Strategy overview

Direct Indexing & Loss Harvesting

Own the index as individual positions and harvest losses continuously to offset gains elsewhere in your financial life.

Code section
ยง1091 (wash sales)
Best for
Taxable portfolios $500K+
Tax effect
Ongoing loss generation
Horizon
Continuous

Direct indexing replaces an index fund with the underlying stocks held individually. Because you own each position separately, the natural dispersion of single-stock returns creates losses to harvest even in years the index is up. Those realized losses offset capital gains anywhere on your return: a business sale, real estate, fund distributions, or concentrated stock sales.

What it actually adds

Industry studies put the incremental tax benefit, often called tax alpha, in the range of 1% to 2% of portfolio value per year in early years, declining as the portfolio's positions appreciate and lockup builds. The benefit is largest for investors who have gains to offset at high rates and who fund the account with cash rather than appreciated securities.

What the marketing leaves out

  • Harvesting mostly defers tax rather than eliminating it. Every harvested loss lowers basis. Unless the position is eventually donated, stepped up at death, or offset against high-rate gains, some of the benefit reverses.
  • The benefit decays. A seasoned direct-index account becomes progressively locked up as positions appreciate.
  • Tracking error is real. Wash sale rules force replacement positions, so returns deviate modestly from the index.

How we use it

We treat direct indexing as the default chassis for taxable equity exposure when there is a pipeline of gains to absorb: an upcoming exit, annual carried interest, or a planned diversification out of concentrated stock. The losses are manufactured on schedule to meet the gains.

This overview is educational and general. Whether this strategy is appropriate, and its actual outcome, depends on individual facts and requires personalized advice and, where trusts are involved, independent legal counsel.
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