In this episode sponsored by Obsidian CIO, hosts Bob Huebscher (Founder of Advisor Perspectives) and Joe Halpern (Managing Partner and CIO of Obsidian CIO) continue their series on tax-aware investing by examining one of the most sophisticated strategies available for managing concentrated stock positions: long/short tax overlay strategies.
Joined by Brent Sullivan, Founder of Tax Alpha Insider, the discussion explores how long/short strategies can help advisors diversify highly appreciated positions, generate tax losses, and potentially create additional portfolio alpha—all while carefully managing risk.
- Understand How Long/Short Tax Strategies Work — Learn how long/short overlays use concentrated stock positions alongside long and short portfolios to improve tax efficiency while managing portfolio risk.
- Compare Today’s Concentrated Stock Solutions — Explore how long/short strategies differ from direct indexing, exchange funds, Section 351 ETFs, options strategies, and other tax-aware diversification tools.
- Generate Tax Alpha While Managing Risk — Discover how harvesting losses from both long and short positions can create additional tax-planning opportunities beyond traditional approaches.
- Evaluate the Costs and Trade-Offs — Understand the role of financing costs, manager expertise, portfolio complexity, and why alpha generation is critical to making these strategies effective.
- Perform Better Due Diligence — Learn what advisors should look for when evaluating long/short managers, including operational experience, risk management capabilities, and track record.
- Expand Your Tax Planning Toolkit — Gain a broader understanding of the growing range of tax-efficient solutions available to help clients diversify concentrated portfolios while preserving after-tax wealth.
Listen to the full Advisor Wars podcast on Spotify.
IMPORTANT DISCLOSURE: Obsidian CIO LLC sponsors the podcast to further education and critical thinking about the factors that affect markets and investing. The podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.
