Has he considered the CRUT option?
It’s not for everyone but if he believes his sales price could appreciate in the next few years and can live with a portion of his assets in a trust, it’s a decent alternative. He donates all or some of his S Corp shares to his CRUT, takes a charitable deduction and the CRUT sells the shares to the acquiring entity which bypasses personal capital gains and he becomes the primary income beneficiary of the trust. Of course, he still would need to pay ordinary income tax rates on the income he receives from the CRUT but depending on his personal circumstances it can make sense for some or all of a sale in the future.
[Post edited by Hoos Operator at 08/10/2020 2:22PM]
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In response to this post by psychobilly)
Posted: 08/10/2020 at 2:13PM