NPT Research · Essay

Our approach to tax-aware long/short.

Prism is NinePointTwo's proprietary tax-aware long/short strategy, offered directly to suitable clients in three configurations.

June 2026

The implementation question

The strategy was developed from our tax-agnostic quantitative long/short equity models, drawing on the same systems that run our Alternatives division. We offer three configurations, called Max, Diversify, and Enhance. They are best understood as three calibrations, or use cases, of one strategy rather than three separate products.

Every configuration runs the same underlying book. Long the stocks our models rate most attractive, short the names they rate weakest. Proceeds from the short sales help finance the additional long exposure, and the return the strategy pursues comes from the spread between the two books rather than from the market's direction. Because up years and down years both leave some part of the book at a loss, there is generally something to harvest, even in the markets where a long-only program eventually runs dry.

Prism Max

Max runs the strategy at its fullest expression. It seeks to generate pre-tax alpha with a high level of tracking error and to realize substantial capital losses (subject to the client's risk parameters).

It fits an investor who wants to add an uncorrelated return stream to their portfolio and has meaningful capital gains arriving. These clients typically do not have another tax loss harvesting program already in place. Their capital gains might come from a business sale, a carry distribution, appreciated equities that need rebalancing, or a steady stream thrown off by other investment managers.

Prism Diversify

Diversify is configured for the single most common problem we see. A low-basis stock has grown to dominate an investor's portfolio. Selling it all at once realizes years of capital gains in one tax year, and holding it leaves their wealth dependent on one company's performance. Diversify runs the long/short program alongside the position and lets realized losses accumulate, so the position can be sold down in stages. What replaces the position after each sale is broad diversified exposure to an agreed‑upon benchmark.

It suits founder stock, early-employee equity, and long-held or inherited equity positions. The concentrated stock essay in our research library walks through the mechanics in greater detail.

Prism Enhance

Enhance is configured for a different premise. The portfolio an investor already owns is broadly the one they want to keep. So we leave much of those holdings in place and overlay the long/short strategy on top of them. The overlay seeks to add a return stream with little correlation to everything else, while realizing losses that may improve the whole portfolio's after-tax characteristics.

It fits investors with no appetite for wholesale restructuring. That may be because the existing portfolio is already generally sound, or because restructuring would itself trigger too much capital gain to effectively optimize the allocation. Enhance is for improving a good portfolio's after-tax outcomes by adding the benefits of an uncorrelated return stream without the typical opportunity costs of funding a long/short program, since the existing holdings stay invested rather than being sold to raise the capital.

Selecting the right approach

In practice the choice comes down to where the gains are coming from and how much of the current portfolio the investor wants to keep. Anticipated capital gains that are not tied to a concentrated position, or that arise outside the portfolio altogether, may point to Max. A single position that is itself the problem may point to Diversify. A generally good portfolio allocation seeking to potentially improve its risk/return characteristics may opt for Enhance.

Exhibit 1One strategy calibrated to three situations.Source: NPT
Prism MaxPrism DiversifyPrism Enhance
The starting pointCapital gains arriving, with no harvesting program working on the investor's behalfA low-basis position that has grown to dominate the portfolioA sound portfolio the investor intends to keep
What the program doesRuns at full strength, seeking pre-tax alpha alongside substantial realized lossesAccumulates the tax capacity to sell the position down in stagesOverlays the long/short strategy on the existing holdings, which stay invested
What changes over timeThe loss base stays ahead of the gains as they arriveOne name becomes diversified exposure to an agreed-upon benchmark, sale by saleThe portfolio stays, and its after-tax character improves
The usual fitBusiness sellers, carry recipients, investors with recurring gains from other managersFounder stock, early-employee equity, long-held or inherited positionsInvestors for whom restructuring would itself trigger the gains they are trying to manage
Note. One quantitative long/short strategy underneath all three configurations. Situations overlap in practice, and a program can move between configurations as circumstances change.

The boundaries are softer than the names suggest. A Diversify program that finishes its sell-down has become, functionally, a Max program. An Enhance overlay can be run harder as a liquidity event approaches. Because the configurations differ only in calibration, moving between them is an adjustment rather than a liquidation.

What none of them do

Harvested capital losses defer tax, they never eliminate it. That said, deferral itself has well-documented value from decades of research. Losses offset capital gains, and can offset ordinary income only up to a small annual allowance, so every configuration assumes the investor has capital gains worth offsetting in the first place. Long/short investing involves shorting, leverage, financing costs, and tracking error that most index funds do not. And Prism has to be a sound investment first, with the tax benefits layered on top of that.

Where to start

We would start by analyzing your entire financial picture. In most of the conversations we have, an investor's situation points to the right configuration fairly quickly.

Important
Disclosures

Regulatory status

NinePointTwo Capital LLC (“NPT”) is a registered investment adviser with the U.S. Securities and Exchange Commission (SEC) and is registered with the National Futures Association (NFA) as a Commodity Trading Advisor (CTA) and Commodity Pool Operator (CPO). Registration does not imply a certain level of skill or training.

Trading in futures contracts and other leveraged derivatives carries a high degree of risk. The risk of loss in trading futures and derivatives is substantial; leverage inherent in these instruments can magnify trading losses as well as gains. Investors should only consider investing in such strategies when the gearing effect of leverage and the risks of loss are fully understood. Past performance is not indicative of future results.

No offer or solicitation

This material is provided by NinePointTwo Capital LLC ("NPT") for informational and educational purposes only. It does not constitute an offer to sell or a solicitation of an offer to buy any security, fund, or investment vehicle. Such offers are made only via a formal Private Placement Memorandum or Investment Management Agreement. Nothing contained herein constitutes investment, legal, tax, or other advice, nor should it be relied upon in making an investment or other decision. NPT is not a law firm or a public accounting firm.

No tax or legal advice

While NPT's tax-aware strategies are designed to generate realized losses for tax-mitigation purposes, the effectiveness of these strategies depends on individual taxpayer circumstances and evolving tax laws. NPT does not guarantee any specific tax outcome or amount of loss harvesting. Clients and prospective clients should consult with their personal tax and legal professionals regarding their specific situation before implementing any strategy discussed herein.

Risks of tax-aware strategies (not exhaustive)

Pre-tax returns of a tax-aware strategy may meaningfully underperform expectations, and negative alpha would erode both growth and loss generation. Realized losses may be smaller than expected, and their value depends on an individual investor's circumstances, including marginal tax rates and the availability of capital gains to offset. Capital losses offset capital gains, not ordinary income beyond a small annual allowance. Gain deferral is not gain forgiveness, and deferred gains may be recognized on liquidation or withdrawal, even after pre-tax losses. Long/short portfolios involve leverage, shorting, financing and transaction costs, tracking error, and operational complexity that index funds do not. The potential tax benefit of any strategy may be lessened or eliminated prospectively by changes in tax law, or retrospectively by an IRS challenge under current law.

Forward-looking statements

Descriptions of NPT strategies reflect how the strategies are designed to operate and what they seek to achieve. There can be no assurance that an investment strategy will be successful, and actual results will differ from objectives. The views expressed reflect the current views as of the date hereof, and NPT does not undertake to advise you of any changes in the views expressed. Forward-looking statements are subject to change without notice.

Geographic availability

This essay is intended only for qualified investors and interested parties residing in jurisdictions in which NPT is qualified to provide investment advisory services. NPT and its affiliates may hold positions (long or short) or engage in securities transactions that are not consistent with the information and views expressed herein.

NinePointTwo Capital

A Los Angeles-based investment management firm. NPT Research publishes periodically and is distributed to clients and qualified prospective investors.

NPT Research
Published · June 2026
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