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Business Owners

Tax and accounting guides for owner-operated and online businesses: S-corp elections and reasonable salary, entity structure, Schedule C deductions, partnerships, retirement plans, and 1099-K reporting.

Choose a topic from the list to see related guides.

Sole Proprietors & Schedule C

Taxes for Content Creators, Influencers, and Freelancers If you earn money on YouTube, Twitch, Patreon, OnlyFans, or freelance platforms, you are running a business, and the IRS treats it like one. Self-employment tax, quarterly payments, gifted-product income, and deductions all change the math.

Schedule C Deductions: What Sole Proprietors and Single-Member LLCs Can Write Off A practical guide to deductible business expenses on Schedule C, including home office, vehicle, contractor costs, self-employment tax, and the QBI deduction for sole proprietors.

Partnerships

Partnership Basis, Allocations, and Capital Accounts How outside basis works in a partnership, what capital accounts track, how special allocations are validated, what guaranteed payments are, and how phantom income can catch partners off guard.

S-Corporations

Late S-Corp Election Relief: When Form 2553 Can Still Be Fixed Missed the S-corp election deadline? In most cases it can still be fixed. Learn exactly who qualifies for late election relief, what the IRS requires, and what breaks the process.

S-Corp Owner Health Insurance, Accountable Plans, and Payroll Cleanup S-corp owners often miss tax savings because health insurance, reimbursements, and payroll were handled casually. The fix is usually not a new entity. It is getting the owner-compensation mechanics right.

S-Corp Basis, Ownership Rules, and Shareholder Loans Who can own S-corp stock, how stock and loan basis work, what limits loss deductions, and why shareholder loans need to be structured correctly to create basis.

S-Corp Reasonable Salary: How to Set It Without Triggering Problems S-Corp owners need a reasonable salary before taking distributions, but the IRS does not use a magic percentage. The right number depends on role, time, comparables, and where the company's gross receipts really come from.

S-Corporation Election: When It Makes Sense (and When It Doesn't) Learn when an S-Corp election saves taxes and when it costs more. Covers the savings calculation, reasonable salary rules, and who should avoid electing.

C-Corporations

C-Corporation Tax Planning: Double Taxation, Retained Earnings, and Owner Compensation How C-corps are taxed at the entity and shareholder level, when retaining earnings at the 21% corporate rate makes sense, how to manage owner compensation versus dividends, and what exit planning looks like.

Choosing & Changing Entity

When to Switch From an LLC to an S-Corp: The Income Threshold That Decides An S-corp election can save thousands in self-employment tax, but only once your profit is high enough to outrun the added payroll, filing, and bookkeeping costs. Here is the math, the breakeven point, and the cases where staying an LLC is the smarter call.

Starting an LLC in Florida: A Tax Guide What a Florida LLC actually means for your taxes: default pass-through treatment, no state income tax, the annual report, sales and reemployment tax, and when to elect S-corp status.

Wrong Form 1099-K After an LLC or S-Corp Change Changed entities and still got a 1099-K under the old tax ID? This mismatch is common after a move from Schedule C to an LLC or S-corp and can create avoidable notice risk if it is not cleaned up.

S-Corp vs. Partnership: Choosing the Right Pass-Through Structure How S-corps and partnerships compare on flexibility, self-employment tax, ownership rules, and economics, and how to decide which structure fits your situation.

Best Entity Structure for Ecommerce Sellers: Schedule C, LLC, or S-Corp Shopify, Amazon, Etsy, Walmart Marketplace, and other ecommerce sellers usually end up choosing between Schedule C, an LLC, and S-Corp treatment. The right structure depends on profit, risk, bookkeeping quality, and growth plans.

Filing & Deadlines

Quarterly Estimated Taxes and the Underpayment Penalty If you have income that is not subject to withholding, the IRS expects you to pay tax four times a year. Miss the safe harbors and you owe an underpayment penalty that is really just interest, currently around 8%, that most people can avoid with a little planning.

2025 Tax Deadlines: Key Filing and Payment Dates Every important IRS filing and payment deadline for the 2025 tax year, including business returns, individual returns, extensions, and estimated tax payments.

Entity & Structure

How to Get a US EIN Without an SSN or ITIN (Form SS-4 for Foreign Owners) Foreign founders do not need a Social Security number or an ITIN to get an EIN for a US company. The online tool will not work for you, but the fax and phone routes will, once you know how to complete the responsible-party line.

Compliance & Reporting

Florida Sales Tax for Online Sellers: Economic Nexus Explained When do out-of-state and online sellers have to collect Florida sales tax? A guide to Florida's $100,000 economic nexus threshold, marketplace facilitator rules, and what sellers must do to comply.

Florida Sales Tax for Small Businesses: Registration, Rates, and Filing A practical guide to Florida sales tax for small businesses: who must register, the 6% state rate plus county surtax, how to collect, and how to file Form DR-15 on time.

Form 1099-K for Ecommerce Sellers: Why Gross Payments Are Not Your Taxable Income Form 1099-K reports gross payments, not profit. Ecommerce sellers have to reconcile platform payouts, fees, refunds, shipping, and inventory before the tax return shows the right income.

Planning Strategies

QSBS (Section 1202): How Founders and Early Investors Can Sell Stock Tax-Free Qualified Small Business Stock can let you exclude millions of dollars of gain from federal tax when you sell C-corporation shares held long enough. The 2025 law expanded the benefit, but the requirements are strict and easy to break years before the exit.

Section 179 and the 6,000-Pound Vehicle Deduction: Writing Off Equipment and Trucks Section 179 and 100% bonus depreciation let a business deduct the full cost of equipment and qualifying vehicles in year one. The heavy-vehicle rule is real, but the weight class, business-use percentage, and recapture traps decide how much you actually keep.

Small Business Tax Strategies: The Augusta Rule, Hiring Your Kids, and Accountable Plans Three legitimate, underused strategies let business owners move money from the taxable column to the deductible one: renting your home to your business tax-free, putting your children on payroll, and reimbursing yourself the right way.

The 83(b) Election and Startup Equity: ISOs, NSOs, RSUs, and Restricted Stock If you receive founder shares or early-exercise your options, the 83(b) election can convert a future ordinary-income tax bill into long-term capital gain. The catch is a hard 30-day deadline that, once missed, cannot be undone.

The QBI Deduction (Section 199A): A 20% Write-Off Most Pass-Through Owners Leave on the Table The qualified business income deduction lets most pass-through owners deduct 20% of their business profit before tax. It is now permanent, but income thresholds, the W-2 wage limit, and the service-business rules decide how much you actually get.

Solo 401(k) vs. SEP-IRA: Which Retirement Plan Is Right for Self-Employed Business Owners? Both plans offer high contribution limits and immediate tax deductions, but the Solo 401(k) lets you save significantly more at lower income levels and includes a Roth option most business owners don't know about.

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