The Pain Trade Podcast

Latest Episodes:

California at a Crossroads: Ethan Penner on Gavin Newsom, Trump, Reform, and Rebuilding the State Oct 13, 2025

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In this episode of Lead-Lag Live, I sit down with Ethan Penner — independent candidate for California governor and a trailblazer in U.S. commercial real-estate finance — to break down what he calls the “collapse of competent governance” in California.

From a radical tax overhaul to fixing housing and energy costs, Penner outlines how he’d reverse decades of political decay — and why he believes Gavin Newsom’s policies have left the state weaker, poorer, and more divided.

In this episode:
– Why Penner says there’s “absolutely nothing” worth continuing from Newsom’s tenure
– How a single-tax system could revitalize California’s economy
– The real drivers of the housing and affordability crisis
– How bureaucratic red tape adds $100K+ to every new apartment build
– Why leadership grounded in empathy and business discipline matters now more than ever

Lead-Lag Live brings you inside conversations with the financial thinkers who shape markets. Subscribe for interviews that go deeper than the noise.

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AI Today: From Chatbots to Humanoid Robots – Investing in the Full Stack Oct 08, 2025

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Imagine the internet’s 20-year curve compressed into a few years: costs plummet, capabilities skyrocket, and adoption leaps from novelty to necessity. That’s where AI stands today. In this episode, we go deep into the evolution of reasoning models—how chatbots are transforming into agents that plan, code, and act across real workflows. Then, we explore the next frontier: physical AI, humanoid robots designed to operate in human spaces, where the “final mile” of automation requires hands, balance, and judgment.

We break down the full AI stack so you can invest with intent:

Digital AI: From semiconductors and data centers to secure data infrastructure, code generation, and multimodal systems connecting perception to action.
Physical AI: Humanoid ecosystems, including integrators, brains, and bodies. We explain why actuators, harmonic drives, tactile sensors, and manufacturing clusters are today’s critical picks-and-shovels plays.
Investment insights: U.S. leadership in intelligence and commercialization vs. Asia’s manufacturing depth, hype vs. investable opportunities, and a practical portfolio approach balancing concentrated and globally distributed AI exposure.

#AI #ArtificialIntelligence #HumanoidRobots #MachineLearning #AgenticAI

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Mastering Options Basics — Long vs. Short, Covered Calls, and Zero DTE Risks | Live Webinar Oct 08, 2025

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Join me as I sit down with Greg Jensen, Founder of OptionsAnimal, and Eric Hale, Founder of Trader Oasis, to break down the foundations of smart options trading. After our last deep dive into the collar strategy, we’re going back to basics to answer the biggest questions every trader faces.

Greg and Eric explain when it’s appropriate to buy long options, why naked calls are among the riskiest trades you can make, and how to think through strategies like short puts vs. covered calls. They also reveal why zero DTE options are attracting retail traders, the hidden dangers behind them, and the adjustments that separate professional traders from gamblers.

In this webinar:

When to buy long calls or puts — and why conviction matters
Why selling options often beats buying them
Naked calls: unlimited risk and real-world horror stories
Covered calls vs. short puts — which strategy really makes sense
The truth about zero DTE options: opportunities vs. catastrophic risks

Lead-Lag Live Webinars give you exclusive access to deep-dive conversations with industry experts, portfolio managers, and strategists. Subscribe now to gain the insights you need to make smarter, more informed investment decisions.

#OptionsTrading #ZeroDTE #CoveredCalls #LeadLagLive #OptionsAnimal

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Beyond 60/40: Alex Shahidi on Diversification, Inflation, and Risk Parity Investing Oct 07, 2025

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In this episode of Lead-Lag Live, I sit down with Alex Shahidi, Managing Partner and Co-Chief Investment Officer at Evoke Advisors, to explore why traditional portfolio construction is failing investors.
From lost decades in the S&P 500 to the dangers of overconcentration, Alex lays out why diversification is more than a buzzword—and how risk parity creates a framework that can withstand both growth and inflation shocks.
In this episode:
– Why owning the S&P 500 alone exposes investors to hidden
– The lessons from the 1970s inflation era and what they mean
– How risk parity differs from traditional 60/40
– The biggest misconceptions investors have about risk
– Practical first steps investors can take to diversify
Lead-Lag Live brings you inside conversations with the financial thinkers who shape markets. Subscribe for interviews that go deeper than the noise.
#LeadLagLive #Diversification #RiskParity #Investing #Inflation #StockMarket

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Why Gold’s Quiet All‑Time High Matters (and How BAR Lowers the Cost of Owning It) Oct 07, 2025

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A record high without the roar—gold has climbed to new territory while the crowd looks elsewhere. We sit down with GraniteShares founder and CEO Will Rind to unpack why this is the most interesting precious metals cycle in years: a quiet surge powered by falling real yields, relentless debt growth, and a decade‑long shift by central banks toward gold as the de facto alternative to the dollar. Will brings rare perspective from building gold ETFs in the UK, stewarding GLD, and launching BAR, a physically backed gold ETF designed to cut costs and increase transparency.
We dig into the mechanics that matter to serious allocators: why BAR’s 0.17% expense ratio compounds an edge over time, how allocated bars and third‑party audits reduce custody risk, and where gold fits on the efficient frontier as a true diversifier with near‑zero equity correlation. Along the way, we pressure‑test common narratives. Bitcoin gets the headlines, yet gold and BTC have moved in step from key points while official reserves tell a different story. We explore how to read the gold price as a mirror of fiat dilution, not just momentum, and why this rally can coexist with rising policy rates when the bigger forces—deficits and credibility—dominate.
The conversation widens to the rest of the complex. Platinum’s breakout, a persistent supply deficit, and a growing role in hydrogen technologies add torque to a metals allocation that often plays catch‑up as gold leads. For investors hunting income without abandoning diversification, we walk through GraniteShares’ options‑based Yield Boost ETFs—weekly distributions generated by defined‑risk put spreads rather than uncovered calls—to complement core holdings like BAR or a platinum sleeve. If your portfolio still leans entirely on stocks and bonds, this is your cue to reconsider what real ballast looks like when passive flows and public debt keep climbing.
Enjoy the episode, share it with a colleague who still thinks gold is only for crises, and subscribe for more candid, research‑driven market conversations. If it helped you think differently about allocation, leave a quick review—it makes a big difference.
#LeadLagLive #Gold #Bitcoin #Investing #fiat #StockMarket

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Building All-Weather Income with Pass-Throughs and HIPS Oct 07, 2025

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Rate cuts change the math on income, but your cash flow doesn’t have to shrink. We invited Will Rind of GraniteShares to unpack a practical way to keep payouts steady as short-term yields slide: a diversified basket of pass-through securities inside the HIPS ETF that aims for an all-weather stream of monthly income. We dig into how REITs, MLPs, BDCs, and fixed income–oriented closed-end funds each respond to different growth and inflation regimes, and why blending them can smooth the ride when markets lurch.
We walk through the index rules that power HIPS—screening for the highest yields and the lowest volatility within each sector, then equal-weighting the results—and why the pass-through structure matters. Because these entities distribute most of their income and avoid corporate tax, more of the cash makes it to investors, and a return of capital component can improve after-tax outcomes. We also get candid about trade-offs: NAV will move with markets, but the fund has paid the same fixed monthly amount for more than a decade, including through the 2020 shock when many dividend strategies cut or suspended payouts.
From portfolio fit to policy risk, we tackle the real questions advisors and investors ask. Should HIPS be core or a satellite? How does it complement the Agg or government bonds without doubling down on duration or credit? What do expense ratios mean when BDCs are involved, and how should you interpret acquired fund fees? We compare liquid, transparent alternative income to private credit’s lockups and opaque marks, then explore pairing HIPS with GraniteShares’ options-based Yield Boost strategies for those seeking weekly distributions and higher-octane cash flow—recognizing the higher volatility that comes with it.
If you’re planning for consistent cash in a falling-rate world, this conversation offers a clear framework, a battle-tested track record, and practical ways to assemble an income sleeve that pays. Subscribe, share this episode with a friend who manages income portfolios, and leave a quick review to tell us what topic you want us to tackle next.
#LeadLagLive #HIPS #AlternativeYield #Investing #Income #StockMarket

Sign up to The Lead-Lag Report on Substack and get 30% off the annual subscription today by visiting http://theleadlag.report/leadlaglive.

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Boom or Bust: Kai Wu on AI CapEx, Concentration Risk, and the Next Phase of Tech Oct 02, 2025

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In this episode of Lead-Lag Live, I sit down with Kai Wu, Founder and CIO of Sparkline Capital, to break down the AI-driven capital cycle reshaping markets.

From Nvidia’s record-shattering deals to hyperscalers pouring trillions into infrastructure, Kai explains why today’s AI boom echoes past capital cycles—and why investors may be missing the real risk.

In this episode:
– Why mega-cap tech is shifting from asset-light to asset-heavy
– The historic link between rapid asset growth and underperformance
– Why concentration in the “Magnificent Seven” is an overlooked AI risk
– Lessons from the dot-com and railroad booms that apply to AI today
– How to position across the full AI adoption cycle

Lead-Lag Live brings you inside conversations with the financial thinkers who shape markets. Subscribe for interviews that go deeper than the noise.

#LeadLagLive #KaiWu #AI #TechStocks #Nvidia #Investing #Markets

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Fed vs Reality: Jay Hatfield on Outdated Data, Rate Cuts, and Where to Invest Now Sep 26, 2025

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In this episode of Lead-Lag Live, I sit down with Jay Hatfield, CEO of Infrastructure Capital Advisors, to unpack why the Fed keeps getting it wrong—and how investors can actually benefit from the new rate-cutting cycle.

From outdated shelter calculations to overlooked leading indicators, Jay explains why monetary policy needs modernization and where the next opportunities lie as markets adjust.

In this episode:
– Why the Fed’s reliance on lagging shelter data distorts inflation
– How the monetary base drives every economic
– Why small caps and financials stand to outperform in a lower-rate
– The case for preferred, high-yield bonds, and MLPs as overlooked
– How AI-driven energy demand is creating a hidden natural gas

Lead-Lag Live brings you inside conversations with the financial thinkers who shape markets. Subscribe for interviews that go deeper than the noise.

#LeadLagLive #JayHatfield #Fed #InterestRates #SmallCaps #Preferreds #MLPs #AI

Sign up to The Lead-Lag Report on Substack and get 30% off the annual subscription today by visiting http://theleadlag.report/leadlaglive.

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Collar Strategies: Protecting Downside While Keeping Upside Alive Sep 19, 2025

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Learn how professional traders use the collar strategy to protect against downside while keeping upside potential alive. In this session, Greg and Eric from Options Animal break down:
How collars act as a dynamic “insurance policy” for your portfolio
Why risk management matters more than stock picking
Real trade examples with Apple & Nvidia
How to think about diversification beyond “more tickers”
Perfect for investors who want smarter strategies, real-world adjustments, and consistent returns without blowing up accounts.

Sign up to The Lead-Lag Report on Substack and get 30% off the annual subscription today by visiting http://theleadlag.report/leadlaglive.

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Access the AI Revolution — How AGIX Gives Investors Pre-IPO Exposure to AI Unicorns Sep 18, 2025

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Join me live as I sit down with Derek Yan, Director at KraneShares, to explore how the AGIX ETF is reshaping AI investing by giving everyday investors exposure to private AI unicorns like Anthropic and xAI—companies powering the foundation models behind the next wave of enterprise AI.

In this expert-led discussion, Derek explains how AGIX combines public equities with late-stage private companies, the proprietary AI scoring system that drives stock selection, and why model companies are the epicenter of the AI value chain. We also cover AGIX’s performance to date, its dynamic quarterly rebalancing, and how it navigates valuation concerns in a fast-moving market.

In this webinar:

How AGIX gives investors rare access to private AI leaders like Anthropic and xAI
Why foundational model companies could capture the lion’s share of AI value
How the AI Score framework identifies true innovators vs. “AI pretenders”
Why enterprise AI could outgrow consumer AI in scale and profitability
How hybrid ETFs unlock private market access with daily liquidity

#AIinvesting #AGIX #AIETF #privateAI #LeadLagLive

Sign up to The Lead-Lag Report on Substack and get 30% off the annual subscription today by visiting http://theleadlag.report/leadlaglive.

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