S-corp pays your health premiums, adds to W-2 (no FICA), you deduct above-the-line — net: pre-tax health.
A >2% S-corp shareholder-employee cannot use pre-tax cafeteria plans for health insurance. Instead: (1) S-corp PAYS the shareholder's health insurance premiums (or reimburses), (2) premiums are added to shareholder's W-2 Box 1 (subject to FIT but NOT FICA/Medicare), (3) shareholder takes an above-the-line §162(l) deduction on Form 1040 Schedule 1. Net effect: pre-tax for FIT purposes and permanently exempt from 15.3% FICA. Missing this step is one of the top S-corp mistakes.
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Front-load depreciation on real estate to slash current-year taxes.
Turn W-2 income into tax-free passive rental losses.
Defer capital gains indefinitely by rolling into bigger real estate.
Defer + eliminate capital gains via OZ funds.
Rent your home to your business up to 14 days/year — tax-free.
Deduct 20% of pass-through business income.
Slash self-employment tax on profits above ~$50K.
Expense equipment, vehicles, and property in year one.