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My Next Move

When Selling Means Surrendering

Capital Gains

The position won. Selling it means handing a share of the win to the IRS. So you hold, and the risk keeps concentrating.

Concentrated stock from years of RSU vests. Founder shares approaching an exit. The building your family bought decades ago. A brokerage account full of winners you can't touch without writing a six-figure check. Appreciation was the goal, until it became the cage.

Diversify, and you realize the gain. Hold, and the concentration risk grows with the position. Give it away, and the basis question follows the asset. No door out of a large embedded gain is costless. There are only doors with different prices.

So most people do nothing. The position gets bigger, the embedded tax gets bigger, and the decision gets harder every quarter it's deferred. Doing nothing feels neutral. It isn't.

Meanwhile the structural windows move without you. Basis step-up rules, QSBS qualification, charitable structures that must be funded before a sale. The code rewards people who act early and ignores everyone else.

You picked right. The tax code punishes you for it.
Eric Cooper, Founder

Why this doesn't solve in isolation

A capital gain is never just a capital gain. It sits inside your estate, your income picture, and (if an exit is coming) your biggest year.

Estate Taxes

Basis steps up at death. Whether an asset should ever be sold during your life is an estate question as much as an investment one.

Liquidity Event

An exit compresses the entire question into one taxable year, and the useful structuring happens years before the close.

Income Taxes

Gains stack on top of ordinary income. NIIT, AMT, and bracket interplay decide what a sale actually costs in a given year.

Sooner's approach

Sooner treats a concentrated position as an engineering problem, not a sales order. Loss harvesting, exchange funds, charitable remainder trusts, opportunity zones, direct indexing. Each is a tool for repositioning without full recognition, and each fits some situations and not others.

Timing matters as much as tooling. Realizations are spread across years and brackets deliberately, coordinated with your CPA, your estate attorney, and every other move in the sequence.

The goal isn't to avoid the tax. It's to stop paying it by accident.

The cost of waiting

Every year the position sits untouched is another year of single-stock risk you're not being paid to take. Every unharvested loss and unstructured sale is recoverable value left to chance.

Concentration built the wealth. It doesn't get to decide what happens to it.

Ninety seconds tells you where to start.

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