March 05, 2026

How To Pay So Little Taxes it Feels Like Cheating

25 minutes

"This is a rule book and the financially savvy who understand the rule book can use it to pay less money in taxes legally."

The U.S. tax code penalizes the least risky financial behavior, earning a W2 salary, with the highest tax rates, while rewarding investment and business ownership with lower rates and a wide range of deductions. Most people overpay because they don't know the rules. This episode walks through the specific strategies available at each level of financial activity.

Jaspreet Singh breaks down the tax advantages that open up as someone moves from W2 income to stock market investing to real estate to business ownership; covering long-term capital gains rates, depreciation, retirement account structures, and small business deductions that most people never use.

In this episode, you'll learn:

How long-term capital gains tax rates (0%, 15%, 20%) compare to ordinary income tax rates (up to 37%) and how earning the same $100,000 from investments versus a job results in dramatically different tax bills

What tax loss harvesting is, how to use realized investment losses to offset gains, and how losses under $3,000 can offset W2 job income directly

How the backdoor IRA allows high-income earners who exceed the Roth IRA income limit to still get money into a Roth account legally

How the SEP IRA lets self-employed individuals and 1099 contractors contribute up to $69,000 per year into a tax-deferred retirement account

How the 27.5-year depreciation schedule on single-family rental properties creates a paper write-off that reduces taxable income even when the property is generating real profit

What accelerated depreciation is and how it can produce a paper tax loss large enough to offset active income from a job or business

Two strategies to unlock full real estate loss deductions above standard income limits: qualifying as a real estate professional, or using short-term rentals like Airbnbs

How small business owners qualify for the 20% QBI deduction and Section 179, including how vehicles over 6,000 pounds used for business can become a deductible expense

Keywords: tax strategy, tax deductions, long-term capital gains, real estate depreciation, SEP IRA, backdoor IRA, tax loss harvesting, QBI deduction, Section 179, small business taxes

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