Convert up to $100K ($50K single) of stock losses from capital to ordinary — huge tax savings if the startup fails.
IRC §1244 lets original-issue shareholders of qualifying domestic small business corps (paid-in capital ≤$1M) treat losses on their stock as ORDINARY (up to $100K MFJ / $50K single per year) instead of capital. Ordinary losses offset W-2, 1099, and business income — worth 3–5× a capital loss in real tax value. No election required, just proper documentation at issuance. Every founder should structure formation to preserve §1244.
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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.