Kristin Gilbertson - Risk, Resilience, and Returns

About this episode

Kristin Gilbertson discusses her journey in investment management and insights on risk and asset allocation.

In this episode, hosts Tano Santos and Michael Mauboussin speak with Kristin Gilbertson, CIO of Access Industries and former CIO of the University of Pennsylvania Endowment. Kristin shares her early interest in economic development and her unique journey through the World Bank, Stanford Management Company, and into managing a major university endowment. She outlines how risk awareness and preparation helped her successfully lead through the 2008 financial crisis and gives detailed insights into asset allocation, manager selection, and the nuances of family office investing. Kristin also discusses career strategies for students interested in the endowment and wealth management space and much more! Key Topics: ● Kristin's early life and interest in economics (3:33) ● Influential professors and academic inspirations at Harvard (4:10) ● Experience at the World Bank and the Young Professionals Program (10:09) ● Joining Stanford Management Company and portfolio repositioning (15:05) ● Moving to Penn and addressing portfolio gaps and alumni engagement (18:26) ● The responsibilities and structure of a university CIO role (22:00) ● Building Penn's VC exposure and getting into Sequoia…

People in this episode

Hosts: Tano Santos, Michael Mauboussin

Guest: Kristin Gilbertson

Topics covered

• risk management
• investment strategies
• endowment management
• career development
• asset allocation
• family office investing

Keywords

• risk awareness
• financial crisis
• portfolio management
• wealth management
• economic development
• CIO role
• investment philosophy

Mentioned in this episode

Organizations: Access Industries, University of Pennsylvania Endowment, World Bank, Stanford Management Company, Sequoia, Harvard

More episodes of Value Investing with Legends

• Jenny Harrington - Dividend Investing, Risk Management, and Building Reliable Income Streams · April 17, 2026 · 1h 2m
• Jenny Harrington - Dividend Investing, Risk Management, and Building Reliable Income Streams · April 17, 2026 · 1h 2m
• Samer Sarraf - Investing in the GCC: Private Equity Discipline in Public Markets · March 13, 2026 · 1h 16m
• Ricky Sandler - Investing Through Perception Shifts and Market Cycles · December 19, 2025 · 56 min
• Robert Robotti - From Pink Sheets to Portfolio Management: Bob Robotti's Value Investing Journey · November 21, 2025 · 1h 2m
• Richard Brekka - From Venture to Secondaries: Richard Brekka on Illiquid Market Advantages · November 7, 2025 · 1h 4m