Investment Wars

Hosted by Obsidian CIO

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Jul 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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August 19, 202646 min

Episode 40: Digital Assets: The Tokenization of Everything

In this episode of Investment Wars , Obsidian CIO Managing Partner and CIO Joe Halpern sits down with Chris Solarz, CIO of Digital Assets at Amitis Capital , to explore one of the potentially most consequential developments in finance: the tokenization of real-world assets. Chris brings an institutional investor’s perspective to a market often dominated by speculation. Before moving into digital assets, he spent more than two decades in traditional finance, including helping allocate nearly $8 billion while at institutional investment consultant Cliffwater. Today, he invests across digital-asset managers and strategies for Amitis Capital. The conversation moves beyond Bitcoin, meme coins and the traditional definition of “crypto” to examine how blockchain technology could change the way investors own, trade, settle, borrow against and access financial assets . Tokenization essentially creates a digital, tradable representation of an asset on a blockchain. Joe and Chris break down why that matters. Traditional securities transactions still involve exchanges, market makers, custodians, clearing systems and settlement processes. Blockchain potentially enables transactions to settle peer-to-peer, around the clock and nearly instantaneously. They also explore a potentially bigger implication: cross-collateralization . Imagine a digital wallet representing multiple financial and real-world assets that could seamlessly be used as collateral for lending and other transactions. That could fundamentally change how credit is created and capital is deployed. In this episode, Joe and Chris ask and answer: What does it actually mean to tokenize a real-world asset? Why could tokenized stocks and bonds be more efficient than today’s financial-market infrastructure? Could tokenization create something approaching a global, 24/7 marketplace for financial assets? How could instantaneous settlement and peer-to-peer transactions reshape investing? Why might putting multiple assets “in one wallet” dramatically improve borrowing and collateral efficiency? What separates Bitcoin and potentially useful digital assets from meme coins and speculative tokens? Where can active investment managers find opportunities as digital-asset markets mature? As Chris puts it, the opportunity he finds most compelling today is the tokenization of real world assets and equities among other assets . Investment Wars is brought to you by Obsidian CIO , helping financial advisors and investors think more clearly, invest more deliberately and build portfolios with institutional discipline—not simply add more products. --- 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.

July 8, 202647 min

Episode 39: Bridging the Liquidity Gap

What happens when a startup employee helps build something valuable—but can’t afford to keep the equity they earned? In this episode of the Investment Wars podcast sponsored by Obsidian CIO , Joe Halpern sits down with Dave Thornton, Co-Founder and CEO of Vested , to explore one of the most overlooked problems in private markets: the liquidity gap facing startup employees with expiring stock options. Dave explains how many rank-and-file startup employees receive equity as a core part of their compensation, only to discover—often after leaving a company—that they have just 90 days to exercise their options or lose them. The result? Billions of dollars in potential employee wealth can disappear simply because the system was not built to finance smaller, fragmented stock-option exercises. Dave shares how Vested pivoted from an equity education platform into a capital provider designed to solve this problem at scale. The conversation also widens into a broader discussion of venture capital, AI-driven capital concentration, vintage-year risk, private-market access, secondary liquidity, and why investors should be cautious about narratives that suggest venture capital is simply about “picking winners.” As always on Investment Wars , the episode challenges the easy story. Private markets are not just about access. They are about structure, liquidity, incentives, risk, and process. We ask and answer: - Why do startup employees often lose the value of the equity they helped create? - Why does the market serve large private-company shareholders better than rank-and-file employees? - How did Vested pivot from equity education to stock-option exercise financing? - How does Vested evaluate private companies without traditional deep-dive underwriting? - What should investors understand about venture capital vintages and AI concentration? - Is venture capital really about picking winners? - What private-market trends are exciting—or concerning—right now? 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.

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 Infrastructure In 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 Information In 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 Covered What 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 Curve Featuring: David Sherman, Founder of CrossingBridge Advisors David 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-taking Why today’s “complicated” market reflects both tightening liquidity and elevated valuations The interplay between real rates, inflation, and policy expectations heading into 2026 Practical frameworks for defining “ballast” in modern portfolios and matching assets to time horizons The importance of liquidity risk—and why many investors still aren’t pricing it correctly Opportunities and risks in global high yield, including the growing appeal of Nordic credit markets Why private credit and direct lending may be less liquid (and less transparent) than investors assume How to rethink risk-free rates, personal cost of capital, and portfolio structure in a high-deficit world 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.

October 3, 2025Episode 3450 min

34. Direct Lending and the Evolution of Private Credit

Debate: Direct Lending and the Evolution of Private Credit Featuring: 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 market How bank consolidation and post-GFC regulation opened the door for asset managers Why institutions embraced private credit for yield, diversification, and inflation protection The five key features of direct lending: income, floating-rate inflation hedge, diversification, low volatility, and resilience Concerns around “too much capital chasing deals”—and why demand still outstrips supply The rise of retail access via non-traded BDCs, interval funds, and innovative structures Why manager selection, track record in avoiding losses, and sourcing advantage are critical for investors 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.

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 Offence Paul 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 matters Why a stable money supply may be better than endless expansion How inflation arises when money growth outpaces productivity What good deflation looks like—and why it’s not necessarily bad The inflationary consequences of government stimulus during crises How education and transparency can empower better financial decision-making Why the current system rewards a few at the expense of many—and what needs to change Is 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 deficits The case for a manufacturing renaissance amid growing geopolitical tensions Labor shortages and their inflationary impact as production returns home The role of Mexico and other nearshoring hubs in a multipolar supply chain How the energy transition is fueling infrastructure demand and CapEx growth Identifying the sectors and regions poised to benefit from strategic reshoring Is 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 surge Can our grid and pipeline systems keep up—or are we already hitting bottlenecks Why U.S. energy needs may diverge from the global picture Where investors should look for the best risk-adjusted opportunities 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.