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 communicate how they’ll handle inevitable issues.

Highlights from this week’s conversation include:

From Hedge Funds And Family Office To Loyola Investment Office (0:30)

What Keeps Mike Interested in Allocating and Fund Investments (3:14)

Advantages of Being a Generalist Across Multiple Asset Classes (5:42)

Shift of Capital Between Private Markets and Hedge Funds (10:30)

Growing Loyola’s Private Capital Allocation and Building from Scratch (13:22)

Early Days Entering Venture During a Hot Fundraising Environment (16:51)

Operational Infrastructure, Disclosures, and Conflicts Framework for GPs (19:20)

Governance Framework and Handling Unforeseen Conflicts of Interest (22:40)

Avoiding Overreliance on Early Venture Track Records and Marks (27:53)

Evaluating Reserves, Follow-On Decisions, and Portfolio Construction (32:14)

Loyola’s Venture Strategy, Emerging Managers, and Fund Size Sweet Spot (34:34)

Advantages of Partnering with Smaller Endowments for GPs (39:16)

Advice to Smaller Endowments Starting a Venture Program (43:20)

Final Thoughts and Takeaways (46:21)

Founded in 1870, Loyola University Chicago is one of the nation’s largest Jesuit, Catholic universities, with nearly 17,000 students.

The University has four campuses: three in the greater Chicago area and one in Rome, Italy, as well as course locations at our Retreat and Ecology Campus in Woodstock, Illinois. The University features 13 schools and colleges, including the Quinlan School of Business, Marcella Niehoff School of Nursing, Stritch School of Medicine, Parkinson School of Health Sciences and Public Health, Arrupe College, College of Arts and Sciences, School of Communication, School of Continuing and Professional Studies, School of Education, School of Environmental Sustainability, School of Law, School of Social Work, and Graduate School.

Consistently ranked a top national university by U.S. News & World Report, Loyola is also among a select group of universities recognized for community service and engagement by prestigious national organizations like the Carnegie Foundation and the Corporation for National and Community Service.

Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com.

Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. 

The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only.

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