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As CIO of DeSouza Family Holdings, Caroline Erickson managed the family’s investment portfolio—a collection of real estate properties, hotels, several small grocery stores, stocks/bonds, and alternative assets. Erickson facilitated quarterly meetings to brief family members on the portfolio. She also reserved time during these meetings for family members to present new investment opportunities. During the July 2020 family meeting, two siblings shared real estate investment proposals. After hearing the details associated with each deal, Erickson was left to consider the two investments on the basis of their risk and expected returns.