How I Invest with David Weisburd

What actually separates great institutional investors from average ones and why does governance matter more than brilliance?

In this episode, I talk with Christopher J. Ailman, former Chief Investment Officer of CalSTRS, about the decisions that shaped one of the largest and most successful public pension funds in the world. Chris reflects on more than two decades leading CalSTRS, why asset allocation and governance drive the vast majority of outcomes, and how building a resilient, low-cost, long-term portfolio matters far more than chasing the latest investment trends. We also discuss culture, decentralization, and what CIOs consistently get wrong when managing people and risk.

Why are humans — not models — still the biggest bottleneck to AI progress, and what happens when that bottleneck becomes a business?

In this episode, I talk with Ali Ansari, Founder and CEO of micro1, about the hidden layer powering today’s AI breakthroughs: high-quality human intelligence. Ali explains how micro1 pivoted from an AI recruiting startup into a critical data infrastructure company for frontier AI labs, why expert-generated data is now the limiting factor in model performance, and what needs to change for AI agents to actually work in production. We also explore how focus, market timing, and ruthless prioritization enabled micro1 to scale more than 30× in a single year.

How should families think about portfolio construction when traditional diversification breaks down?

David Weisburd speaks with Michael Phipps about building New Republic Partners, designing portfolios around growth, income, and diversification, and why open architecture matters in multifamily offices. Michael discusses common portfolio mischaracterizations, the role of alternatives and co-investments, and how families can better align risk, liquidity, and long-term objectives.

How do experienced LPs evaluate venture managers in an increasingly crowded and bifurcated market?

David Weisburd speaks with Kate Simpson about her career as a venture allocator, her move to GEM to lead venture investing, and how institutional LPs assess sourcing, portfolio construction, and power-law dynamics. Kate explains how reference calls, fund sizing, access, and long-term relationships shape conviction in venture manager selection.

How does one of the world’s largest pension funds shift its culture, governance, and investment process at scale?

David Weisburd speaks with Nicole about her transition from Ontario Teachers’ Pension Plan to serving as CIO of CalPERS, implementing a total portfolio approach, and leading organizational change during a period of market and operational disruption. Nicole shares lessons on governance, board alignment, co-investing, and building long-term investment institutions.