Concentrated Stock

The Problem

Three routes out of a concentrated position

An investor holding a large appreciated position faces an unattractive pair of options. Selling generates a substantial capital gains bill. Holding leaves their wealth dependent on the fortunes of one company, or on one narrow set of bets.

Three structures are commonly proposed as a middle path. A tax-aware long/short separately managed account realizes losses that absorb the gain as the position is sold down. A Section 351 conversion moves securities into a newly launched ETF. An exchange fund pools positions from many investors into a partnership. All three defer the tax rather than eliminate it, and each carries costs of its own.

The first question is usually eligibility rather than preference, because the three have very different entry requirements. What follows describes typical structures rather than any specific fund, and nothing here is tax or legal advice.

Mechanics

How each structure works

01

Tax-Aware Long/Short

Accepts
Any position
Timing
Any time
Liquidity
Daily, no lockup

A tax-aware long/short program is a separately managed account rather than a pooled vehicle. The concentrated position stays in the investor's own account. Alongside it, the manager runs a long/short equity portfolio built to realize losses through its normal trading. That capacity does not depend on a falling market.

Realized losses accumulate and may offset the gains from selling the concentrated stock. The position is sold down in stages over several years. Proceeds move into a diversified portfolio the investor owns directly.

There is no eligibility test on the position and no lockup. The program does require capital or borrowing capacity alongside the position. It also requires a tolerance for the risks of short selling and leverage.

02

Section 351 ETF Conversion

Accepts
Diversified portfolios only
Timing
Sponsor launch windows
Liquidity
Daily, as ETF shares

Section 351 of the tax code allows property to move into a corporation in exchange for its stock without triggering tax. The condition is that the transferors together control the corporation immediately afterward. At the launch of a new ETF, a group of investors contributes securities and receives ETF shares. Gain is generally not recognized at that moment, and the original cost basis carries over.

There is a significant restriction. A transfer to an investment company is generally taxable when it diversifies the transferor's interests. The contributed portfolio must therefore already be diversified. The test allows no more than 25 percent of value in one issuer and no more than 50 percent in the five largest. A single concentrated position usually cannot be contributed on its own.

A 351 conversion therefore fits a different investor than the name suggests. It suits a diversified but low-basis portfolio, often a legacy managed account or an index portfolio with decades of embedded gains. Contributions are possible only during a sponsor's launch window. The timing is the sponsor's rather than the investor's.

03

Exchange Funds

Accepts
Concentrated positions
Timing
Periodic subscriptions
Liquidity
Seven-year lockup

An exchange fund is a limited partnership. Investors contribute appreciated stock and receive partnership units. Under Section 721 the exchange generally does not trigger tax. The fund pools positions from many investors alongside a sleeve of qualifying assets, often real estate. The sleeve preserves the partnership's tax treatment.

The tax code discourages early exits. An investor who redeems within seven years generally receives their original shares back. After seven years, redemption can be taken as a diversified basket of stocks drawn from the pool. The original cost basis carries into that basket, and the gain stays embedded until those shares are sold.

Unlike a 351 conversion, an exchange fund is built to accept the concentrated position itself. The tradeoff is a seven-year lockup and no say in what the pool holds.

Comparison

Where the structures differ

Seven dimensions cover most of what investors ask. The first two rows rule a route in or out more often than the rest combined.

What you can contribute

Tax-Aware Long/Short

Any position. There is no eligibility test on the position itself, though the economics depend on its size relative to the capital funding the program.

351 Conversion

An already diversified portfolio. No more than 25 percent in any one issuer and no more than 50 percent in the top five. A single concentrated position generally does not qualify on its own.

Exchange Fund

A concentrated position in a stock the fund is willing to accept. Eligibility standards vary by sponsor.

Timing

Tax-Aware Long/Short

Any time. The program starts when the investor is ready.

351 Conversion

Only during a sponsor's ETF launch window. The investor does not choose when.

Exchange Fund

Subscription periods set by the sponsor, generally more frequent than an ETF launch.

What you end up owning

Tax-Aware Long/Short

A diversified portfolio held directly in the investor's own account, designed around their broader situation.

351 Conversion

Shares of the ETF and its strategy, held alongside every other contributor. Individual positions are no longer separable.

Exchange Fund

Partnership units, and after seven years a basket of stocks drawn from the pool. The composition reflects what others contributed.

Liquidity

Tax-Aware Long/Short

Daily liquidity in a separately managed account. The strategy can be scaled back or unwound at any time, though exiting early cuts the tax benefit short.

351 Conversion

ETF shares trade daily. Selling them realizes the deferred gain, but the investor is not locked in.

Exchange Fund

Typically a seven-year holding period. Redeeming early generally returns the original shares and can unwind much of the benefit.

Tax treatment

Tax-Aware Long/Short

Harvested losses may offset gains as the position is sold, with deferral showing up as reduced basis in the long/short portfolio. Loss generation depends on market conditions and is not guaranteed.

351 Conversion

Contribution is generally tax-free and basis carries into the ETF shares. The fund's in-kind redemption mechanism can work off low-basis lots over time. Gain remains embedded until shares are sold.

Exchange Fund

Contribution defers tax and the original basis carries into the redemption basket. The gain stays embedded until those shares are sold.

Control and customization

Tax-Aware Long/Short

Full. The investor sees every holding, keeps them in their own account, and sets the pace of the sell-down with the manager.

351 Conversion

None after contribution. The investor owns a share of a common strategy and cannot harvest losses on individual holdings.

Exchange Fund

None. The underlying holdings, early-exit treatment, and final basket composition are set by the fund.

Costs

Tax-Aware Long/Short

An advisory fee on the account, plus the trading and financing costs of running a long/short portfolio. No pooled vehicle and no placement fee.

351 Conversion

The ETF's ongoing expense ratio. No placement fee and no lockup charge.

Exchange Fund

Ongoing management fees on the pooled vehicle, and in some cases placement fees or early-redemption charges.

Suitability

Where each structure fits

No structure dominates the others. A 351 conversion or an exchange fund is often a better answer than ours, and we say so when it is.

Where tax-aware long/short works

  • Priority on daily liquidity and transparency
  • A destination portfolio built around the investor
  • Spare capital available to fund the program
  • Gains elsewhere that harvested losses could offset
  • Tolerance for short selling and leverage

Where a 351 conversion works

  • A diversified but low-basis portfolio
  • Comfort owning one common strategy
  • Daily liquidity valued over customization
  • Timing that happens to match a launch window
  • No appetite for an ongoing program

Where an exchange fund works

  • A genuinely concentrated position to diversify
  • No spare capital to commit alongside the position
  • Comfort with a seven-year holding period
  • Deferral aimed at a basis step-up at death
  • One transaction preferred over an ongoing program

FAQ

Common Questions

What is a Section 351 exchange?

Section 351 of the Internal Revenue Code allows property to move into a corporation in exchange for its stock without recognizing gain. The condition is that the transferors together control the corporation immediately after the exchange. In the fund context this is used at the launch of a new ETF. A group of investors contributes securities, receives ETF shares, and generally does not pay tax at that moment. The original cost basis carries over, so the gain is deferred rather than forgiven. Whether any particular transfer qualifies depends on facts specific to the investor and should be reviewed with a tax advisor.

Can I contribute a single concentrated stock position to a 351 ETF conversion?

Usually not on its own. The rules governing transfers to investment companies generally make the exchange taxable if it results in diversification of the transferors' interests. A contribution avoids that outcome when the portfolio being contributed is already diversified. The test allows no more than 25 percent of value in one issuer and no more than 50 percent in the five largest. A single large position fails that test. This is the most common misunderstanding we encounter. An investor holding one appreciated stock is typically looking at an exchange fund or a tax-aware long/short program instead.

How is a 351 conversion different from an exchange fund?

They solve different problems. A 351 conversion suits an already diversified but low-basis portfolio and produces liquid ETF shares with no lockup. An exchange fund is built to absorb a genuinely concentrated position and requires a seven-year commitment in return. A 351 conversion is also only available during a sponsor's launch window, while exchange funds subscribe more regularly.

Does any of these structures eliminate the tax?

No. All three defer tax rather than eliminate it. A 351 conversion and an exchange fund both carry the original basis forward. In a long/short program, losses used to offset a sale are typically paired with reduced basis elsewhere in the portfolio. Deferral still has value, because the portfolio compounds on a larger base in the meantime. Separate provisions of the tax code can prevent deferred gains from ever being realized. The basis step-up at death and charitable gifts of appreciated stock are the common examples, and all three structures leave them available.

Can these structures be combined?

Yes. They are not mutually exclusive. Some investors contribute part of a position to an exchange fund and apply a tax-aware long/short program to the remainder. Others use the program's harvested losses against gains realized elsewhere. That includes gains from selling ETF shares received in a 351 conversion.

How long does a tax-aware long/short sell-down take?

It depends on the size of the position relative to the capital funding the program. Market conditions and the pace of loss generation matter as well, and none of these is guaranteed. The sell-down typically takes one to three years. The expected path is typically modeled with the client before anything is implemented.

What happens if an investor needs to exit an exchange fund early?

Terms vary by fund. Early redemption generally returns the investor's original shares, and some funds return the lesser of the value at contribution or at redemption. Charges may apply, and the diversification benefit largely unwinds. This is the structural price of the tax treatment and applies across sponsors.

What are the main risks of the long/short approach?

Short selling and leverage introduce risks that a long-only pool does not carry, including the possibility that the long/short portfolio loses money. Tracking error against broad market indexes can be significant, and the tax outcome depends on individual circumstances and evolving tax law. These strategies are not suitable for all investors.

Disclosures

This page is a general comparison provided for informational purposes only. It does not describe any specific fund, and terms vary by sponsor. Nothing here is tax or legal advice. The tax treatment of any transaction depends on facts specific to the investor. Consult your own tax advisor before acting.

Investing involves substantial risk, including the possible loss of principal. Tax-aware long/short strategies involve unique risks, including short selling and leverage, 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.

Contact

Talk through a specific position

Which route fits depends on what you hold, its basis, your other assets, and your liquidity needs. We are direct with prospective clients about the cases where a 351 conversion, an exchange fund, or simply selling is the better answer.