Cultivating a Venture Program Without Chasing the Hype

About this episode

The episode discusses building a modern venture program at Loyola University Chicago with insights from Mike Kakenmaster.

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. Also, Chuck Daly of Sidley focuses on how first-time fund managers should thoughtfully build their operational and governance infrastructure, especially around disclosures and conflicts of interest, so they can run a real business, protect LPs, and clearly…

People in this episode

Hosts: Earnest Sweat, Alexa Binns

Guest: Mike Kakenmaster

Topics covered

• venture capital
• private capital allocation
• investment strategies
• fund management
• risk assessment
• emerging managers

Keywords

• venture program
• private capital
• hedge funds
• investment office
• fund managers
• portfolio construction
• market cycles

Mentioned in this episode

Organizations: Loyola University Chicago, Sidley

More episodes of Swimming with Allocators

• DDQ: Celebrating 100 Episodes with Swimming with Allocators · June 3, 2026 · 49 min
• What It Takes to Win With Institutional LPs · May 20, 2026 · 49 min
• How Denmark Built a Big-Tech Future From a Small-Country Base · May 13, 2026 · 55 min
• A New Playbook for Deep Tech Fund Investing · May 6, 2026 · 46 min
• Aligning Capital With Community Impact · April 29, 2026 · 46 min
• Rethinking the Venture Co-Investment Playbook · April 22, 2026 · 40 min