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The Albatross: Daily Summaries Delivered
by Brent Sullivan
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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- Today20 min
Landing the long/short plane with BlackRock's Taotao Cai
For tax-aware long/short strategies, some see the leverage as cost-effective, amplified exposure to the underlying manager, while others need to have a plan to land the plane, or to remove the leverage, thoughtfully and without making a costly risk or tax error.BlackRock's Taotao Cai joins The Albatross to talk about end-to-end planning with long/short strategies.He reminds us along the way that long/short is a powerful tool, but it is not the only tool.
- 3 days ago32 min
IRS on "solid ground" going after suspicious §351 transactions - Bob Elwood and Ray Holst
Last week, Treasury released Notice 2026-62 and Rev. Rul. 2026-20 concerning IRC §351 transactions, nowadays popularly used to seed new exchange-traded funds (ETFs) in-kind.Bob Elwood is the founder of Practus and he and his partners, including Ray Holst, have collectively structured more than 100 §351 transfers over the past several years. In this episode, Bob and Ray talk about the difference between routine and aggressive planning using §351, and the nuances of some of the key words in the new revenue ruling.Bob and Ray are tax attorneys, but they are not your tax attorneys. For specific and personalized guidance, hire tax counsel. This content is education only.
- 1 weeks ago18 min
Too much tax alpha, too little diligence with Steve Curley
There's a flavor of financial adviser that understands how powerful tax alpha sounds to prospects and clients, but who hasn't thought too much about what could go wrong.Steve Curley has seen this before with the hype around market timing strategies, private investments, crypto and now... tax alpha.His point is NOT that these things are bad, only that they require increasing levels of diligence, and he cautions that some folks recommending these products simply haven't done the work.
- 1 weeks ago10 min
Abusive §351 is dead, long live routine §351
For the last few years, the ETF industry has used Section 351 of the Internal Revenue Code to let investors seed new exchange traded funds with appreciated securities, mostly stocks and other ETFs, without recognizing the gains.On Monday, September 28, 2026, Treasury and the IRS threw cold water on the most egregious uses of 351 with Notice 2026-62 and Revenue Ruling 2026-20. While some folks are nervous about this, others are exuberant. In their minds, finally, Treausury has provided a little clarity around what routine usage of section 351 looks like.The key thing is knowing the difference.
- 2 weeks ago22 min
Exchange Fund Replication using Options with BlackRock's Eric Metz
Exchange fund replication is a hidden gem in the concentrated public stock de-risking toolkit.Exchange fund replication is a 4-legged options trade that collars a single stock for risk management (2 options), and creates index-like exposure with a synthetic long position (another 2 options).Eric Metz, CIO of SpiderRock, a BlackRock company joins The Albatross to explain how it works, why no one has heard of it despite its relative simplicity, and how it could pair nicely with other risk and tax management strategies like tax-aware long/short.
- 3 weeks ago29 min
Covered Calls Are Not For Hedging With Roy Haya
Covered calls are in the single-stock management canon, but not because they meaningfully hedge risk.Roy Haya, Partner and Head of Derivative Solutions at Fort Point Capital Partners, tells us covered call writing means income today, truncated upside, and often just a small premium for downside cushion. For some clients covered call writing is simply a disciplined way to exit a stock.We talk about the straddle rules, structuring the call to reach Qualified Covered Call status so straddle loss deferral falls away, and why dividends might lose their preferential tax treatment. We close by considering how all of this applies to bitcoin.
- 3 weeks ago22 min
The Cost of Holding a Concentrated Position with Antti Petajisto
Antti Petajisto and I talk about concentration drag resulting from the many, many, many public companies that go bust, and the tiny slice of the market that vastly outperforms. These two phenomena expand the chasm between a simple equal-weight fund and picking individual stocks, resulting in concentration drag, which Antti measures in his research.
- Sep 3, 202626 min
Opportunity Zones Won't Save a Bad Deal, But Can Accelerate a Good One
The biggest criticism of Qualified Opportunity Funds is that the tax tail is wagging the dog so hard that investors completely lose sight of investment viability.Nick Rosenthal, co-CEO of Griffin Capital Company, thinks that if investors do due diligence on QOFs as they would without the tax incentives, the program can be an important tool in the single-stock de-risking playbook.
About The Albatross
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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