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 for generating value through operational expertise, alignment of interest, and AI-driven insights. They also address diversification risks, executive underwriting, and maintaining discipline while scaling responsibly.

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 health and wellness, mental health pressures tied to technology, and strategies for asset allocation, diversification, and tax-efficient planning in the wake of concentrated liquidity events.

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 investors can tap into innovation without traditional barriers like high minimums and illiquidity. Andreas also reflects on trust, transparency, and the future of capital markets.

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 markets, and the future of leadership in an increasingly tech-enabled world.

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.