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Keep More: Tax Strategies for the Self-Employed Trade

The practical tax playbook for contractors, tradespeople, and service operators who want to stop overpaying and start keeping what they earn.

98 min · 30 video lectures · quizzes · assignments · workbook

Most self-employed tradespeople and service operators overpay their taxes by hundreds or thousands of dollars every year — not because they are doing anything wrong, but because nobody ever showed them the full picture of what they are legally entitled to deduct and how to structure their business to keep more of what they earn. This course covers the tax fundamentals that apply across every trade and service business: plumbers, electricians, landscapers, cleaners, mobile operators, contractors, and independent service providers of every kind. You will learn how your business structure affects your tax bill, which deductions tradespeople and service operators routinely miss, how to handle vehicle and home office deductions correctly, how to calculate and pay quarterly estimates without penalty, and how to use retirement accounts to reduce taxable income while building long-term wealth. Each section connects directly to real decisions you make in your business: how you pay yourself, how you classify your vehicle expenses, which receipts you need to keep and why, and how to work productively with an accountant so you are not paying for time spent reconstructing records you should have maintained year-round. This is educational content covering general tax principles applicable to self-employed individuals in the United States and Canada. It is not tax advice or legal advice, and nothing here replaces a qualified tax professional who knows your specific situation. The welcome lecture repeats this clearly. The goal of this course is to make you a better-informed client when you do sit down with a professional, and to help you stop leaving legally available deductions on the table. No accounting background required. No complex software. Just clear, specific, actionable content built for people who work with their hands and run their own operations.

What you'll learn

  • You will be able to evaluate whether a sole proprietorship, LLC, or S-corp structure is appropriate for your income level and risk profile
  • You will be able to identify the vehicle deduction method — standard mileage versus actual costs — that produces the larger deduction for your situation
  • You will be able to build a home office deduction calculation if you use a dedicated workspace for your business
  • You will be able to calculate your quarterly estimated tax payments and set up a payment schedule that avoids underpayment penalties
  • You will be able to identify at least five deduction categories that tradespeople commonly miss or underreport on their returns
  • You will be able to open and fund a SEP-IRA or Solo 401(k) to reduce taxable income while building retirement assets
  • You will be able to organize your receipts, mileage logs, and expense records into a year-round system your accountant can use efficiently
  • You will be able to evaluate whether your current accountant is a genuine tax strategist or simply a return preparer, and ask the right questions to find out

Course curriculum

Section 1: Section 1: Business Structure — LLC, S-Corp, and What the Choice Costs You

Section 2: Section 2: The Deductions Tradespeople Miss

Section 3: Section 3: Vehicle, Tools, and Home Office Deductions

Section 4: Section 4: Quarterly Estimates and Avoiding Penalties

Section 5: Section 5: Retirement Accounts and Income Smoothing

Section 6: Section 6: Working with an Accountant Effectively

Built for the Self-employed tradespeople and contractors who suspect they are overpaying taxes but are not sure where to start

This course is the operator's playbook for the industry it serves. Pair it with: