Concentrated Stock Risk for Your Retirement

A concentrated stock position feels like a problem you'd love to have. And if you've built one, you probably have a number in your head, the tax bill, that keeps you from doing anything about it. Adam and Andy have seen this play out many times. The first question they ask isn't about tax strategy. It's simpler: if this position dropped 80% tomorrow, would it derail your retirement? If the answer is yes, no tax optimization strategy changes what you actually need to do. In the latest episode of Long Story Short, they walk through three approaches people use to manage concentrated positions and explain why sometimes the most straightforward move is also the right one. Listen to the full #LongStoryShort podcast episode “529s, Concentrated Stock, and AI in Investing” on Spotify, Apple Podcasts, or YouTube.

Added 16 Apr 2026