Gregory Halsted Okonkwo — Senior Retirement Planner

Gregory has run retirement plans for roughly 400 households over two decades, with a recent concentration in clients aged 52 to 64 who accumulated most of their wealth through RSU vestings and a long-held ESPP position at a single public employer. His planning horizon starts earlier than traditional retirement work, usually at age 50, because concentrated-stock households need a much longer unwind runway than diversified households do.

The plan he builds most often starts with a 58-year-old senior director sitting on $6.4M of employer stock, $1.1M in a 401(k) with about 40% in company stock inside the plan, and a target retirement at 62. The 401(k) company-stock piece is a candidate for net unrealized appreciation treatment: distributed in kind to a taxable account at retirement, the basis portion is taxed as ordinary income today and the appreciation converts to long-term capital gain on future sale, often a 15 to 20 percentage point arbitrage. Gregory sequences the NUA distribution against the client’s first low-income year in retirement, runs Roth conversions against the remaining 401(k) balance across the years before age 65 Medicare IRMAA lookback kicks in, and schedules concentrated-stock sales to land in 0% and 15% capital-gains brackets where possible.

He reviews content on concentrated-stock drawdowns, NUA, and retirement-income sequencing.