CashFlow Quest Episode 13
NIL Insights and California Insurance Flaws | Risks and Rewards in Changing Industries (Ft. Pat Kilkenny)
In this episode of CashFlow Quest, hosts Blake Comfort and Jennifer Purcell are joined by Ben Schuster and guest, Pat Kilkenny, a serial entrepreneur, philanthropist, and former University of Oregon Athletic Director. Pat shares his incredible journey from bootstrapping an insurance business to building billion-dollar companies, his experiences in private equity, and his deep involvement in collegiate sports. He also discusses key challenges in the insurance industry, the impact of California’s wildfires, and the future of college athletics in the age of NIL (Name, Image, and Likeness) deals.
Pat Kilkenny is a visionary entrepreneur, philanthropist, and former Athletic Director at the University of Oregon. Over four decades, he built and scaled insurance giants like Arrowhead and K2 Insurance into multi-billion-dollar enterprises. Kilkenny later revitalized Oregon athletics, leading the construction of a $200M basketball arena and reinstating the baseball program. Through the Lucky Duck Foundation, he remains deeply committed to philanthropy and community impact.
Listeners can learn more about Pat Kilkenny and the Luck Duck Foundation
Blake Comfort
Blake Co-Founded Comfort Communities in 2008 and began working to acquire manufactured home communities in order to build the investment and management company that exists today. Comfort Communities first manufactured home community was purchased in 2009 and has continued to grow and purchase many more manufactured home communities ever since. Blake currently handles all the business development & acquisitions for Comfort Communities.