Educational Alpha

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.

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.