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How We Helped
Equity Compensation Analysis — Took stock of all the different forms of equity (ISOs, NSOs, and RSUs) and modeled the tax treatment of each tranche, including AMT exposure on ISO exercises and the short-term vs. long-term capital gains windows for each lot.
Multi-Year Tax Projection — Built a forward-looking tax model spanning the next several years to map income spikes from RSU vests, option exercises, and planned share sales.
Tax Planning & Minimization Strategies — Implemented a coordinated plan that included tax-loss harvesting in their diversified portfolio, charitable giving via a Donor-Advised Fund using their most highly appreciated shares, and timing exercises and sales to stay in the most favorable marginal brackets and manage AMT. The coordinated tax strategy saved them over 15% on their tax bill.
Disciplined Sell Schedule — Mapped specific share lots to specific goals (home purchase, education funding, long-term diversification) so the client knew exactly which shares to sell and when. Tying sales to concrete dollar needs removed the emotional pull of holding out for a "better price" on stock the client was personally invested in after years at the company.
Education Planning With New Liquidity — Front-loaded 529 plans for both children using 5-year accelerated gifting (superfunding) to lock in tax-advantaged growth while liquidity was abundant.
Home Purchase Budgeting With New Liquidity — Modeled different home price points & renovation costs against their post-tax cash position, expected mortgage payments, and ongoing diversification plan.
Outcome
They diversified the majority of their concentrated employer stock on a tax-efficient multi-year glide path, fully funded their kids' future education, and purchased a new home. Just as importantly, the framework removed the day-to-day stress of watching the stock price. Sales decisions had been made up-front and tied to family goals, not market timing.
Back to Top ↑How We Helped
Holistic Net Worth Review – Assessed all assets and liabilities to quantify concentration risk and how much of their net worth was tied to employer stock.
Home Affordability Analysis – Modeled different home price points based on their down payment, expected mortgage payments and what that means for the cashflow.
Tax-Optimized Diversification Strategy – Created a multi-year RSU sale plan with tax-budget targets to reduce volatility and spread gains across several years.
Charitable Giving Optimization – Established a Donor-Advised Fund (DAF) and funded it with their most highly appreciated shares for a large charitable deduction.
Smart Investing With Direct Indexing – Built a diversified portfolio that excluded their employer stock and used direct indexing to aggressively harvest tax losses and reduce taxes on the RSU capital gains.
College Savings Framework – Developed a 529 savings strategy to ensure they were on track for future education costs for their two children.
Retirement Plan Review & Optimization – Evaluated both spouses’ 401(k) plans and recommended maxing pre-tax deferrals, utilizing after-tax 401(k) contributions, and implementing a mega backdoor Roth strategy to accelerate long-term tax-free retirement savings.
Outcome
In addition to accomplishing their primary goals of diversifying their RSUs and purchasing a home, we were also able to help them further optimize their taxes, save for kids future education, and maximize their retirement savings.
Back to Top ↑How We Helped
Financial Independence Modeling — Calculated their FI number using realistic current and projected family spending, then stress- tested withdrawal rates with Monte Carlo simulations and historical sequence-of-returns scenarios to identify a realistic FI date.
Asset Location Optimization — Restructured ongoing contributions across taxable, tax-deferred, and Roth accounts so they would have enough accessible cash and non-retirement assets to bridge the gap to age 59½ without early withdrawal penalties.
Roth Conversion Ladder Strategy — Designed a multi-year Roth conversion ladder to take advantage of low-income years after they step away from work, allowing penalty-free access to converted funds in early retirement.
Healthcare Bridge Planning — Modeled ACA premium subsidies tied to managed taxable income post-FI, since healthcare is typically the largest unknown cost for early retirees.
Concentration & Equity Management — Built a diversification glide path for their RSUs and employer stock to systematically reduce single-stock risk as they approach their FI target.
College Savings Coordination — Layered 529 contributions and a college funding plan for both kids into the broader FI timeline so education costs wouldn't push back their independence date.
Outcome
They now have a clear, dated path to financial independence, a tax-efficient withdrawal sequence, a healthcare bridge, and a kids' college plan that doesn't conflict with the FI timeline. They can confidently make career decisions (downshifting, sabbatical, starting a business, etc) without worrying about derailing their long-term financial security.
Back to Top ↑How We Helped
Cashflow System & Business Framework – Designed a structure showing how much cash to keep in the business for working capital and how much to distribute for personal use and investments.
Optimize Cash Reserves – Moved excess cash out of business checking into higher yielding savings.
Tax-Efficient Business Setup – Transitioned the business to an S-Corp, implemented payroll, and started saving strategically for taxes.
Retirement & Savings Infrastructure – Set up a Solo 401(k) allowing pre-tax and after-tax (mega backdoor Roth) contributions.
Goal-Based Investment Plan – Created an investment framework aligning funds with key goals, including a goal of financial freedom.
Outcome
They now have a streamlined financial system, predictable tax savings, and a clear roadmap that supports both their creative work and long-term goals.
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