A business sale can be one of the most significant financial events of your lifetime, and can also be one of the most heavily taxed — which can be strategically planned for. 

The tax code treats different components of a sale differently: some portions may be taxed as ordinary income, others as capital gains, and still others may qualify for special treatment (like QSBS exclusions). 

One aspect founders overlook is waiting until the closing table to think about taxes. But even so, planning techniques exist to offset capital gains no matter when planning starts. Through tax-focused planning, founders can navigate their lifetime tax considerations, with the goal of creating a tax efficient portfolio for the next chapter of life.

Many professionals accumulate a large portion of their net worth in company stock through RSUs, ESPPs, options, or long-term tenure. 

While this can create tremendous upside, it also creates concentration risk — the kind that can wipe out decades of work if the company stumbles.The challenge is that diversification often triggers taxes, and most people assume they must choose between reducing risk or tax efficiency. 

In reality, we can help with both. Through enhanced restructuring of your current portfolio, you can help gradually reduce concentration while pursuing a tax efficient strategy. The goal is simple: manage your wealth, address portfolio volatility, and maintain long-term flexibility — with a focus on balancing your long-term goals.

Pairing Roth conversions with strategies that may generate ordinary income offsets can impact the taxes associated with converting. This creates a rare opportunity: move pre-tax assets that have grown tax deferred into a tax advantaged vehicle — with a focus on tax efficiency.

For investors who expect higher future tax rates, want to reduce RMDs, or plan to leave tax free assets to heirs, Roth conversions are already compelling. The challenge is the upfront tax bill. By integrating offset strategies that produce deductions or losses, investors can neutralize that cost and convert more efficiently.

This approach can turn Roth conversions from a heavy tax decision into a strategic planning tool — one that can impact long term after tax wealth.

Levered long/short strategies can do more than seek alpha — they can help investors manage capital gains in a tax efficient way. For clients with large, embedded gains or ongoing realization liquidity events, these strategies can help manage the tax impact of rebalancing, diversification, or selling appreciated assets.

The benefit isn’t just the offset itself. By reducing the tax friction of realizing gains, investors can potentially regain control and flexibility: they may be able to reposition portfolios and change risk profiles amid a changing investment landscape or, one can potentially unwind concentrated positions with the goal of reducing idiosyncratic risk  without triggering an outsized tax bill.


For investors with recurring capital gains — from business sales, real estate, or active portfolio turnover — this approach can be a powerful tool for smoothing tax liabilities while maintaining market exposure.


And spoiler alert. Long/short strategies can be used in different asset classes that will not only introduce a return stream that behaves differently from traditional equities, but also introduce a different tax benefit—namely offsetting individual ordinary income.

Tax loss harvesting is valuable, but can only one piece of a broader tax efficient investment strategy that high income investors increasingly need. Harvesting losses helps reduce taxable gains, but it doesn’t address ordinary income, concentrated positions, or the ongoing tax drag created by distributions and turnover.

Relying solely on harvesting can also leave investors exposed in years when markets rise and losses are scarce. A more complete approach layers in durable offset strategies with thoughtful portfolio construction to potentially reduce taxes across multiple categories — not just capital gains.

The goal isn’t to “beat the IRS,” but to build a portfolio that compounds more efficiently over time. Tax loss harvesting is a great start, but it’s not the finish line.