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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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- Yesterday28 min
Midterm results are about 2029 not 2027 with Tax Foundation's Andrew Lautz
In 2027, Democrats will control both chambers of Congress.Advisers want to know what, if anything, could change with President Trump holding veto authority.Tax Foundation's Andrew Lautz joins the podcast, where we discuss...Possible changes to step-up in basisEqualizing capital gains and ordinary ratesThe efficacy of wealth taxesAndrew says he's watching committee hearings for hints about possible policy changes if one party achieves a trifecta in 2029.
- 6 days ago20 min
Exchange funds from scratch with Cache's Srikanth Narayan
Building an exchange fund from scratch with Cache's Srikanth Narayan, why a 7-year "lockup" isn't quite right, and why managing risk is one of their core value propositions.This is part 1 of 2 with Srikanth. In part 2, we discuss how Cache uses Section 351 for risk management and their comments and recommendations to Treasury following Notice 2026-62 and Rev. Rul. 2026-20.
- 1 weeks ago24 min
Transferrable tax credits can offset passive income tax liability with Jason Prince
The Inflation Reduction Act (2022) made it easier than ever to transfer tax credits, but most investors don't know anything about how this works.Jason Prince of Giraffe Financial takes us through buying tax credits at a discount and applying them against a passive income tax liability.
- 1 weeks ago29 min
Former SpaceX engineer on divesting a windfall
Soon after SpaceX announced it would go public, a former company engineer, who wishes to remain anonymous, reached out to me on social media. He was looking at an 8-figure outcome, and wanted to chat about modeling various divestment strategies.Part of his decision was considering whether or not to work with a financial adviser. I asked him if I could record his thought process. This episode is our discussion.
- 2 weeks ago27 min
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 remainder trust (CRT), specifically its variant, the charitable remainder unitrust (CRUT), and, heck, its variant, the net income makeup charitable remainder unitrust (NIMCRUT).Simone Devenny, J.D., Head of Private Wealth Strategies at Allworth Financial, joins the Albatross to talk about why, what, and how people give.
- 2 weeks ago24 min
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 Treasury should rescind the temporary 1988 regulation, making trader fund investors passive investors.
- 3 weeks ago24 min
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).
- 3 weeks ago33 min
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.
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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