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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Expert guide on filing IRS Section 83(b) elections as a non-US person. Includes 30-day deadline mechanics, TIN/ITIN procedures, AMT implications, and why FEIE won't save you.
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 Alternative Minimum Tax (AMT) planning for ISO stock options. Learn how to calculate your AMT crossover point, avoid the $200K+ tax trap on paper gains, recover AMT credits via Form 8801, and coordinate exercises with RSU/NSO to minimize exposure.
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.
Expert guide on ISO qualifying vs disqualifying dispositions. Learn the 2-year and 1-year holding rules, tax implications of each, and when to sell for optimal tax treatment.
Decision framework for exercising ISO options: same-day sale vs hold. Compare tax outcomes, cash requirements, AMT risk, and when each strategy makes sense.
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 how forward and reverse stock splits and share buybacks affect RSUs, stock options, ESPPs, and your tax obligations. Covers anti-dilution adjustments, the 1% buyback excise tax, ISO $100K limit recalculations, and real-world examples from Apple, Google, Tesla, and Amazon.
Complete guide to the One Big Beautiful Bill Act's impact on equity compensation in 2026. Covers permanent AMT exemptions, expanded QSBS exclusions, SALT cap increases, estate tax exemption updates, and actionable planning strategies for ISO exercises, startup exits, and estate planning with stock options and RSUs.
Step-by-step guide to reporting equity compensation on your 2025 tax return. Covers Form 8949, Schedule D, cost basis corrections, W-2 codes, Forms 3921/3922, AMT Form 6251, and the most common filing mistakes for RSUs, ISOs, ESPPs, and NSOs.
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.
Expert analysis of AI startup equity compensation in 2026. Covers OpenAI and Anthropic equity structures, Profit Participation Units, capped-return equity, 100% refresh rates, secondary tender offers at sky-high valuations, QSBS eligibility, and how to evaluate AI equity offers vs traditional tech.
Practical guide to finding a qualified tax advisor for stock options, RSUs, and equity compensation. Covers questions to ask, red flags, CPA vs EA vs tax attorney, fee structures, and when DIY is sufficient vs when you need professional help.
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.
Compare RSUs (restricted stock units) with ESPP (employee stock purchase plan) and how people use 'ESOP' in job offers. Tax timing, discount vs free shares, $25k ESPP limit, and when to use an ESPP tax / total-return calculator.
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.
How prior-year AMT becomes a credit, how Form 8801 works conceptually, why ISO exercises create credits, and how recovery interacts with future regular tax vs tentative minimum tax. Educational—not filing instructions.
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.
When a company spins off a subsidiary or carves out a division, employee equity may be adjusted, converted, or split. Learn common treatment patterns for ISO preservation, RSU conversion, cash-in-lieu, and why tax timing follows the transaction structure.