Swimming with Allocators · 2026-05-27 · 48 min
This week on Swimming with Allocators, Earnest and Alexa welcome Mike Kakenmaster, Director of Investments at Loyola University Chicago, to discuss how a small endowment builds and scales a modern private capital and venture program. Mike shares his journey from hedge funds and a family office to Loyola, explaining how being a generalist across asset classes (hedge funds, buyout, credit, venture) helps him see risks, opportunities, and market cycles more clearly. The conversation covers the shift of LP attention between private markets and hedge funds, how Loyola doubled its private capital allocation, and why they moved deliberately into venture instead of rushing into brand-name funds. Mike also explains why early-stage track records can be misleading, how he evaluates managers (portfolio construction, reserves, access, networks, and founder/company quality), and why smaller and emerging managers can be especially compelling.
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