CASE STUDY
Two employers' worth of equity. One clear plan.
A senior software engineer with RSUs, ISOs, and appreciated stock from a previous job — plus a costly tax filing error nobody had caught.
How We Can Help
How We Can Help
✓ Balance the tradeoff between living well today, paying down debt, and investing for the future.
✓ Rent vs. buy decisions.
✓ Analyzing and optimizing your employer benefits.
✓ Evidence-based investing that fits your goals and time horizon.
✓ Full analysis and game plan for your equity compensation (ISOs, NSOs, ESPP, RSUs).
✓ Help budgeting and saving for upcoming big expenses and goals.
✓ Strategies to reduce your tax liability — tax prep is included as part of your financial planning fee.
We've helped clients understand and plan around equity at these companies (and more)
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This is a hypothetical, composite scenario based on situations we commonly see across clients. It does not represent an actual, identifiable client, and past results — hypothetical or actual — do not guarantee future outcomes.
AGE
35
LOCATION
New York City
PROFESSION
Senior Software Engineer
NAME
Alex
The Situation
Alex had equity from both a current and a previous employer — RSUs and ISOs from the current job, plus appreciated stock from an earlier position. It was a meaningful part of their net worth, but it created real problems.
01 Managing tax liabilities on RSU vesting and ISO exercise.
02 Diversifying out of old company stock that had grown substantially.
03 Fixing inaccuracies in prior tax filings to avoid overpaying on taxes.
What We Did
● Integrated Direct Indexing
For Alex's old employer's stock, we implemented a direct indexing strategy to exclude that position from the index — maintaining diversification while systematically selling shares using a targeted tax-band approach.
● Tax Return Review
While reviewing Alex's tax return, we discovered the cost basis on RSUs had been reported incorrectly — causing Alex to pay taxes twice on the same income. We worked with the tax preparer to amend the return and recover the overpayment.
● Equity Planning & Diversification
We built a step-by-step plan to sell RSUs from the current employer and reinvest the proceeds into a diversified portfolio. For the ISOs, we created a phased exercise plan specifically to avoid triggering AMT.
$9,000+
Recovered from a prior-year tax overpayment
Diversified
Portfolio rebalanced to reduce risk and align with long-term goals, including a home purchase
$25,000+
Saved in taxes in year one through targeted equity and tax strategies