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 14 guides in Strategies & advanced topics
Expert guide on equity compensation for startups vs public companies. Covers tax implications, strategies, IRS rules, and practical examples for tech employees and expats.
Expert guide on section 409a valuation: understanding your stock's fair market value. Covers tax implications, strategies, IRS rules, and practical examples for tech employees and expats.
Guide to selling startup equity before an IPO. Covers tender offers, secondary markets, 409A valuation, tax treatment (capital gains vs compensation), and SEC compliance.
Expert guide to phantom stock and stock appreciation rights (SARs) taxation. Covers Section 409A compliance, payout triggers, tax withholding, FICA timing, and comparison with traditional stock options and RSUs.
Expert guide to Non-Qualified Deferred Compensation (NQDC) plans for tech executives. Covers Section 409A compliance, deferral elections, rabbi trusts, distribution rules, bankruptcy risk, and strategies to optimize deferred compensation alongside equity compensation.
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.
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.
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.
If your employer files for bankruptcy, stock options, RSUs, and shares can be wiped out, restructured, or stuck in court. Learn Chapter 7 vs 11, unsecured creditors, ISO/NSO/RSU treatment, and what to document now.
Understand SAFEs vs priced rounds, cap and discount, pro rata side letters, and how early-employee equity sits alongside convertible instruments. Founder and employee framing for dilution and liquidation preferences.
Build scenario probabilities for IPO, M&A, stay-private, and shutdown; apply dilution haircuts; convert grants to fully diluted ownership; compare to liquid salary. Includes mental models—not investment advice.
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.
If a company’s Section 409A valuation is challenged or defective, option strike prices may be off—triggering immediate income inclusion, penalties, and bad tax outcomes. Learn IRS Section 409A penalties, correction programs, and how employees get caught in the middle.