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Working Paper

Liquidity without Liquidation

August 28, 2026 - Stanley Krasner Joseph Liberman Nathan Sosner Sydney Brenner

This paper shows that investors may be able to access meaningful liquidity from tax-aware strategies while preserving the remaining portfolio’s tracking error, leverage, and pre-tax return potential. An adaptive withdrawal process may also better manage capital-gain realization than a fixed withdrawal schedule.

Journal Article

Are Completion Portfolios Effective for Managing Concentrated Stock Risk?

August 31, 2025 - Stanley Krasner Joseph Liberman Nathan Sosner Marcus Stevens

This paper investigates the most effective ways to manage the risk of concentrated stock positions.

Journal Article

Levering Up to Do Good: Direct Long-Short Investing and Charitable Giving

August 31, 2024 - Stanley Krasner Joseph Liberman Nathan Sosner Sydney Brenner

We use historical strategy simulations to evaluate the advantages of donating appreciated stock in the context of tax-aware long-short factor strategies. We find long-short strategies exhibit several advantages over long-only investments.

Journal Article

Loss Harvesting or Gain Deferral? A Surprising Source of Tax Benefits of Tax-Aware Long-Short Strategies

April 30, 2024 - Stanley Krasner Nathan Sosner

We explore the mechanism for how tax-aware long-short factor strategies, within their first three years since inception, can realize cumulative net capital losses exceeding 100% of initially invested capital, all while generating a significant pre-tax alpha – a result shown in previous research. Surprisingly, we find in these strategies that net capital losses arise not from an increased realization of capital losses but rather from the deferral of capital gains, especially short-term gains on long positions.

Journal Article

Beyond Direct Indexing: Dynamic Direct Long-Short Investing

August 31, 2023 - Joseph Liberman Stanley Krasner Nathan Sosner Pedro Freitas

On average, net losses realized by direct indexing loss-harvesting strategies taper off within the first few years after their inception, and these strategies also exhibit a high dispersion of net loss outcomes. We show that long-short strategies motivated by factor investing can significantly outperform direct indexing strategies from both a pre-tax and tax perspective.

Journal Article

The Tax Benefits of Direct Indexing: Not a One-Size-Fits-All Formula

May 19, 2022 - Nathan Sosner Michael Gromis Stanley Krasner

An investor holding a direct indexing portfolio can obtain tax benefits by harvesting losses on individual stock positions. We show that investors with allocations to hedge funds and derivatives are the most likely category of investors to have systematic short-term capital gains in their portfolios and, therefore, benefit the most from losses harvested by direct-indexing strategies. We show how tax benefits are affected by equalizing the tax rate applicable to long-term and short-term capital gains.

Journal Article

Tax-Efficient Portfolio Transition: A Tax-Aware Relaxed-Constraint Approach to Switching Equity Managers

January 31, 2021 - Nathan Sosner Stanley Krasner

For a taxable investor with a highly appreciated equity portfolio, replacing the portfolio manager is likely to trigger substantial tax liabilities. We find that a tax-aware relaxed-constraint post-transition strategy significantly outperforms a traditional tax-agnostic long-only strategy in its ability to preserve and grow the investors after-tax wealth over the long term.

Journal Article

The Tax Benefits of Relaxing the Long-Only Constraint: Do They Come from Character or Deferral?

January 31, 2019 - Nathan Sosner Stanley Krasner Ted Pyne

Are there tax benefits from relaxation of the long-only constraint? If so, what are the sources? To answer these questions, we decompose the total tax benefit (or liability) of a strategy into two components.