Concentrated Stock
Selling a large, low-basis holding at once would generate a substantial capital gains bill. The account realizes losses that can absorb the gain as the position is sold down over time.
Compare the three routesProprietary long/short equity extension strategies, from 130/30 to 300/200, that seek better after-tax returns.
Tax-aware long/short adds tax impact as a variable in the same quantitative process behind NinePointTwo's long/short equity strategies. It seeks to keep market exposure in place, add diversification and potential alpha, and realize tax losses along the way. Holding positions on both sides of the market lets it keep harvesting losses after conventional tax loss harvesting and direct indexing have slowed.
The structure is often called a long/short extension strategy. Implementations range from 130/30 to 300/200. At 130/30, each $100 invested supports $130 of long positions and $30 of shorts, so net market exposure stays at $100. Every account is a separately managed account (SMA) held in the client's name.
Tax-aware investing is most relevant for taxable U.S. investors seeking to improve their after-tax wealth. Three situations come up most often.
Selling a large, low-basis holding at once would generate a substantial capital gains bill. The account realizes losses that can absorb the gain as the position is sold down over time.
Compare the three routesThe long/short overlay runs on NinePointTwo's expected return models and seeks returns with low correlation to the rest of the portfolio. The same positions realize tax losses along the way.
Read the research primerA company sale, a founder's liquidity event, or carried interest is often visible years before it arrives. Losses realized in advance may offset those gains.
Read the founder's tax problemTax-Aware Long/Short adds systematic long and short equity extensions to a client's existing portfolio, based on NinePointTwo's proprietary forecasts of expected returns. The existing portfolio does not need to be sold first.
Illustration of structure only. Higher configurations generally realize losses faster and diversify a position sooner, with larger deviations from the market along the way.
Runs alongside existing holdings or cash. Appreciated positions stay in place, with no forced sale.
Selected by NinePointTwo's quantitative models, signals, and factor research.
Stocks the models expect to underperform, sized to offset the long extensions so the overlay adds no net market exposure.
Adjusted over time to each client's needs, with the goal of maximizing after-tax returns.
Conventional tax loss harvesting works inside a long-only portfolio. The table compares long/short with the two most common alternatives.
| Feature | Tax-Aware Long/Short | Direct Indexing | Exchange Fund |
|---|---|---|---|
| Loss harvesting in rising markets | Designed to continue, since short positions can decline as markets rise | Generally slows as holdings appreciate | Not designed to harvest losses |
| Starting point | Cash or existing holdings | Cash or existing holdings | Stock contributed to the fund |
| Lockup | None | None | Typically seven years |
| What the client owns | Positions in an SMA in their own name | Positions in an SMA in their own name | Units of a pooled partnership |
| Source of pre-tax return | Market exposure plus a long/short alpha overlay | Market exposure, held close to the index | The pooled portfolio's holdings |
| Eligibility | Accounts generally from $1M | Varies by provider | Accredited investors, often qualified purchasers |
Loss harvesting in rising markets
Tax-Aware Long/Short
Designed to continue, since short positions can decline as markets rise
Direct Indexing
Generally slows as holdings appreciate
Exchange Fund
Not designed to harvest losses
Starting point
Tax-Aware Long/Short
Cash or existing holdings
Direct Indexing
Cash or existing holdings
Exchange Fund
Stock contributed to the fund
Lockup
Tax-Aware Long/Short
None
Direct Indexing
None
Exchange Fund
Typically seven years
What the client owns
Tax-Aware Long/Short
Positions in an SMA in their own name
Direct Indexing
Positions in an SMA in their own name
Exchange Fund
Units of a pooled partnership
Source of pre-tax return
Tax-Aware Long/Short
Market exposure plus a long/short alpha overlay
Direct Indexing
Market exposure, held close to the index
Exchange Fund
The pooled portfolio's holdings
Eligibility
Tax-Aware Long/Short
Accounts generally from $1M
Direct Indexing
Varies by provider
Exchange Fund
Accredited investors, often qualified purchasers
Describes typical structures rather than any specific fund or provider. Nothing here is tax or legal advice.
Enter a position value and cost basis to compare selling today with a tax-aware long/short account that defers the gain. The full tool also sets the horizon, leverage, and tax rates.
Hypothetical illustration. Assumptions and disclosures appear with the results.
In 2026 the two largest retail custodians restricted new tax-aware long/short accounts. Fidelity paused new openings. Schwab now requires $10 million for certain new accounts and allows only Regulation T margin, which generally limits a new account to about 150/50. NinePointTwo custodies accounts at Interactive Brokers, which has announced no comparable restriction. New accounts open from $1 million, at configurations up to 300/200. The provider comparison lists the sources.
About Interactive Brokers
Source: Interactive Brokers Group. Total equity as of 30 June 2026 (second-quarter 2026 results). Client equity and client accounts as of 31 August 2026 (monthly brokerage metrics, released 1 September 2026). Index membership per S&P Dow Jones Indices, effective 28 August 2025. Checked September 2026.
The strategies are proprietary and run in-house on the same quantitative long/short infrastructure behind NinePointTwo's Alternatives division. NinePointTwo works directly with each client to design, calibrate, and adjust the strategy over time.
Uses the expected return models from NinePointTwo's unconstrained long/short strategies.
Tuned to each client's risk tolerance, goals, time horizon, and tax situation.
Work directly with the portfolio managers, with or without an advisor.
One all-in management fee between 0.50% and 2.00%, negotiated by account size and configuration.
The goal of our tax-aware long/short strategies is to offer suitable taxable U.S. investors direct access to our quantitative strategies in a tax-efficient manner. The strategies have the potential to add additional alpha to portfolios and improve diversification characteristics.
Yes. The portfolio can appreciate in value while simultaneously generating realized losses on specific positions. Losses are a tax construct tied to individual transactions, not a reflection of overall portfolio performance.
Losses are generated as a byproduct of the investment process and are not tied to any specific event. They may be applied against capital gains from any source, including real estate transactions, business sales, carried interest, and more.
Yes, however a portfolio that defers taxes compounds on a larger base each year. Over long time horizons, that compounding advantage may generate significantly more after-tax wealth than a tax-inefficient portfolio, even after paying all deferred taxes at liquidation.
No. The strategy works with cash or any existing portfolio.
Traditional tax-loss harvesting captures losses only when holdings decline, so as a long-only portfolio appreciates, harvestable losses generally become scarce. A long/short portfolio holds positions on both sides of the market, and at any given time some longs and some shorts trade below cost. The strategy may realize those losses as its models rotate out of positions they no longer favor, and the replacements are chosen for expected return rather than to mimic what was sold. Short positions lose value when markets rise, which is why a long/short book may continue to harvest losses in rising markets after a long-only program has run out. Our expected return models select the positions, not tax reasons alone, so the same book also seeks pre-tax alpha and diversification.
Yes, these strategies go by many names, including tax-managed long/short, tax-efficient long/short, and long/short tax loss harvesting, but are typically all long/short implementations of quantitative equity strategies. A long/short extension strategy adds long and short positions on top of varying levels of market exposure. Ours ranges from 130/30 up to 300/200 depending on the client's risk tolerance and objectives. We offer our tax-aware long/short through separately managed accounts rather than a pooled fund, so the client's funds remain completely segregated with a standard 1099 for tax reporting.
A long/short SMA is a separately managed account that runs a long/short strategy in the client's own name. The client directly owns the positions rather than units of a pooled fund. Realized tax losses in the account belong to the client and arrive on a standard 1099.
Yes. Accounts generally begin at a $1M minimum. Please contact us directly to discuss whether the strategy is appropriate for your situation.
NinePointTwo does not publish performance for Prism, its tax-aware long/short strategy, on its website or in other public materials, consistent with its compliance policies. Prospective clients and their advisors can request that performance information directly. NinePointTwo has managed quantitative strategies since 2018 and tax-aware long/short strategies since 2025. Prism draws on the same in-house models. Tax-aware long/short managers generally do not publish live results for these separately managed accounts on their public websites.
NinePointTwo sizes each account's leverage to its collateral and monitors margin daily. Adding cash or other holdings to the account increases the buffer.
There is no lockup. The client can lower the account's leverage or close it at any time. Unwinding the positions realizes whatever gains or losses are embedded in them. The preferred route is for NinePointTwo to move the account to long-only direct indexing, a transition that may be managed without a tax impact.
The account reports on a standard 1099. A long/short account generates many more transactions than a long-only portfolio, so the 1099 runs longer. Most tax software and tax preparers import 1099 data directly, so a longer form is not necessarily more work.
Tell us which approach interests you and we will follow up to arrange a conversation.
Investing involves substantial risk, including the possible loss of principal. Tax-aware long/short strategies involve unique risks and may not be suitable for all investors. The effectiveness of tax management strategies depends on individual taxpayer circumstances and may vary. Past performance is not indicative of future results. See our Disclosures page for additional important information.
We work with a select number of clients on a direct basis. We welcome a conversation to explore whether Tax-Aware Long/Short may be a suitable fit for you.