Exchange Funds vs 351 ETFs: The Millionaire's Guide to Tax-Free Diversification

Picture of Mark Stancato, CFP®, EA, ECA, CRPS®

You're sitting on a stock that changed your life. Maybe it was your startup equity, or a lucky bet on Nvidia or Tesla. The problem? You’re also sitting on a massive tax bill if you try to sell. A concentrated stock position may have helped you build your wealth - but now it’s a risk you can’t afford, and you feel trapped.

This is where advanced tax strategies come into play - specifically Exchange Funds and 351 Conversion ETFs. These aren’t everyday tools. They’re sophisticated legal strategies used by ultra-high-net-worth individuals and family offices to diversify without triggering capital gains tax.

In this article, we’ll break down both strategies in depth, explore real-world use cases, and help you understand when each strategy makes sense. If you’ve got $5M, $25M, or even $100M of low-basis stock, this is the kind of chessboard you should be playing on.

The Capital Gains Conundrum

Let’s say you hold $20 million in Nvidia stock with a $2 million basis. That’s an $18 million unrealized gain. Selling would likely cost you:

  • Federal LTCG tax (20%) = $3.6 million
  • NIIT (3.8%) = $684,000
  • State tax (e.g., California ~13.3%) = $2.4 million

Total tax hit: over $6.6 million.

So you don’t sell. But you’re overexposed, under-diversified, and potentially one earnings call away from a disaster. You need a way out that doesn’t set fire to your gains.

Enter Exchange Funds and 351 ETFs.

Strategy 1: The Exchange Fund

What It Is

An Exchange Fund is a pooled investment vehicle—usually structured as a limited partnership—where multiple investors contribute their concentrated stock holdings. Over time, they receive a diversified basket of stocks, without triggering a sale.

These funds are governed under Section 721 of the Internal Revenue Code and are typically offered by firms such as Goldman Sachs, Eaton Vance, or Morgan Stanley.

How It Works

  1. You contribute $5M–$10M+ of a single low-basis stock (e.g., Apple).
  2. Others do the same with their stock.
  3. You receive LP units in a diversified fund.
  4. After 7 years, you can redeem your pro-rata share of the diversified basket.

Tax Consequences

  • The initial contribution is non-taxable.
  • The exchange after 7 years is also non-taxable, provided the structure follows IRS rules.
  • You retain carryover basis in the stocks you receive - so tax is deferred, not erased.

Costs Involved

  • Management Fees: Typically 0.75%–1.25% annually
  • Performance Fees: Some funds may charge a back-end or performance-based fee
  • Opportunity Cost: Limited customization and 7-year lockup
  • Administrative Costs: Built into the fund’s NAV; not always transparent

Pros

  • Simple to implement through institutional platforms
  • No need to create a new legal entity
  • Built-in diversification

Cons

  • 7-year lockup
  • No control over fund holdings
  • Illiquidity
  • Mismatched strategies possible

Strategy 2: The 351 ETF Conversion

What It Is

A 351 Conversion ETF is a bespoke, publicly traded ETF created by contributing appreciated assets under Section 351 of the IRC, which allows tax-free transfers of property into a corporation. White-label firms, such as Tidal, Exchange Traded Concepts, or Alpha Architect, commonly structure these ETFs.

This strategy enables you to create an ETF, seed it with your low-basis stock, and utilize in-kind transactions to rebalance into a diversified portfolio—all without incurring capital gains tax.

How It Works

  • You or your advisor creates a new ETF (via a white-label platform).
  • You contribute $25M+ of appreciated stock (e.g., Snowflake, Palantir).
  • The ETF is launched with your holdings.
  • Within days or weeks, the ETF rebalances via in-kind heartbeat trades into something like SPY or AGG.
  • You now own diversified ETF shares—with no tax triggered.

Tax Consequences

  • Initial contribution is non-taxable (Section 351).
  • Rebalancing trades within the ETF are non-taxable (in-kind swaps).
  • You now hold ETF shares with a carryover basis.
  • Tax is deferred until the ETF is sold.

Sample Client Scenario

Let’s say Sarah holds $25M in Snowflake (basis $3M). She funds a custom ETF with the position. The ETF then swaps Snowflake for SPY and a few fixed income ETFs. Sarah now owns ETF shares worth $25M with a $3M basis—fully diversified, fully liquid, no tax paid.

What Can Be Held Inside a 351 ETF?

  • Single stocks (e.g., Snowflake, Nvidia)
  • Other ETFs (e.g., SPY, AGG, sector ETFs)
  • Fixed income ETFs
  • Individual bonds (e.g., Treasuries, corporates, munis)

Using ETFs inside the 351 fund helps satisfy the IRS’s 25/50 diversification rule:

  • 25% Rule: No single position can be more than 25% of the portfolio
  • 50% Rule: The top 5 positions cannot collectively exceed 50% of the portfolio

ETFs and bond funds naturally spread exposure across dozens or hundreds of securities, helping the ETF pass this test and qualify for non-recognition under Section 351.

Costs Involved

  • ETF Formation/Legal Setup: $100K–$200K upfront
  • White-label platform onboarding: $50K–$100K
  • Annual Operating Expenses: $100K–$300K per year (compliance, audit, board, legal)
  • Custom Fund Management: If outsourced, expect advisory fees
  • Tax Compliance: Ongoing cost to track basis and file fund returns

Pros

  • No lockup
  • Full control and customization
  • Transparent and liquid
  • Diversification within days
  • Flexibility in asset selection

Cons

  • High setup and ongoing costs
  • Requires careful tax and basis tracking
  • Legal and operational complexity

What Happens After the Conversion?

Option 1: Keep the ETF Open and Publicly Tradable

  • The ETF continues trading.
  • You, as the original seeder, hold ETF shares that you can sell at any time (taxable event).
  • Fund manager (or white-label platform) continues maintaining it.
  • Other investors could theoretically buy into it, but often they don’t — it's not marketed.

This is the most common path for clients who want:

  • Liquidity
  • Ongoing tax deferral
  • Custom index-like exposure

Option 2: Wind Down the ETF

Once the strategic tax move is done (i.e., your appreciated stock has been exchanged for diversified assets), you may decide to:

  • Liquidate the fund
  • Redeem ETF shares in-kind
  • Shut down the ETF shell

This could make sense if:

  • The ETF has served its purpose (e.g., post-diversification)
  • You want to reduce the costs of maintaining the ETF
  • You’ve sold or donated your ETF shares elsewhere
  • You don't want to deal with compliance and board governance long-term

⚠️ Important:

Any liquidation or redemption must be carefully structured to avoid turning the transaction into a constructive sale or triggering gain. This is where a strong tax counsel and fund legal team are absolutely essential.

What Does ETF Closure Look Like?

If you decide to shut down the fund:

  • File termination paperwork with the SEC.
  • Distribute assets to remaining shareholders (usually just you or your family office).
  • Dissolve the legal entity.
  • File a final return and issue final shareholder tax reports (cost basis, NAV at closure, etc.).

It’s not unlike shuttering a mutual fund or private fund. The key is that:

  • You don’t trigger a deemed sale
  • Basis tracking is preserved
  • Any remaining assets are distributed in-kind (not cash) if you want to avoid recognition

Planning Tip:

Many clients hold the ETF for years, integrating it into their broader portfolio:

  • Can be transferred to trusts
  • Used for tax-loss harvesting pairs
  • Or held until death for step-up in basis

But if you want to unwind it, you can — you just have to do it intentionally, not casually.

Summary

Side-by-Side Comparison

Feature Exchange Fund 351 ETF Conversion
Tax Deferral Yes Yes
Contribution Type Stock only Stock, ETFs, Bonds
Lockup 7 years None
Minimum ~$5M per investor $25M+ total seed
Liquidity None until redemption Fully liquid ETF shares
Control None Full control
Customization Low High
Transparency Low High
Use of ETFs/Bonds No Yes
Carryover Basis Yes Yes
Step-Up at Death Yes Yes
Setup Cost Low–Moderate High
Ongoing Costs Moderate High

When to Use Each Strategy

Use an Exchange Fund if:

  • You're contributing $5M–$10M and don’t want to deal with creating a new fund
  • You're OK with a 7-year lockup
  • You're looking for a passive, plug-and-play solution

Use a 351 ETF if:

  • You have $25M+ in appreciated assets
  • You want full control over the portfolio
  • You need diversification quickly, not in 7 years
  • You want liquidity and exit flexibility
  • You’re a family office or highly sophisticated investor with tax counsel
  • You're willing to absorb higher upfront and ongoing costs for greater flexibility

Estate and Tax Planning Implications

Carryover basis must be tracked manually
Sale of ETF shares triggers gains unless offset with:
  • Charitable giving
  • Loss harvesting
  • Lower-tax-bracket years
Step-up in basis at death remains available
Can integrate with:
  • CRUTs
  • IDGTs
  • Donor-Advised Funds
  • Family partnerships

Sidebar: What Is a Heartbeat Trade?

A heartbeat trade is a strategy used by ETFs to remove appreciated securities without triggering capital gains.

Here’s how it works:

  1. A large investor (or authorized participant) contributes cash or securities to the ETF — an inflow.
  2. The ETF uses that inflow to swap out appreciated positions via an in-kind redemption with the same participant — the outflow.
  3. These paired inflows and outflows create a “heartbeat” pattern in the ETF’s daily fund flows.

🔁 Because the ETF doesn't sell anything — it simply exchanges securities — no taxable event occurs.

Why it matters:
Heartbeat trades are critical for 351 ETFs because they allow rapid, non-taxable rebalancing away from the original low-basis stock — and into diversified ETFs or bonds — without tripping capital gains.

Visual Flowchart: How a 351 ETF Works

Client w/ $25M in low-basis stock
Forms ETF via Section 351 with white-label provider
Seeds ETF with appreciated assets
(e.g., Snowflake, Palantir)
ETF launches with concentrated holdings
Heartbeat trades: in-kind inflows & outflows initiated
ETF swaps original stocks for diversified ETFs
(e.g., SPY, AGG)
Client now owns ETF shares worth $25M
Key Details:

✔️ Same $25M value

✔️ Same $3M basis (carryover)

✔️ No tax triggered

Hypothetical Case Study: Before vs. After Portfolio

BEFORE: Concentrated Portfolio

Client: Sarah, a tech executive with a highly concentrated brokerage account.

Holding Value Cost Basis Unrealized Gain
Snowflake $15,000,000 $1,500,000 $13,500,000
Palantir $10,000,000 $1,000,000 $9,000,000

Total Portfolio Value: $25,000,000

Estimated Tax Liability if Sold: ~$6M–$7M (depending on state)

AFTER: 351 ETF Conversion + Heartbeat Trade

Strategy: Sarah contributes appreciated shares into a custom ETF.

Snowflake and Palantir shares are contributed to a newly formed ETF.
ETF rebalances into:
  • $15M in SPY (broad market index)
  • $5M in AGG (core bonds)
  • $5M in sector ETFs (e.g., clean energy, healthcare)

Sarah now holds:

  • $25M of ETF shares
  • Same $2.5M cost basis (carryover)
  • Zero tax triggered

Result: Fully diversified. Liquid. Tax deferred. Strategic optionality preserved.

Summary: Deferral is the New Alpha

Wealthy investors aren’t dodging taxes. They’re deferring them—strategically, legally, and with precision.

If you’re sitting on a massive low-basis position, the game isn’t just about beating the market. It’s about utilizing the tax code in your favor. Whether you choose an Exchange Fund or a 351 ETF conversion, you’re playing a different game entirely and doing it with purpose.

At VIP Wealth Advisors, we don’t do boilerplate plans. We do battle-tested, bespoke strategy. If you’re ready to reposition your wealth without triggering a tax minefield, it’s time to talk.

💼 Thinking About Diversifying Without Paying the IRS?

If you’re sitting on a massive low-basis stock position and want to explore advanced strategies like Exchange Funds or 351 ETFs, we can help.

At VIP Wealth Advisors, we help high-net-worth tech professionals and founders navigate the tax code with precision—no boilerplate plans, just smart strategy.

📅 Book Your Private Strategy Call

 


ABOUT THE AUTHOR

Mark Stancato, CFP®, EA, ECA, CRPS®

Mark Stancato, CFP®, EA, ECA, CRPS® has over 20 years of experience advising high-net-worth clients, including tech executives, real estate investors, and entertainment professionals. He specializes in tax strategy, equity compensation, and multi-stream income planning—offering white-glove guidance and highly personalized financial solutions.

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