Sell appreciated assets inside a tax-exempt trust, defer the gain across a payout stream, and take a deduction up front.
A charitable remainder unitrust (CRUT) is a tax-exempt trust. You contribute an appreciated asset, the trust sells it, and no capital gains tax is due at the sale. The full pre-tax proceeds are reinvested and the trust pays you a fixed percentage of its value each year, between 5% and 50%, for a term of up to 20 years or for life. Whatever remains at the end passes to charity, which must be at least 10% of the initial contribution on an actuarial basis.
The value comes from compounding the deferred tax. Sell $5M of zero-basis stock outright at a combined 30% rate and you reinvest $3.5M. Sell it inside a CRUT and $5M compounds. You pay tax gradually as distributions come out, under ordering rules that treat payouts as income first. In long-duration, high-return scenarios the trust route can produce meaningfully more after-tax wealth than an outright sale, and you receive a charitable deduction in year one for the present value of the remainder interest.
We compare an outright sale against multiple trust designs using your basis, state residency, expected return, and payout preferences, and we present the comparison with the assumptions visible. If the structure clears the bar, we coordinate drafting counsel and the trustee, and we manage the trust's portfolio inside your overall allocation.
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 →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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