Company stock options can feel overwhelming, and for good reason. They’re not simple, they’re not standardized, and depending on how they’re handled, they can either create real opportunity or serious tax headaches. Today I’ll walk through the most common types of company stock options, including ISOs, NSOs, RSUs, restricted stock awards, employee stock purchase plans, and stock appreciation rights, so you understand what you actually have and how each one works.

I also get into the tax implications behind each option, using real-world examples to show how timing, holding periods, and strategy can dramatically change your outcome. Company stock often feels like a bonus, but it comes with real decisions and real consequences. This episode is about understanding those tradeoffs so the stock you earn actually works for you, not against you.