Timeless Lessons from a Trend Following Legend | Jerry Parker

In this episode of Excess Returns, Jerry Parker joins us for a deep dive into the philosophy and practice of trend following. As one of the original Turtle Traders, Jerry shares lessons from Richard Dennis and Bill Eckhardt, explores how trend following has evolved over the decades, and offers timeless wisdom on markets, psychology, and risk management. From his early days in the Turtle Trading program to running Chesapeake Capital today, Jerry explains what it takes to survive and thrive as a systematic trader in an uncertain world.Topics covered:• The origins of the Turtle Trading program and what Jerry learned from Richard Dennis and Bill Eckhardt• How trend following has evolved from short-term to longer-term systems• Why trading psychology is harder than following the rules• The role of discomfort and doing “hard things” in successful investing• The design and diversification of a robust trading universe• Risk management, drawdowns, and letting profits run• Why trend following belongs alongside a 60/40 portfolio• How ETFs are expanding access to managed futures strategies• Incorporating crypto and new markets into trend following systems• The internal truths of trend following and why smooth returns can be dangerousTimestamps:00:00 Trading should be hard02:00 The origins of the Turtle Trading program08:00 Evolution of trend following systems12:00 The psychology of following rules16:00 The famous Turtle Trader true/false test20:00 Could the Turtle program work today?23:00 Building a diversified trading universe28:00 Risk management and position sizing32:00 How trend following complements 60/40 portfolios38:00 Managed futures, stocks, and diversification41:00 The rise of trend-following ETFs45:00 Incorporating crypto and futures48:00 Where the strongest trends are now52:00 AI and systematic investing53:30 The internal truths of trend following56:00 The belief Jerry holds that most investors would disagree with

Subscribe on Spotifyhttps://open.spotify.com/show/5IsVVM27KWP6SUW6KN2ifeSubscribe on Apple Podcastshttps://podcasts.apple.com/us/podcast/the-100-year-thinkers-long-term-compounding-in-a-short-term-world/id1845466003Subscribe on YouTubehttps://youtube.com/@excessreturns

Warren Pies joins Excess Returns to discuss why he believes we’ve entered a “Debasement Regime,” what that means for investors, and how it differs from the post-GFC deflationary era. He explains the psychology behind this shift, how it’s changing market behavior, and what it means for asset allocation, gold, bonds, small caps, and the Federal Reserve. This conversation covers macro strategy, portfolio construction, and how investors can adapt to a world focused on protecting purchasing power rather than principal.Main topics covered• The shift from deflation to debasement and what defines this new regime• Why protecting purchasing power is replacing the fear of losing principal• Fiscal policy, deficits, and how politics drive the debasement dynamic• The cyclical vs. secular forces shaping markets today• Labor market analysis and the idea of “malignant stasis”• How bonds fit in a debasement era and when they hedge equities again• Valuations, bubbles, and why Warren sees room for the S&P 500 to rise further• Gold as the key debasement asset and how to manage the trend• Portfolio construction in a 60/40-is-dead world• AI, productivity, and the longer-term implications for growth and inflation• What could ultimately break the debasement regimeTimestamps00:00 Debasement vs. deflation and the new investor mindset07:40 Fiscal deficits, policy shortcuts, and the debasement channel10:25 Reacceleration or illusion: the cyclical economic outlook16:42 The labor market’s “malignant stasis” and what it signals21:17 How Warren values bonds and equities in this environment29:34 Bond vigilantes and the likelihood of a true bond revolt34:00 Valuations, bubbles, and the path to S&P 7,00038:27 Why small caps remain a short against large caps41:37 Value stocks, energy, and timing hard asset rotations45:08 Gold’s breakout and how to manage the position50:00 Portfolio construction in a debasement era54:32 AI’s potential to reshape productivity and demographics57:13 What could end the debasement regime59:46 Managing risk with technicals and conviction with fundamentals

Andy Constan returns to Excess Returns to break down today’s macro environment using his Four-Pillar Framework — growth, inflation, risk premia, and flows. Drawing on lessons from his time at Bridgewater and Brevan Howard, Andy explains how he blends systematic and discretionary approaches to form a clearer picture of markets. He discusses the AI-driven CapEx boom, the economic effects of tariffs, Fed independence under Trump, and why the current setup could produce extreme outcomes in either direction.Topics covered:Systematic vs. discretionary macro investingAndy’s Four-Pillar Framework: growth, inflation, risk premia, and flowsHow AI CapEx is driving growth — and what happens when it stopsTariffs, policy shifts, and their impact on inflation and growthThe Fed’s independence and what it means for marketsRisk premia, volatility, and asset allocation in uncertain environmentsHow major flows and corporate buybacks shape market directionWhy Andy sees a “digital” macro environment with binary outcomesTimestamps:00:00 Intro and setup02:00 Systematic vs. discretionary macro investing14:00 The Four-Pillar Framework explained22:00 Growth outlook and AI-driven CapEx boom33:00 The real impact of tariffs on the economy39:00 Thinking in probabilities and constructing macro portfolios40:00 Fed independence and policy alignment47:00 Labor market dynamics and AI uncertainty48:30 Risk premia and asset allocation56:00 Flows, buybacks, and corporate debt01:00:00 What Andy’s watching next01:06:00 Why macro outcomes have never been more digital

In this episode of Excess Returns, macro strategist Julian Brigden of MI2 Partners joins the show to break down today’s volatile market landscape. Brigden discusses why he believes we’re in one of the most fertile environments for macro investors in decades, the forces driving dollar weakness, inflation, and capital rotation, and how investors can position amid shifting policies, labor constraints, and AI’s uncertain impact. He also explains the risks of U.S. exceptionalism, the fragility of equity markets, and why he’s long everything not tied to the U.S.Topics covered:The role of macro as a “supporting actor” that becomes essential at tops and bottomsWhy this may be the best macro environment in 40 yearsThe policy and market implications of tariffs, immigration, and a weaker dollarPositioning for U.S. underperformance and the case for international assetsHow Brigden uses price confirmation and technical signals in his processThe dollar’s impact on equity and sector leadershipInflation, labor markets, and the “no firing, no hiring” phenomenonWhy AI’s economic impact will take longer than expectedThe probabilities of recession, inflation, and soft landing scenariosFiscal dominance, debt, and the future of financial repressionWhy bonds are “a crap place to have your cash”The fragile reflexive cycle of passive investing and U.S. equitiesLessons for individual investors about thinking independently and avoiding industry “cheerleaders”Timestamps:00:00 Macro at extremes and U.S. underperformance risk02:00 How Brigden uses macro analysis to time markets06:00 Why this is a generational macro opportunity08:00 Tariffs, growth, and the policy shift under Trump12:00 Price confirmation and process discipline15:00 The case for non-U.S. assets and sector rotation20:00 Inflation waves and the labor market’s fragility26:00 AI, uncertainty, and hiring hesitation36:00 Recession vs. reacceleration probabilities42:00 The debt problem and fiscal dominance47:00 Sector positioning and the weak dollar playbook51:00 Passive flows and market reflexivity56:00 The hyper-financialized U.S. economy01:00:00 AI, equity valuations, and risk of disappointment01:01:00 Lessons for investors and independent thinking

Katie Stockton, founder and managing partner at Fairlead Strategies, joins us for her quarterly technical outlook on markets, sectors, and asset classes. In this episode, Katie breaks down what her indicators are showing for equities, discusses the implications of new DeMark signals on the S&P 500 and Nasdaq, and explores opportunities across sectors like healthcare, utilities, and energy. She also analyzes key macro charts including gold, oil, Treasury yields, and the dollar, and explains how investors can use technical analysis to manage risk and identify trends heading into year-end.Main topics covered:• The current technical setup for the S&P 500 and how Katie reads market momentum• The role of moving averages, MACD, and DeMark indicators in her process• Breadth, sentiment, and seasonal factors influencing market direction• Why the AI and tech rally may be entering a more selective phase• Sector analysis: healthcare, utilities, energy, and consumer staples• Trends in financials and what’s driving sector rotations• Overview of the Fairlead Tactical Sector ETF (TACK) and its positioning• The broadening theme, mega-cap leadership, and market concentration• Technical outlooks for gold, oil, Treasury yields, and the dollar• How correlations between bonds and equities are evolving• Key risk metrics Katie is watching into year-endTimestamps:00:00 Introduction and S&P 500 setup04:15 How Katie uses key technical indicators07:00 Reading trend strength through moving averages10:00 Balancing short- and long-term signals12:00 Seasonality and sentiment in the current market15:00 DeMark sell signals on the S&P and Nasdaq18:30 What a correction could mean for the AI trade20:20 Sector rotation and using technicals for allocation23:30 Opportunities in healthcare and energy25:30 Utilities and countertrend setups27:20 Consumer staples and defensive positioning29:00 Financials and recent weakness31:00 Inside the TACK ETF and its strategy34:10 Market breadth and mega-cap concentration37:00 Gold’s breakout and sell discipline using technicals41:00 Oil’s setup and resistance levels43:15 10-year Treasury yield analysis46:20 The dollar index and its key levels48:15 Relationship between stocks and bonds51:10 Final takeaways and closing

In this episode of Excess Returns, we’re joined by Rob Thummel of Tortoise Capital to discuss the critical intersection of energy and technology. Rob explains why “electricity is the new oil” as AI and data center demand reshape global power needs. We explore the future energy mix, investment opportunities across natural gas, nuclear, and renewables, and how investors can position for decades of transformation in the energy ecosystem.Topics covered:How AI is driving a new era of electricity demandThe evolving U.S. energy mix: oil, gas, nuclear, and renewablesWhy electricity is becoming the new oilThe scale of power needed to support AI and data centersOpportunities and challenges in renewables and battery storageThe resurgence of nuclear and the role of natural gasHow U.S. shale transformed inflation and global energy marketsEnergy infrastructure and why it offers steady returnsHow the TCAI ETF captures the “AI infrastructure” opportunityRisks and resilience of the U.S. power gridLessons from 30 years investing in energyTimestamps:00:00 Electricity is the new oil and the future of AI energy demand02:00 The evolving U.S. energy mix and global demand growth08:00 Why electricity, not oil, will power the next economic era11:00 How much power AI and data centers will need15:00 Can renewables meet rising energy demand?20:00 The comeback of nuclear and its challenges25:00 How U.S. shale changed global energy and inflation32:00 Why energy infrastructure is less volatile than commodities36:00 Inside Tortoise’s new AI infrastructure ETF (TCAI)43:00 The rise of digital and electricity infrastructure plays45:00 How Tortoise evaluates investments and valuations49:00 The resilience and future expansion of the U.S. grid52:00 Closing lessons: contrarian investing and energy’s importance

In this episode of Excess Returns, Matt Zeigler sits down with investor and author Bogumil Baranowski to discuss one of investing’s most important mindset shifts: moving beyond cheap stocks to paying up for quality and exceptional opportunities. Drawing on lessons from Warren Buffett, Ben Graham, and his own journey, Bogumil explains how value investing evolves across three key phases—buying cheap, buying good, and learning to pay up. The conversation explores patience, conviction, dead money periods, family wealth stewardship, and how to think about value versus price in a noisy world.Topics covered:• The “cheapest dentist” analogy and why investors chase bargains• The three phases of investor evolution: cheap, good, and exceptional• Lessons from Buffett, Munger, and Graham on paying up for quality• How to hold through drawdowns and dead money periods• Why patience and conviction are the hardest investing skills• Frugality, compounding, and lessons from his grandmother• How long-term family investors think about wealth and stewardship• The difference between price and value in modern markets• How to know when cheap is too cheap and quality is worth paying for• Why great investments are often simple to explain• The story behind his Wall Street Journal essay “The Expensive Truth About Cheap Investments”Timestamps:00:00 Introduction – The cheapest dentist analogy03:00 Why investors love cheap stocks07:00 The evolution from bargain hunter to quality investor09:00 Examples from Ben Graham, Buffett, and Facebook15:30 Conviction, drawdowns, and dead money19:00 Judging success by business progress, not stock price27:00 Lessons from grandma on value and frugality31:00 How Buffett evolved from cheap to quality45:00 Investing for future generations49:00 Invisible wealth and stewardship52:00 The value investor dilemma58:00 Equal-weight vs market-cap indexes59:00 Lessons for the average investor1:02:00 How much research you really need1:04:30 How his WSJ essay came to life and final takeaways

In this episode of Excess Returns, we sit down with Matt Zenz of Longview Research Partners to explore factor investing, evidence-based strategies, and the challenges and opportunities in today’s markets. Matt shares insights from his engineering background, his time at DFA, and his current work running the Longview Advantage ETF (EBI). We cover the nuances of value, momentum, size, implementation, and how investors can think more effectively about long-term returns.Topics covered:Matt’s journey from engineering to investingLessons learned at DFA and the foundation of evidence-based investingDefining factors and what makes them credibleThe role of value, momentum, quality, and size in portfoliosThe challenges of intangibles and redefining valueLarge cap tech dominance, mean reversion, and whether the world has changedFactor timing, valuation spreads, and Cliff Asness’ “sin” frameworkHow momentum can be integrated with value tiltsPortfolio construction: combining factors vs sleeve approachesImplementation challenges for large vs small managersHow Longview manages liquidity, turnover, and trading costsThe potential impact of AI on factor investingFuture opportunities in implementation alpha and ETF designMatt’s biggest investing belief most peers disagree withThe key lesson he would teach the average investorTimestamps:00:00 Value vs returns and factor investing basics03:00 From engineering and Boeing to investing06:15 Time at DFA and lessons in evidence-based investing07:30 What evidence-based investing really means09:25 Defining factors and what makes them valid12:00 Using value, profitability, size, and momentum16:00 Large cap tech dominance and future returns18:00 Mean reversion and whether the world has changed20:00 How long does value need to struggle before it’s “dead”?22:30 Should value be redefined for intangibles?25:30 Intangibles, R&D, and why adjustments add noise27:00 Value’s performance across economic cycles and migration30:00 Interest rates, growth, and value performance32:00 Factor timing and valuation spreads34:15 The role of momentum in timing and implementation35:00 How Longview applies passive-aggressive tilts36:30 Combining factors vs sleeve approaches39:00 How momentum is used in practice41:30 Factor migration and average holding periods43:00 The size premium and whether it still exists44:30 The benefits of being nimble vs large fund families47:30 Liquidity challenges in small cap value52:00 The role of AI in investing54:00 Where implementation adds the most alpha55:30 One belief Matt holds that peers may disagree with57:20 The one lesson for the average investor

In this episode of Excess Returns, we’re joined by Noel Smith, co-founder and CIO of Convex Asset Management. Noel shares his unique journey from biochemistry and the military to market making, high-frequency trading, and running a volatility-focused hedge fund. We dig deep into volatility, regime models, income strategies, dispersion, tail hedging, and more, offering a rare look inside the world of professional options and volatility trading.Topics covered:Noel’s background: biochemistry, military, market making, HFT, hedge fund launchHow markets have evolved since the 1990sWhy volatility is the best source of market informationRegime shift modeling and its role in strategy selectionUsing options for income and the trade-offs investors should understandVolatility harvesting and risk-defined short vol strategiesThe impact of zero DTE options on marketsDispersion trading and correlation dynamicsBond vol arbitrage and volatility surfacesOpportunistic trades like GameStop and meme stocksTail hedging, its costs, and how to monetize hedgesLessons on flexibility, risk, and never being married to positionsTimestamps:00:00 Intro and Noel’s unique background06:00 How markets have changed behind the scenes07:00 Why volatility is the best information source09:00 Regime shift model explained19:00 Using options for income – benefits and risks24:30 Volatility harvesting strategies29:10 What the VIX does (and doesn’t) tell you30:30 Zero DTE options and systemic risk33:20 Dispersion trading explained42:00 Bond vol arbitrage45:00 Opportunistic trades: GameStop and beyond51:30 Tail hedging and rebalancing54:30 Lessons on flexibility and risk management