Charitable remainder trusts for divesting concentrated stock with Simone Devenny

In late September 2026 Treasury and IRS released Notice 2026-62 and Rev. Rul. 2026-20, requesting comment from industry about some tax-aware funds, and cautioning that certain uses of Section 351 ETF seeding could result in capital gain recognition.They also mentioned an "exchange fund variant" where investors would contribute individual shares to a partnership, and the partnership would contribute a slice of its portfolio to an ETF via Section 351. Cache pioneered this approach and so founder Srikanth Narayan joins The Albatross again to talk about the long-standing approach used by the exchange fund industry, how Cache's approach is similar and different, and how they're getting Treasury up to speed.

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.

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.

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).

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.

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 Wealth financial adviser, Cliff Cornell. Part 1: Why transfer BTC into an ETF?Part 2: How to transfer BTC into an ETF (mechanics, tax)