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The Albatross

The Albatross

Author: Brent Sullivan

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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.
18 Episodes
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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.
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.
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.
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.
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.
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