Guides — Cliff & Vest

01 Guide Double-trigger RSUs, and the bill that arrives at IPO Private-company RSUs need two things to happen before you own anything: time, and a liquidity event. That structure protects you from being taxed on shares you cannot sell — and stores up several years of income to land in a single tax year when the company finally goes public.
02 Guide What changed for equity compensation in 2026 Two provisions that matter enormously to people holding startup equity were rewritten in July 2025, and both took effect for 2026. One makes exercising incentive stock options more expensive at high incomes. The other makes founder stock dramatically more valuable — but only if it was issued after a particular Friday.
03 Guide The tax forms your equity generates Equity compensation produces a small pile of paperwork every spring, most of it informational and one piece of it actively misleading. The 1099-B your broker files frequently reports a cost basis of zero on shares you have already paid tax on, and correcting it is on you.
04 Guide How equity compensation is taxed Four instruments, four completely different answers. What decides your tax is not how much your equity is worth but which of the four you hold, and at which of the four possible moments the tax code decides to notice it.
05 Guide What happens to your options when you leave Resigning starts two clocks at once. One gives you ninety days to find the cash to exercise or lose the options entirely. The other, which almost nobody is told about, quietly converts incentive stock options into non-qualified ones on day ninety-one.
06 Guide When to exercise your stock options The strike price is fixed and the deadline is years away, so exercising feels like a decision you can defer indefinitely. It is not: every year you wait usually raises the valuation, and the tax you will owe rises with it. Here is what actually drives the timing.