Tax strategy for people who actually file their own returns.

Specific, numbered guides for self-employed people, LLC owners, and freelancers. Real numbers. Real forms. No vague "consult your CPA" filler.

Deduction Discovery

The deductions most self-employed people miss — and the errors that cost them refunds.

Founder Story

Form 8829 Home Office: The $1,046 Error I Found on My Own Return

I filed my 2024 taxes in March. Two months later, I ran the return through a tool I was building and it flagged a single line — rent. The number was off by $10,200.

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Reference

17 Deductions Self-Employed People Miss (With Real Numbers)

A ranked list with dollar stakes. If you're DIY-ing your return, read this before you file.

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Comparison

Simplified vs Actual Home Office Method: Which Wins in 2025?

The simplified method caps at $1,500. Most people who use it leave money on the table.

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How-To

Can You Deduct Your Phone Bill? (Yes, Here's How Much)

The IRS allows a business-use percentage of your personal phone. Most people skip it entirely.

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Rules

Business Meals 2025: The 50% vs 100% Rules That Still Confuse Everyone

The 100% deduction window closed in 2022. Here's what's still deductible and at what rate.

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Above-the-Line

Self-Employed Health Insurance Deduction

An above-the-line deduction most DIY filers skip. Could be worth $3,000+ depending on your premium.

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Decision

Section 179 vs Bonus Depreciation: Which Saves More in 2025?

Bonus depreciation phased down to 40% in 2025. Here's how to pick between the two.

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Decision

Vehicle Deduction: Standard Mileage vs Actual Cost

When to switch, and why switching mid-vehicle-life can cost you.

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Edge Case

The QBI Deduction Trap: When a Bigger Expense Costs You Money

QBI is 20% of qualified income. Which means a large deduction can actually shrink your refund. Here's when.

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First Year

Startup Costs Deduction: The $5,000 First-Year Rule

If you started your business this year, you can deduct up to $5,000 of pre-launch costs. Most solo filers miss this entirely.

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Self-Employed Fundamentals

The boring but load-bearing stuff. Get these right before optimizing anything fancy.

Explainer

Self-Employment Tax Explained: What the 15.3% Actually Pays For

Social Security + Medicare, on both the employer and employee halves. Here's how the math works and where the deduction kicks in.

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Penalty Avoidance

Quarterly Estimated Taxes: The Safe Harbor Rule That Saves the Penalty

Pay 100% of last year's tax (110% if high income) and you're safe. Here's the calculation nobody explains.

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Walkthrough

Schedule C Line by Line: A Plain-English Walkthrough

Every line of Schedule C, what it means, and where the common mistakes live.

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Reference

1099-NEC vs 1099-MISC: Who Gets What in 2025

The 1099-NEC came back in 2020. Here's which payments go on which form.

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Decision Tree

Do I Need an EIN? A 5-Question Decision Tree

Sole proprietor, SMLLC, contractors, retirement plan — each triggers a different answer.

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System

Tracking Expenses Without QuickBooks: The CSV + Spreadsheet System

The system I use for my own LLC. Zero subscription cost, 1 hour a month, audit-ready.

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Red Flag

Business Bank Account vs Personal: The IRS Commingling Red Flag

Mixing funds doesn't disqualify your deductions — but it can pierce the LLC veil and trigger audits.

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Recovery

Mixing Business and Personal Expenses: How to Untangle at Tax Time

If you already commingled, here's the process to clean it up before filing.

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Retirement for Self-Employed

How to shelter $60k–$300k a year from tax, legally, using plans almost no W-2 worker has access to.

Decision

SEP-IRA vs Solo 401k: The $60,000 Decision Nobody Explains Right

For most solo LLC owners, the Solo 401k wins by a wide margin. Here's why — and when SEP-IRA still beats it.

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Calculator

SEP-IRA Max Contribution Calculator for 2025

Enter your net self-employment income. We'll show the exact max you can contribute.

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Tax Math

Why 20% Is the Real SEP-IRA Rate (Not 25%) for Self-Employed

The IRS publications all say 25%. For self-employed people it's actually 20%. Here's the circular math.

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Strategy

Solo 401k Loan: Using Retirement Money to Buy a Business Asset

You can loan yourself up to $50k from your Solo 401k. Here's the mechanics and when it makes sense.

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Broker Review

E*TRADE vs Fidelity vs Schwab: The Only SEP-IRA Comparison You Need

Fees, features, loan support, and which one actually lets you do a Solo 401k loan.

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Advanced

Backdoor Roth for LLC Owners: The Step-by-Step

High-income self-employed people can't contribute to Roth directly. Here's the legal workaround.

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50+

Catch-Up Contributions at 50+: The Self-Employed Edition

$7,500 extra on a Solo 401k. $8,000 on an IRA. Here's how to stack them.

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High Earner

Defined Benefit Plan: The Retirement Hack for $200k+ Solopreneurs

Contribute $200k+ per year, fully deductible, if you qualify. Here's who does.

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Entity Structure

LLC, S-Corp, partnership, sole prop. The choice matters more as income grows.

Decision

LLC vs S-Corp: The Income Threshold Where Election Pays Off

Below $50k, don't bother. Above $80k, almost always worth it. Here's the actual math.

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Deadline

S-Corp Election: Form 2553 Deadlines & Late-Election Relief

Miss the March 15 deadline? There's a retroactive relief option. Here's how to use it.

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Audit Risk

Reasonable Salary for S-Corp Owners: How the IRS Actually Decides

Pay yourself too little and the IRS reclassifies distributions as wages. Here's the benchmark.

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Basics

Single-Member LLC Taxes: 3 Paths, 1 Form, 0 Confusion

Disregarded entity, S-Corp election, or C-Corp election. Here's which applies to you.

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Form 1065

Multi-Member LLC: Partnership Return Basics

Adding a partner triggers Form 1065 and K-1s. Here's what the first year looks like.

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Exit

Dissolving Your LLC: The Final Tax Return Nobody Talks About

Close the LLC wrong and you'll get IRS letters for years. Here's the shutdown checklist.

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Compliance Trap

Foreign-Owned Single-Member LLC: The Form 5472 Trap

Non-US owners of SMLLCs face a $25,000 penalty for missing Form 5472. Here's who owes it.

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Contractors & International Payments

Paying people across borders. What the IRS wants, what your contractor owes, and how to pay cheaply.

Form

Hiring International Contractors: Form W-8BEN Demystified

The form your overseas contractor signs so you don't have to file a 1099 for them.

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Deadline

1099 Filing Deadline Survival Guide (Jan 31 — No Extensions)

Penalties start at $60 per missed form. Here's the 10-day sprint to get them out on time.

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Process

Paying Contractors in Thailand, Philippines, Colombia: Tax Checklist

The documentation you collect up front saves you a panic-filled January.

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Comparison

Wise vs PayPal vs Wire: Cheapest Way to Pay Overseas Contractors

Wise wins on FX. PayPal loses on fees. Wires lose on speed and receiving cost. The numbers.

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Filing

Form 1042-S: Do I Really Need to File for My Overseas Worker?

Usually no — if the work is performed outside the US. Here's the full decision tree.

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Amended Returns & Corrections

Found an error? Three years to fix it. Here's how.

Walkthrough

Form 1040-X Walkthrough: Amending Without Panic

What changes, what stays, how to explain the change in Part III, and how to file electronically.

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Statute

How Far Back Can You Amend a Tax Return?

Three years from filing or two years from payment, whichever is later. With exceptions.

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How-To

IRS Transcript 101: How to Pull Yours Free

What's in a Wage & Income transcript vs Account transcript. How to use them to find missed 1099 income.

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Patience

Amended Return Refund Timeline: Why It Takes 16 Weeks

Humans process 1040-X, not machines. Here's how to track yours and when to worry.

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We're building a tool that checks your return for these errors.

Free. Upload your PDF, get a list of missed deductions and miscalculations. Launches January 2027.