Tech Equity Windfall: Strategic Planning for the Mitchells’ Charitable and Family Goals
Current State of Finances
Ethan and Claire Mitchell, a married couple in their mid-40s, have reached a pivotal financial moment. Ethan works for a rapidly growing tech company and recently experienced a substantial equity event tied to an early grant of stock options and RSUs. Between his and Claire’s salaries, their annual household income sits above $750,000. The couple currently rents their primary residence but owns undeveloped land in a more rural region where they plan to build a long-term home. They also have a modest seasonal property abroad for family getaways.
A recent liquidity event allowed Ethan to sell a portion of his equity, bringing their invested assets to just under $2 million. However, with additional vested equity potentially worth more than $15 million, and further unvested grants on the table, they face increasingly complex decisions. They are debt-free and planning significant personal and family expenses, including home construction and the cost of growing their family through surrogacy over the next few years.
The Mitchells are deeply committed to charitable giving. Ethan has pledged to donate a substantial portion of his initial equity grant, and the tech company he works for provides a generous 3:1 match on half of that commitment. Their giving goals are ambitious, focused, and long-term—they want to support a specific scientific area they believe is underfunded and overlooked. With limited liquidity windows for company stock and a looming valuation reset that could impact tax strategy, they are looking for urgent and highly specialized planning.
Financial Advisor Insights: What are we thinking about?
Equity Strategy and ISO Optimization
Ethan’s early ISO grant creates a time-sensitive planning opportunity. With a potential increase in fair market value on the horizon and a blackout window approaching, we are working closely with their CPA to determine how much he can exercise before year-end without triggering significant AMT exposure. This will allow him to maximize long-term capital gains treatment and create more flexibility for future charitable giving, especially using donated shares. Exercising too little may limit future options, while exercising too much could reduce liquidity or increase tax risk—so this balancing act is critical.
Charitable Planning with Matching Programs
The Mitchells’ pledge to give away a meaningful portion of their equity—and the company’s 3:1 match—creates an incredible opportunity for impact, but also adds complexity. We’re developing a multi-year charitable giving strategy that blends cash and stock donations, with a focus on tax efficiency, liquidity constraints, and maximizing match potential. We’re also helping them explore vehicles like donor-advised funds (DAFs) and charitable LLCs that can give them flexibility and long-term control over grantmaking.
Liquidity Event Readiness and Cash Flow Planning
Future liquidity events are likely but capped and unpredictable. That means any short-term financial plans—like building their home, growing their family, or ongoing investing—must be built on a conservative baseline of liquidity. We are modeling how much they can safely allocate to personal goals while still preserving the runway for long-term philanthropic and retirement planning, even if additional liquidity is delayed. With the broader market closely watching potential public offerings in the AI space, the Mitchells are preparing for possible liquidity windows that could arise in the coming years—even if the timing and terms remain uncertain.
Real Estate and Lifestyle Planning
With plans to build a home over the next two years, the Mitchells are budgeting several hundred thousand dollars annually for construction. We’re factoring this into their cash flow plan and investment strategy, helping them preserve cash for these lump-sum expenses while keeping their long-term investments growing in the background. As they build their family, they also want flexibility to travel and enjoy their time together, so we’re stress-testing their spending plan for future income variability.
Confidence Through Coordination
The Mitchells are sophisticated but busy professionals who want to delegate the technical modeling and receive clear, strategic guidance. Our goal is to provide a comprehensive roadmap—one that simplifies their decision-making, allows them to act confidently before tax and valuation deadlines, and ensures their wealth supports the causes and family they care most about.
What’s Next?
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