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 10 guides in Strategies & advanced topics
Section 83(b) election for restricted stock and early-exercised options: must file within 30 days of transfer, official IRS Form 15620, Treasury Regulation §1.83-2, what Pub. 525 covers, and why 83(b) does not apply to typical RSUs.
Expert guide to negotiating equity compensation in tech. Covers RSU packages, stock option grants, refresh grants, vesting acceleration, and counter-offer strategies with real-world frameworks.
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.
Comprehensive guide to SEC Rule 10b5-1 trading plans for corporate insiders. Covers the 2023 amendments, cooling-off periods, plan structures, blackout period navigation, tax optimization strategies, and compliance requirements for employees with equity compensation.
Expert guide to profits interests in LLCs—the primary equity compensation alternative when stock options aren't available. Covers Rev. Proc. 93-27 safe harbor, capital gains treatment, 83(b) elections, K-1 reporting, vesting, and comparison with phantom stock, SARs, and traditional stock options.
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.
Guide to equity compensation tax implications when getting married. Covers MFJ vs MFS, marital property classification, spousal consent in community property states, and planning strategies for couples with stock options and RSUs.
Guide to equity compensation for new parents. Covers vesting during parental leave, RSU tax withholding, estimated tax payments, and strategies to avoid underpayment when income drops during leave.
Companies may claw back cash or equity for restatements, misconduct, or competition. Understand SEC rules for executives, typical contract triggers, and what to negotiate before you sign.
How the One Big Beautiful Bill (2025) affects AMT, QSBS, capital gains, NIIT, and withholding for tech employees with ISOs, NSOs, RSUs, and ESPP. Practical planning notes and what to verify each tax year.