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Equity compensation, in depth
Plain-English walkthroughs of the topics our calculators run on. Written for tech employees with real equity at stake, with the math, the trade-offs, and the landmines spelled out.
Alternative Minimum Tax
Five AMT mistakes you can still fix before December 31
Exercising $1M of ISOs in one year can cost $200K of AMT; splitting the same exercise across years, or shifting it from late December to early January, can save most of it. Five common timing and structure traps shape whether your ISO exercise nets out at a free lever or a six-figure surprise. We price each trap, with the calculator to find your specific crossover.
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Non-qualified stock options
Six NSO mistakes your tax advisor probably won't mention
Did you know brokerages may actually underreport your true NSO cost basis (per IRS basis-reporting rules)? Many tax software products and advisors miss this small detail. This and five other common NSO mistakes may cost you a small fortune. We price each trap, with the calculators to run your own grant.
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Restricted stock units
Five RSU mistakes that quietly grow your April tax bill
Your employer withholds federal tax on every RSU vest at 22%. Your true marginal rate is probably 32% or 35%. The gap shows up as a four-to-six-figure April surprise. This and four other common RSU traps determine what you owe at filing. We price each trap, with the calculator to find your specific gap.
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Concentration and diversification
Five costly stock concentration mistakes
Over 90 years of US stock data, the median individual stock returned less than one-month Treasury bills (Bessembinder 2018). Concentrated equity exposure has a wider distribution of outcomes than gut feel suggests. Five common traps decide whether de-concentration costs more in tax than the risk it eliminates. We size each trap, with the calculator to run your own numbers.
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Hedging concentrated positions
Five hedging mistakes that erase the protection you paid for
A typical 3%-per-year protective-put premium on a single-stock position compounds to roughly 26% of position value over a decade. The zero-cost collar fixes that, but introduces its own traps. Five common mistakes decide whether your hedge actually protects you or grows the bill it was meant to prevent. We price each trap, with the calculator to run your specific position.
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Calculators
Run the numbers on your own grant
Every article above pairs with a free calculator that takes your grant data and produces an answer. No signup.