Former SpaceX engineer on divesting a windfall

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)

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.

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.