In June 2023, the Commonfund Institute hosted 36 nonprofit leaders on the campus of Yale University for our premier educational event -- the Investment Stewardship Academy (ISA). Much has changed since the last convening in 2019 -- a global pandemic, a deep racial reckoning, war in Ukraine, inflationary pressures, ongoing and distressing impacts of the climate crisis, and more. At the same time, the need for fiduciaries to shepherd endowment capital into the future to support their institutions has not changed. Throughout the three-day program, external thought leaders gathered with Commonfund experts to present their most insightful thoughts on how to be the most effective stewards of long-term capital. Participants spanned 34 institutions, 3 countries, 19 states, in addition to Washington D.C. and the Virgin Islands. The value of diversity of thought and experience was apparent throughout the program. Participants representing different types of institutions, from community foundations to nonprofit hospital systems, higher education, and holding various positions, from CFO to investment committee member to board chairs, raised questions for enlightening discussion to help all in attendance to understand the nonprofit ecosystem and all its complex, interconnected challenges. Key takeaways are presented in this report.