The Stacking Benjamins Show · Friday, October 30, 2026
Panelists discussed strategies for managing a concentrated company stock position when it triples in value to 38% of a portfolio. Paula Pant advised trimming it to 10% if it is earmarked for retirement, while OG suggested considering momentum, writing options, or building savings elsewhere to lower the percentage without triggering capital gains taxes.
“If this is money that has, if it's earmarked for retirement, if it's money that you need, then you sell. You get the hell out of the basement. You go running for the hills and you whittle that down to 10% of your portfolio.”
“I wouldn't sell a stock that was up a whole bunch. And you paying the tax man if I don't have to. So I would probably let it ride and maybe build outside of it to get the percentage down”