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Many portfolios are built with one primary goal in mind: Performance. Taxes are often treated as an afterthought, addressed once the year is over and the 1099s arrive.
For many investors, tax planning means sending paperwork to a CPA and hoping for the best. But by that point, most of the decisions that drive the tax outcome have already been made.
Investment management shouldn’t simply report taxes after the fact. When done well, it should help shape them.
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This becomes important during major financial earnings peaks or years with unusually large capital gains, concentrated stock positions or upcoming liquidity events.
In these moments, proactive coordination between investment strategy and tax planning can deeply impact how much an investor ultimately keeps.
Facing a large capital gains year
The most common large-capital-gains scenario I see involves a long-held investment that has appreciated far beyond its original allocation. This could be a stock that performed exceptionally well, the sale of an investment property or a partial business liquidity event that creates a one-time spike in taxable income.
Ideally, planning begins at least 12 to 24 months before a known or expected gain. That window provides greater flexibility, particularly for loss harvesting, asset location decisions and coordinating with broader tax strategies.
If someone anticipates a large gain in the next year or two, the most impactful step they can take today is to review their portfolio through a tax lens, not just a performance lens. That means understanding embedded gains, identifying potential offsets and stress-testing different timing scenarios.
One common mistake investors make in high-capital-gains years is reacting too late. Selling assets without a coordinated plan, or ignoring tax exposure altogether, often leads to unnecessary erosion of after-tax returns.
Managing a concentrated stock position
Concentrated stock positions often develop gradually. They can come from employer stock, founder equity or a single investment that outpaced the rest of the portfolio.
At a certain point, concentration simultaneously becomes a risk to the investment and a tax problem. Procrastinating too long can leave investors feeling trapped between the tax cost of selling and the risk of staying too exposed.
We’re aiming for controlled chaos to a degree. The goal is rarely to eliminate the position all at once, but rather to reduce risk in a measured, intentional way.
One frequently missed opportunity occurs when investors delay action until the position becomes uncomfortably large. By then, fewer planning tools are available, and the tax consequences are often more severe.
Our team urges weighing the tax cost against the concentration risk, which requires reframing the decision. The question isn’t simply how much tax will be paid, but what level of risk the investor carries by doing nothing. The true enemy is inaction.
Preparing for a sale or other liquidity event
While business sales and private-equity events are common, there are a range of situations that can trigger significant tax shifts of which to be aware. For instance, the vesting of equity compensation, the exercise of stock options, real estate sales or significant portfolio rebalancing.
A potential sale or exit is something a tax-focused investment strategy should prepare for well before a formal deal is on the table. Once a transaction is imminent, the available planning options narrow considerably.
Proactive investment management moves such as repositioning assets to create flexibility, managing liquidity intentionally and aligning the portfolio with the investor’s anticipated post-event tax profile can also support a future event.
These strategies might include adjusting risk exposure, revisiting asset location or ensuring the portfolio isn’t inadvertently compounding the event’s tax impact.
A common mistake when a liquidity event is on the horizon is focusing solely on the transaction itself, without considering how the rest of the balance sheet interacts with the tax outcome.
Coordination with a CPA or tax adviser is essential during this phase, as investment decisions and tax strategy are tightly interconnected.
Advisory that is focused primarily on pretax performance is easy to measure and easy to discuss. After-tax results, however, are harder to quantify but far more meaningful.
When investment management and tax planning operate in silos, opportunities are missed. In coordination, especially during periods of change, investors gain more control of outcomes that truly matter: flexibility, risk and what they ultimately get to keep.
