Diligence Dialogues

On this episode of Diligence Dialogues, host Sara Chertoff sits down with Melissa Strait, former Chief Compliance Officer at Coinbase to explore how the crypto space presents both new and also familiar risks, exciting opportunities, and compliance challenges that come with innovation. They discuss navigating the evolving regulatory landscape and the critical role of due diligence in this rapidly developing investment vertical. 

On this episode of Diligence Dialogues, host Sara Chertoff sits down with Stephanie Pries, Founder of Endowment Legal Services and former Director of Compliance at The Notre Dame Investment Office. Together, they explore how university endowments are navigating the balance between returns, reputation, and responsibility – and how their approach to risk is evolving in 2025. From crypto and AI to geopolitical pressures and governance, Stephanie shares key insights on the forces shaping endowment investing today.

On this episode of Diligence Dialogues, host Sara Chertoff discusses the critical role of Operational Due Diligence (ODD) in investment risk assessment with Brad Stehle, Founder of Illume Partners. They explore the evolution of ODD, its importance in identifying operational risks, and the impact of technology and COVID-19 on due diligence practices. Brad shares insights on assessing risks, identifying red flags, and the future of ODD, emphasizing the need for continuous monitoring and the growing significance of ODD in investment strategies.

How do investment firms keep on top of emerging trends? What role is AI playing within the alternative investment space? What does risk mitigation look like in an increasingly complex market? What are some of the unique challenges for institutional investors? We dig into these topics and more with Zack Siddique, Vice President of Operations at Accolade Partners.