The Mack Podcast Structuring Portfolios for After-Tax Efficiency
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Mar 5, 2026 Brent Sullivan, independent industry analyst and author of Tax Alpha Insider who advises on tax-aware portfolio design for high-net-worth families. He breaks down tax loss harvesting frameworks and using volatility as opportunity. He explains coordinating tax-aware structures across households and entities. He covers direct indexing, crypto quirks, leverage to amplify tax alpha, and tech needed to monitor lots and wash sales.
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Crypto Harvesting Carries Substance Over Form Risk
- Crypto can be harvested like stocks but carries unique costs and legal risk.
- No formal wash sale rule yet, so document profit-seeking rationale to defend against substance-over-form challenges.
Coordinate Harvesting Across Household Accounts
- Coordinate accounts across household entities to avoid accidental wash sales and suboptimal harvesting.
- Feed brokerage data into a unified platform so managers can choose when to harvest or harvest gains in other accounts strategically.
Direct Indexing Balances Tracking Error And Tax Alpha
- Direct indexing lets managers harvest at the individual-stock level while keeping benchmark exposure via a subset of names.
- Trade-off is tracking error versus tax alpha; replacement selection should consider existing exposures and factors.