Christopher Ailman
The Steward
Legacy, values and the long now, leadership as care and continuity.
Christopher Ailman embodies The Steward archetype through his decades-long custodianship of CalSTRS, a fund serving over a million public school teachers. Throughout this interview, Ailman frames every allocation decision around long-term accountability to beneficiaries, not short-term performance optics. He tightened strategic asset allocation ranges to prevent speculative drift, championed passive equity as a disciplined cost-control measure, and articulated a philosophy of corporate engagement rooted in permanence rather than exit. His extended tenure, which he personally committed to the board upfront, reflects a steward's orientation toward institutional continuity over personal ambition. Ailman's language of riding out storms, maintaining infrastructure assets, and voting as a long-term capital partner all reinforce a fiduciary identity built on durability and trust. He openly admits the emotional weight of losing beneficiaries' money, treating that vulnerability not as weakness but as the moral core of his role.
“I'm a steward of a million teachers money. I want to be able to tell them what we're invested in. I want to know what we own and what we don't own.”
“As long as there are public school teachers in the state of California, we're going to own their stock, which means we're going to own their stock a lot longer than they're going to be CEO.”
“Losing other people's money is actually by far the toughest thing to do. It just hollows you out. It hurts in the heart.”
Money Maze Podcast: “CalSTRS: How the $300+ Billion Pension Fund is Allocating in 2023 - With Christopher Ailman, CIO”
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