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Tax Matters
CRUTs, Tax-Aware Strategies, and Concentrated Stock Diversification
April 1, 2025
When implemented well, CRUTs can be a valuable tool, combining wealth preservation with philanthropy. Our latest papers are meant to help investors maximize the benefits of these strategies.
Tax Matters
The Enduring Appeal of Gain Deferral, Part 4
March 19, 2025
Our first post in this series showed the power of deferral for building wealth; our second showed how robust the value of deferral is to changes in future tax rates on capital gains; our third considers whether deferral is still the right choice if an investor is able to find a strategy with a higher expected return. Here, we build on Part 3 by adding a tool investors and advisors increasingly have access to: tax-aware transition.
Working Paper
A Brief Guide to the Mathematics and Taxation of Charitable Remainder Unitrusts
March 18, 2025
We provide a practical guide for financial planners and wealth management professionals on charitable remainder unitrusts (CRUTs).
Working Paper
Combining Charitable Remainder Unitrusts and Tax-Aware Strategies to Diversify Low-Basis Stock
March 18, 2025
We show how combining charitable remainder unitrusts (CRUTs) with tax-aware strategies can help investors diversify low-basis stock and enhance after-tax wealth accumulation. Our findings suggest that investors and their advisors should integrate philanthropy and investment management to optimize wealth preservation and charitable impact.
Tax Matters
The Enduring Appeal of Gain Deferral, Part 3
March 12, 2025
Our first post in this series showed the power of deferral for building wealth, and our second showed how robust the value of deferral is to changes in future tax rates on capital gains. But what if you’re able to find a new investment with a higher expected return?
Tax Matters
Our Research into Tax-Aware Long-Short Investing
January 28, 2025
As the concept of tax-aware long-short investing becomes a mainstay of private wealth planning, we wanted to clearly articulate some core findings of our research, and help parse the jargon of this rapidly growing but sometimes confusing area.
Journal Article
A Brief Guide to Pricing and Taxation of Variable Prepaid Forwards
November 6, 2024
Variable prepaid forward (VPF) contracts have been developed as a solution to hedging the risk of concentrated low-basis stock. Using options pricing theory, we develop a VPF pricing model that helps understand the VPF prepayment amount and the cash flows and tax liabilities upon VPF rolls.
Tax Matters
Can Capital Losses Offset Gains from the Sale of Low-Basis Real Property?
November 1, 2024
In general, capital losses realized on stocks or other assets may offset capital gains, but not ordinary income, from the sale of a property. Therefore, it is important to understand which portion of the gain from the sale would be treated as capital gain and which would be treated as ordinary income.
Tax Matters
Separating the Wheat from the Chaff
October 8, 2024
Investors seeking tax efficiency must look for strategies motivated by a pre-tax investment rationale, otherwise known as “economic substance.”
Tax Matters
Levering Up to Do Good
July 9, 2024
Long/short tax aware strategies can be a win-win for the charitably inclined: larger donations for the charity and larger tax benefits for the donor.