Writing· Series
Equity Explainers
Plain-language notes on the tax and investment decisions behind startup equity — exercising options, the AMT, selling into liquidity, and how ISOs and NSOs differ. An ongoing series; new topics get added as they come up.
Before You Exercise: The Questions That Matter More Than TaxesExercising stock options is an investment decision before it's a tax decision. The four questions worth answering first.The AMT Breakeven: Exercising ISOs Without a Surprise Tax BillHow ISO exercises interact with the Alternative Minimum Tax, and how modeling the exercise first can bring the AMT bill to zero.Selling Early: Tender Offers, Disqualifying Dispositions, and What Holding Gets YouWhat happens tax-wise when ISO shares are sold before the holding periods run, why tender offers force the timing question, and what patience (including QSBS) actually rewards.NSOs: The Default Option, ExplainedNon-qualified stock options trade the AMT puzzle for a straightforward income hit at exercise. Why they show up alongside ISOs, what exercising really costs, and how they can make ISO planning work better.