Foundation
Holistic tax planning for equity
Your equity compensation doesn't live in a vacuum — it lives inside a tax picture that also includes ordinary income, capital gains, state residency, retirement contributions, and estate planning. This is how the pieces fit together, and where equity sits inside the wider frame.
The Reading List
Articles, in order.
Work through them sequentially, or jump to the one most relevant to your situation.
- 01Opinion— TAX STRATEGIES
Why Tax Planning Matters
Smart tax planning typically saves 3-8% (sometimes up to 37%) on a stock-comp household's tax bill — break the work into knowing what taxes apply, learning the strategies, and choosing wisely.
3 MIN3 MIN - 02Reference— TAX STRATEGIES
13 Types Of Tax
An overview of the 13 federal, state, FICA, capital gains, AMT, estate, and QSBS tax types that can apply to stock-based compensation.
2 MIN2 MIN - 03Reference— TAX STRATEGIES
Equity/Stock Tax Strategies
An index of equity/stock tax strategies — holding for LTCG, tax-loss harvesting, lot management, relocation, hedging, opportunity zones, ING trusts, and exchange funds.
2 MIN2 MIN - 04Reference— TAX STRATEGIES
Income Tax Strategies
An index of income tax strategies — deductions, bracket management, stacking, DAFs, deferred comp, state taxation, Social Security optimization, and uncommon offsets.
1 MIN1 MIN - 05How-to— TAX STRATEGIES
Manage Your Capital Gains Tax Bracket
Time gains, harvest losses, and reduce taxable income to keep long-term capital gains in the 15% (or 0%) bracket instead of jumping to 20% plus NIIT.
3 MIN3 MIN - 06Reference— TAX STRATEGIES
Understanding and Optimizing for State Taxation
States vary on AMT, QSBS conformity, and Opportunity Zones — know your state's rules before choosing a tax strategy, especially in California.
4 MIN4 MIN - 07Reference— TAX STRATEGIES
50+ Tax Strategies
A menu of 50+ tax strategies for stock-based-comp, organized by instrument and category, each linking to a one-page deep dive.
8 MIN8 MIN - 08Reference— TAX STRATEGIES
Estate/Trust Tax Strategies
An index of estate and trust tax strategies — gifting to lower brackets, step-up at death, CRUTs, GRATs, and spousal transfers.
1 MIN1 MIN
Talk to a 30/40 Advisor
Want this applied to your situation?
A 30-minute consult tells you whether the frameworks in this reading list cleanly apply to your equity package — and if so, what the first three moves are. No pitch.
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