The sale of a business is usually the largest taxable event of an owner's life, and the most plannable. Entity structure, timing, and pre-sale transfers drive the outcome.
Years before a sale: entity review (C corporation status opens Section 1202; S corporations and partnerships have their own routes), compensation and retirement plan design, and income timing across years. As a sale becomes realistic: GRATs and installment sales to grantor trusts move appreciation out of the estate at pre-deal values, and QSBS stacking multiplies exclusions where the stock qualifies.
At the sale itself: installment treatment, charitable remainder trusts for low-basis interests, opportunity zone reinvestment of the gain, and state residency and situs questions that can swing the bill by double-digit percentages.
After the sale: the proceeds become a portfolio problem. Asset location, direct indexing against the realized gain, and estate structures for the next generation. We manage that full arc rather than handing you off at the wire transfer.
Sell appreciated assets inside a tax-exempt trust, defer the gain across a payout stream, and take a deduction up front.
Read the overview →Multiply the Section 1202 exclusion by gifting shares to non-grantor trusts, each with its own per-issuer cap.
Read the overview →Transfer the upside of an appreciating asset at near-zero gift tax cost. The classic pre-liquidity estate freeze.
Read the overview →Roll a realized gain into a qualified opportunity fund to defer the tax and eliminate tax on the fund's own appreciation after a 10-year hold.
Read the overview →Own the index as individual positions and harvest losses continuously to offset gains elsewhere in your financial life.
Read the overview →A first meeting covers your situation, the strategies that plausibly apply, and what we would need to review before recommending anything.
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