Direct Indexing for Tax Management

What if you could own the SP 500 but harvest tax losses on individual stocks throughout the year? That is direct indexing - owning the individual components of an index rather than an ETF, enabling continuous tax-loss harvesting that can add 30 basis points annually to after-tax returns (Parametric, 2023). For high earners in taxable accounts, the tax savings can exceed the higher management fees.

The durable lesson: Direct indexing is not about beating the market. It is about harvesting losses you cannot access inside an ETF. The strategy shines when you have large capital gains to offset or expect to have them in the future.

How Direct Indexing Works

Traditional index investing:

• Buy one ETF (VOO for SP 500)
• Own fractional interest in 500 stocks
• If Apple falls 20%, you have no loss to harvest - your ETF is still positive overall

Direct indexing:

• Own all 500 stocks individually (or weighted subset)
• If Apple falls 20%, you sell Apple, harvest the loss
• Buy a similar stock (Microsoft, Google) to maintain market exposure
• Repeat across hundreds of positions throughout the year

The result: You capture the market return while generating tax losses impossible to access in an ETF.

The Tax Alpha Math

Parametric Study Findings:

• Daily tax-loss harvesting generates ~30 basis points more tax alpha than monthly harvesting
• Benefit highest in first 5-10 years, then diminishes as cost basis rises
• Benefit resets if you have future capital gains to offset

Example:

Your situation:

• 500,000 taxable portfolio
• 20% long-term capital gains bracket
• Direct indexing harvests 30,000 in losses per year

Tax savings:

• 30,000 losses x 20% = 6,000 annual tax savings

Cost:

• Direct indexing fee: 0.30% of 500,000 = 1,500
• VOO fee: 0.03% of 500,000 = 150
• Net additional cost: 1,350

Net benefit: 4,650 per year (6,000 savings - 1,350 higher fees)

The point is: Direct indexing makes sense when tax savings exceed fee premium.

Who Benefits Most

Ideal candidates:

High earners in top tax brackets

• 20% LTCG + 3.8% NIIT = 23.8% tax rate
• Every dollar of losses saves 23.8 cents

People with concentrated stock positions

• Large unrealized gain from employer stock or successful investment
• Need losses to offset when diversifying

Business owners expecting liquidity event

• Building loss carryforward before sale
• 100,000+ in losses can offset 23,800+ in taxes on sale

Those in high-tax states

• State taxes on capital gains can add 5-13% to federal rate
• California investor at 37.1% combined rate saves 3,710 per 10,000 in losses

Minimal benefit for:

• Low tax bracket investors (limited tax savings)
• Retirement account investors (no capital gains taxes anyway)
• Small portfolio investors (fees exceed savings)

The Wash Sale Constraint

The rule: Cannot claim loss if you buy substantially identical security within 30 days before or after the sale.

Direct indexing solution:

• Sell Apple at loss
• Buy Microsoft (similar large-cap tech, not substantially identical)
• Maintain market exposure while harvesting loss

Tracking complexity:

• With 500 positions, wash sale monitoring is constant
• This is why you need software and professional management
• Personal attempt at this scale would be extremely difficult

Customization Beyond Taxes

ESG exclusions:

• Remove fossil fuels, tobacco, weapons, etc.
• Still track index closely with remaining stocks

Employer stock:

• Exclude your company (already have concentration risk)
• Avoid wash sales with vesting RSUs

Sector tilts:

• Overweight or underweight sectors based on views
• Maintain approximate index risk characteristics

The trade-off: More customization = more tracking error vs. benchmark

Cost Comparison

Expense Ratios:

• VOO (SP 500 ETF): 0.03%
• Fidelity Direct Indexing: 0.40%
• Vanguard Personalized Indexing: 0.25% (250K minimum)
• Parametric: 0.30-0.45%
• Schwab: 0.40%

Minimum investments:

• Fidelity: 5,000
• Vanguard: 250,000
• Schwab: 100,000
• Parametric: 250,000+

Break-even calculation: Fee premium of 0.37% (0.40% - 0.03%) requires tax savings of at least 0.37% of portfolio to break even.

At 500,000 portfolio: Need 1,850 annual tax savings to break even. At 20% tax rate: Need 9,250 in annual loss harvesting.

Tracking Error: The Trade-Off

Definition: How much your returns differ from the target index

Sources of tracking error in direct indexing:

• Tax-loss harvesting substitutions (Apple replaced with Microsoft)
• Timing of trades
• Customization exclusions
• Transaction costs

Typical tracking error: 0.2-0.5% annually

The perspective: If you save 1% in taxes but underperform by 0.3%, you are still ahead by 0.7%.

The Diminishing Returns Problem

Year 1-5: Abundant opportunities for loss harvesting (volatility creates losses)

Year 5-10: Cost basis has risen; fewer positions have losses to harvest

Year 10+: Most positions have large embedded gains; harvesting opportunities rare

The reset button:

• New cash added can be harvested
• Major market corrections create new opportunities
• Large gain events (business sale) reset the benefit calculation

The durable lesson: Direct indexing front-loads tax benefits. Do not expect 30 bps forever.

Implementation Considerations

Account requirements:

• Must be taxable account (no benefit in IRA/401k)
• Need to handle hundreds of positions
• Tax reporting complexity (1099s with hundreds of transactions)

Integration with other accounts:

• Coordinate with wash sale rules across all taxable accounts
• May need to avoid same stocks in direct indexing and other accounts

Exit strategy:

• Positions accumulate gains over time
• Transferring to heirs gets step-up in basis
• Selling creates large gain (may want to hold)

Common Mistakes

Starting direct indexing in retirement accounts Zero tax benefit - retirement accounts already tax-advantaged. Waste of higher fees.

Expecting permanent 30+ bps benefit Tax alpha diminishes as cost basis rises. Plan for reduced benefit over time.

Ignoring wash sale rules across accounts Buying the same stock in your 401k within 30 days kills the loss in direct indexing account.

Choosing high-cost provider for small account 500 portfolio with 0.40% fee = 2,000 annual cost. Unless you harvest 10K+ in losses annually, the math does not work.

Checklist

Before starting direct indexing:

• Account is taxable (not retirement)
• In 15%+ capital gains bracket (20%+ ideal)
• Have or expect significant capital gains to offset
• Portfolio size large enough for fees to make sense
• Can coordinate wash sale rules across all accounts
• Understand tracking error and are comfortable with it
• Have realistic expectations about diminishing benefits over time

References

• Parametric (2023). Tax-Loss Harvesting: The Case for Daily.
• Fidelity (2024). Direct Indexing Overview.
• Vanguard (2024). Personalized Indexing.