Legacy at a Crossroads: Inheritance, Impact, and Intentional Planning for the Herreras
Current State of Finances
Diego Herrera is in his mid-30s when he receives an inheritance: approximately $20 million in assets from his late father, a successful investor and philanthropist. The estate includes multiple family-owned real estate properties, a charitable trust, individual stocks with varying cost basis details, and a substantial cash reserve. He and his siblings co-own much of the real estate, and the assets have been structured across multiple entities and trusts over the years—making clarity and coordination a challenge.
With young children, a still-active professional life, and a desire to honor his family’s charitable legacy, Diego isn’t simply asking “what do I do with the money?” He’s asking:
What is this wealth for?
How do we steward it well—for our lives, our kids, and the causes we care about?
He comes to us not just for portfolio advice—but for a long-term thinking partner. He’s trying to make thoughtful decisions with real implications: Should the family keep the real estate? Who buys whom out? Can they afford to maintain properties long term? And what about the foundation—how much can they give away without compromising their own future?
Financial Advisor Insights: What are we thinking about?
Clarifying Structure, Ownership, and Liquidity
The first challenge is making sense of the inheritance’s structure. We analyze real estate holdings co-owned with siblings, assessing cost to maintain, income potential, and the emotional weight of keeping them. After detailed modeling, the family decides to sell the properties—unlocking liquidity and simplifying shared ownership dynamics. This creates more deployable cash, reducing potential friction and freeing each sibling to pursue their own financial path.
We also map out embedded gains in inherited securities. Because many holdings have low cost basis and would trigger large capital gains if sold, we develop a plan to hold them longer term while managing risk through broader portfolio diversification.
Strategic Giving: Balancing Legacy with Lifespan
The biggest question on Diego’s mind is how to honor the family’s charitable values without overcommitting. He wants to give meaningfully—but he’s still young, with a long life and evolving financial needs ahead.
We help him define how much he can afford to give now without compromising future flexibility. Together, we design a strategy that includes an early lump-sum gift to the family foundation and a multi-year charitable giving plan that matches his income, investment growth, and tax profile over time. We also preserve optionality—so if life circumstances change, the plan can adjust.
Importantly, Diego wants to be actively involved in giving, not just funding it. We advise him on how to evaluate nonprofit partners—focusing on operational sustainability, measurable impact, and internal governance—so his investments in the philanthropic space are thoughtful, aligned, and built to last.
Planning Around Purpose and Uncertainty
A major undercurrent in Diego’s planning is identity. With financial independence now secure, the question becomes: Should I keep working? If not, where do I direct my time and energy? We don’t answer that for him—but we help build a plan that supports either path.
Whether he chooses to grow his foundation work, pursue new projects, or take time to explore, his financial model accounts for both flexibility and security. That includes maintaining a personal financial plan independent of the charitable vehicles—so giving remains a choice, not a burden.
We also layer in complexity like international giving, travel plans, and education goals for his children—creating a plan that holds space for ambition, spontaneity, and deeply held values.
What’s Next?
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