S3: Conversation with Jennifer Fonstad, Managing Partner, Owl Capital
In this episode, Bill speaks with Jennifer Fonstad, seasoned venture investor and co-founder of Owl Capital. With nearly 30 years in venture capital, Jennifer shares her journey from Bain and Harvard Business School to investing in companies like SpaceX, Tesla, and Chime. They examine the evolving landscape of early-stage VC, the value of diverse teams, and the unique community-driven model at Owl Capital. Jennifer also discusses the firm's long-term, evergreen funding approach backed by family offices, and offers insights into evaluating startups, emerging AI applications, and the real metrics of investment potential.
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35:40
S3: Conversation with Eoin Motherway Independent Chair and INED to Funds, Management Companies, Fin/RegTechs, eMoney Institutions and Digital Assets/Tokenisation
In this episode, Bill welcomes Eoin Motherway, a seasoned finance professional whose career spans investment banking, fund accounting, and digital asset management. Eoin recounts his path from chartered accountant to head of a major asset management platform, and now, to a portfolio career bridging TradFi and DeFi. They explore the impact of regulatory change, the rise of tokenization, and the increasing intersection of technology and finance. Eoin also shares insights on board governance, financial literacy, and the evolving role of independent directors in today's tech-driven financial landscape.
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39:51
S3: Conversation with Annelise Osborne, Chief Business Officer, Kadena
In this episode, Bill sits down with Annelise Osborne, author of From Hoodies to Suits and a veteran in both traditional finance and the evolving digital asset space. Annelise shares her journey from commercial real estate and structured finance at Moody’s to becoming a leading voice in blockchain innovation. They explore the institutional adoption of crypto, the role of blockchain in transforming back-office operations, and the shifting attitudes of younger generations toward investing. The discussion also covers tokenization, stablecoins, permissioned blockchains, and the broader technological convergence with AI and DeFi.
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37:56
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.
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44:15
S3: Conversation with Steve Novakovic, Managing Director, Educational Programs, CAIA Association
In this episode, Bill welcomes Steve Novakovic, Managing Director of Educational Programs for CAIA Association, to discuss the evolving nature of endowment investing, the growing role of total portfolio approaches (TPA), and the shifting responsibilities of asset allocators. Steve shares his journey from working at the Cornell University Investment Office to shaping the CAIA curriculum, emphasizing how events like the global financial crisis and modern portfolio theory shaped his views. They also explore the role of diversification in portfolio construction, the importance of due diligence and manager selection, the rising impact of retail democratization, and the ethical foundation needed to support long-term credibility in the profession. Steve further outlines how CAIA is adapting its curriculum, introducing proprietary ethical principles, and leading with new educational tools like the UniFi platform.
Listen in on conversations with host Bill Kelly and an eclectic group of guests within the world of finance. Hear about their professional or personal journeys, career and life advice, and perspectives on the industry. There’s always more to the story …
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