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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.

Highlights:

• Why governance is the most underrated driver of returns
• Asset allocation as ~90% of long-term performance
• Borrowing from the Canadian pension model
• Building in-house capabilities to reduce costs
• Why chasing “shiny objects” destroys net returns
• Cost discipline as a competitive advantage at scale
• Culture as a hidden source of alpha
• Centralized vs. decentralized decision-making
• Portfolio resiliency and downside protection
• Why great investors come from wildly different backgrounds

Guest Bio:

Christopher J. Ailman is the former Chief Investment Officer of CalSTRS, where he served for more than 23 years and helped grow the fund into one of the largest and most respected institutional investors globally. Over a 30+ year career in institutional investment management, Chris became widely recognized as one of the world’s top CIOs. He is now the founder of Ailman Advisers, where he focuses on coaching and mentoring CIOs and institutional investors, as well as teaching and public speaking. He also serves as Chair of The 300 Club of global CIOs and is Chair Emeritus of the Milken Global Capital Markets Committee.

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Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

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X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Christopher Ailman:

LinkedIn: https://www.linkedin.com/in/christopherailman/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:06) Key decisions and achieving above median returns (2:18) Lowering investment costs and borrowing ideas (5:36) Avoiding fads and building a world-class culture (10:51) Governance and crisis anticipation in portfolio strategy (13:34) Hiring and unique due diligence strategies (17:37) Future of asset allocation and special GP encounters (21:18) Closing remarks