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S-Corp Strategist

Tax Planning for Growth-Stage Businesses

The S-Corp Advantage: Self-Employment Tax

Unlike a Sole Proprietorship where 100% of profit is subject to Self-Employment (SE) tax, an S-Corp allows you to split earnings into W-2 Salary (subject to SE tax) and Distributions (not subject to SE tax). Use the sliders below to estimate your potential tax reduction.

Net profit before owner's pay.

Must be "reasonable" for your role.

47% of Profit

Estimated SE Tax Savings

$0

Annual savings vs. Sole Prop.

Tax Liability Comparison

Sole Proprietorship vs. S-Corp Split

Advanced Planning Strategies

Beyond the basic tax split, S-Corps offer specific mechanisms for Health, Retirement, and Timing that require careful execution.

The >2% Shareholder Rule

For S-Corp owners owning more than 2% of shares, health insurance premiums are handled differently than for regular employees. They are not tax-free fringe benefits. However, if structured correctly, you can still deduct 100% of the premiums.

The Critical "Wage Gross-Up"

To take the deduction on your personal 1040, the S-Corp must pay the premium (or reimburse you) and include the amount in your W-2 wages (Box 1 and Box 14).

Correct Reporting Workflow

1

Company Pays Premium

S-Corp pays insurer directly or reimburses owner via accountable plan.

2

Report on W-2

Add cost to Box 1 (Wages) and Box 14 (Info). Subject to Income Tax, but exempt from FICA (if plan is qualified).

3

Deduct on 1040

Owner takes "Self-Employed Health Insurance Deduction" on Schedule 1, offsetting the income tax impact.