Case Studies

The Situation

Sarah had approximately $2 million of company-linked wealth, including owned shares, vested NQSOs, and $300,000 of unvested RSUs scheduled to vest over the next 18 months.

While she knew she likely had enough to retire, she was concerned about how much of her net worth was tied to a single stock: her employer. Could she depend on the company’s growth for the foreseeable future, or should she diversify ahead of retirement?

Sarah also needed to evaluate her retirement timeline. She wanted to understand whether unvested RSUs would continue vesting, accelerate, or be forfeited under the plan’s retirement eligibility provisions. She also needed to know whether vested stock options had to be exercised within a limited post-termination window or were eligible for an extended retirement exercise window.

Our Approach

First, we modeled Sarah’s retirement income using diversified assets, excluding any assumed future appreciation from company stock. We also estimated Social Security benefits based on her earnings record and filing age, so she could see how much of her lifestyle would be supported by guaranteed income versus portfolio withdrawals.

Then, we calculated a couple scenarios comparing how her financial situation would change if she retired now or waited 18 months. We found that waiting would allow her to capture roughly $300,000 in additional vested RSUs.

We found that waiting the additional 18 months also gave us time to create an exercise strategy for those vested NQSOs, enabling us to exercise them before her employment was terminated and she left valuable options on the table.

Because she would need to rely on her portfolio in retirement, we developed a phased diversification plan that reduced company stock exposure while still preserving some upside participation for the company she cared deeply about.

We used the sale proceeds from selling some of her company stock to build a retirement portfolio more aligned with her income needs, risk capacity, and tax considerations for retirement.

Results

As retirement approaches, the question often shifts from "How much wealth can my company stock create?" to "How much of my retirement should depend on one stock and what happens to my stock when I retire?" By building out a retirement income plan for Sarah, we helped her determine how much risk is necessary and how much risk is optional.

Together, we helped Sarah:

• Capture additional RSU vesting value by considering a modest retirement delay.
• Develop a strategy for exercising vested stock options before post-termination deadlines became a problem.
• Reduce company stock concentration from more than 40% of investable assets to about 20%.
• Confirm that retirement success did not depend on the future performance of a single stock.

The Situation

Michael is overwhelmed by the complexity of coordinating 10b5-1 planning, NQDC, ownership requirements, RSUs, performance shares, tax exposure, and retirement timing.

He knows he should diversify, but the mechanics are complicated. Selling stock requires navigating blackout periods, insider-trading restrictions, stock ownership policies, performance share timing, and tax consequences.

Doing nothing leaves his retirement too tied to the performance of one company. Selling too aggressively could lead to unnecessary taxes, compliance concerns, or conflict with ownership requirements.

Our Approach

We began by identifying the minimum required company stock position under executive ownership guidelines. From there, we projected his RSU and performance share vesting schedule over the next five years and used a Rule 10b5-1 trading plan to create a systematic, defensible diversification process. This would allow us to help Michael sell shares and diversify his portfolio while adhering to strict insider trading regulations.

From there, we coordinated his NQDC distribution elections with his anticipated retirement spending needs and other sources of taxable income.

Finally, we reinvested the sale proceeds from his company stock into a diversified portfolio that better supported his long-term income needs.

Results

For executives like Michael, diversifying concentrated company stock requires a coordinated strategy that takes into consideration compliance, compensation design, tax planning, cash flow, governance, and retirement readiness.

Together, we helped Michael:

• Reduce company-linked wealth from roughly 60% of investable assets to approximately 25% over four years.
• Maintain compliance with ownership requirements and trading policies.
• Use NQDC distributions to support retirement cash flow needs and reduce pressure to sell during unfavorable periods.
• Create a repeatable diversification plan that did not rely on last-minute trading decisions.

Before the IPO, most of Emily's wealth existed only on paper. After the IPO, the numbers are life-changing, but the planning decisions have also become much more urgent and emotionally charged.

She’s excited to participate in the company’s future growth, but she also understands that her financial independence could be at risk if the stock price falls before she diversifies. She must coordinate new challenges, including lockup expiration, ISO exercise decisions, AMT exposure, RSU settlement, NQSO taxation, and cash needs.

Our Approach

We created a post-IPO equity inventory of all of Emily’s grants, including strike prices, vesting schedules, exercise windows, lockup timing, and tax attributes.

Because a significant portion of company stock was in the form of ISOs, we also helped Emily understand the AMT exposure that came with exercising and holding ISOs. This way, we could review several exercise scenarios with the full tax picture.

We created a plan around her post-IPO lockup and trading windows in preparation of generating liquidity. We took time to define her target liquidity buckets, which included emergency reserves, near-term goals, taxes, diversification, and retained company stock.

When trading windows allowed, we sold a predetermined percentage of shares at staged intervals. That helped Emily avoid making one emotional, all-or-nothing decision.

Results

An IPO can create wealth quickly, but lasting wealth usually comes from the decisions made after liquidity. Our goal for Emily was to convert concentrated opportunity into a durable, tax-aware, intentionally allocated financial plan.

Together, we helped Emily:

• Convert a meaningful portion of paper wealth into diversified assets within two years of the IPO.
• Manage AMT and ordinary income exposure through proactive scenario planning.
• Track potential AMT credits and incorporate them into future tax planning.
• Build cash reserves for taxes and near-term lifestyle goals.
• Retain a defined amount of company stock for upside participation.

Years of accumulated shares have created a portfolio that is difficult to understand, emotionally hard to sell, and increasingly disconnected from David’s retirement income goals.

Some shares have very low basis and large unrealized gains. Others have high basis and can be sold with a smaller tax impact.

David needs to decide which shares to sell, which to hold, which might be donated, and how to balance tax costs against concentration risk.

Our Approach

We built a complete tax-lot inventory of David’s company stock, which included each lot’s acquisition date, source, holding period, cost basis, embedded gain, and current value.

We then segmented shares into high-basis sale candidates, low-basis hold or donation candidates, and strategic retention shares. This helped determine the best course of action for each lot based on concentration risk, tax cost, and David’s broader retirement plan.

We then coordinated strategic stock sales with David’s retirement income needs, projected tax brackets, charitable giving goals, and estate planning priorities.

With the sale proceeds, we built an income-oriented retirement portfolio.

We reviewed David’s plan annually to adjust as needed, because we did not want to recreate his concentration challenges when future RSUs vested or ESPP purchases were made.

Results

Long-time employees like David often struggle to organize and leverage their accumulated wealth in a tax-efficient way, especially when they believe in the value and future potential of their company stock.

Together, we helped David:

• Reduce company stock exposure gradually without triggering one large tax event.
• Improve retirement cash flow flexibility by converting selected shares into diversified assets.
• Use charitable giving strategies for some low-basis shares where appropriate.
• Shift his decision-making from grant-by-grant reactions to an intentional portfolio allocation process.