Educational Alpha

In this episode, host Bill Kelly sits down with Brett Hickey, Founder and CEO of Star Mountain Capital, to explore the landscape of lower middle market private credit. Brett shares how his early experiences shaped his approach to entrepreneurship, leadership, and long-term investing. The conversation covers the evolution of private credit post-GFC, structural inefficiencies in the lower middle market, and Star Mountain’s strategy f...

In this episode, host Bill Kelly welcomes Tad Fallows and Matt Shechtman from Long Angle, a private community of high-net-worth individuals focused on wealth preservation, personal growth, and alternative investing. Tad and Matt share their entrepreneurial backgrounds, discuss how Long Angle fosters unbiased peer learning, and explore the value of collective access to private market investments. The conversation also touches on hea...

In this episode, host Bill Kelly speaks with Andreas Bezner, CEO and Co-Founder of Stableton, to explore how secondary markets are transforming access to late-stage private tech companies. Andreas shares his entrepreneurial journey, the evolution of Stableton, and the creation of the Top 20 Unicorn Index Fund. The conversation unpacks the value of secondary market access, the convergence of public and private equity, and how invest...

In this episode, host Bill Kelly is joined by global business executive and commentator Ryan Patel. Known for his cross-industry influence, Ryan shares how his multifaceted experience helps him assess innovation, leadership, and the evolving workplace. The conversation explores the future of AI, ethical governance, global cooperation, and quantum computing. They also discuss long-term thinking in policy, the complexity of financial...

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 chal...

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 gover...

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 con...

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 ...

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 t...

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 ...

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 sh...

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-le...

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 financ...

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 industr...

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 impa...

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 adop...

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 alte...

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 navigat...

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...