Peter Tolman, a first-generation investment professional, debated which family office strategy to adopt for managing his family's assets. As the sole steward of his family's wealth, he sought to conserve and grow his family's wealth for him, his wife, and his two very young sons. However, being left unsatisfied with large multi-family offices' template-based approaches to managing intergenerational wealth, he sought out a more liberal investment philosophy tailor-made for his needs and wants. What was the best path forward for allocating his family's wealth? Should he establish a single-family office, pursue another multi-family office, or devise a new hybrid approach? What implications would his precedent-setting decisions hold for his children's futures?