
Hosted by Dean Curnutt · EN

I was excited to host this conversation with Rob Flatley, Founder and CEO of TS Imagine, on prediction markets, AI-driven workflows, and the structural changes reshaping financial market infrastructure. We begin with Rob’s path from software engineering into capital markets, including leadership roles at Bank of America and Deutsche Bank during the rise of electronic trading and through the Global Financial Crisis. That experience informs a broader perspective on how market infrastructure evolves during periods of stress and technological transition. The conversation then turns to artificial intelligence and the distinction between large language models and reinforcement learning systems. Rob explains why traditional deterministic workflows in settlement and collateral management create different challenges than probabilistic systems such as risk management. He argues that the next phase of AI adoption will focus less on generating language and more on learning and automating complex workflows across financial systems. We also explore prediction markets, an area where Rob and his team have spent significant time building infrastructure and risk frameworks. He discusses how markets tied to elections, Fed policy, GDP, inflation, and geopolitical outcomes are beginning to move from retail experimentation toward institutional relevance. We also discuss tokenization and settlement infrastructure. Rob outlines how stablecoins, digital ledgers, and atomic settlement could reshape financing, custody, collateral mobility, and the economics of intermediated finance. We discuss the implications for prime brokerage, repo, clearinghouses, and 24-hour trading environments. I hope you enjoy this episode of the Alpha Exchange, my conversation with Rob Flatley.

It was a pleasure to host a conversation with Hari Krishnan, Head of Volatility Strategies at SCT Capital, on the changing nature of volatility markets, portfolio hedging, and why commodities may offer increasingly valuable diversification in today’s environment. Hari reflects on his book Second Leg Down, which explores practical approaches to tail-risk hedging and the cyclical nature of volatility. He discusses how investors often ignore protection in calm periods, only to rush toward hedges after markets have already repriced risk. That dynamic leads to a broader conversation on planning, budgeting, and approaching hedging as an ongoing portfolio discipline rather than a reactive decision. We then turn to option markets more broadly, including volatility risk premium, skew, and the challenge of protecting against fat-tailed outcomes. Hari explains why moderately out-of-the-money options often embed persistent premium, while deeper tail risks can be difficult to price with confidence. The conversation then shifts to commodities, where Hari sees a differentiated opportunity set. We discuss how producer hedging, end-user demand, and forward-curve dynamics create a very different volatility ecosystem than that in equities. He outlines a strategy focused on gaining long exposure to select commodities while using options structures to reduce carry costs and preserve upside convexity. We close with a discussion on cross-asset dislocations, the recent divergence between oil, gold, and equities, the role of commodities in a world where bonds may be less defensive, and how AI tools are accelerating research, customization, and hypothesis testing across markets. I hope you enjoy this episode of the Alpha Exchange, my conversation with Hari Krishnan.

It was a pleasure to welcome Rob Kaplan, Vice Chairman of Goldman Sachs, and former President of the Dallas Fed, to the Alpha Exchange. We begin with Rob’s reflections on his time at the helm of the Dallas Fed from 2015 to 2021, a period spanning rate liftoff, fiscal stimulus, and the COVID crisis. He outlines how his perspective as a business practitioner led him to focus on structural forces—demographics, globalization, and technology—rather than relying solely on cyclical data and economic models. We then turn to the current environment, where the Fed faces a more complex trade-off between inflation and employment. Rob highlights the limits of monetary policy, emphasizing that broader economic outcomes are increasingly shaped by fiscal policy, regulation, and structural trends beyond the Fed’s control. The conversation also explores changes in financial markets, including the diminished influence of Fed policy on the long end of the yield curve, the growing importance of supply and demand for Treasuries, and the implications of a more leveraged global economy. We close with a discussion on regulation, private credit, and the impact of geopolitical shocks, as well as how AI-driven disruption is influencing corporate behavior and risk management across industries. I hope you enjoy this episode of the Alpha Exchange, my conversation with Rob Kaplan.

It was a pleasure to welcome Wayne Dahl, Co-Portfolio Manager of Global Credit Strategy at Oaktree Capital Management, to the Alpa Exchange. We begin with Wayne’s path through convertible arbitrage, structured credit, and multi-asset investing, and how that foundation informs a framework centered on understanding sensitivities across rates, credit, and equity exposures. Convertible arbitrage, in particular, serves as an entry point into managing multiple dimensions of risk simultaneously, reinforcing a core principle: avoiding large losses is essential to long-term compounding. We explore Oaktree’s consistent investment philosophy—one that prioritizes credit fundamentals over macro forecasting and emphasizes patience in periods of compressed risk premiums. Wayne reflects on environments like 2021, where low yields and tight spreads challenge investors to remain disciplined, and contrasts that with the more attractive all-in yields that have emerged following the shift in rates since 2022. The conversation next considers today’s landscape. Here, Wayne walks through how the firm is positioning across liquid credit markets, highlighting areas such as residential mortgage-backed securities and shorter-duration, high-income instruments as ways to balance yield with risk control. We close with a discussion on AI-driven dispersion, energy-driven uncertainty, and the importance of portfolio construction across geographies, sectors, and structures in navigating an increasingly complex environment. I hope you enjoy this episode of the Alpha Exchange, my conversation with Wayne Dahl.

Welcome to Episode 250 of the Alpha Exchange. To celebrate the milestone, I asked my dear friend, Jon Kalikow, to host the conversation, switching seats and having me as the guest. I launched the podcast in 2018 with a simple idea: to create space for long-form conversations that explore how market practitioners think about risk. Rather than focusing on predictions, the goal has always been to understand frameworks—how investors process information, respond to uncertainty, evolve through cycles. In this episode, we also explore some of my own thinking on risk. Here, I outline a simple framework built around four categories: economic, monetary, financial, and geopolitical. While distinct, these risks are deeply interconnected and understanding how they interact is critical in assessing market outcomes. Today’s market dynamics are fascinating in this context. We close the discussion with a look ahead—toward expanding the Alpha Exchange platform through live events, educational initiatives, and continued conversations that emphasize intellectual honesty, humility, and the ongoing exchange of ideas. I feel as convicted as ever about the business model which aims to create value through engagement. I hope you enjoy this episode and appreciate your ongoing support of the Alpha Exchange.

The “risk-free” rate figures prominently in how we’ve all been taught the foundations of finance. To price a security, start with the asset that is the safest and soundest and then add compensation for bearing uncertainty. It has always been self-evident that the global risk-free benchmark was the Treasury market. Deep, liquid and viewed as default free, US government bonds have been the recipient of capital during times of stress. And the reason is that the US has long been viewed as not just the world’s strongest economy but also a stabilizing force in global affairs. In this discussion, and with the help of four recent expert guests on the Alpha exchange, I argue that this is changing and the US is now becoming a chief source of risk. In the process, the Treasury market may be losing one its most important characteristics: the insurance feature. That is, its capacity to be durable to and even benefit from market shocks. We’ve all got to be asking, “how can US government bonds be a shock absorber when the US government is the source of the shock?” The implications for asset prices that result from a less stable US are significant and there are important questions to consider. I hope you find this discussion useful.

Kris Abdelmessih, author of the MoonTower Substack and founder of the options analytics firm MoonTower.ai., has spent years thinking about option pricing, volatility regimes, and the mental math traders use to translate volatility into price. In this context, it was great to welcome him back to the Alpha Exchange to explore his thought process. We begin with developments in commodity markets, particularly crude oil, and silver, where geopolitical tension and speculative flows have led to sharp changes in volatility surfaces. Kris explains how option skew in underlyings like oil can reprice rapidly during shock events, leading to inverted termstructure and a well bid call skew. These dynamics create unusual behavior in vertical spreads and probabilities implied by option prices. Kris describes how the relationship between spot moves and volatility changes across market environments, emphasizing that traders must continually recalibrate their models. What appears to be a stable relationship—such as the familiar beta between the S&P 500 and the VIX—can shift quickly depending on positioning and market structure. A major focus of our conversation is on the mental math traders use to interpret option prices without relying on models. Kris walks through several shortcuts that allow traders to move quickly between volatility, straddle prices, and probability estimates. These approximations help traders identify when prices look unusual and whether options markets imply probabilities that diverge from other markets. Finally, we discuss the work Kris is doing on financial education. Inspired by teaching his own children about investing and compounding, he has begun running small classes for students and sharing the materials publicly. The goal is simple: introduce younger investors to concepts like time value of money and long-term compounding earlier in life. I hope you enjoy this episode of the Alpha Exchange, my conversation with Kris Abdelmissih.

As Chairman and CEO, Zach Buchwald leads Russell Investments, a firm overseeing $370bln in client assets and celebrating its 90th anniversary in providing portfolio management services to institutions and individuals. Zach details the open-architecture model utilized at Russell, explaining how portfolios are constructed by combining best-of-breed managers and strategies across asset classes. He shares how these portfolios are managed through an outsourced chief investment officer framework, providing institutions with integrated portfolio construction, manager selection, and risk management. A central theme in our discussion is retirement, a large focus at Russell on behalf of its client base. Zach highlights the long-term shift from defined benefit pensions to 401(k) plans, and the structural and behavioral challenges individuals face in saving for retirement and the growing responsibility they now bear in planning. We discuss the power of compounding, the importance of staying invested through market volatility, and the role that portfolio design can play in helping investors avoid costly behavioral mistakes. While the 401(k) structure can work well when participants save early and remain invested, Zach notes that many Americans have not accumulated the assets necessary for retirement and that compounding requires both time and consistent exposure to the market. Default investment options, diversified portfolios, and disciplined asset allocation can help individuals remain invested through periods of volatility and capture the long-term growth of capital markets. I hope you enjoy this episode of the Alpha Exchange, my conversation with Zach Buchwald.

Amidst these very uncertain times in the economy, geopolitics, and asset prices, it was excellent to welcome Alberto Gallo, founder and CIO of Andromeda Capital Management, back to the Alpha Exchange. Our conversation first considers the long arc of post-crisis monetary policy. Here, Alberto argues that extended quantitative easing, while stabilizing in the short run, carried structural side effects over time—capital misallocation, corporate consolidation, and widening inequality. He notes that central bank balance sheets remain large and that markets today send mixed signals: stability in rates and credit alongside strength in precious metals. We then turn to Andromeda’s approach to finding value in credit markets. Alberto frames bonds as embedded short-volatility instruments and describes a strategy that seeks asymmetric gain-to-loss profiles, liquidity, and convexity. A major focus is the rapid expansion of private credit—five-year lockups, high-single-digit returns achieved in benign conditions, sector concentration in technology, and insurer ownership structures. With spreads near multi-decade tights, he questions whether investors are adequately compensated for default, liquidity, and volatility risk. We close on AI-driven capex, fiscal dominance, and elevated debt levels. Alberto frames the future as a distribution with meaningful tails and argues that current pricing reflects limited uncertainty at a moment of structural transition. You can learn more about the firm at https://andromedainvestors.com/

With early exposure to Paul Tudor Jones and then stints on the sell-side in credit research, Michael Contopoulos is now Deputy CIO of Richard Bernstein Advisors, a macro-oriented asset manager overseeing roughly $20 billion across long-only portfolios. Our discussion centers on portfolio construction in an era of extreme equity concentration and shifting global leadership.On the equity side, the firm is under-weight the most concentrated segments of U.S. equities and overweight international markets, citing valuation gaps, earnings acceleration abroad, and under-ownership by investors.Using his background in quantitative credit strategy and a Merton framework for modeling spread risk, Michael brings a structural lens to today’s corporate debt markets. Our conversation focuses on the surge in long-dated issuance tied to AI infrastructure build-outs. He argues that history rarely rewards lenders who finance capital-intensive growth booms at their peak.Drawing parallels to late-1990s telecom boom, Michael questions whether investors are being adequately compensated for duration and technology risk embedded in 40- and 50-year debt issued by hyperscalers building data centers. The core concern is twofold: that AI-driven revenue gains may not justify the scale of investment, and that infrastructure built today may not remain technologically relevant decades from now.I hope you enjoy this episode of the Alpha Exchange, my conversation with Michael Contopoulos.Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)