All Chapters

Options vs. RSUs vs. restricted stock. ISOs and NSOs. The vocabulary you need before anything else makes sense.

The numbers that actually matter, vesting schedules, the exercise window gotcha, and what your percentage really means.

409A valuations, the common stock discount, running bear/base/bull scenarios, and comparing offers apples-to-apples.

How funding rounds shrink your slice, the option pool shuffle, and red flags to watch for.

AMT traps, the 83(b) election, QSBS (the holy grail), capital gains timing, and what to actually do.

What's negotiable, how to make the ask, using market data, and the exact scripts to use.

Why your equity doesn't stop after year 4. Performance, promotion, and market correction refreshes.

The structural, communication, and situational red flags to check before you sign anything.

The 90-day clock, good leaver vs. bad leaver, layoffs vs. resignation, and acquisition scenarios.

How to sell private shares before an IPO. Platforms, tax implications, and who's eligible.

The decision framework for comparing a startup offer against Big Tech RSUs. Risk adjustment and scenario modeling.

Five questions, a pre-sign checklist, and the mental model to carry with you for every offer.