking, and Payroll

• Bookkeeping Systems for Small Business: Software, Routines, and Who Does What
• Setting Up a Business Bank Account: Documents, Account Types, and Structure
• Business Credit Cards and Personal Guarantees: What Owners Are Really Signing
• Cash vs Accrual Accounting: Which Method Fits Your Small Business?
• Chart of Accounts Basics: How to Organize Your Categories for Clean Books and Taxes
• Independent Contractor vs Employee: How Classification Really Works
• The Small Business Month-End Close Checklist
• Owner Draws vs Distributions vs Salary: Paying Yourself by Entity Type
• Payroll for New Employers: A First-Hire Checklist
• Payroll Tax Deposits and Filings: Forms 941, 940, W-2, and State Returns Explained
• Separating Personal and Business Finances: A Practical System for Owners

Deductions and Owner Reimbursements

• Accountable Plans: How to Reimburse Owners and Employees Tax-Free
• Business Meals and Travel Deductions: What Qualifies, What Is Limited, and What to Record
• Hiring Your Spouse or Family Members: Tax Rules, Wages, and Documentation
• Hiring Your Children in the Family Business: Payroll Exemptions, Limits, and Proof
• The Home Office Deduction: Rules, Methods, and Common Mistakes
• Is It a Business or a Hobby? The Profit Motive Test and What It Means for Deductions
• Depreciation, Section 179, and Bonus Depreciation: A Small Business Primer
• The Self-Employed Health Insurance Deduction: Who Qualifies and How It Works
• Startup and Organizational Costs: What You Can Deduct Before Opening Day
• Vehicle Deductions for Business Owners: Standard Mileage, Actual Expenses, and Records

Retirement Plans for Business Owners

• Cash Balance Plans for Business Owners: How They Work, Costs, and Who They Fit
• HSAs for Business Owners: Eligibility, Limits, and Entity-Specific Rules
• Retirement Plans for S-Corp Owners: How W-2 Salary Shapes Your Contributions
• SEP IRA Guide: A Simple Owner Retirement Plan and Its Trade-Offs
• SIMPLE IRA Guide: A Practical Retirement Plan for Small Employers
• Solo 401(k) Guide: Contribution Limits, Eligibility, and Setup for Owners Without Employees
• Solo 401(k) vs SEP IRA: Which Fits Your Income, Entity, and Plans to Hire?

Tax Basics for Business Owners

• Estimated Taxes for Business Owners: Due Dates, Safe Harbors, and How to Calculate
• 1099-NEC, 1099-K, and W-9: Information Return Basics for Small Businesses
• Pass-Through Entity Tax (PTET) Elections: The State Tax Workaround for Business Owners
• The QBI Deduction (Section 199A): How the 20 Percent Pass-Through Deduction Works
• Sales Tax Nexus Basics: When Your Business Must Collect and Remit in Other States
• Self-Employment Tax Explained: Rates, Calculation, and Ways It Differs by Entity
• The Small Business Tax Calendar: Deadlines by Month for Owners, Payroll, and Entities
• State Income Tax, Nexus, and Remote Employees: What Changes When You Hire Across State Lines
• Tax Basis Basics for Business Owners: Why It Determines Gain, Loss, and Deductions

Buying, Selling, Real Estate, and Entity Cleanups

• Adding or Removing an Owner: Tax and Structural Consequences for LLCs and S-Corps
• Due Diligence Checklist for Buying a Small Business: Financial, Tax, Legal, and Operational
• Buying a Business: Asset Purchase vs Stock or Equity Purchase
• Catching Up on Unfiled Returns and Behind Bookkeeping: A Practical Recovery Plan
• How to Dissolve an LLC or Close a Business Properly: Filings, Taxes, and Final Steps
• Earnouts and Seller Financing: Structuring Deferred Payments in a Business Sale
• Entity Cleanup Guide: Fixing Mismatched Elections, Missing Records, and Tangled Structures
• Owning Your Business Building Through a Separate LLC: Lease Terms, Taxes, and Traps
• Purchase Price Allocation in a Business Sale: Classes, Form 8594, and Why It Matters
• Qualified Small Business Stock (QSBS) Basics: Section 1202 for Founders and Early Investors
• Real Estate in an LLC or Your Personal Name? Liability, Financing, Taxes, and Costs
• Selling Your Business: Tax Basics for Owners of Small Companies

Structuring Marketing, Consulting, and Creative Agencies

• Agency Ad Spend: Recording Pass-Through Media Costs Gross or Net
• Agency Client Contracts and Intellectual Property: Ownership, Licenses, and Work for Hire
• Agencies, Freelancers, and Employees: Classification, Contracts, and Cost Comparison
• Paying International Contractors: W-8BEN, Withholding, and Compliance Basics for U.S. Agencies
• Agency Owner Pay and Profit: Salary, Distributions, Retained Earnings, and Reserves
• Agency Retainers, Prepayments, and Revenue Timing: Cash vs Accrual for Recurring Work
• Structuring a Consulting Business: Entity, Liability, Pricing Model, and Taxes
• From Freelancer to Agency: The Structural and Tax Changes When You Start Hiring
• Entity Structure for a Marketing Agency: LLC, S-Corp, and Multi-Entity Options
• Selling Your Agency: What Buyers Look At and How to Prepare Years Ahead
• Quarterly Entity Review for Agency Owners: A Practical Checklist