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Tax Matters
Regardless of How You Deal with Low-Basis Stock, Long-Short Strategies Can Help
June 23, 2022
Most investors recognize that concentrated stock holdings are risky, but the outright sale of a low-basis stock incurs a punitive tax burden. In this post, we highlight several tax-efficient alternatives to an outright sale and explore how long/short strategies can help enhance this tax efficiency.
Working Paper
When Fortune Doesn’t Favor the Bold: Perils of Volatility for Wealth Growth and Preservation
May 12, 2022
Entrepreneurs and executives holding much of their wealth in a highly appreciated single stock face either the high risk of idiosyncratic volatility and potentially catastrophic losses, or selling stock and facing an immediate, punitive tax burden. This paper evaluates this choice and explains how it relates to classic betting strategies and economic theory, finding tax-efficient techniques might strike the balance between the urgency to diversify concentrated risk and aversion to taxes.
Tax Matters
Can Your Loss-Harvesting Strategy Still Harvest Losses?
February 28, 2022
As equity portfolios appreciate over time, opportunities to harvest losses become few and far between. Whether you’ve been invested in a passive equity portfolio or in a Direct Indexing strategy, you’ve likely found that harvesting losses was much easier in the first few years after inception. Beyond that, not only does harvesting losses become a challenge but even keeping up with index reconstitutions might be difficult without recognizing capital gains. Appreciated portfolios—once a benefit—become a liability later in their life-cycle.
Journal Article
Taxes, Charity, and Hedge Funds: Tax Implications of Charitable Contributions of Leveraged Partnership Interests
January 10, 2022
As a result of recent Treasury regulations, investors in investment partnerships, such as hedge funds, might end up recognizing capital gains when they contribute their partnership interests to a charity. We explain how such taxable gains upon charitable contributions arise and quantify how punitive they might be.
Tax Matters
Why You Might Defer Your Gains, Even When Tax Rates Are About to Increase
November 17, 2021
With the current proposals for (and the future expectations of) various tax rate hikes, investors with appreciated portfolios might feel like sailing into a storm and wondering, is it still better to defer gains if tax rates were to increase?
Tax Matters
The Value of Integrating Income and Estate Planning
September 2, 2021
In this post, we discuss challenges of wealth preservation and growth faced by high net worth families. While a family that invests with income tax and estate tax efficiency in mind is more likely to achieve its financial legacy goals, the numerical advantages of tax efficiency are quite striking. In addition, we show that there is a significant value in integrating income tax efficiency and estate tax planning.
Tax Matters
Does Tax Efficiency Just Delay the Tax Burden?
July 28, 2021
We often hear the sentiment that tax-efficient investing just delays the inevitable: Eventually, a day will come when the tax-efficient investor will have to true up on years of deferred taxes. And, with the proposed Biden Tax Plan sending many investors scrambling to plan for higher taxes, we feel that now is as good a time as any to put this long-standing myth to bed.
Tax Matters
Improving Direct Indexing: 130/30 and 150/50 Strategies
July 6, 2021
In this post, we expand on our analysis which studies the tax benefits of a hypothetical tax-aware direct indexing strategy with 1% tracking error.
Tax Matters
Direct Indexing and the Proposed Biden Tax Plan
June 9, 2021
There are two basic ways to invest in a stock market index: you can buy an index fund, or you can directly buy a stock portfolio that tracks the index. If you are a taxable investor, a benefit of the direct approach is that you can harvest losses on individual positions. But how high are those benefits—and what happens to them under the proposed Biden Tax Plan?
Tax Matters
Tax-Efficient Portfolio Transition, or How to Rejuvenate Ossified Equity Portfolios
May 12, 2021
We discuss portfolio transition techniques that could alleviate the tax costs of switching managers for a taxable investor.