The Albatross

Brent Sullivan

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About

The Albatross is about managing concentrated wealth. Each week, I interview an expert, and we discuss the risks of holding public and private single-asset positions and the numerous ways of exiting thoughtfully. This includes tax-loss harvesting, hedging with options and variable prepaid forwards, exchange funds, qualified opportunity funds, numerous charitable strategies, estate planning vehicles, and several other solutions for private stock and other assets.

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Recent episodes

  • Landing the long/short plane with BlackRock's Taotao CaiOct 9, 2026 · 21 min
  • IRS on "solid ground" going after suspicious §351 transactions - Bob Elwood and Ray HolstOct 5, 2026 · 33 min
  • Too much tax alpha, too little diligence with Steve CurleyOct 1, 2026 · 19 min
  • Abusive §351 is dead, long live routine §351Sep 30, 2026 · 11 min
  • Exchange Fund Replication using Options with BlackRock's Eric MetzSep 25, 2026 · 23 min
  • Covered Calls Are Not For Hedging With Roy HayaSep 18, 2026 · 29 min
  • The Cost of Holding a Concentrated Position with Antti PetajistoSep 14, 2026 · 23 min
  • Opportunity Zones Won't Save a Bad Deal, But Can Accelerate a Good OneSep 3, 2026 · 27 min
  • Investing in Three Dimensions with Paul BoucheyAug 28, 2026 · 33 min
  • A Good ProblemAug 14, 2026 · 2 min

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