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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Showing 20 guides in Strategies & advanced topics
ISO vs NSO explained: incentive stock options vs non-qualified stock options—ordinary income vs capital gains, AMT on ISO exercise, NSO withholding, $100K ISO limit, and 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.
Tax-loss harvesting for shares acquired from RSUs or stock options: capital losses after vest or exercise, offsetting gains, $3,000 ordinary income net, IRC §1091 wash sales—not IRS Publication 525 RSU wage income at vest. Links to RSU tax guide and ESPP tools.
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.
Employee-focused guide to IRC Section 409A valuations: how FMV sets your strike price, what happens when the 409A moves, ISO limits, and how to read your grant alongside the company’s appraisal.
How IRS Revenue Ruling 2007-49 applies to early-exercised stock options: substantial risk of forfeiture, Section 83 inclusion timing, and interaction with Section 83(b) elections for startup employees.
Canadian tax overview for tech employees with US equity: stock option deduction (110(1)(d)), RSU taxation as employment income, cross-border US citizens, and coordination with employer withholding.
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.
Technical guide to the ISO $100,000 annual limitation under IRC 422(d) and Treasury Regulation §1.422-4: first-exercisable shares, grant-date FMV, ordering rules, and automatic NSO conversion—plus links to calculators.
Decode Form W-2 Box 14 labels for RSUs, options, and ESPP: how they relate to Boxes 1 and 12, broker 1099-B basis, and common employer-specific codes.
How France taxes US-issued RSUs and stock options for residents: employment income timing, social charges, PFU vs progressive tax, and US-French treaty coordination for Americans in Paris and remote tech workers.
How California taxes equity compensation for remote workers and employees relocating mid-vest—FTB sourcing by service days, allocation periods, and the California Equity Source Days Calculator.