Entity structure confusion. Reasonable salary questions. Payroll tax surprises. Year-end planning gaps. Every small business tax issue in one place — free tools, clear answers, 2026 rates.
Four high-stakes tax questions every small business owner gets wrong — and what to do instead.
Most owners wait too long to elect S-Corp status — or never do it at all. At $100K net income, the typical savings are $5,400–$7,200 per year. The 2026 election deadline for calendar-year businesses is March 15. Late election relief exists but costs time and money.
Compare entity structures →Setting your W-2 salary too low is the #1 IRS audit trigger for S-Corp owners. Too high eliminates the tax advantage. The IRS compares you to market wages for your role. Industry, hours, and revenue all factor in — and the answer isn't 50% of net income for every business.
Generate S-Corp election package →Underpayment penalties hit small business owners hard. The 2026 quarterly deadlines are April 15, June 16, September 15, and January 15, 2027. If your 2025 AGI exceeded $150,000, you must pay 110% of last year's tax to use the safe harbor — not just 100%.
Calculate estimated taxes →Your first hire triggers employer FICA (7.65%), FUTA, and state unemployment taxes — adding $3,800–$5,000 per year in employment taxes per $50K employee. It also affects your Section 199A deduction, which adds a W-2 wage limitation above income thresholds of $197,300 (single) or $394,600 (joint).
Model your tax picture →Small business tax liability by entity type. Same income, dramatically different outcomes.
The comparison above uses $150K, California, single filer. Your income, state, and filing status change the math significantly. Run the Entity Comparison Calculator with your actual numbers — it covers all 50 states and all three entity types with 2026 tax law built in.
Four tools in the right order. Each builds on the last. No CPA required to get started.
Compare LLC vs S-Corp vs C-Corp. Enter your income, state, and filing status. See exact 2026 tax liabilities and breakeven point for S-Corp election.
Generate a complete Form 2553 cover letter, board resolution, and state-specific filing checklist. Includes reasonable salary guidance and all 50 state requirements.
Calculate your 2026 quarterly payments with safe harbor thresholds, payment schedule, and underpayment risk analysis. Supports S-Corp salary splits.
Full AI-generated tax strategy for your business: entity analysis, deduction maximizer, quarterly plan, year-end action roadmap, and state-specific notes. $39 — or more with your CPA.
Generic advice costs small business owners thousands. These tools are built around the real decisions — not textbook scenarios.
The One Big Beautiful Bill Act restored 100% bonus depreciation and R&D expensing. SE tax rates, FICA limits, and QBI thresholds all changed. Every calculator reflects current law, not last year's numbers.
You don't need a spreadsheet that generates more questions. Every tool produces a clear recommendation — and where TaxStackHub says "talk to your CPA," it tells you exactly what to bring to that conversation.
The calculators, entity comparison, and document generators are free — no paywall, no signup required. Premium is reserved for deep personalized analysis that would cost $2,000+ with a CPA.
Weekly insights on entity structure, deduction strategy, quarterly planning, and hiring tax implications — written for owners, not accountants. Free.
Specific answers to the tax questions small business owners are actually searching for.
An LLC should elect S-Corp when net self-employment income consistently exceeds $50,000–$80,000 per year. At $100,000 net income, the typical S-Corp saves $5,400–$7,200 annually by splitting income between a W-2 salary and an S-Corp distribution — the distribution portion avoids the 15.3% SE tax. The Form 2553 deadline for 2026 is March 15 (15th day of the 3rd month of the tax year). Late election relief is available under Rev. Proc. 2013-30. You'll also need to set up payroll and file quarterly payroll returns. Source: IRC § 1362(a), IRS Form 2553.
The IRS requires S-Corp owner-employees to pay themselves a "reasonable salary" comparable to what you'd pay a third party to do the same work. For service businesses, reasonable salary is typically 40–60% of net S-Corp income. At $150,000 net income, a $65,000–$90,000 salary is common. Factors include industry, geography, hours worked, and qualifications. Setting salary too low is the #1 S-Corp audit trigger and can result in reclassification of distributions as wages plus penalties. Setting it too high eliminates the tax advantage. Use the S-Corp Election Generator to get guidance specific to your business. Source: IRS Publication 15-A, IRC § 3121.
For a small business with 1–10 employees generating $100K–$1M net income, the S-Corporation is generally optimal. An S-Corp saves SE tax on distributions above the owner's salary — up to the $184,500 Social Security wage base in 2026. At $250,000 net income with a $100,000 salary, an S-Corp saves ~$14,000/year vs. a sole prop or single-member LLC. C-Corps have a flat 21% rate but create double taxation on dividends. Multi-member LLCs face full SE tax on each partner's share. The right answer depends on your specific income, state, and filing status — use the Entity Comparison Calculator. Source: TaxStackHub 2026 entity calculator, IRC §§ 1362, 1401, 11.
Small business owners must pay quarterly estimated taxes if they expect to owe $1,000 or more. 2026 due dates: April 15 (Q1), June 16 (Q2), September 15 (Q3), January 15, 2027 (Q4). Safe harbor: pay 90% of current year tax OR 100% of 2025 tax (110% if 2025 AGI exceeded $150,000). Quick estimate: set aside 25–35% of net income each month for taxes, with the high end for self-employed owners who haven't yet elected S-Corp. Use the Estimated Tax Generator for precise quarterly payment amounts. Source: IRS Publication 505.
Hiring your first employee triggers: (1) Employer FICA: 7.65% of wages (6.2% SS up to $184,500 + 1.45% Medicare). (2) FUTA: 6% on first $7,000 wages, often reduced to 0.6% with state unemployment credits. (3) State unemployment insurance (SUI): 1–5% depending on state. (4) Payroll tax deposits: monthly or semi-weekly based on your lookback period. Total employer tax cost: ~$3,825 per $50K employee in FICA alone. Hiring also affects your Section 199A deduction — W-2 wages paid by the business become relevant above income thresholds of $197,300 (single) / $394,600 (joint). Source: IRS Publication 15, IRC §§ 3111, 3301, 199A.
The Section 199A QBI deduction lets pass-through owners (sole props, S-Corps, partners) deduct up to 23% of qualified business income from taxable income (raised from 20% under OBBBA). In 2026, the phase-out for specified service businesses (consulting, law, accounting, health, etc.) begins at $197,300 (single) and $394,600 (joint). Above the phase-out, the deduction is limited to 50% of W-2 wages paid OR 25% of W-2 wages + 2.5% of qualified property — whichever is greater. S-Corp owners with employees often qualify for a higher QBI deduction than sole props because W-2 wages paid count. Source: IRC § 199A, OBBBA, IRS Publication 535.
Commonly missed deductions in 2026: (1) Section 179: deduct up to $1,160,000 of equipment/property in year of purchase. (2) 100% bonus depreciation, restored under OBBBA for property placed in service 2025–2029. (3) Home office: $5/sq ft simplified ($1,500 max) or actual expenses. (4) Vehicle: $0.70/mile standard rate or actual expenses. (5) Health insurance premiums: 100% deductible for self-employed. (6) Retirement: SEP-IRA up to $70,000; Solo 401(k) up to $70,000 + $7,500 catch-up if 50+. (7) R&D expenses: 100% expensing restored under OBBBA. Source: IRC §§ 162, 168, 179, 199A, IRS Pub. 535.
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Guides
Guide
LLC vs S-Corp vs C-Corp: The 2026 Comparison
Real tax math at $75K, $150K, and $250K income. Know which entity structure wins for your situation.
Read entity guide →
Guide
S-Corp Election: When to Elect & How to File Form 2553
The $50K–$80K profit threshold, reasonable salary rules, and the compliance costs to model in.
Read S-Corp guide →
Guide
Self-Employment Tax 2026: The Full Breakdown
15.3% SE tax, the 50% deduction, and how entity structure changes everything for business owners.
Read SE tax guide →