The Albatross
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.
Episodes
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Charitable remainder trusts for divesting concentrated stock with Simone Devenny
Most people know about giving to charity for the tax deduction. They also know about giving appreciated stock to a donor-advised fund to take the deduction now and choose the recipient later. Some may even set up a private foundation. But one of the most powerful giving vehicles is the charitable...
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Trader funds and Treasury's Own Goal with Prof. Daniel Hemel
In 1988, Treasury issued a temporary regulation that persists to this day. It allowed trader fund investors to escape the passive activity rules that would normally require hundreds of hours of material participation for any losses to offset nonpassive income. NYU Prof. Daniel Hemel thinks…
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Box spreads could be taxed like ordinary income - NYU Prof. Daniel Hemel
Box spread ETFs attempt to replicate something like the Treasury bill return without the annual taxable income. NYU Prof. Daniel Hemel thinks Treasury could use IRC §1258 to make investors treat their gains on sale as ordinary income (if industry challenges to new regulations fail).
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Pt. 2 How to transfer BTC into an ETF with Teddy Fusaro and Cliff Cornell
Bitcoin can transfer in and out of a spot bitcoin ETF just like a gold bullion ETF. There are details! Thankfully Cliff Cornell (Bona Fide Wealth) and Teddy Fusaro (Bitwise Asset Management) walked me through it.
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Pt. 1 Why transfer BTC into an ETF with Teddy Fusaro and Cliff Cornell
Bitcoin made many investors rich. Now, they're wondering how to hedge and monetize, and transfer to charities, non-financial spouses, and kids. Transferring to an ETF might help. Part 1 of this 2-parter is a conversation with President of Bitwise Asset Management, Teddy Fusaro, and Bona Fide…
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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...
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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…
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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...
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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...
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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).…
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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...
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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...
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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...
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Investing in Three Dimensions with Paul Bouchey
Paul Bouchey is the Editor of the Journal of Wealth Management, Managing Director of Applied Research at Morgan Stanley, and the former Chief Investment Officer at Parametric Portfolio Associates. He tells us how Parametric went from active manager in the 1980s to $600 billion AUM passive...
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A Good Problem
The Albatross is about navigating concentrated wealth. Markets are at all-time highs, and founders, executives, early employees, and investors have become rich... but highly concentrated. Many are unable or unwilling to diversify. Solutions exist: selling, hedging, tax-loss harvesting,...
About this show
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.
Hosted by
Brent Sullivan