Educational Alpha

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.

In this episode, Bill welcomes Ruth Yang, Global Head of Private Market Analytics at S&P Global Ratings. Ruth shares her extensive background in credit and leveraged finance, highlighting her unique perspective on the expansion of private credit markets. They explore how private credit has evolved, the role of club deals, rating methodologies, and the growing involvement of high-net-worth investors. Ruth also discusses the impact of documentation quality, the rise of lender-on-lender conflicts, and the critical role of thought leadership and generative AI in shaping the future of private market analytics.

In this episode, Bill welcomes Andre Maciel, founder of Volpe Capital and former leader of SoftBank’s Latin America operations. They explore the evolution of venture capital in the region, from post-dot-com investments to today’s AI-fueled innovations. Andre reflects on his career at J.P. Morgan and SoftBank, the rise of Latin American startups, and the importance of timing in tech investing. The conversation also addresses AI adoption, due diligence in emerging markets, regional challenges like bureaucracy, and the potential for AI to transform inefficiencies. They wrap with insights on regulation, talent, and Brazil’s growing investment ecosystem.

In this episode, Bill sits down with George Aliferis, founder of Orama, host of the Investology podcast, and a fellow CAIA Member, to explore the evolving dynamics of private markets, democratized investing, and the importance of long-term thinking. George shares his unconventional path—from financial markets to filming Michelin-star chefs, and back into fintech content creation. Together, they probe the marketing practices in alternative investing, the pitfalls of liquidity and wrappers, and the critical role of education and governance in a more accessible financial landscape. The episode also features reflections on Swensen-style investing, the challenges of retail access to alts, and whether fractional ownership of wine or art is more hobby than portfolio play. Check out Bill's interview with George on Investology: https://open.spotify.com/episode/75aukPhzZi7Su6aQiN7SWA?si=DLQdcQ-yQYKyy_-VnQazqg

In this episode, Bill welcomes Fernando De Leon, founder of Leon Capital Group, to explore the intricacies of private capital, real estate investments, and long-term wealth creation. Fernando shares his unique upbringing along the U.S.-Mexico border and how it shaped his approach to business and investment strategy. He discusses his early career at Goldman Sachs, his transition into entrepreneurship, and how he successfully navigated the financial crisis to build a diversified, multi-sector investment firm. The conversation highlights Leon Capital’s evolution from special situations investing to an operator-led model spanning real estate, healthcare, and financial services. Fernando offers insights into his approach to patient capital, the role of alternative investments, and the importance of adapting to market inefficiencies. He also discusses the firm’s recent expansion into fund management via iCapital, as well as the role of technology and data analytics in shaping investment decisions. The episode concludes with a deep dive into Leon Capital’s scholarship program, emphasizing the importance of investing in future generations and staying connected to evolving trends in business and technology.

In this episode, Bill welcomes Independent Directors Council Managing Director Thomas Kim to explore the evolving role of independent fund directors in today’s financial landscape. They discuss the history and growth of the mutual fund industry, the importance of fiduciary responsibilities, and the growing complexities of investment oversight. Tom shares his perspective on how governance has changed since the introduction of the 40 Act, the impact of ETFs, the importance of professional fund management, and the increasing need for financial education for investors. The conversation also touches on the future of asset management, the role of technology and AI in investing, and how independent directors can prepare for the challenges of tomorrow.

In this episode, Bill welcomes Daniel Liebau, an expert in blockchain and decentralized finance, to discuss the evolving world of Decentralized Autonomous Organizations (DAOs). Daniel shares insights into his background in traditional finance and technology, his transition into blockchain research, and his work in the DAO space, including co-authoring a book on the subject. The discussion covers key aspects of DAOs, their governance structures, and real-world applications. If you're looking to deepen your understanding of DAOs and their role in the future of finance, this episode is a must-listen.