Technical deep-dives on equity compensation taxation
Our comprehensive guides cover every aspect of stock options taxation, including RSU (Restricted Stock Units), ISO (Incentive Stock Options), NSO (Non-Qualified Stock Options), ESPP (Employee Stock Purchase Plans), 83(b) elections, and international tax planning strategies for tech professionals with equity compensation.
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Equity compensation is a significant part of total compensation for tech professionals, but the tax implications can be complex. Our guides cover the essential topics including:
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ISO vs NSO compared for employees: ordinary income vs capital gains paths, supplemental withholding and payroll taxes on NSOs, AMT on ISO exercise, the ISO/NSO split under the $100K rule, and early-stage startup considerations. Links to calculators for NSO tax and ISO AMT.
Expert guide on stock options in mergers and acquisitions. Covers IRC Section 424, accelerated vesting, cash-out vs substitution, ISO preservation, tax treatment by deal structure, and strategies to minimize tax liability in M&A transactions.
Complete guide to early exercise break-even analysis for stock options. Learn when to exercise before vesting, calculate break-even points, and optimize tax outcomes with 83(b) elections.
Beginner-friendly guide to stock options for employees. Learn what stock options are, how they work, key terms, tax basics, and what to do when you receive your first grant.
Complete tax guide to equity compensation for independent contractors, consultants, and startup advisors. Covers NSO-only eligibility rules, warrant structures, 1099 vs W-2 tax treatment, Section 409A compliance, self-employment tax, advisory share agreements, and vesting considerations.
Complete guide to the 3.8% Net Investment Income Tax (NIIT) on equity compensation. Learn which equity income triggers NIIT, how RSU sales, ISO dispositions, NSO exercises, and ESPP sales are treated, plus strategies to minimize the surtax.
Compare cash exercise, cashless (same-day sale), sell-to-cover, and net exercise (share withholding). Tax and ISO qualification notes, plus link to net exercise vs cashless calculator for how many shares you keep.
Expert guide on calculating correct cost basis for RSUs, ISOs, NSOs, and ESPPs. Learn why your 1099-B is wrong, how to use Form 8949 adjustment codes, and how to fix already-filed returns to avoid paying tax twice on equity compensation income.
Complete guide to the ISO $100,000 annual limit under IRC 422(d). Learn how options exceeding the limit are bifurcated into ISO and NSO, FMV at grant date, vesting order rules, and strategies to maximize tax benefits.
Understand IRC Section 422(d): how the $100,000 per-year limit on incentive stock options works when grant FMV times first-exercisable shares exceeds the cap—and how excess is treated as NSO.
When valuations fall, new 409A FMV may drop—changing future option exercise prices and AMT exposure. Learn what resets do and do not change for ISOs, NSOs, RSUs, underwater options, and repricing risks.
When companies reprice underwater options or offer stock-for-option exchanges, tax and qualification rules shift. Learn ISO preservation tests, ordinary income risks on NSOs, accounting-driven structures, and diligence questions before you consent.
How Social Security, Medicare, and Additional Medicare apply to RSU vesting, NSO exercises, and ISO exercises. Wage base limits, withholding gaps, and why equity can trigger surprise payroll taxes.