You built the position. The question is how much of it survives the sale. We plan exits so that tax is deferred, reduced, or eliminated where the Internal Revenue Code allows it, and we quantify the trade-offs of each route before you commit.
A concentrated position with a large embedded gain has four basic exits: sell and pay, defer, exclude, or diversify without selling. Each has a different after-tax outcome, a different liquidity profile, and a different set of risks. Our job is to run the math on all four for your specific facts and hold periods, then implement the one you choose.
At 2026 federal rates, a top-bracket seller gives up 23.8% of a long-term gain (20% capital gains rate plus the 3.8% net investment income tax), before state tax. In a high-tax state the combined figure can exceed 37%. That is the hurdle every strategy below is measured against.
Sell appreciated assets inside a tax-exempt trust, defer the gain across a payout stream, and take a deduction up front.
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 →Diversify a concentrated stock position without a sale by pooling shares with other investors in a partnership.
Read the overview →Sold qualifying stock before the holding period was met? Roll the proceeds into new QSBS within 60 days and keep the clock running.
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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