Investment Wars

Hosted by Obsidian CIO

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Jun 2026

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We all love stories - telling them and hearing them. We tend to construct narratives incorporating data points and information that reinforce our point - only capturing a part, and perhaps the wrong part, of the full story within the dynamic and complex investing world. How do we know if the narrative is right? How do we know how the story will end? Subscribe to Investment Wars on YouTube, Apple Podcasts and Spotify to ensure you never miss an episode. For guest opportunities or to share feedback, contact us at ocio@obsidiancio.com. — IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

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38 recent

June 8, 202651 min

Episode 38: Planes, Trains, and Automobiles: Mobility, Automation, and the Future of Infrastructure

Planes, Trains, and Automobiles: Mobility, Automation, and the Future of InfrastructureIn this episode of Investment Wars sponsored by Obsidian CIO, Joseph Halpern sits down with Andrew Miller, a transportation consultant, author, speaker, and writer of the Changing Lanes Substack.This is a wide-ranging conversation about how transportation systems actually work — and why the future of mobility may look very different than the simple narratives around high-speed rail, robotaxis, autonomous trucks, and airport security suggest.We explore why America’s “bad” passenger rail system may be the flip side of one of the world’s best freight rail systems, why autonomous trucking is already here, how robotaxis could reshape cities, and why flying could become dramatically better if we rethink the assumptions that make air travel so miserable today.In this episode, we ask and answer:Why are American passenger trains so slow — and is that actually the wrong question?How soon will autonomous trucking change logistics, labor, truck stops, and the economics of moving goods?Could automated trucks compete with trains — or make rail and trucking more powerful together?What needs to happen for robotaxis to become more than a novelty in San Francisco, Phoenix, and Austin?Will cities help or block the robotaxi future — and what can Boston, Seattle, Austin, and Phoenix teach us?Can autonomous shuttles solve the “last mile” problem for public transit?Who benefits most from self-driving cars: cities, suburbs, or rural communities?Why might airports matter more than high-speed rail for intercity travel?Is much of modern airport security still solving yesterday’s problem?Where should investors and market watchers look next — robotaxis, automated warehouses, freight logistics, or mobility infrastructure?This episode cuts through the easy narratives. High-speed rail is not always the obvious answer. Autonomous vehicles are not a distant fantasy. Public transit may need automation to survive.The future of transportation may depend less on the technology itself than on governance, incentives, infrastructure, and the willingness to let better systems emerge.Subscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode.If you are a financial advisor interested in partnering with Obsidian CIO or would like to suggest a future guest, reach out at ocio@obsidiancio.com.---IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing. The podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

May 6, 2026Episode 241 min

Episode 37: Prediction Markets: Forecasting, AI, and the Future of Information

Prediction Markets — Forecasting, AI, and the Future of InformationIn this episode of Investment Wars, Joe Halpern sits down with Zvi Mowshowitz, a deep thinker with hands-on experience in professional trading, prediction market design, and AI, for a wide-ranging conversation on what prediction markets are, what they're actually good for, and where they're headed.Prediction markets get a lot of hype. But are they genuinely useful economic tools or just sophisticated entertainment?This episode cuts through the noise, exploring how well-designed questions create real informational value, where prediction markets outperform traditional hedges, and why AI may be the next great participant, not the replacement, for these markets.Key Topics CoveredWhat Makes a Good Prediction Market Question: Why specificity, measurability, and verifiability are everything, and why questions like "Is Jesus coming back?" generate nothing but risk-free arbitrage, while questions like "How many ships will pass through the Strait of Hormuz by [date]?" can be genuinely valuable.Real-World Hedging Use Cases: How a shipping company like Maersk could use a well-structured prediction market as a direct, targeted hedge, perhaps more efficient than buying oil futures, which measure far too many variables at once.The Insider Trading Debate: Why insider trading, so clearly harmful in equity markets, is far more nuanced in prediction markets and why thinkers like Robin Hanson argue it should be permitted, since insiders reveal information the market needs.Super Forecasters vs. AI vs. Prediction Markets: Zvi defines super forecasting, explains where super forecasters excel (most near-term political and geopolitical questions) and where they reliably fail (long-range predictions, fat-tail events, and AI capabilities). He then explains how well-prompted AI is now outperforming all but the very top human forecasters and what that means for prediction markets going forward.The Centaur Model of Decision-Making: Drawing on the arc of chess, from human dominance, to AI dominance, to a brief window of human-AI centaurs outperforming both, Zvi explains why we're in the centaur phase of forecasting right now. The winning approach: challenge the AI, push back on its logic, and let the best reasoning win.World Models and Decision Systems: Why building a causal, gear-level model of how the world works, rather than relying on vibes or headlines, is the foundation of better investing and better decisions. Not just for professionals. For everyone.The Real Costs of Participating in Prediction Markets: Beyond bid-ask spreads and platform fees, Zvi makes the case that mental transaction costs, time, focus, and the risk of addiction, are the most underappreciated barriers to participation. His framework: trade when the market justifies those costs, and not a moment before.Why Markets Are Still the Best Aggregators: Even as AI improves, prediction markets may become more powerful, not less, because they synthesize inputs from humans and AIs alike, including sources that hold private information they'd only reveal in exchange for profit.Subscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode.Hear more from Zvi Moshshowitz, subscribe to Don’t Worry About the Vase on SubStack.If you are a financial advisor interested in partnering with Obsidian CIO or would like to suggest a future guest, reach out at ocio@obsidiancio.com.---IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing. The podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

April 2, 2026Episode 3647 min

Episode 36: Private Credit: Navigating Bumps in the Road

In this episode of Investment Wars, Episode 36, sponsored by Obsidian CIO, host Joe Halpern (Managing Partner and CIO of Obsidian CIO) sits down with Robert Grunewald — a 30-year veteran of middle market finance — to deliver a ground-up education on private credit and direct lending.Private credit has been making negative headlines as of late. Investors are asking hard questions about valuations, covenants, defaults, and whether the risks are fully understood. This episode goes beyond the headlines, walking through how these deals actually work from origination to exit, and having an honest conversation about where the real risks and opportunities lie. Key Topics Covered: • How Direct Lending Works: A real-world deal walkthrough of a Texas metal plate rental company, how equity and debt are structured, what happens when a loan goes bad, and why first lien senior secured debt is fundamentally different from what imploded in 2008. • The PE Buyout Engine: Why 70–80% of direct lending is PE-sponsored, how add-on acquisitions generate repeat lending opportunities, and how private equity incentives may actually protect lenders.• The Vehicle Landscape: Public BDCs, private BDCs, interval funds, institutional separately managed accounts, and CLOs — how a single loan gets distributed across vehicles and why over half of all private credit loans end up in CLOs.• Size of Market & Covenant Risk: The $1.5 trillion private credit market, how rapid asset gathering by mega-managers has softened covenant protections, and why that matters for returns and downside protection.• The 2022 Vintage Problem: Why loans originated just before the rate hiking cycle have seen elevated losses, and how vintage diversification protects a portfolio.• Software Exposure & AI Disruption: Software is roughly 25% of the private credit market. Equity values are down ~25%; debt has moved from par to ~90 cents. How to think about concentration risk and why first lien positioning still provides meaningful protection.• Default Rate Reality: Default rates spiked from ~2% to ~5% but are now tracking back toward 3%. Why long-term investors should expect this volatility and not confuse cyclical stress with structural impairment.• The Illiquidity Premium: Private credit can offer 300+ basis points over publicly traded high yield. How to think about the return tradeoff, proper portfolio sizing, and realistic liquidity expectations. Subscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. If you are a financial advisor interested in partnering with Obsidian CIO or would like to suggest a future guest, reach out at ocio@obsidiancio.com. -- IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing. The podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

November 10, 2025Episode 3546 min

35. Liquidity, Valuation, and the Return of the Yield Curve

Debate: Liquidity, Valuation, and the Return of the Yield CurveFeaturing: David Sherman, Founder of CrossingBridge AdvisorsDavid Sherman joins Investment Wars for a wide-ranging discussion on navigating today’s complex fixed income and equity markets—from the aftermath of a decade of zero interest rates to the reemergence of inflation, tighter liquidity, and shifting policy dynamics. In this conversation, we explore how investor behavior evolved in an era of “easy money,” what lessons were learned when rates abruptly reversed, and how to think about liquidity, valuation, and ballast in a world of persistent uncertainty.In today’s episode, we explore:How the decade of zero and negative rates conditioned investor behavior and risk-takingWhy today’s “complicated” market reflects both tightening liquidity and elevated valuationsThe interplay between real rates, inflation, and policy expectations heading into 2026Practical frameworks for defining “ballast” in modern portfolios and matching assets to time horizonsThe importance of liquidity risk—and why many investors still aren’t pricing it correctlyOpportunities and risks in global high yield, including the growing appeal of Nordic credit marketsWhy private credit and direct lending may be less liquid (and less transparent) than investors assumeHow to rethink risk-free rates, personal cost of capital, and portfolio structure in a high-deficit worldSubscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. For guest opportunities or to share feedback, contact us at OCIO@obsidiancio.com.—IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

October 3, 2025Episode 3450 min

34. Direct Lending and the Evolution of Private Credit

Debate: Direct Lending and the Evolution of Private CreditFeaturing: Alona Gornick, Managing Director & Senior Investment Strategist at Churchill Asset Management (an affiliate of Nuveen, the $1 trillion asset management arm of TIAA) Alona Gornick joins Investment Wars to break down one of the fastest-growing corners of alternative investing: direct lending to private U.S. companies. In a wide-ranging conversation, she explores the history of private credit, how regulation and bank consolidation created opportunity for asset managers, and why institutions and now individual investors are turning to the space for income, diversification, and resilience. From the role of private equity sponsors to the rise of retail-friendly structures, this episode demystifies a complex but increasingly essential part of the investment landscape. In today’s episode, we explore:The growth of private credit from niche strategy to a $2 trillion marketHow bank consolidation and post-GFC regulation opened the door for asset managersWhy institutions embraced private credit for yield, diversification, and inflation protectionThe five key features of direct lending: income, floating-rate inflation hedge, diversification, low volatility, and resilienceConcerns around “too much capital chasing deals”—and why demand still outstrips supplyThe rise of retail access via non-traded BDCs, interval funds, and innovative structuresWhy manager selection, track record in avoiding losses, and sourcing advantage are critical for investorsSubscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. For guest opportunities or to share feedback, contact us at ocio@obsidiancio.com.—IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

July 16, 2025Episode 3346 min

33. Interest Rates and Economic Distortions

Debate: Interest Rates and Economic Distortions Featuring: Paul Musson, Former Senior Portfolio Manager at Mackenzie Investments & Author of Capital OffencePaul Musson joins Investment Wars to unpack one of the most misunderstood forces shaping modern markets: interest rates. In a thought-provoking conversation that touches on inflation, money supply, and the consequences of government intervention, Musson makes the case for economic education and a return to first principles. From the natural rate of interest to the dangers of debt-fueled consumption, this episode offers a sharp critique of how policy distorts the economy—and what investors need to understand to navigate it.In today’s episode, we explore: The difference between the natural and neutral rates of interest—and why it mattersWhy a stable money supply may be better than endless expansionHow inflation arises when money growth outpaces productivityWhat good deflation looks like—and why it’s not necessarily badThe inflationary consequences of government stimulus during crisesHow education and transparency can empower better financial decision-makingWhy the current system rewards a few at the expense of many—and what needs to changeIs it time to rethink everything we’ve been taught about inflation, interest, and economic intervention?Subscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. For guest opportunities or to share feedback, contact us at ocio@obsidiancio.com.—IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

June 9, 2025Episode 3236 min

32. Trade Imbalance – Is Reindustrialization the Key to U.S. Economic Resilience?

Debate: Trade Imbalance – Is Reindustrialization the Key to U.S. Economic Resilience?Featuring: Eli Horton, Senior Portfolio Manager & Investment Committee Member at TCW.Eli Horton joins Investment Wars to debate one of the most pressing economic challenges of our time: the U.S. trade imbalance and the industrial response it demands. In a conversation spanning global supply chains, national security, and the race to rebuild domestic manufacturing, Horton explores how public and private capital expenditures (CapEx) and reshoring strategies are reshaping the investment landscape.In today’s episode, we explore:The economic and strategic implications of America’s persistent trade deficitsThe case for a manufacturing renaissance amid growing geopolitical tensionsLabor shortages and their inflationary impact as production returns homeThe role of Mexico and other nearshoring hubs in a multipolar supply chainHow the energy transition is fueling infrastructure demand and CapEx growthIdentifying the sectors and regions poised to benefit from strategic reshoringIs this the dawn of a new industrial era—or are we underestimating the challenges ahead? Subscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. For guest opportunities or to share feedback, contact us at ocio@obsidiancio.com.—IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

May 16, 2025Episode 3141 min

31. Energy Infrastructure – Will It Double in the Next Decade?

Debate: Energy Infrastructure – Will It Double in the Next Decade?Featuring: Robert Thummel, Senior Portfolio Manager & Investment Committee Member at Tortoise Capital.As the U.S. power grid strains under the weight of rising demand, AI-fueled data centers, and shifting global energy dynamics, one sector stands at the center of it all: energy infrastructure. In this episode, we break down the critical—and often misunderstood—backbone of the modern energy system. With insights from industry veteran Rob Thummel, we explore: In today’s episode, we explore:What qualifies as “energy infrastructure”Why energy demand, flat for nearly two decades, is now set to surgeCan our grid and pipeline systems keep up—or are we already hitting bottlenecksWhy U.S. energy needs may diverge from the global pictureWhere investors should look for the best risk-adjusted opportunitiesSubscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. For guest opportunities or to share feedback, contact us at ocio@obsidiancio.com.—IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

April 28, 2025Episode 3043 min

30. How to Measure and Navigate Market Uncertainty

Debate: How to Measure and Navigate Market UncertaintyFeaturing: Professor Nick Bloom is the William Eberle Professor of Economics at Stanford University, Senior Fellow at SIEPR, and Co-Director of the Productivity, Innovation, and Entrepreneurship Program at the National Bureau of Economic Research.Uncertainty is one of the most critical—and elusive—forces shaping markets today. How is it measured? How does it affect economic and financial market behavior? And what strategies can help investors navigate periods of high uncertainty? On Wednesday, April 2nd — “Liberation Day” — President Trump announced sweeping tariffs targeting countries with which the U.S. has trade imbalances. The tariffs, which disproportionately affected key allies, sent markets into a tailspin. In just 48 hours, U.S. equity markets suffered the greatest two-day destruction of market wealth on record. But even more troubling were the developments in the bond market, which ultimately triggered a 90-day policy pause. While the direct math of tariffs implies rising inflation and falling consumption—raising risks of a recession or worse—the more complex and destabilizing element is uncertainty. In today’s episode, we explore:How uncertainty is measuredIts real-world impact on the economy and financial marketsStrategies for navigating uncertain market environmentsDon’t miss our discussion of the Economic Policy Uncertainty Indexes, co-developed by Professor Bloom and referenced throughout the episode. Subscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. For guest opportunities or to share feedback, contact us at ocio@obsidiancio.com.—IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

April 1, 2025Episode 2946 min

29. How Do I Select the “Right” ETF?

Debate: How Do I Select the “Right” ETF?Featuring: Adam Patti is the Co-founder and CEO of Vistashares, an ETF issuer designed to provide pure exposure to disruptive technology-driven supercycles. He is an industry pioneer and insider with vast ETF development and construction knowledge.There are at least 24 artificial intelligence-themed ETFs in the market. How can we differentiate one from the other and make an appropriate decision about which to buy? What factors should we be considering?In today’s episode, we explore:A brief history of the ETF marketHow ETFs revolutionized the capability to achieve tailored exposure among other benefitsAreas of focus when analyzing whether to buy an ETFSubscribe to Investment Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. For guest opportunities or to share feedback, contact us at ocio@obsidiancio.com.— IMPORTANT DISCLOSURE: Obsidian CIO sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.