Educational Alpha

In this episode, host Bill Kelly sits down with Matt Curtolo to unpack the evolving dynamics between LPs and GPs, and what changing investor profiles mean for private markets. Matt shares highlights from his two-decade career across firms like Hamilton Lane, MetLife, and Allocate, offering key insights on secondary markets, manufactured liquidity, transparency, and the future of venture capital investing. They also explore the challenges and opportunities in democratizing access to private markets and how to equip investors with the right tools and education for long-term success.

In this episode, Bill Kelly speaks with Winston Ma, adjunct professor at NYU and former managing director at CIC, to unpack the intersection of tech, law, and finance in today’s AI-driven economy. Winston shares his career trajectory across legal, investment banking, and sovereign wealth fund sectors, highlighting how these disciplines now converge in shaping U.S. industrial policy. The conversation probes the growing role of government in private markets, focusing on strategic investments in rare earth materials, semiconductors, and AI. Winston offers perspective on the evolving U.S. sovereign wealth fund model, the influence of geopolitics on capital flows, and what this all means for institutional investors.

In this episode, host Bill Kelly welcomes Aaron Filbeck of the CAIA Association for a wide-ranging discussion on the growing momentum behind expanding access to private market investments within retirement plans. They explore the implications of a recent executive order focused on 401(k) access, the structural differences between DB and DC plans, and the potential benefits and risks of democratizing private market exposure. The conversation probes the importance of fiduciary responsibility, the role of innovation in target date funds, and the evolving narrative around long-term investing and investor protection.

In this episode, Bill Kelly is joined by Kane Brenan, CEO of TIFF, and Anne Duggan, Managing Director at TIFF, to explore the firm’s origins, investment philosophy, and the evolving landscape of institutional investing. Kane and Anne share how TIFF was founded to deliver institutional-quality returns to endowments and foundations, the structural advantages that drive their manager access, and the firm’s strategic approach to asset allocation. The conversation covers macroeconomic influences, the impact of new endowment taxes, liquidity considerations, and why private equity and hedge funds remain critical to long-term portfolio performance. They also examine the nuances of manager selection, structural premiums in private markets, and the challenges of adapting sophisticated institutional strategies for retail investors.Disclaimer: Kane Brenan is the CEO at TIFF Investment Management, and Anne Duggan, CAIA, is the Managing Director, Client CIO Group at TIFF Investment Management. All views expressed by them on this podcast are solely their opinions and do not reflect the opinions of TIFF. You should not treat any opinions expressed by Kane or Anne as a specific endorsement to make a particular investment. References to any securities are for informational purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Any past performance discussed is not indicative of future results. Please keep in mind that investment in a fund entails a high degree of risk, including the risk of loss. Please note that the ads featured in this podcast are not endorsed by TIFF, and TIFF is not a sponsor of these ads.

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.

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.

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.

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.

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.

In this episode, Bill welcomes Roger Vincent, founder of Summation Capital, to explore the evolving private equity landscape. Roger shares insights from his 30-year career, including his pivotal role at Cornell’s Endowment and his motivation for creating Summation to deliver institutional-quality private equity access to high-net-worth investors. They address private equity’s shift from an exclusive asset class to a complex industry, the challenges of democratization, the critical role of manager selection, and the importance of fee structures. Roger also discusses the future impact of AI in investment strategies and portfolio construction.