The taxable wealth revolution

Happy Fourth of July

Jul 04, 2025

Taxable wealth: What I’m reading…

Taxes and the American Revolution
Quisenberry, Welch (2005): Increasing the Tax-Effectiveness of Concentrated Wealth Strategies (variable prepaid forwards + direct indexing)
Santa Barbara Management: A Wealth Strategy for Taxable Families
AQR: Combining Charitable Remainder Unitrusts and Tax-Aware Strategies to Diversify Low-Basis Stock
AQR: A Brief Guide to the Mathematics and Taxation of Charitable Remainder Unitrusts (notes on NIMCRUTs)
Wealthfront has just filed for an initial public offering
Double (consumer direct indexing) is winding down ($3.9 VC raised)

Variable prepaid forwards on my mind…

AQR’s paper Combining VPFs and Tax-Aware Strategies to Diversify Low-Basis Stock is worth a read if you serve qualified purchaser investors with concentrated stock positions.

The gist is that the prepayment from the VPF can be invested in a tax-aware long/short strategy (like those shown below) to generate pretax alpha and capital losses than can offset the gains realized when the VPF expires (typically 2-5 years).

Tax-aware long/short strategies go quite a bit further than the VPF realization usually requires. See the following image from their paper.

Double Down

Double is a YC-backed company that raised $3.9mm in late 2024. They charged $1/month for their consumer direct indexing product, and initially said they would add on other services later.

It didn’t work.

“The simple reason is that we did not attract enough customers to be on a path towards building a sustainable business. In the world of investing, a company must ultimately stand on its own feet. Despite our best efforts, it has become clear that the demand for our particular low cost approach to automated portfolio investing is not sufficient to do so.” (wind down blog)

My guess is that the founders are simply pivoting to something completely unrelated. There’s no way they burned through that seed capital in ~6 months.