Isabel Monroe Asante , JD, LLM Taxation

Isabel’s charitable-planning practice sits inside a regional firm that serves tech executives and founders. Most of her engagements start in November, when a client who has just had a liquidity event realizes they are looking at a seven-figure federal tax bill and wants to reduce it through a large current-year contribution. She pushes clients to separate two questions they tend to collapse: how much to give this year, and what vehicle to give through.

The structure she runs most often is a contribution of long-held appreciated public stock to a donor advised fund in the year of a large income event. A director sells $4M of vested RSUs at a $240 share price into a 10b5-1 window, producing $3.8M of ordinary and capital income on top of an already $800k base comp year. Contributing $600k of separate long-held shares to a DAF produces a federal deduction at fair market value, capped at 30% of AGI, with a five-year carryforward. The deduction offsets ordinary income at the 37% bracket while the embedded capital gain on the donated shares disappears entirely, a combined tax value of roughly 56 cents per dollar donated. For clients with more to give and a longer horizon she runs the charitable remainder trust analysis against the DAF and often lands on a CRUT when the client wants an income stream.

She reviews content on DAFs, CRTs, and gifts of private stock.