The IPO Lockup Playbook
The lockup lifts, your double-trigger RSUs vest all at once, and the 22% flat withholding doesn't cover what you'll actually owe. Here's the IPO game plan.
Tag: stock-options
All the articles with the tag "stock-options".
QSBS: The $10M Tax Break
QSBS lets qualifying startup stock skip federal capital gains tax on millions in profit, but exercise late or structure a buyout wrong and you lose it entirely.
The 83(b) Election: Your 30-Day Window
The 83(b) election has a strict 30-day deadline with no extensions. File it and a future tax bill shrinks to pocket change. Miss it and it can cost six figures.
ISO vs NSO: Options and the AMT Trap
ISOs and NSOs are taxed completely differently. Get it wrong and you owe a six-figure AMT bill on stock that's now worthless. Here's the full breakdown.
Stock Options vs RSUs: Which Is Better?
ISOs, NSOs, RSUs, your offer letter has all three and explains none of them. Here's what each type means, how it's taxed, and which you actually want.