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Sales Tax
Sales Tax Nexus Checklist
16 questions that reveal whether you owe sales tax in states you haven't registered in — before a state finds you first.
Tax Planning
Small Business Tax Planning Guide
The five moves that separate business owners who plan from those who just file — entity structure, quarterly payments, deductions, and more.
Bookkeeping
2026 Bookkeeping & Tax Deadline Calendar
Every federal deadline that matters this year, quarter by quarter — plus the monthly habits that keep your books audit-ready.
New resources added monthly. Check back — or get in touch if there's a topic you'd like us to cover.
Sales Tax
Sales Tax Nexus Checklist
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Physical Presence
Economic Nexus
Registration & Compliance
Warning Signs
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Your entity determines your tax bill. Sole proprietors pay self-employment tax on every dollar of profit. An S-Corp election can change that math significantly once profits are consistent.
The S-Corp question is about timing, not just savings. Elect too early and payroll costs eat the benefit. Too late and you've overpaid for years.
An S-Corp requires paying yourself a reasonable salary. Set it too low and the IRS notices. This is where professional guidance pays for itself.
Review your structure annually. The right answer at $40K of profit is often the wrong answer at $150K.
Four deadlines: April 15, June 15, September 15, January 15. Miss them and you owe underpayment penalties — even if you pay in full at filing.
Use the safe harbor. Pay 100% of last year's tax (110% if your income was over $150K) and you avoid penalties no matter what this year brings.
Set aside a percentage of every deposit. A separate tax savings account, funded automatically, means April is never a crisis.
Recalculate mid-year. If your income jumped, your Q3 and Q4 payments should too.
Home office, vehicle, and mileage — legitimate, valuable, and only defensible with records kept as you go, not reconstructed in April.
Retirement contributions cut taxes twice. A SEP-IRA or Solo 401(k) lowers this year's bill while building your future.
Equipment purchases can be deducted faster. Section 179 and bonus depreciation let you write off qualifying purchases now instead of over years.
Don't forget the QBI deduction. Many pass-through owners can deduct up to 20% of qualified business income — but the rules around it are exactly where planning matters.
Separate accounts, always. Mixing business and personal is the fastest way to lose deductions and credibility with the IRS.
Every deduction needs a paper trail. Receipts, invoices, mileage logs — digital copies are fine, missing copies are not.
Reconcile monthly, not annually. Clean books each month means tax season is a formality, not an archaeology project.
Document the "why" on unusual expenses. A note today beats an explanation you can't remember in three years.
Timing is a tool. Deferring income or accelerating expenses in December can shift your tax bill meaningfully — but only if you act before the year closes.
Buy needed equipment before year-end to capture the deduction this year instead of next.
Open retirement plans by their deadlines. Some plans must exist before December 31 even if you fund them later.
Do a November tax projection. Knowing your number in November leaves time to change it. Finding out in April doesn't.
This guide is educational and general in nature — it isn't tax advice for your specific situation. That's what the consultation is for.
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Q4 2025 estimated tax payment dueFinal quarterly payment for the prior tax year.
Jan31
1099-NEC & W-2 filing deadlineForms due to contractors, employees, and the IRS. Late filing penalties add up per form.
Mar16
S-Corp & Partnership returns dueForms 1120-S and 1065 (or extension requests). March 15 falls on a Sunday in 2026.
Apr15
Individual & C-Corp returns due + Q1 estimated paymentForm 1040 and 1120 filing deadline — and the first quarterly payment for 2026 is due the same day.
Jun15
Q2 estimated tax payment dueSecond quarterly payment — only two months after Q1, which surprises people every year.
Sep15
Q3 estimated payment + extended S-Corp/Partnership returns dueTwo deadlines in one day: your third quarterly payment, and the final deadline for extended 1120-S and 1065 returns.
Sep30
Ideal window for a mid-year books cleanupThree full quarters of data — the perfect time to fix messy books while there's still time to act on what they show.
Oct15
Extended individual & C-Corp returns dueThe final deadline — no more extensions after this.
Nov30
Run your year-end tax projectionKnow your number while there's still time to change it.
Dec31
Last day for most year-end tax movesEquipment purchases, certain retirement plan setups, income/expense timing — all close with the year.
Every Month, No Exceptions
Reconcile every bank and credit card account
Review outstanding invoices and unpaid bills
File sales tax returns due that month (frequency varies by state)
Save and categorize receipts — don't let them pile up
Glance at your P&L: does this month make sense?
Federal deadlines shown; weekend/holiday shifts applied for 2026. State deadlines vary.
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