Equity Compensation
Equity compensation goes wrong in two predictable ways: a reporting error that taxes the same income twice, and a concentration problem where your portfolio and your salary depend on the same company. Both are avoidable, and both need deciding before you exercise rather than after.
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How an ESPP Is Taxed: Qualifying and Disqualifying Dispositions
Two holding-period clocks, four worked sales of the same shares, why the qualifying rule saves less than it sounds, and the 1099-B basis error that taxes the discount twice.
Read the article →Non-Qualified Stock Options: How They're Taxed
Two taxable moments, one costly reporting error, and a withholding rate that is usually too low. What to check before you exercise, and what to check on your 1099-B afterwards.
Read the article →How RSUs Are Taxed: Vesting, Withholding and the Shortfall Nobody Mentions
RSUs are wages the day they vest, and the 22% withholding usually falls short. A worked 2026 example, the 1099-B basis error, and why selling at vest costs nothing extra.
Read the article →Incentive Stock Options and the AMT: How Much You Can Exercise Before It Bites
No regular tax at exercise, but the spread counts for the AMT. Finding your 2026 crossover, the AMT credit, and the December sale that undoes a bad exercise.
Read the article →Net Unrealized Appreciation: The Tax Break for Company Stock in Your 401(k)
Take employer stock out of a 401(k) as shares and most of its growth becomes long-term capital gain. When it beats a rollover, when it loses, and the mistake that forfeits it.
Read the article →Too Much of Your Net Worth in One Stock: How to Reduce It Without a Huge Tax Bill
Why one stock is riskier than it feels, what selling really costs in tax, and the tools for bringing it down: staged sales, gifts, exchange funds, hedges and 10b5-1 plans.
Read the article →Want this applied to your own situation?
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