The Tab You Keep Closing (And Why You Need to Open It)

What's in this episode

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. — There's a tab a lot of tech professionals have open right now. It's from Fidelity or E-Trade, it shows how much company stock they're sitting on, and most of them close it without doing a thing. Because the moment you start thinking about selling, it gets complicated. In this episode, Scott and Nick break down what to actually do when a big chunk of your net worth is tied to your employer's stock, whether that's RSUs, ISOs, ESPPs, or some combination of all three. They walk through why concentration happens quietly and compounds fast, especially when you're getting promoted, the stock is climbing, and new grants keep coming in. And they explain why "just diversify" is technically correct advice that leaves out everything that actually matters. The real conversation is about sequencing. How to unwind a concentrated position across multiple years, in a tax aware way, without triggering a bill you didn't plan for. That means looking at your income year by year, understanding which shares to sell first, knowing