Pod Street Week
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THIS WEEK · 15 PODCASTS · WEEK OF MAY 1, 2026
This week we bring you fifteen exceptional podcasts spanning Bill Ackman’s Pershing Square USA IPO and market outlook, Lloyd Blankfein on wealth inequality and the 2008 lessons, Jacob Pozharny’s systematic sentiment analysis revealing Asian energy stress and defense stock mispricings, Cem Karsan’s evidence that the V-bottom was orchestrated by the administration, Ben Felix on index investing and the 5% rent-vs-buy rule, Clem Chambers on 9% structural inflation and the Nokia/Fluor nuclear conviction, BlackRock COO Rob Goldstein on the enterprise AI megatrend, Moez Kassam on fading the crowd in cannabis and SpaceX, Jamie Dimon on cyber risk and the coming bond crisis, Paul Tudor Jones on dollar-yen and AI watermarking as the most important policy intervention, Jason Landau on why the energy trade is mispriced, Ken Griffin on Citadel’s winning culture and regulated industry AI moats, Peter Grandich on his most extreme 42-year bearish conviction, Jon Alterman on how China is winning the Iran war, and a new academic paper on the AI Layoff Trap. Each summary is designed to be immediately actionable — whether you are allocating capital, running a business, or simply trying to understand the forces reshaping the world around you. We hope you enjoy them.
THIS WEEK’S LINEUP
EP 1 Pershing Square’s Ackman Talks IPO, State of Markets — Bill Ackman — Pershing Square CEO & Founder
EP 2 Why the Stock Market Has Become a Casino | Lloyd Blankfein — Lloyd Blankfein — Former Goldman Sachs CEO
EP 3 Why Fundamentals Don’t Work For “New Economy” Stocks | Jacob Pozharny — Jacob Pozharny — Bridgeway Capital Management Co-CIO
EP 4 The Market Is Being Managed (And That Tells You Something) | Cem Karsan — Cem Karsan — Kai Wealth & Kai Volatility Advisors
EP 5 Stock Expert: Becoming Rich Is Simple, But You Won’t Do It! | Ben Felix — Ben Felix — PWL Capital CIO & Rational Reminder Host
EP 6 9% Inflation For 10 Years, The Assets That Win Or Break Revealed | Clem Chambers — Clem Chambers — ADVFN Founder
EP 7 Next Megatrends in Finance | BlackRock’s Rob Goldstein — Rob Goldstein — BlackRock COO
EP 8 Fading the Crowd: How Anson Funds Finds Alpha in Market Chaos | Moez Kassam — Moez Kassam — Anson Funds CIO
EP 9 Biggest Challenges Ahead: Geopolitics, Private Credit, Cybersecurity and AI | Jamie Dimon — Jamie Dimon — JPMorgan Chase CEO
EP 10 AI Risk, Bubbles and Buffett | Paul Tudor Jones — Paul Tudor Jones — Tudor Investment Corp Founder
EP 11 Everyone is Getting the Energy Trade Wrong: $4 Billion Hedge Fund Manager
— Jason Landau — Warah Capital Advisors CIO
EP 12 Creating the Winning Strategy and Culture | Ken Griffin — Citadel — Ken Griffin — Citadel Founder & CEO
EP 13 Stock Market Refuses to Fall? Most Extreme Conviction in 42 Years | Peter Grandich — Peter Grandich — Veteran Market Analyst & Author
EP 14 How China Is Winning the Iran War | Jon Alterman — Jon Alterman — CSIS Zbigniew Brzezinski Chair in Global Security
EP 15 The AI Layoff Trap — Academic Paper — Brett Hemenway Falk & Gerry Tsoukalas — Authors
Full summaries with actionable insights and investment focus for each podcast follow on the pages below.
EP 1 - Pershing Square’s Ackman Talks IPO, State of Markets
Bill Ackman — Pershing Square CEO & Founder
Bill Ackman, CEO and founder of Pershing Square, appeared on live television to mark the IPO of Pershing Square USA (PSUS), a closed-end fund structured as an investment holding company. Ackman described the IPO as the beginning of a long compounding journey, with $5 billion raised and capital expected to be deployed within weeks. He argued that PSUS, which has delivered a 24.9% annualised return over eight years, deserves to trade at a premium to book value rather than at the traditional closed-end discount, given its track record, low fees, and the transparency that comes with its SEC-registered structure. Ackman also expressed bullishness on the broader market, calling specific dips “stupidly cheap” and projecting a forward IRR still in the mid-twenties for his existing portfolio companies such as Uber and Meta.
Actionable Bullet Points
• PSUS Is the Lowest-Cost, Most Transparent Version of Pershing Square: No incentive fees, quarterly shareholder calls, full SEC transparency, and a 24.9% eight-year track record make PSUS the most accessible and cheapest way to invest alongside Ackman. For investors seeking concentrated, long-duration equity exposure, this is the entry point.
• Closed-End Discount Logic Does Not Apply: PSUS should be valued like any high-ROIC business. Ackman’s argument: businesses that earn 19% on equity over 22 years trade at 2–3x book, not at a discount. If performance holds, the fund should trade at a premium. The structural downside risk is limited by permanent capital and liquid underlying holdings.
• Fannie and Freddie Are Core to the Thesis: Ackman is deeply involved with the administration on the Fannie/Freddie privatisation process. This is a multi-year, potentially very large catalyst that could generate significant returns for Pershing Square’s capital base.
• Uber and Meta Are Still Cheap at Today’s Prices: Despite significant gains, Ackman believes these businesses are still undervalued relative to their earnings power. He views recent multiple compression as an opportunity rather than a warning. Model forward earnings for both, not trailing sentiment.
• The Geopolitical Risk Is Temporary; the AI and Capital Investment Story Is Structural: Ackman believes the Iran war is close to resolution and that once it clears, the Fed will be able to cut rates. Massive AI capex, energy investment, and a supportive tax bill all form the backbone of a bullish multi-year thesis for US equities.
Investment Focus
Ackman’s investment framework: own the best large-cap businesses in the world at moments of price dislocation, stay long, and let compounding do the work. The actionable implication is to monitor PSUS at or near book value as the ideal entry point, treat the Fannie/Freddie situation as a free option on a significant multi-year event, and continue to hold or initiate positions in high-quality compounders like Uber and Meta that are still priced below their intrinsic earnings power.
EP 2 - Why the Stock Market Has Become a Casino | Lloyd Blankfein
Lloyd Blankfein — Former Goldman Sachs CEO
Lloyd Blankfein, former CEO of Goldman Sachs who steered the firm through the 2008 financial crisis, discussed wealth inequality, the disconnect between markets and the real economy, and the structural inevitability of credit cycles. He argued that the US economy has significant tailwinds — stimulus from the tax bill, elevated equity markets, likely rate cuts — but that the distributive failure is profound: the gains are going almost entirely to asset owners while wage earners stagnate. He drew explicit parallels between regulatory over-corrections after 2008 and the reduced capacity of regulators to act in the next crisis.
Actionable Bullet Points
• Asset Inflation Is the Core Driver of Inequality — and the Biggest Political Risk: Blankfein was direct: those with assets are getting richer, those without are not. This is not a solvable problem through monetary policy alone. The political response — redistribution, populism, higher taxes — will shape the investment environment for a decade. Reduce exposure to businesses whose pricing power depends on stable consumer sentiment.
• The Market Is Not the Economy — But It Increasingly Drives It: Equities have become reflexive inputs into consumption via the wealth effect and collateral values. A market that reacts to social media posts and ceasefire rumours is functioning as a sentiment machine, not an economic signal. Do not trade on index moves; trade on fundamentals within the noise.
• The Next Crisis Will Be Harder to Manage: Blankfein warned that post-2008 regulatory over-correction removed tools and capital flexibility from regulators and institutions. The political infrastructure to respond quickly is weaker than in 2008. This argues for structuring portfolios with higher-than-average liquidity and avoiding deep illiquidity without commensurate premium.
• Goldman’s Role as Market Maker Is Frequently Misunderstood — and That Misunderstanding Creates Opportunity: The Paulson trade discussion highlights a perennial market opportunity: when public outrage and regulatory narrative create stigma around an asset class or strategy, sophisticated investors can step in at distressed pricing. The short-selling stigma and private credit narrative both create structural mispricings today.
• The Probability of Stagflation Is Not Zero: Blankfein acknowledged the list of structural inflationary pressures — the Iran war, government deficits, military spending — while stopping short of a strong call. He cited stagflation as the worst case scenario. Position a portion of the portfolio explicitly for this outcome through real assets and commodity exposure.
Investment Focus
Blankfein’s framework is sobering: we have good macro tailwinds now, but the structural inequality, political dysfunction, and reduced institutional capacity to respond to the next shock are real long-term risks. The actionable implication is to participate in the equity rally while maintaining a clear exit framework, own real assets as a stagflation hedge, and think carefully about the political economy of the businesses you own — who benefits from the current distribution and who is vulnerable to redistribution policy.
EP 3 - Why Fundamentals Don’t Work For “New Economy” Stocks | Jacob Pozharny
Jacob Pozharny — Bridgeway Capital Management Co-CIO
Jacob Pozharny, co-CIO at Bridgeway Capital Management, presented a systematic, data-driven framework for stock selection that bifurcates the investment universe into “old economy” (where fundamental analysis works) and “new economy” companies (where sentiment analysis and intangible-asset-adjusted metrics must dominate). His Computex-based textual analysis of 150,000+ sentences from CEO/CFO earnings calls and regulatory filings reveals that Asian energy companies are experiencing significant negative sentiment shifts driven by the Iran war’s supply disruption, while specific defensive names like BAE Systems show positive unpriced sentiment. His model requires only a 53–55% batting average to generate meaningful alpha.
Actionable Bullet Points
• Traditional DCF Breaks Down for Intangible-Heavy Companies: Pharma, semiconductors, software, and healthcare companies cannot be valued using classical price-to-book or return-on-equity frameworks because R&D investment distorts both earnings and book value. Apply sentiment analysis as the primary input for these names, and reserve fundamental analysis for old-economy names like autos, real estate, and consumer durables.
• Asian Energy Is Showing Its Most Negative Textual Sentiment Since COVID: Across 150,000 sentence extractions from CEO/CFO calls and filings in the Asian energy sector, sales-related language has turned sharply negative. This is the leading indicator of earnings deterioration and should inform underweight or short positions in Asian energy importers and their downstream buyers.
• BAE Systems and Northrop Grumman Have Positive Unpriced Sentiment: Both defence names have experienced strong positive sentiment shifts that are not reflected in their price returns. This represents a long opportunity in both names. The market has not yet connected the escalating defence budget reality to the stocks’ current valuations.
• Orient HK (Shipping) Has Negative Sentiment That Is Not Priced In — Short Opportunity: Orient HK’s negative sentiment around container shipping disruption has not been reflected in its price. This is a short-side opportunity, driven by the disruption of Asian shipping lanes caused by the Iran war.
• Sell-Side Analyst Dispersion Is a Predictable Alpha Source: Poorly-performing sell-side analysts systematically follow the better ones with a lag. By identifying who the leading analysts are on any given stock, Bridgeway can predict where consensus EPS estimates are heading before the street’s consensus adjusts — a genuinely actionable edge available with public data.
Investment Focus
Pozharny’s framework should reshape how investors approach stock research for intangible-heavy businesses. The direct actionable implications are: (1) go long BAE and Northrop on positive unpriced sentiment, (2) go short Orient HK on negative unpriced sentiment in Asian container shipping, (3) overweight Japan energy companies where sentiment, quality, trend, and value align, and (4) use Bridgeway’s approach as a template for bifurcating your own research process by intangible intensity.
EP 4 - The Market Is Being Managed (And That Tells You Something) | Cem Karsan
Cem Karsan — Kai Wealth & Kai Volatility Advisors
Cem Karsan, volatility expert and macro strategist, argued that the extraordinary 15% equity rally from a 5–10% drawdown has no historical precedent and can only be explained by active, proactive market management by the US Treasury — not by organic market forces. He laid out a specific mosaic of crisis-preparedness actions taken by the administration in April 2026: emergency private credit meetings, cyber security gatherings with AI leaders and bank CEOs, Jones Act energy deregulation, domestic grid infrastructure prioritisation, military auto production conversions, military budget increases, and Hank Paulson floating the idea of a Treasury market backstop facility. The UAE’s exit from OPEC fits the same pattern: a geopolitically necessary bolstering of critical alliances under pressure.
Actionable Bullet Points
• The V-Bottom Was Orchestrated, Not Organic — This Has Critical Implications: Karsan documented the March 29–31 sequence: the apocalyptic tweet, followed within 12 hours by ‘peace in our time,’ timed precisely at quarter-end when JP Morgan gamma positioning made a squeeze maximally effective. The administration is managing markets as a tool, not observing them as an output. This is the most important single insight for positioning: own convexity, not directionality.
• Every Preparedness Action Points to Something Much Worse Than the Market Is Pricing: Emergency meetings on private credit, cyber, Treasury market fragility, military conversions, and a $1 trillion defence budget increase all point to an administration that knows the geopolitical situation is getting worse, not better. The market rallying is the inflation management strategy, not a reflection of the underlying reality.
• Brent Oil at 104 Is the Real-World Signal — Not the S&P at 7,175: The US is incentivised to keep domestic oil prices low while allowing Brent to rise — this pressures China, forces dollar demand, and creates leverage. Brent moving from 85 to 104 while the market rallied confirms the physical reality is deteriorating while the financial reality is being managed. Position: long Brent, long commodity exporters, short Asian importers.
• The Shorts Are Exhausted — The Market Has Less Fuel for a Further Squeeze: CTAs are back in, short positioning has normalised, and the administration’s capacity to engineer another squeeze is declining. Karsan’s base case: slow mean reversion back toward previous levels, managed by headline diplomacy but gravity-constrained. The risk-reward for directional equity longs has deteriorated significantly from the trough.
• Volatility Compression Into June–August Is the Base Case — But a Kinetic Escalation This Month Could Break It: June OPEX vol compression is Karsan’s structural base case for the summer. But May is the most dangerous period: news is turning genuinely bad, the administration’s ability to manage the squeeze is diminishing, and if kinetic escalation occurs, they may not have sufficient firepower to prevent a 4–5% decline. Buy OTM calls on any such dip as the administration will respond.
Investment Focus
Karsan’s framework is the most operationally specific of any macro guest this week. The direct playbook: (1) own convexity via OTM calls rather than directional equity exposure, (2) be long Brent oil and commodity exporters as the real-world signal, (3) short Asian energy importers (Korea, Philippines, India), (4) avoid direct equity shorts while the administration has managed volatility capacity remaining, and (5) treat any 4–5% equity decline in May as a tactical long opportunity — the administration will respond. The medium-term structural trade (inflation, fiscal dominance, dollar erosion) remains unaffected.
EP 5 - Stock Expert: Becoming Rich Is Simple, But You Won’t Do It! | Ben Felix
Ben Felix — PWL Capital CIO & Rational Reminder Host
Ben Felix, CIO at PWL Capital and host of the Rational Reminder podcast, delivered a systematic, research-grounded overview of the most important personal finance and investing principles, from renting versus owning a home to asset allocation to the 10 biggest financial mistakes people make. His central thesis: investing has been essentially solved by index funds, and the hard part is executing the simple strategy through psychology, not finding alpha. His “5% rule” for rent-versus-buy decisions and his endorsement of a 100% equity, globally-diversified portfolio (1/3 domestic, 2/3 international) based on the most controversial paper in finance are his most operationally specific contributions.
Actionable Bullet Points
• Investing Has Been Solved — Execution Is the Problem: A globally diversified low-cost index fund portfolio has historically outperformed the vast majority of professional stock pickers after fees. The only remaining variable is your ability to hold through volatility without selling. The most valuable investment skill today is psychological, not analytical.
• The 5% Rule: When Renting Is Financially Superior to Owning: Multiply the home price by 5%, divide by 12. If you can rent an equivalent home for less than that monthly number, renting is the better financial decision after accounting for mortgage interest, property taxes, maintenance (likely over 2%), opportunity cost of equity, and renovation spending. For most urban markets at current prices, renting wins.
• 100% Equities, 1/3 Domestic, 2/3 International Is the Academically Optimal Long-Term Portfolio: Based on a paper simulating one million potential lifetimes across 39 countries since 1890, the portfolio that maximised retirement consumption and bequest utility was 100% equity — not target-date or 60/40. Bonds are riskier for long-horizon investors because they are devastated by inflation. Apply this as your baseline asset allocation.
• Covered Calls and Thematic ETFs Are Wealth-Destroying Products: Covered call ETFs sacrifice huge amounts of upside for the psychological comfort of income, at enormous implied cost. Thematic ETFs are consistently launched after an asset class has already peaked in valuation. Both are products designed to capture investor biases rather than generate returns. Avoid both categories entirely.
• Earn More, Invest in Rare Skill Stacks, and Optimise Tax First: The single largest financial lever is earning more through human capital investment. The second is holding investments in tax-advantaged accounts (TFSA, RRSP, Roth IRA, 401k) before taking any investment risk elsewhere. Both are higher leverage than stock selection or market timing for most people.
Investment Focus
Felix’s framework is the most practically applicable for individual investors managing their own or their clients’ personal finances. The actionable template: (1) use the 5% rule to evaluate rent versus own, (2) allocate long-term savings to low-cost global equity index funds at ~1/3 domestic and ~2/3 international, (3) maximise tax-advantaged account contributions before taking any taxable investment risk, (4) avoid covered call ETFs and thematic funds entirely, and (5) invest in income-generating skills before chasing investment returns — the compounding on human capital is faster and more reliable than the compounding on financial capital in the early career stages.
EP 6 - 9% Inflation For 10 Years, The Assets That Win Or Break Revealed | Clem Chambers
Clem Chambers — ADVFN Founder
Clem Chambers, founder of ADVFN and a long-standing contrarian macro commentator, made the case for 7–9% structural inflation for the next 5–10 years, driven by the combination of AI-driven capital investment, defence rebuilding, domestic infrastructure, and the Fed’s eventual capitulation to political pressure. He argued that the new Fed chair has already telegraphed dovishness by citing deflation risk — a framing he views as preparation to print money. He is most bullish on Nokia (AI-enabled 6G infrastructure) and Fluor Corp (nuclear construction) as the highest-conviction long ideas, and most cautious on passive investors who will be crushed by inflation while active investors in productive hard assets will thrive.
Actionable Bullet Points
• Structural Inflation of 7–9% for 5–10 Years Is Coming — Position Now: The combination of AI data centre build-out, US military expansion, domestic energy infrastructure, and inevitable Fed monetisation of deficits creates sustained inflationary pressure that passive cash or bond holders will not survive. Hard assets, productive equities, and inflation-linked instruments are the only defence.
• Nokia Is the Highest-Conviction Long — Nvidia Just Put $1 Billion In: Nokia is building out 6G infrastructure with Nvidia’s backing, is European-listed at a historically low valuation, and is one of the few credible non-Chinese mobile infrastructure companies. This is a multi-year theme around AI-enabled mobile infrastructure. Buy Nokia before the market catches up.
• Fluor Corp Is the Nuclear Construction Play — Few Competitors, Massive Demand: Energy security and AI data centre power demand are forcing a nuclear renaissance. Fluor Corp is one of the very few companies that can actually build nuclear power stations at scale. Their order book will grow dramatically; the stock has not fully priced this in.
• The Fed Will Print Aggressively While Claiming to Fight Deflation: Chambers’ reading of the new Fed chair’s language is that ‘deflation risk’ is the cover story for aggressive easing. This is the playbook for monetising government debt. The investment implication is to be short long-duration bonds and long everything that benefits from monetary debasement: gold, real assets, energy infrastructure, and productive equities.
• Gold Is for War — Wait for Taiwan Risk to Clarify Before Re-Entering: Chambers made a specific and unusual call: gold’s recent weakness is correlated with the apparent postponement of a Taiwan invasion following a reported Xi-PLA falling-out. If Xi and the PLA reconcile, gold goes significantly higher. Use dollar-cost averaging to build a position and watch the Taiwan-PLA signals for timing.
Investment Focus
Chambers’ framework is the most inflationary bull case presented this week. The actionable template: (1) buy Nokia as a high-conviction AI infrastructure play, (2) buy Fluor Corp as the nuclear construction winner, (3) be short long-duration government bonds, (4) own energy infrastructure, hard assets, and gold via dollar-cost averaging, and (5) watch Taiwan-PLA news as the signal for when gold is ready to make its next major move. The passive investor holding cash or bonds will see their real wealth erode at 7–9% annually; the active, inflation-aware investor has significant opportunities.
EP 7 - Next Megatrends in Finance | BlackRock’s Rob Goldstein
Rob Goldstein — BlackRock COO
Rob Goldstein, COO of BlackRock, appeared on Odd Lots to discuss the four megatrends reshaping finance — the rise of the buy side, the dominance of technology, the growth of private markets, and the winner-takes-most dynamics of large firms. He described how Aladdin is evolving from a closed expert system to an open, agent-accessible platform, argued that enterprise AI implementation is still in its pre-game phase, and explained how the explosive growth in code being written is the most underappreciated structural change in the financial technology landscape. He also outlined what constitutes edge for investors and asset managers going forward.
Actionable Bullet Points
• Enterprise AI Implementation Has Not Started — The National Anthem Is Still Being Played: Despite individual productivity gains, AI has not yet been implemented meaningfully at the enterprise level. This means the next 2–3 years of AI adoption at major financial institutions will look nothing like the past 2 years. The investment implication: AI-enabling infrastructure (compute, data, integration platforms) has significantly more growth ahead than current valuations imply.
• The Amount of Code in the World Is Going to 10x by 2030 — Multiply All Downstream Implications: BlackRock’s technology portfolio manager predicted code volume increasing by a factor of 10 by 2030, driven by AI coding tools. Every industry that runs on software — which is all of them — will be transformed at a pace and scale not currently priced into most valuations. Underweight businesses whose only moat is software convenience without proprietary data.
• Convenience SaaS Is Structurally Disrupted — Regulatory Moats Are Safe: Goldstein drew a clear line: SaaS businesses that aggregate public information and make it convenient are in trouble; enterprise platforms with proprietary data, deep workflow integration, regulatory compliance, and permission management (like Aladdin and Bloomberg) are structurally advantaged and will become more valuable, not less.
• The Whole Portfolio Approach Is the New Edge: The asset management industry was historically organised around asset class silos. The next wave of growth goes to firms that can manage the whole portfolio — public equities, fixed income, private credit, infrastructure, real assets — in an integrated way. This explains the strategic logic of every major acquisition in the industry.
• Information That Has Not Been Digitised Yet Is the Last Alpha Source: As AI models ingest all available data, the edge shifts to information that is not yet in a model — local contacts, on-the-ground channel checks, conversations with executives in regions where data is sparse. This is the ultimate argument for human network investment and why old-fashioned relationship banking and regional expertise retain their value.
Investment Focus
Goldstein’s framework offers the best inside view of where AI is actually going in finance. The actionable implications: (1) underweight convenience SaaS without proprietary data or deep workflow lock-in, (2) overweight enterprise platforms with regulatory moats, proprietary data, and workflow integration (Aladdin, Bloomberg, Salesforce FS, SS&C), (3) invest in infrastructure that enables the 10x code growth — compute, storage, chip design tools, (4) prioritise firms with genuine whole-portfolio capability for future M&A and partnership potential, and (5) rebuild human information networks in regions and sectors where data is sparse — this is where the last remaining undigitised alpha lives.
EP 8 - Fading the Crowd: How Anson Funds Finds Alpha in Market Chaos | Moez Kassam
Moez Kassam — Anson Funds CIO
Moez Kassam, CIO of Anson Funds, a multi-strategy hedge fund known for its short-selling and activism, shared his current framework for finding alpha by going where the crowd isn’t. His highest-conviction new position is US cannabis companies following genuine descheduling progress, which he believes could deliver 400% returns for the MSOS ETF over a couple of years. He is cautiously watching the SpaceX IPO for both supply dynamics and index rebalancing plays, is rotating into select beaten-down software names on free cash flow, and has moved away from digital asset treasuries as sentiment normalised. His fundamental principle: the expected value of any investment decreases as consensus grows.
Actionable Bullet Points
• US Cannabis Is the Highest-Expected-Value Contrarian Trade Right Now: DEA descheduling removes the 280E tax burden (potentially billions in refunds for multi-state operators), enables banking access, credit card processing, interstate commerce, and institutional custody of shares. MSOS could return 400% from current levels as the regulatory unlock flows through. Buy MSOS or individual multi-state operators now — before the news is fully priced in.
• SpaceX IPO: Buy Pre-Index Inclusion, Sell Day Nine: NASDAQ will add SpaceX to its index on day 10 of trading. The actionable trade: buy before or on IPO, sell on day nine before the index rebalance is fully executed and the rumour becomes news. After day 10, the marginal buyer disappears. Early investors with potentially relaxed lockup structures add supply at the same time.
• Beaten-Down Software at Free Cash Flow Multiples Below the S&P Is a Buy: The market sold off software indiscriminately on AI disruption fears. Companies with recurring free cash flow trading at half the S&P’s multiple, whose cash flow has not actually declined, represent asymmetric long opportunities. The thesis: sentiment recovers before cash flows are impacted, so the re-rating happens before the fundamentals fully prove out.
• Short the SpaceX Also-Rans: The market has bid up dozens of small space, quantum, and AI-adjacent companies on retail euphoria. These companies lack the R&D depth, investor base, and competitive moat to survive competition with the real players. Look for retail-driven price dislocations, absence of institutional ownership, and meme-like trading dynamics as short signals.
• Sentiment Analytics at Scale Is the Only Reliable Edge in Contrarian Positioning: Kassam uses quantitative sentiment tracking — Twitter/Reddit sentiment ratios, institutional trading patterns, short interest dynamics — to identify when consensus has reached an extreme of 90:10 bullish or bearish. At those extremes, anyone who would sell has sold and any catalyst creates a disproportionate move in the other direction.
Investment Focus
Kassam’s framework is the most explicitly contrarian this week. The actionable playbook: (1) buy MSOS or individual US cannabis MSOs as the highest-expected-value contrarian trade given genuine descheduling progress, (2) IPO strategy for SpaceX: buy early, sell day nine, (3) selectively buy beaten-down software with durable free cash flow at below-market multiples, (4) short speculative space/quantum/AI-adjacent names with retail ownership and no institutional backing, and (5) track sentiment metrics at the extremes — a 90:10 sentiment reading in any direction is the primary contrarian entry signal.
EP 9 - Biggest Challenges Ahead: Geopolitics, Private Credit, Cybersecurity and AI | Jamie Dimon
Jamie Dimon — JPMorgan Chase CEO
Jamie Dimon, CEO of JPMorgan Chase, spoke at a conference in Oslo on corporate culture, the risks facing the global economy, the European Union’s structural underperformance, and the implications of AI for financial services and labour markets. He emphasised that cybersecurity is his single biggest institutional concern, that private credit standards have quietly deteriorated across a wide spectrum, and that a bond crisis is probable unless governments act now. He called for a free trade deal between the US and EU as the single most impactful thing that could strengthen the western alliance and arrest Europe’s relative economic decline.
Actionable Bullet Points
• Cybersecurity Is the Single Biggest Risk to Financial Institutions — Not Geopolitics, Not Credit: Dimon cited cyberattacks enabled by AI as the most acute near-term threat to JPMorgan and the financial system. Bad actors are getting stronger and more capable. The investment implication is structural: cybersecurity spending is non-discretionary and growing for every financial institution in the world. Long Palo Alto, CrowdStrike, and any enterprise cyber platform with strong government and financial sector relationships.
• Private Credit Standards Have Deteriorated Across a Wide Spectrum — A Credit Cycle Is Coming: Dimon was precise: assumptions are too aggressive, leverage is a little higher, ratings arbitrage is excessive, covenants are weaker, PIK is more prevalent. Not a catastrophe, but worse than people think when the credit cycle turns. The actionable implication: avoid vehicles with undisclosed private credit exposure and demand explicit mark-to-market from any private credit manager you are allocated to.
• A Bond Crisis Is Coming If Governments Don’t Act First: Government debt refinancing needs are enormous; the foreign buyer base has shrunk; private credit is crowding out Treasuries in some yield zones. Dimon said it plainly: there will be a bond crisis; the question is whether governments act first or wait for markets to force their hand. Remain underweight long-duration government bonds and structure fixed income exposure at the short end of the curve.
• Europe Is Slowly Walking Into a Serious Problem — The Answer Is the Draghi Report: European GDP has declined from 100% to 70% of the US over 25 years. The single market is unfinished; capital markets union has not been completed; regulation is anti-growth. Dimon proposed a comprehensive US-EU free trade agreement as both the economic solution and the geopolitical glue to hold the west together against China and Russia. Long European companies that would benefit from regulatory harmonisation and single-market completion.
• AI Will Be Deployed Aggressively but Labour Dislocation May Happen Faster Than Society Can Adjust: JPMorgan has thousands of AI use cases in production across risk, fraud, marketing, AML, and KYC. Dimon made an unusually honest acknowledgment that AI displacement may occur faster than prior technological revolutions because of the internet’s instantaneous deployment capability. Invest in retraining, manage AI implementation with a focus on redeployment — and be cautious about businesses with high white-collar headcount at risk of rapid AI substitution.
Investment Focus
Dimon’s framework carries the authority of someone running the world’s most systemically important financial institution. The actionable template: (1) structurally overweight cybersecurity — it is the only truly non-discretionary tech spending category, (2) demand transparency on private credit exposure from any manager or vehicle you allocate to, (3) remain underweight long-duration government bonds, (4) long European companies positioned to benefit from potential regulatory harmonisation, and (5) be cautious about white-collar-heavy service businesses facing AI displacement — the productivity upside for lean, AI-enabled competitors is enormous.
EP 10 - AI Risk, Bubbles and Buffett | Paul Tudor Jones
Paul Tudor Jones — Tudor Investment Corp Founder
Paul Tudor Jones, founder of Tudor Investment Corp and one of the most celebrated macro traders in history, discussed the difference between trading and investing, the case for dollar-yen as the next big macro trade, the structural AI safety crisis, and his belief that we are at or near a bubble in US equities at 252% of GDP market cap to GDP. He credited Warren Buffett as the OG of compound interest and offered rare self-criticism about his own short-termism. His most actionable contribution: an urgent call for mandatory AI watermarking as the single most impactful policy intervention available, and a specific dollar-yen trade driven by Japan’s new prime minister as the catalytic event.
Actionable Bullet Points
• Long Dollar-Yen Is the Next Big Trade — Japan Has Its Own Reagan Moment: Japan’s new prime minister has the characteristics of a structural economic reformer — Japan-first, entrepreneurial, Thatcher-like. Japan has $4.5 trillion in net international investment position, mostly unhedged dollar assets. A strong reform mandate causes a currency re-rating. The yen is grossly undervalued. This is a high-conviction macro trade with a clear catalytic moment.
• US Equities at 252% of GDP Are in Dangerous Territory — The Historical Exit Rate Is Brutal: At 252% of stock market cap to GDP, we are far above the 65% of 1929, 85% of 1987, and 170% of 2000. A mean reversion to long-run average PE implies a 30–35% decline, which represents 80–90% of GDP in lost wealth — a catastrophic feedback into consumption, tax revenues, and the deficit. Own equities selectively, not passively.
• Mandatory AI Watermarking Is the Single Most Important Policy Intervention — Advocate for It: Jones made a specific and actionable policy call: make all AI-generated content mandatory to watermark, make violations a felony. This is the minimum required to restore epistemic trust in public information. As an investor, allocate to companies building AI authentication and content verification infrastructure — this will become a regulated requirement.
• The IPO Supply Flood Is the Structural Bear Case for Tech: Jones identified that IPOs (SpaceX, others) will add 5–6% of market cap in new equity supply. For 10 years, buybacks have been retiring 2–3% of market cap annually, creating structural demand. Reversing this flow while hyperscaler capex also consumes their cash flow means tech faces a structural supply-demand headwind. Underweight mega-cap tech on a 12–18 month view.
• The ‘Build-Break-Iterate’ AI Development Model Is the Greatest Unregulateable Risk of Our Era: Jones documented that leading AI scientists at major frontier model companies told him explicitly that meaningful safety intervention will not happen until 50–100 million people die in an AI accident. This is not hyperbole — it is the consensus within the community. The investment implication: own companies that are building AI safety and verification infrastructure, and discount the long-term value of companies whose entire value chain depends on unconstrained AI deployment.
Investment Focus
PTJ’s framework combines the urgency of a genuine macro warning with specific, actionable trades. The actionable template: (1) go long dollar-yen as Japan’s new prime minister creates the catalytic moment for a significant re-rating, (2) reduce overall equity exposure as the supply-demand dynamics for tech deteriorate with the IPO wave, (3) invest in AI watermarking and content verification companies — regulatory mandate will create a large new market, (4) own convexity (via options) rather than outright beta, and (5) do not be long the S&P 500 passively at 252% of GDP — historical evidence says 10-year expected returns from this level are negative.
EP 11 - Everyone is Getting the Energy Trade Wrong: $4 Billion Hedge Fund Manager
Jason Landau — Warah Capital Advisors CIO
Jason Landau, CIO of Warah Capital Advisors, a $4 billion Canadian hedge fund with a 16-year track record, argued that the energy market is materially mispriced because the consensus believes the Iran war will end quickly, discounting the new structural risk premium that should permanently embed in oil prices when 20% of the world’s supply runs through a 16-mile chokepoint that can be shut by a non-military power with drones. He is specifically long Canadian energy producers with long reserve life (CNQ, Tamarack), long Cheniere Energy as an LNG infrastructure toll, and long Welltower as a senior housing demographic play. He has largely exited software, preferring to focus on areas where he has genuine edge.
Actionable Bullet Points
• The Left Tail in Energy Is Massively Mispriced — The War Ceasefire Trade Is a Mistake: Markets are pricing a near-certain quick resolution to the Iran war and a sharp drop in oil prices. Landau argues this probability chain is wrong. Even after a ceasefire, tanker crews need safety confidence, LNG facilities take years to restore, and a permanent risk premium for Hormuz closure should be embedded in all oil models. Go long Canadian oil producers with 30–50-year reserve life.
• Cheniere Energy Is the Definitive LNG Infrastructure Buy: Cheniere is a toll business — they earn a fixed fee to convert US natural gas into LNG and ship it. They have no commodity exposure, ~90% contracted revenue, and are building two additional expansion terminals. Qatar’s LNG facilities being damaged for 3–5 years means the world needs to source LNG from somewhere safer. Cheniere is that somewhere. Long LCNG as a structural position.
• Welltower Is the Demographic Mega-Trend Trade: One in five Americans is now over 65, up from one in eight in 2004. Welltower owns premium senior housing in the US, Canada, and UK where they can raise prices 10% annually and reprice units every two years as residents turn over. This is an inflation-passthrough business with structural demographic tailwinds for the next 20 years. Own it as a core position.
• Software Is Not the Right Hunting Ground Right Now — Warah Replaced Six-Figure Software in Five Days with AI: Landau shared that his two-person risk team vibe-coded a replacement for six-figure enterprise software in five days using AI tools. This is the lived experience that informed his decision to be effectively absent from software as an investment. He simply does not know which companies will survive or die, so he stays away and hunts elsewhere.
• Dollarama Is a Long-Term Compounding Machine — Wait for USMCA Clarity: Dollarama is one of the highest-ROIC businesses in Canada with massive international expansion runway (11 Mexican stores vs 1,700 Canadian stores in a population three times the size of Canada). The near-term risk is USMCA tariff uncertainty affecting China-sourced goods. Wait for negotiation clarity, then accumulate. Long-term target implies 60–70% upside.
Investment Focus
Landau’s framework is the most specific equity-level framework for the energy trade this week. The direct actionable portfolio: (1) long Canadian Natural Resources (CNQ) and Tamarack Valley as long-reserve-life Canadian oil producers, (2) long Cheniere Energy (LCNG) as the definitive LNG infrastructure toll play, (3) long Welltower (WELL) as a demographic compounding machine in senior housing, (4) accumulate Dollarama after USMCA clarity, (5) short space/quantum also-rans with retail ownership and no institutional backing. Avoid software until a clear winner-loser framework emerges — the AI disruption makes it too uncertain to underwrite.
EP 12 - Creating the Winning Strategy and Culture | Ken Griffin — Citadel
Ken Griffin — Citadel Founder & CEO
Ken Griffin, founder and CEO of Citadel, spoke at the Norwegian Government Pension Fund’s conference on how to build a genuine winning culture in a large organisation — one where the most junior person closest to the information makes the decision, where winning is explicitly named as a core value, and where the top 1% talent density creates a self-reinforcing excellence loop. He discussed Citadel’s disciplined approach to GenAI (killing 195 of 200 proposed projects to focus on 5), the importance of aspirations over ambitions when hiring, and the underappreciated competitive advantage of being in a highly regulated industry when AI is the central technology.
Actionable Bullet Points
• Regulated Industries Have a Structural AI Moat — Finance Is Advantaged, Not Disadvantaged: Griffin made a counterintuitive argument: the compliance, permissions, controls, and regulatory infrastructure that regulated industries consider a burden are actually a competitive advantage in the AI era. They create natural human-in-the-loop checkpoints that make AI deployment safer and more trustworthy for clients. This validates the investment case for regulated financial technology platforms versus consumer AI plays.
• GenAI Productivity at Citadel: One Discussion → Functional Prototype in Days: Griffin described a session where a product meeting was recorded, transcribed into a functional specification via AI, debugged autonomously, and delivered as a working prototype in days rather than months. This collapse of the prototype-to-production timeline is the real enterprise AI productivity story — it is about code velocity, not headcount reduction. Own picks-and-shovels infrastructure for this workflow.
• Kill 195 of 200 AI Projects — Focus Wins: Griffin reduced Citadel’s 200 GenAI projects to 5, executed them intensively, and found success in over half. The lesson for capital allocators: diversified AI investment is the wrong strategy. Concentrated, intensively managed AI projects with clear success criteria outperform scattered experimentation. Apply this to how you assess AI strategy at the companies you own.
• The Most Junior Person Closest to the Information Should Make the Decision: Griffin’s management philosophy is the opposite of hierarchy: empower the closest-to-information decision maker, give negative consent (no response = go), and treat agency as a talent development tool. Companies where this is the culture will outperform on execution speed in AI-enhanced environments. Use this as a management quality screen.
• Hire for Aspirations, Competitive Track Record, and Resilience — Not Just Intelligence: Griffin’s hiring filter: people who have competed in any arena (sports, music, debate), have clear long-term aspirations that do not include a magic number at which they stop, and have demonstrated resilience through failure. The best portfolio managers are right 53% of the time and can still come back the next day. Character is the limiting variable, not IQ.
Investment Focus
Griffin’s framework offers the clearest inside view of how the world’s most sophisticated hedge fund is actually thinking about AI and culture. The actionable implications for investors: (1) systematically prefer regulated financial technology platforms over consumer AI plays in your portfolio — regulation is a moat, not a handicap, (2) as a management quality test, ask whether the company’s culture empowers junior decision-makers or creates hierarchy bottlenecks — this predicts execution speed on AI integration, (3) when evaluating AI strategy at portfolio companies, look for concentration and intensity rather than diversification and experimentation.
EP 13 - Stock Market Refuses to Fall? Most Extreme Conviction in 42 Years | Peter Grandich
Peter Grandich — Veteran Market Analyst & Author
Peter Grandich, a 42-year market veteran who called the 1987 crash, the 2000 bubble, and numerous other major dislocations, expressed his most extreme bearish conviction in his entire career. He cited the convergence of passive investing complacency, corporate bond market fragility (particularly the $5 trillion in BBB-rated bonds, 5x the size of the pre-GFC market), a $10 trillion Treasury refinancing requirement, shrinking foreign demand for US debt, and an equity market underpinned entirely by the mechanical flow of passive investment. He argued that process and preparation — not prediction — are the critical edges in the current environment.
Actionable Bullet Points
• The Corporate Bond Market Is the Overlooked Systemic Risk: Triple-B rated investment-grade bonds have grown to $5 trillion — five times larger than at the 2009 crisis. Downgrade to junk for even a portion of this would create a cascade of forced selling across pension funds, insurance companies, and passive bond ETFs. Model your portfolio for this outcome. Be very selective in fixed income allocation and avoid any vehicle with significant BBB credit exposure.
• Passive Investing Has Created the Largest Structural Bull Market Support — and the Largest Potential Trigger for a Crash: Grandich argued that passive investment flows have mechanically supported equities regardless of fundamentals, creating a self-reinforcing illusion of safety. When retail sentiment shifts or redemptions begin, passive managers have no discretion — they must sell. This is the most underappreciated structural risk in the market today.
• Process Beats Prediction in Every Volatile Market: Grandich’s most important lesson: in 42 years, his biggest mistakes have all been emotional — breaking from process under pressure. His framework: write the process before the decision (what triggers entry and exit), execute mechanically, and never decide in the heat of the moment. This applies as much to portfolio management as to trading.
• Private Credit Problems Are Already Unfolding — 1.7 to 2 Trillion in Potential Losses: Grandich cited $1.7–2 trillion in private credit at risk of investors not recovering what they expected. This is consistent with warnings from Howard Marks, Chris Whalen, and Jamie Dimon this week. Treat any private credit vehicle without transparent marks and monthly liquidity as effectively locked capital with unknown duration.
• 42 Years of Bearish Fundamentals at Their Extreme Convergence — This Is Not a Normal Cycle: Grandich was unequivocal: he has never seen more bearish fundamental signals simultaneously than he does today. Passive complacency, record BBB bond supply, Treasury refinancing demand, foreign buyer retreat, equity valuation extremes, geopolitical escalation. None of these is individually fatal, but the convergence is unprecedented in his career.
Investment Focus
Grandich’s framework is the clearest bearish warning of this week’s lineup. The actionable implications: (1) build and follow a written investment process — do not make decisions during the emotional peak of market moves, (2) significantly reduce BBB corporate bond exposure — the downgrade risk is systemic, (3) exit or reduce any private credit vehicle where you cannot access transparent marks and liquidity, (4) maintain high cash or short-duration equivalents as the hedge against passive-driven cascade selling, and (5) do not mistake the mechanical support of passive flows for fundamental value — the two are not the same.
EP 14 - How China Is Winning the Iran War | Jon Alterman
Jon Alterman — CSIS Zbigniew Brzezinski Chair in Global Security
Jon Alterman, former special assistant to the Secretary of State for Near Eastern Affairs and current CSIS chair in global security, provided the most detailed geopolitical analysis of the Iran war available this week. His central argument: the Trump administration systematically underestimated Iran’s grit and the range of tools available to a country that has been preparing for this confrontation for 50 years. Iran’s political economy is embedded with incentives to maintain its pariah status. China is the primary strategic beneficiary — every day the US is committed to the Middle East is a day China can operate freely in the Western Pacific. A ceasefire-by-negotiation is more likely than an outright military victory, and the post-war world may include Iran extracting payment for strait access.
Actionable Bullet Points
• China Is the Strategic Winner of the Iran War — and Has No Incentive to End It Quickly: Every week the US military is committed to the Gulf is a week China operates unchallenged in the Western Pacific. China has observed US weapons systems, exhausted US munitions stockpiles, and allowed an adversary to spend its political capital with allies globally. Position as if the US-China strategic rivalry is intensifying, not stabilising, and own assets that benefit from that intensification: defence, energy independence, US-allied technology supply chains.
• Iran’s Political Economy Is Structured Around Being a Pariah State — The Pathway to Reform Is More Complex Than Assumed: Iranian Revolutionary Guard and clerical foundations profit directly from sanctions circumvention. Removing sanctions without a complete political restructuring may actually strengthen the bad actors within the Iranian system. This means the US is structurally unable to offer Iran the combination of economic relief and political survival that would make a deal viable. Prepare for a longer conflict than the market is pricing.
• The Speed of Military Action Has Outpaced the Speed of Political Change — This Is the Structural Challenge: The US has destroyed 20,000 targets with extraordinary precision and minimal collateral damage, but has not created the political conditions for Iranian capitulation. This mismatch between military capability and political outcome is the core failure. It argues for continued uncertainty and elevated commodity prices regardless of military developments.
• The Strait May Eventually Become a Revenue Source for Iran — A Worse Long-Term Outcome Than Most Model: Alterman raised a scenario where Iran extracts payment for allowing shipping through the strait — effectively a private tax on global energy trade. This would be a profound and permanent change to global energy infrastructure economics. Model this outcome in long-term oil and LNG infrastructure valuations.
• The US-European and US-Canadian Relationship Rupture Will Have Permanent Scars: Alterman was direct: regardless of who wins the next election, the damage to US alliances — Europe, Canada, and key Asian partners — will leave lasting institutional scars. The western alliance’s credibility as a predictable partner has been undermined. This argues for geographic diversification away from US-dependent supply chains and financial systems, and long-term investment in non-US developed market equities.
Investment Focus
Alterman’s framework is the most important geopolitical contribution this week for macro and portfolio investors. The direct actionable implications: (1) position for a US-China strategic rivalry intensification — long defence, energy independence, non-China semiconductor supply chains, (2) extend your Iran war timeline significantly from current market pricing and position commodity exposure accordingly, (3) take the strait-as-revenue-source scenario seriously in long-term LNG and energy infrastructure valuations, (4) begin the process of geographic portfolio diversification away from US-centric supply chains and alliances, and (5) long European and Canadian equities that benefit from the political incentive to rebuild non-US partnerships.
EP 15 - The AI Layoff Trap — Academic Paper
Brett Hemenway Falk & Gerry Tsoukalas — Authors
A new academic paper, “The AI Layoff Trap,” argues that competitive market dynamics will drive firms to automate beyond the socially and economically optimal level. The logic is precise: each firm captures the full cost savings from labour automation, while the demand destruction from reduced consumer income is distributed across the whole market. This creates a classic negative externality — no single firm has the incentive to stop automating, even as the collective over-automation destroys the aggregate demand that all firms depend on. The authors propose a Pigouvian automation tax equal to the demand damage imposed on the rest of the economy as the only structurally correct intervention.
Actionable Bullet Points
• The Automation Arms Race Is Self-Defeating in Aggregate — Firms May Destroy the Demand Their Profits Depend On: The mechanism is clean: workers are consumers. As firms replace workers with AI en masse, they reduce their cost base but also reduce the income base of their customer pool. Each firm’s savings are private; each firm’s demand destruction is socialised. The incentive structure creates systematic over-automation. This is the first rigorous theoretical framework for why AI-driven layoffs may be economically self-defeating.
• Standard Policy Fixes (UBI, Retraining, Capital Taxes) Do Not Address the Core Problem: The authors argue that popular remedies — UBI, worker equity schemes, capital taxes — may help workers but do not correct the incentive for firms to over-automate relative to the social optimum. Only a tax specifically tied to the demand externality would directly address the mechanism.
• A Pigouvian Automation Tax Is the Theoretically Correct Policy Response — Monitor for Adoption: If regulators in any major jurisdiction begin seriously discussing an automation tax tied to labour displacement and demand destruction, this is a significant policy risk for highly automated businesses. Monitor EU, UK, and Scandinavian policy developments closely. Own businesses with pricing power sufficient to pass through such a tax if it materialises.
• More Competition and Better AI Make the Problem Worse, Not Better: The paper’s most counterintuitive finding: as AI improves and competition intensifies, the over-automation problem becomes more severe, not less, because competitive pressure makes firms even less willing to be the first to stop automating. This is the structural case for why AI regulation will eventually become necessary, and why early investment in automation-tax-compliant infrastructure has a structural option value.
• The Biggest Risk Is Not AI Replacing Workers — It Is the Speed of the Replacement Destroying Aggregate Demand: This framing is the most important reframe from the paper. The scenario to model is not mass unemployment per se, but rather a demand destruction feedback loop where automated savings fail to materialise because customers can no longer afford the products. Long pricing power; short volume-dependent consumer businesses in sectors with high AI substitution rates.
Investment Focus
The paper’s framework has direct portfolio implications. The actionable template: (1) long businesses with strong consumer pricing power that can maintain margins even as overall consumer income pressure builds, (2) underweight volume-dependent consumer discretionary businesses in sectors with high white-collar AI substitution rates — the revenue risk is more severe than most currently model, (3) monitor regulatory developments on automation taxation in the EU and UK as an early warning system for the policy response to this paper’s predictions, (4) own companies building AI compliance and audit infrastructure — if automation taxes become policy, firms will need measurement systems to calculate their liability, and (5) apply this demand-destruction framework as a stress test to your portfolio companies’ revenue models: what happens to demand if AI displaces 20% of their customers’ income?
Unlistenable. AI voice is just awful.
Good compilation of topics, thanks!