In this episode, I spoke with Anurag Chandra, Chief Investment Officer of a single-family office and longtime trustee and former Investment Committee Chair of the San Jose Federated City Employees’ Retirement System (FSERS). Over the past decade, Anurag has helped transform FSERS from one of the worst-performing pension plans in the U.S. into a top-decile performer. He’s also an experienced operator, venture capitalist, and accidental allocator—with hard-won insight into everything from re-risking public portfolios to model delivery and tax-loss harvesting.

In our conversation, Anurag shared how EQ, team dynamics, and governance structure often outperform raw IQ in investing—and how he helped rebuild a $2.2B pension plan through careful governance reform, luck, and great timing. We also covered how he now applies those same principles at a nimble family office, blending institutional rigor with operational agility.

Guest Bio:

Anurag Chandra is currently the Chief Investment Officer of a single-family office based in the Bay Area. He previously served for nearly a decade on the board of the San Jose Federated City Employees’ Retirement System, including several years as Chair of the Investment Committee. Under his leadership, the pension plan went from being one of the lowest-performing in the country to a consistent top-decile performer. Anurag has also worked as a venture capitalist, operator, and advisor, with 25+ years of professional experience across legal, investment, and entrepreneurial roles.

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David Weisburd: @dweisburd

David Weisburd: https://www.linkedin.com/in/dweisburd/

Anurag Chandra: https://www.linkedin.com/in/anchandra/

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(0:00) Episode preview

(1:11) The Value of EQ and Resourcefulness in Business

(11:40) Anurag Chandra's Career and San Jose Pension Fund Turnaround

(19:14) Governance and Manager Selection Challenges in Pension Funds

(23:45) Applying Pension Fund Lessons to Family Office Management

(26:52) Strategies in Tax Optimization and Asset Allocation

(30:05) Model Delivery Concerns in Asset Management

(30:58) Integrating Skills for Better Investment Decisions

(34:41) Cross-functional Experience and First Principles Thinking

(35:05) The Role of a Board Member and Opinion Strength

(37:02) Closing remarks