Masters of Risk

In this episode of Masters of Risk, host Stewart Webster sits down with Matthew Tuttle, CEO and Chief Investment Officer of Tuttle Capital Management, to discuss how investors can navigate an increasingly thematic market shaped by artificial intelligence, geopolitical shifts, and evolving investment risks.

With more than two decades of investment experience and a reputation for challenging conventional portfolio construction, Matt shares why he believes many traditional investment frameworks no longer reflect today's market realities. He introduces his HEAT investment philosophy, an approach centered on Hedge, Edge, Asymmetry, and Theme, designed to help investors manage risk while identifying emerging opportunities.

As AI investment accelerates across industries, Matt explains why the next generation of winners may extend far beyond the well-known technology giants. From memory and photonics to energy, utilities, materials, and even space infrastructure, he explores how investors can identify critical bottlenecks powering the AI economy and uncover opportunities before they become consensus trades.

Stewart and Matt also examine several of the market's most pressing questions, including whether rising valuations present a growing risk to investors, how consumers may fare in a higher-rate environment, and what signals could indicate that AI-driven capital spending is beginning to slow. The conversation also explores the growing role of thematic ETFs, digital asset exposure, and the risks surrounding private credit products entering the ETF marketplace.

Looking further ahead, Matt shares his perspective on emerging investment themes ranging from aerospace and defense to the rapidly developing space economy, where long-term opportunities may be created by the infrastructure required to support next-generation technologies.

A thought-provoking discussion for investors, portfolio managers, risk professionals, and market participants seeking fresh perspectives on thematic investing, ETF innovation, portfolio risk management, and the forces shaping tomorrow's market opportunities.

More S&P Global Resources:

• Proactive Risk Intelligence | S&P Global
• The Definitive Risk Conference | S&P Global
• ⁠Masters of Risk | Season 4 Episode 5 Video: Beyond Diversification: Strategic Risk Insights for Mod…
• ⁠Masters of Risk | Season 4 Episode 6: Private Credit Under Pressure: Liquidity, Distress, and Oppor…

Credits:

• Host: Stewart Webster, CFA
• Guest: Matthew Tuttle, CEO & Chief Investment Officer, Tuttle Capital Management
• Editor: Carl Schmidt
• Producer: Caitlin Bray
• Published with Assistance From: Sophie Carr and Feranmi Adeoshun

In this episode of Masters of Risk, host Stewart Webster speaks with Lionel Jolie, Partner and Head of Credit at J.F. Lehman & Company, about the growing tensions beneath today's private credit markets and the opportunities emerging for disciplined investors.

As private credit assets have expanded rapidly in recent years, liquidity pressures, redemption requests, and shifting market dynamics are reshaping the landscape for business development companies (BDCs), direct lenders, and secondary credit investors. Lionel explains how his team navigates both public and private credit markets, providing liquidity to lenders while evaluating stressed, illiquid, and often misunderstood opportunities.

Drawing on more than two decades of credit investing experience, Lionel discusses the evolution of the BDC market, the rise of liability management exercises, and why traditional refinancing strategies are becoming increasingly difficult in a higher-rate environment. He also explores how investors can distinguish between companies facing temporary liquidity challenges and those caught in a true operational decline.

Together, Stewart and Lionel examine the sectors attracting capital today—including aerospace, defense, and industrial infrastructure—and discuss how government spending, supply chain constraints, and asset scarcity can influence credit outcomes. They also unpack the growing popularity of private credit ETFs, the risks of liquidity mismatches, and why market stress may be more nuanced than the headlines suggest.

A timely conversation for institutional investors, credit professionals, risk managers, and allocators seeking deeper insight into private credit, secondary markets, and the risks shaping the next phase of the credit cycle.

More S&P Global Resources:

• Proactive Risk Intelligence | S&P Global
• The Definitive Risk Conference | S&P Global
• Masters of Risk | Season 4 Episode 5 Video: Beyond Diversification

Credits:

• Host: Stewart Webster
• Guest: Lionel Jolie, Partner, Credit, F. Lehman & Company
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• Editor: Carl Schmidt
• Producer: Caitlin Bray
• Published with Assistance From: Sophie Carr and Feranmi Adeoshun

In this episode of Masters of Risk, host Stewart Webster sits down with Karan Sood, Co-Founder and CEO of Vest, to challenge one of the most widely accepted principles in investing: diversification.

Karan introduces the concept of "outcomes-based investing" and explains how Vest is leveraging derivatives to engineer defined outcome ETFs—investment strategies that explicitly shape risk and return profiles. By capping upside, buffering downside, and stabilizing income, these products aim to give investors something markets rarely offer: predictability.

Drawing on his deep experience in structured products and options-based strategies, Karan breaks down how derivatives can function as a form of "insurance" within portfolios—transferring risk rather than simply spreading it. He also explores the hidden fragility beneath modern portfolios, arguing that traditional diversification may create a false sense of security in a world where correlations spike precisely when protection is needed most.

Together, Stewart and Karan unpack the structural risks embedded in today's markets—from concentration within major indices to the growing illusion of diversification—and discuss why investors may be overcrowding the very strategies they believe mitigate risk.

A thought-provoking conversation for asset managers, risk professionals, and financial advisors seeking to rethink portfolio construction, challenge long-held assumptions, and build more resilient investment strategies in an increasingly interconnected market.

Credits:

• Host: Stewart Webster • Guest: Karan Sood, Co-Founder and CEO of Vest • Editor: Carl Schmidt • Producer: Caitlin Bray • Published with Assistance From: Sophie Carr and Feranmi Adeoshun

In this episode of Masters of Risk, host Stewart Webster sits down with Kareem Saleh, Founder and CEO of FairPlay AI, to unpack one of the most critical and underexamined risks in modern finance: algorithmic bias. As artificial intelligence becomes central to everything from lending decisions to fraud detection, Kareem explains why the promise of "objective" algorithms often falls short—and how hidden biases can quietly shape outcomes at scale.

Drawing on his experience across global credit markets, Kareem reveals how unfairness enters AI systems—from flawed data to model design to real-world deployment—and why organizations that fail to address it are exposing themselves to financial, regulatory, and reputational risk.

Together, Stewart and Kareem explore the misconception that fairness comes at the expense of performance, showing instead how more equitable models can unlock growth, improve accuracy, and expand access to capital. They also dive into the future of work in the age of AI, the need for modern governance infrastructure, and why fairness is quickly becoming a defining competitive advantage.

A compelling listen for executives navigating AI adoption, risk leaders rethinking model governance, and anyone seeking to build more responsible—and more profitable—AI systems.

Credits:

• Host: Stewart Webster
• Guest: Kareem Saleh, Founder and CEO of FairPlay AI
• Editor: Neri Reyes
• Producer: Caitlin Bray
• Published With Assistance From: Sophie Carr, Feranmi Adeoshun, Patrick Moroney, Barb Dalumpines, Cassandra Rowe

In this episode of Masters of Risk, host Stewart Webster sits down with Chrystina Howard, ERM leader for the Complex Risk Practice at HUB International, to explore how enterprise risk management is transforming in an era defined by volatility, interdependence, and systemic shocks. Chrystina brings decades of experience at the intersection of insurance, strategy, and complex risk, helping organizations navigate everything from geopolitical tensions and climate extremes to cyber escalation and workforce instability.

Together, Stewart and Chrystina examine why ERM can no longer be treated as a compliance exercise and how leading organizations are using it as a strategic capability, one that unifies risk awareness, drives resilience, and strengthens competitive advantage. Their conversation spans the full risk horizon: alternative risk financing, the resurgence of parametric insurance, global regulatory pressures, the fragility of traditional insurance markets, and the critical role of culture in building risk‑mature organizations.

Chrystina also shares a candid look at the risks keeping leaders up at night, from escalating cyber threats to declining employee wellness, and explains why the organizations positioned to thrive aren't the ones predicting every disruption, but the ones preparing to adapt to any disruption.

A must-listen for executives seeking to modernize their approach to risk and unlock the full potential of ERM in a world where crises rarely occur alone.

Credits:

• Host: Stewart Webster
• Guest: Chrystina Howard
• Editor: Feranmi Adeoshun
• Producer: Caitlin Bray
• Published With Assistance From: Sophie Carr

In this episode of Masters of Risk, host Stewart Webster sits down with Ali Hassan, investor, entrepreneur, and founder of Perceptive Capital, to dissect the accelerating institutional movement into digital assets. Ali reflects on the early misconceptions surrounding Bitcoin and crypto and shares how risk frameworks have evolved as the market matures, infrastructure hardens, and regulatory uncertainty fades.

Their discussion spans the full risk universe: exchange fragility, leverage, custody, smart‑contract vulnerabilities, the role of Decentralized Finance (DeFi) in global financial inclusion, and the growing belief that Bitcoin represents one of the most asymmetric return opportunities of our time.

Stewart and Ali also look ahead to 2045, exploring which digital assets will survive, which will vanish, and what a world built on programmable money might mean for investors. A compelling roadmap for anyone seeking clarity in a rapidly shifting financial ecosystem.

Credits:

• Host: Stewart Webster
• Guest: Ali Hassan
• Editor: Feranmi Adeoshun
• Published With Assistance From: Sophie Carr and Caitlin Bray

Kicking off Season 4 of Masters of Risk, host Stewart Webster sits down with risk expert Michelle Sartain, President, Marsh US and Canada, for a deep dive into the volatile U.S. risk landscape They explore the top threats identified by business leaders, including economic uncertainty, declining workforce health, the rapid spread of misinformation, the dual-edged sword of Artificial Intelligence, and systemic supply chain fragility.

The conversation emphasizes the profound interconnectedness of these modern risks, where vulnerabilities in one area can trigger cascading consequences across social, operational, and political domains. Stewart and Michelle discuss the critical need for organizations to build resilience and adopt cross-functional strategies to anticipate, manage, and mitigate shocks in an unpredictable world. Don't miss this essential guide to navigating the complex fragilities of today's business environment.

Credits:

• Host: Stewart Webster
• Guest: Michelle Sartain
• Editor: Feranmi Adeoshun
• Published With Assistance From: Sophie Carr and Caitlin Bray

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In this episode of Masters of Risk, host Stewart Webster engages with Michael Brawer, the CEO of Transparency Analytics. With a wealth of experience in executive positions within the financial services industry, Michael has leveraged his insights to establish his own firm. Stewart explores the motivations behind Michael's entrepreneurial journey, the risks he has faced, and the challenges of raising funds to realize his vision. Don't miss this insightful conversation.

More S&P Global Content:

• Masters of Risk | Season 3 Ep. 2: AI or Not: How Do We know What is Real or Not
• Masters of Risk | Season 3 Ep. 3: Nc'Nean Whisky Breaking the Barriers
• Are Credit Chatbots Worth the Resources?
• Tariffs in Transition: The Impacts of Trade on Credit Markets - Part 1
• Balancing Risks and Rewards in the EU-US Tariff Landscape - Part 2
• Navigating Global and Asia-Pacific Economic Prospects Amid U.S. Policy Changes and Tariffs – Part 3 Credits:

• Host: Stewart Webster
• Producer and Editor: Alisha Rappaport
• Guest: Michael Brawler

In this episode of "Masters of Risk" host Stewart Webster engages in the second part of a compelling conversation with Wish Bakshi, Founder & AI Systems Engineer of AQ Energy. In this two-part episode they have an in-depth conversation about AI data centers, digital infrastructure, the complex energy systems behind them in a world where the demand is high and the risks are increasing. Wish gives us two episodes to unpack all the intricacies from grid stress and financial risk to supply chain pressures. Tune into this insightful discussion.

More S&P Global Content:

• Masters of Risk | Season 3 Ep. 2: AI or Not: How Do We know What is Real or Not
• Tariffs in Transition: The Impacts of Trade on Credit Markets - Part 1
• Balancing Risks and Rewards in the EU-US Tariff Landscape - Part 2
• Navigating Global and Asia-Pacific Economic Prospects Amid U.S. Policy Changes and Tariffs – Part 3
• Credit Memo Automation: Where AI Meets Analyst Efficiency

Credits:

Host: Stewart Webster

Producer and Editor: Alisha Rappaport

Guest: Wish Bakshi

In this episode of "Masters of Risk" host Stewart Webster engages in a two-part compelling conversation with Wish Bakshi, Founder & AI Systems Engineer of AI Systems in Energy & Power. In this two-part episode they have an indepth conversation about AI data centers, digital infastructure, the complex energy systems behind them in a world where the demand is high and the risks are increasing. Wish gives us two episodes to unpack all the intricacies from grid stress and financial risk to supply chain pressurse. Tune into this insightful discussion.

More S&P Global Content:

• Masters of Risk | Season 3 Ep. 2: AI or Not: How Do We know What is Real or Not
• Tariffs in Transition: The Impacts of Trade on Credit Markets - Part 1
• Balancing Risks and Rewards in the EU-US Tariff Landscape - Part 2
• Navigating Global and Asia-Pacific Economic Prospects Amid U.S. Policy Changes and Tariffs – Part 3
• Credit Memo Automation: Where AI Meets Analyst Efficiency

Credits:

• Producer and Editor: Alisha Rappaport
• Host: Stewart Webster
• Guest: Wish Bakshi