S3: Conversation with Jon Caplis, Founder and CEO, PivotalPath

In this episode, Bill speaks with Jon Caplis, founder and CEO of PivotalPath, to explore how his firm is redefining hedge fund transparency and trust for institutional investors. Jon walks through his career path—from early hedge fund experience to founding PivotalPath—and the core challenges investors face when accessing reliable hedge fund data. They examine the systemic flaws in commercial databases, the necessity of strategy-level insight, and the foundational importance of data integrity, relationships, and peer benchmarking. The discussion also touches on the evolving role of due diligence, the use of AI in fund evaluation, the relevance of portable alpha, and the lessons learned from attempts to democratize hedge fund investing through liquid alternatives.