Investment Portfolio Case Competition: A challenge beyond portfolio construction

I used to think of investment strategy mainly as a matter of balancing risk and return. That view changed when I competed in the 2026 Cornell Investment Portfolio Case Competition (IPCC), hosted by Scott Stewart, the faculty co-director of the Parker Center for Investment Research. Over 10 intense days, my teammates, Liang-Min Ou Yang, Maggie Huang, Anthony Chu and I were asked to design a comprehensive wealth, tax and asset-allocation plan for Andrea and Francis, a cross-border couple navigating an amicable divorce.

What made the experience so meaningful was the complexity behind every decision. The goal was not simply to identify the highest-return portfolio, but to build a recommendation that could work in practice. Each choice had to balance competing priorities, including differing tax regimes, uneven liquidity profiles, future living expenses, family obligations, and long-term wealth preservation. Working through those layers gave me a much deeper understanding of how investment decisions are shaped not only by markets, but also by the constraints and goals of individuals.

Turning collaboration into a structured asset split

This case was not simply about maximizing returns. The challenge was to build a solution that could hold up in real life. Because the family’s assets, income and future plans spanned the United States and Switzerland, differences in how each country taxes income, capital gains and wealth meant that even strong investment ideas had to be evaluated through an after-tax lens.

To navigate this, our team organized the work around three key priorities: future cash-flow needs, after-tax outcomes, and long-term financial stability. What stood out most to me was how much stronger our solution became through the combination of our unique perspectives. Whether in tax reasoning, portfolio construction, modeling, or strategic framing, these differences allowed us to evaluate trade-offs thoughtfully and develop a well-rounded approach.

Rather than trying to arrive at a perfect answer, we refined our strategy through an iterative process, continuously challenging and building on one another’s ideas. This led us to an asset split recommendation that was not only numerically equitable but also optimized for tax efficiency and tailored to each individual’s cash-flow needs and liquidity profile.

Designing tailored portfolios

Arriving at the asset split gave us a clear foundation, but it also raised the next question: How should each portfolio be managed going forward?

Andrea’s Swiss trust structure provided substantial and stable cash flow, which meant liquidity was less of a concern, but it also placed her under significant taxable income exposure. We designed a portfolio that minimized dividend and interest payouts and instead emphasized steady capital appreciation. The goal was to reduce unnecessary tax drag while still maintaining flexibility and minimizing the probability of a liquidity shortfall.

Francis’s circumstances were different. Because a large portion of his wealth was tied up in private equity holdings, he faced near-term illiquidity even though those assets were expected to generate liquidity over time. As a result, we proposed a portfolio with a heavier allocation to bonds so that he could generate periodic interest income to support near-term cash needs. We also incorporated a dynamic direct indexing strategy to harvest tax losses, offset future capital gains and generate tax alpha over time. Rather than treating tax management as a separate exercise, we built it directly into the portfolio design.

As we developed these strategies, it became clear that our recommendations could not remain static. We incorporated rebalancing throughout the forecast period to reflect the fact that both spouses’ financial situations would evolve as assets were liquidated and future obligations changed. To test the robustness of our recommendations, we back-tested the proposed portfolios using Monte Carlo simulations and compared them with the original asset allocation. The results showed meaningful improvements across several measures, including annual return, shortfall probability, Sharpe ratio and Sortino ratio.

What made this process especially meaningful to me was seeing how an investment strategy becomes more powerful when it is tailored to an individual’s circumstances. In our case, the objective extended beyond preserving each spouse’s current wealth. We also incorporated a family trust concept to help transfer wealth across generations without imposing an excessive inheritance tax burden. One valuable lesson I took away was that strong investment decisions are most effective when investment strategy, tax planning and estate planning are considered together in one cohesive framework; that way of thinking applies not only to case competitions, but also to real financial decisions.

Making a complex strategy understandable

After days of modeling and refining our strategy, we only had 10 minutes to persuasively present a highly technical and multilayered recommendation. This forced our team to step back from the details and ask ourselves a different set of questions: What matters most? What is the clearest way to explain our logic? How do we make the audience understand what we recommend and why? The Q&A portion pushed this even further, requiring us to defend our recommendations and explain tax implications. It reinforced an important lesson: The ability to communicate under pressure depends on how deeply a team understands the logic behind each decision.

A challenge worth taking

IPCC gave me not only technical experience, but a broader perspective on investing. The competition showed me that investment decision-making is rarely straightforward; it is complex, deeply interconnected, and ultimately shaped by the institutional, financial, and personal realities.

The long hours were certainly demanding, but that made the experience so memorable. I genuinely enjoyed building something meaningful alongside my teammates and seeing how much we could accomplish together in a short period of time.

For future participants

For students considering IPCC in the future, I would strongly encourage you to take the opportunity. IPCC pushes you to move beyond classroom frameworks and confront ambiguity. The questions are not neatly structured; the trade-offs are real; and the strongest solutions require not only technical skill, but also judgment, creativity and the ability to see how different pieces of a problem connect.

IPCC was an opportunity to sharpen how I think, work and communicate under pressure. It is an opportunity to grow and experience finance in a way that extends beyond the classroom. That is what makes the experience so worthwhile and why I would wholeheartedly encourage future students to pursue it.

About the author

Erica Chiang, MPS ’26, is pursuing a master’s in applied economics and management. Her concentration is behavioral finance. On campus, she is a sector analyst for The Cayuga Fund, the student-led investment fund.