The Game Was Rigged in Their Favor. 28% Went Bust Anyway | Kris Abdelmessih on How to Size Bets

Barry Ritholtz, Dave Nadig and Matt Zeigler explore why AI's real productivity gains don't automatically translate into an investing edge. From stock picking and market concentration to the financing behind the AI buildout, they separate enthusiasm for the technology from the economics of owning it.Subscribe to Click Beta on Spotify⁠⁠⁠⁠⁠⁠Subscribe to Click Beta on Apple PodcastsIn this episode of Click Beta, Barry Ritholtz and Dave Nadig join Matt Zeigler for a conversation about where AI is already changing their work and where investors should ask harder questions. Barry shares how his team uses AI to analyze portfolio drift and identify clients who may need a rebalance. The discussion also covers client relationships, consumer pricing, creative side projects, and why Barry is increasingly enthusiastic about bonds without calling an end to the equity bull market.Topics covered:Why widely available AI tools may improve research without creating a lasting stock-picking advantageMarket breadth, mega-cap concentration, and the potential impact of large tech IPOsData center financing, credit quality, and the risk of rapid technological changeBarry Ritholtz's use of AI to analyze allocation drift, taxes, and household circumstancesHow better meeting records can strengthen the human side of financial adviceLearning to collaborate with AI and asking better questionsThe debate over dynamic pricing, consumer data, and whose interests AI agents serveBaseball tools, astronomy dashboards, music discovery, and the joy of experimentingDeciding which tasks to automate and which activities are worth doing yourselfBarry Ritholtz's case for bonds, municipal income, and avoiding the reach for yieldFind our guests:Barry Ritholtz — The Big Picture - https://ritholtz.comRitholtz Wealth Management - https://www.ritholtzwealth.comBarry Ritholtz on X - https://x.com/RitholtzDave Nadig's work at etf.com - https://www.etf.comDave Nadig on X - https://x.com/DaveNadigTimestamps:00:00 Meet Click Beta: AI and the stock-picking question05:14 AI concentration and market breadth10:08 Tech IPO valuations and data center financing15:22 Barry Ritholtz: AI and portfolio rebalancing analysis20:58 Can AI improve the human side of financial advice?25:49 Better client questions and better prompts30:13 The AI imagination gap: collaboration versus search36:48 Dynamic pricing and the consumer-retailer arms race41:26 Consumer data and the incentives behind AI agents45:54 Astronomy, music, and testing your assumptions51:18 Automating busywork to make room for curiosity55:39 Creative experiments and choosing what to automate01:00:11 Why Barry Ritholtz is excited about bonds01:04:37 Bonds versus equity income and closing thoughtsLearn more about the Excess Returns podcast network:https://excessreturns.coNo information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

Chris Davis and Robert Hagstrom explore the tension between holding great businesses and keeping a winning stock from becoming too much portfolio risk. Why do two investors who believe in letting winners compound also use 10% position limits?On this episode of 100 Year Thinkers, Chris Davis of Davis Funds and Robert Hagstrom of EquityCompass join Matt Zeigler and Bogumil Baranowski to discuss position sizing, selling mistakes, index concentration and the cost of growth. From Chris Davis’s experience selling Costco to the debate over who will capture AI’s economic benefits, they examine what it takes to hold a business through uncertainty without ignoring risk. Stay for Matt and Bogumil’s closing discussion of the lessons for investors.Subscribe to the 100 Year Thinkers of Spotify⁠⁠⁠⁠Subscribe to the 100 Year Thinkers of AppleTopics covered:Why selling a genuinely great business can be an investor’s most expensive mistakeHow client behavior and fund constraints influence 10% position limitsChris Davis’s concerns about index concentration, momentum and future IPO incentivesRobert Hagstrom on trimming positions as the margin of safety shrinksThe bull-case pre-mortem: asking what could make selling today a mistakeWhat Chris Davis missed about Costco’s growth and ability to adaptWhy identical earnings growth can produce different shareholder returnsWhether AI spending builds durable pricing power or delivers more value to usersHow customer trust and restraint on margins can strengthen competitive advantagesBalance sheets, circular financing and the humility required to size a position⁠Chris Davis / Davis Funds⁠⁠Robert Hagstrom / EquityCompass⁠Chapters:00:00 Holding great businesses and the case for position limits06:47 Robert Hagstrom on concentration and client risk12:40 Index concentration, momentum and IPO incentives19:03 Trimming winners, margin of safety and the Costco lesson30:09 Valuation, return on capital and the cost of growth36:01 Is AI’s capital spending cycle temporary?40:10 AI pricing power: builders versus users45:35 Competitive advantage, margins and customer trust51:45 Balance sheets and circular AI financing55:53 Evaluating the AI investment cycle01:00:23 Matt and Bogumil’s takeaways: position sizing and AI01:10:25 Being an AI user versus an AI investor Learn more about the ⁠Excess Returns podcast network⁠.No information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

Katie Stockton of Fairlead Strategies explains why the S&P 500 can reach record highs while many individual stocks struggle. She sees the bull market as intact, but weaker participation raises an important question for diversified investors: is the pullback creating opportunity, or signaling a more lasting change?In this episode of Excess Returns, Katie Stockton joins Matt Zeigler and Justin Carbonneau to examine market breadth, rising Treasury yields, sector leadership and the signals that would change her outlook. She also explains why the Fairlead Tactical Sector ETF holds roughly half its assets in equities at the time of the conversation, and walks through the charts for gold, oil and Bitcoin.Topics covered:Why narrow leadership can sustain the index while diversified portfolios lagThe difference between an overbought market and a downturn in momentumWhy weak breadth alone is not a reliable market-timing signalSmall-cap support levels and the difference between a relief rally and a lasting recoveryThe Treasury-yield breakout and credit spreads as a longer-term risk gaugeSector relative strength, technology leadership and international market concentrationHow the TACK ETF's rules-based approach produces more defensive positioningGold's role as a potential hedge despite a weakening price trendCrude oil's support and resistance levels and Katie Stockton's Bitcoin outlookThe BNAV ETF's tactical Bitcoin strategy and the risk signals to watch into year-endLearn more about Fairlead Strategies.Follow Katie Stockton on X.Chapters:00:00 The bull market and weakening breadth06:02 Narrow leadership and small-cap weakness13:43 Treasury yields, breakouts and resistance18:56 Credit spreads and sector leadership24:53 TACK positioning, semiconductors and international stocks30:22 Gold, oil and Bitcoin: reading the trends35:30 Bitcoin indicators and the BNAV strategy39:47 Credit, volatility and tech: the year-end risk watch Learn more about the Excess Returns podcast network.No information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

Tom Maher of Hilton Capital Management explains what is changing for small-cap stocks as earnings improve and AI spending reaches beyond big tech. After years of justified large-cap leadership, he sees reasons to revisit smaller companies while remaining selective about business quality, financing needs and valuation.In this episode of Excess Returns, we explore the physical infrastructure behind AI, the case for diversifying beyond the largest stocks, and how Tom Maher finds businesses with improving fundamentals. We also discuss the effects of passive investing, opportunities in reshoring, and why knowing more about a company does not always lead to a better investment decision.Topics covered:Why stronger earnings helped justify large-cap leadership and what could change that balanceHow AI construction and equipment spending can benefit smaller industrial companiesWhy some small companies grow into large caps while others remain smallSelf-funding businesses versus companies that depend on outside capitalUnprofitable index constituents, private equity and the changing IPO marketHow interest rates affect financing costs, valuations and portfolio decisionsWhy ETF flows can move a stock independently of its business fundamentalsFinding improving businesses without mistaking a low valuation for an opportunityEvaluating management incentives, consistency and acquisition decisionsTom Maher's lessons on taking partial profits and reading unexpected stock-price reactionsLearn more about Hilton Capital Management.Chapters:00:00 Tom Maher's outlook: earnings, valuations and risk05:26 Small-cap earnings and AI infrastructure spending11:41 Defining small caps and why some companies stay small16:45 Active management and business quality22:03 Small-cap index quality and companies staying private27:15 Combining stock selection with a macro view32:58 Higher interest rates and portfolio decisions37:04 Passive investing and ETF-driven stock moves41:33 Finding stocks with improving fundamentals51:13 Valuation, consistency and management quality56:39 Reshoring and the industrial recovery01:01:14 Research, profit-taking and investor expectations Learn more about the Excess Returns podcast network.No information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

Ed Yardeni of Yardeni Research explains why he still sees the S&P 500 reaching 10,000 by 2029, even as higher oil prices and bond yields make him more cautious near term. His destination hasn't changed, but the timetable has: he has pushed his 8,400 target to mid-2027 while retaining his Roaring 2020s outlook.In this conversation with Justin Carbonneau and Jack Forehand, Ed distinguishes an earnings-led bull market from a speculative melt-up, explains why retiring baby boomers keep spending, and makes the case for AI's benefits spreading beyond the Magnificent Seven. He also weighs the return of the bond vigilantes, diesel's inflation impact, global diversification and the risks that could challenge his optimistic base case.Topics covered:Ed Yardeni's FEMO: fabulous earnings momentum versus fear of missing outWhy strong earnings can support stocks even as valuation multiples fallThe assumptions behind Ed Yardeni's S&P 500 target of 10,000 by 2029Retiree wealth, consumer spending and Ed Yardeni's G-shaped economyAI, productivity and data as a fourth factor of productionWhy Ed Yardeni favors the “impressive 493” as potential AI beneficiariesCloud revenue, compute demand and the returns on AI capital spendingBond vigilantes, fiscal deficits and the difference between growth-driven yields and a debt crisisHow diesel costs could feed into core inflationGlobal diversification and the bond market's role in guiding Fed policyChapters:00:00 Ed Yardeni's bull case and near-term caution04:26 The Roaring 2020s and retiree spending08:53 Technology and the productivity thesis13:06 AI, economic growth and data as a resource18:22 Why the economy is more than AI spending24:10 AI returns and the impressive 49329:48 Valuations, S&P 10,000 and rising bond yields38:42 Government debt and demand for Treasuries43:34 Diesel inflation and global diversification47:41 Fed policy and signals from the bond market51:55 Yardeni Research's process and tools56:19 Why Ed Yardeni favors a G-shaped economyLearn more about the Excess Returns podcast network:https://excessreturns.co

Andy Constan, Brent Kochuba and Eric Pachman examine rising bond yields, options positioning and the inflation risks facing stocks. What happens if the rate relief traders are betting on never arrives?On this month's Last Call, Jack Forehand and Matt Zeigler connect three perspectives on the market. Andy Constan explains why stronger growth and debt supply can push yields higher without signaling a bond crisis. Brent Kochuba examines options flows that suggest traders are still leaning toward a rebound. Eric Pachman traces the path from refinery constraints and diesel shortages to freight costs and consumer inflation. Jack and Matt close with the investment implications of AI spending, efficiency and adoption.Follow Last Call on Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Last Call on Apple Podcasts⁠Topics covered:Andy Constan on growth, AI capital spending and the supply of debtWhy Andy Constan sees more attractive bonds without calling for a recessionHow higher yields can constrain stock returns even when growth remains strongBrent Kochuba on bond volatility, calm equities and bets on falling yieldsWhy Brent Kochuba is watching both upside surprises and downside riskEric Pachman on crack spreads and why cheaper crude may not mean cheaper fuelHow diesel prices can flow through freight bills into CPIEric Pachman on wage inequality and what national averages missAI spending, productivity and the difference between slower growth and contractionThe practical obstacles to bringing AI agents into everyday lifeChapters:00:00 Rising yields and the outlook for stocks05:26 Andy Constan: Growth, debt supply and higher yields12:01 Why bonds look more attractive after the selloff18:33 Brent Kochuba: Options flows and bets on rate relief23:21 Equity complacency and risks in both directions31:12 Eric Pachman: Diesel shortages, crack spreads and inflation40:06 Wage inequality and the limits of average inflation44:40 AI capital spending, productivity and investment returns50:34 AI adoption, automation and everyday obstaclesLearn more about the Excess Returns podcast network:⁠https://excessreturns.co⁠No information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

Michael Baron of Baron Capital explains his case for AI beneficiaries beyond the biggest tech stocks, including software companies the market fears will be disrupted. He joins Matt Zeigler and Justin Carbonneau to discuss how competitive advantages, management quality, and a long investment horizon shape the firm's growth portfolios.Baron Capital's co-president and portfolio manager walks through the firm's investments in Tesla and SpaceX, from vertical integration and autonomous driving to reusable rockets, Starlink, and the potential for AI infrastructure in space. He also explains why proprietary data may strengthen some software businesses, how the firm manages positions as winners grow, and what would make him sell. The conversation closes with lessons from Ron Baron on curiosity, primary research, and building conviction.Topics covered:Finding growth opportunities across technology, financial services, real estate, and consumer businessesWhy Michael Baron believes some apparent AI losers could become beneficiariesProprietary data and the investment cases for Shopify, Guidewire, FactSet, MSCI, and GartnerTesla's evolution, energy business, and the potential economics of autonomy and softwareSpaceX's reusable rockets, Starlink, and Michael Baron's vision for AI infrastructure in spaceValuing businesses over a long horizon and assessing reliance on key leadersLessons from Ron Baron and the importance of management relationships during market stressLetting winners run while managing concentration, leverage, and portfolio correlationsDistinguishing portfolio trims from selling when a competitive advantage deterioratesWhy Michael Baron believes AI will increase the importance of investment judgmentLearn more about Baron Capital:https://www.baroncapitalgroup.com/Chapters:00:00 Michael Baron on finding growth beyond technology04:16 AI disruption and the opportunity in software10:54 Tesla, Elon Musk, and vertical integration18:33 Long-term valuation and key-person risk23:28 SpaceX, Starlink, and AI infrastructure in space34:11 Lessons from Ron Baron and the firm's future40:08 Evaluating management and competitive advantages47:11 Time as an edge and managing growing positions54:11 When to trim a position and when to sell58:11 Curiosity, primary research, and convictionLearn more about the Excess Returns podcast network:https://excessreturns.coNo information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

How much of your portfolio does a good investment idea deserve? Kris Abdelmessih of Moontower joins Matt Zeigler to explain why having an edge is only part of the decision: position size can determine whether favorable odds translate into long-term growth or damaging losses.Through a coin-flipping experiment and everyday examples, Kris makes the Kelly Criterion accessible without a complicated derivation. The conversation explores the difference between expected returns and compounded wealth, why growth-maximizing bets can still be uncomfortable, and how uncertain probabilities make a case for betting less. From portfolio decisions to insurance and extended warranties, the goal is to build better intuition about how much risk to take.Topics covered:How a favorable coin-flipping game exposed costly mistakes in bet sizingWhy maximizing the expected payoff of one bet differs from maximizing long-term compounded growthHow oversized bets can undermine an otherwise profitable opportunityThe Kelly Criterion's three inputs: probability of winning, probability of losing, and payoffWhy a constant percentage of your bankroll means changing the dollar amount after wins and lossesHow different payoffs change the appropriate size of a betApplying the framework to hypothetical self-insurance and extended-warranty decisionsWhy full Kelly can involve substantial drawdowns, and the tradeoffs of fractional KellyWorking backward from a position size to the odds needed to justify itAllowing for uncertainty in your estimates and preserving capital for future opportunitiesThe essay behind this conversation:After this post you will be sizing bets in your headhttps://www.panoptica.com/after-this-post-you-will-be-sizing-bets-in-your-head/Research discussed:Rational Decision-Making Under Uncertainty: Observed Betting Patterns on a Biased Coinhttps://arxiv.org/abs/1701.01427Kris Abdelmessih's Moontower newsletter:https://moontower.substack.com/Moontower:https://moontower.ai/Kris Abdelmessih on X:https://x.com/KrisAbdelmessihChapters:00:00 Position sizing and the favorable coin-flip experiment04:45 Why a good bet can produce bad outcomes13:49 The Kelly Criterion formula explained18:10 Adjusting your bankroll and accounting for the payoff23:03 Applying Kelly to a self-insurance decision30:25 Full Kelly, drawdowns, and reasons to bet less34:59 Working backward from bet size and evaluating warranties41:09 Volatility drag, uncertain odds, and the experiment's results46:09 How much capital does your edge deserve?Learn more about the Excess Returns podcast network:https://excessreturns.coNo information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

What are headline jobs and inflation numbers missing about the economy investors actually face? Eric Pachman of Data 4 The People joins Matt Zeigler to examine how a changing workforce, rising fuel costs, and differences in household spending could affect inflation, consumer demand, and corporate margins.Using interactive data tools, Eric looks beneath monthly payroll reports, maps changes in America's labor force, and traces how diesel prices can work their way into retail prices. He also shares a grocery-price study that challenged his own assumptions about CPI and explains how he is using AI to make rigorous data journalism more accessible.Topics covered:Why monthly jobs reports need context, including survey uncertainty and revisionsHow to spot unusual industry-level payroll changes and assess the quality of jobs addedWhat county-level labor force trends reveal about aging and rural AmericaEric Pachman's research on foreign-born workers and the limits of replacement assumptionsHow a shrinking supply of workers could create pressure on service pricesHow diesel costs flow through freight surcharges, retailer margins, and consumer pricesWhat to watch for in retailer earnings calls as companies weigh price increasesWhy household income, driving habits, and spending patterns change the experience of inflationWhat Eric Pachman's Kroger study found about CPI, the Thrifty Food Plan, and store brandsUsing AI to test assumptions and expand access to data journalismExplore Eric Pachman's research and interactive tools:https://www.data4thepeople.com/The Men Who Vanished: Testing Labor Market Displacementhttps://www.data4thepeople.com/p/the-men-who-vanishedHow do the government's grocery prices stack up against the real ones?https://www.data4thepeople.com/p/kroger-shelf-vs-cpi-thrifty-food-plan/Chapters:00:00 Introduction and Data 4 The People's mission09:20 Spotting unusual changes in the jobs data18:27 Mapping America's changing labor force27:00 Foreign-born workers, aging, and labor supply34:51 Energy costs and the path to consumer inflation47:49 Why your inflation experience differs from CPI56:12 Personal inflation tools and testing grocery prices1:02:36 AI, data journalism, and challenging your own bias1:11:17 Where to find Eric Pachman's work and toolsLearn more about the Excess Returns podcast network:https://excessreturns.coNo information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

Jack Raines turned $6,000 into roughly $400,000 trading SPACs, then lost $157,000 in three minutes after taking a very different bet. The author of Young Money joins Matt Zeigler to discuss what that experience taught him about investing risk, the urge to chase more, and the time a growing portfolio can cost you.The conversation follows Jack Raines from SPAC warrants and market narratives to a broader question: how do you allocate money, time, and risk to build a life you actually want? They explore the limits of a trading edge, why cheap stocks can get cheaper, and how debt, career choices, and status shape the decisions investors make beyond their portfolios.Young Money: A Field Guide to Wealth and Purpose in Your Twentieshttps://amzn.to/4AtUsDoJack Raines' Young Money newsletterhttps://www.youngmoney.co/Jack Raines on Xhttps://twitter.com/Jack_RainesTopics covered:How Jack Raines grew his Roth IRA through SPAC warrants and pre-merger common shares, and why those positions carried different risks.Why an edge in one corner of the market did not translate into a successful concentrated earnings bet.How a million-dollar target and constant account checking changed Jack Raines' relationship with money and time.What SEC filings, Discord research, and market narratives contributed to his trading process.Why Jack Raines bought Figma after questioning the market's AI narrative and speaking with designers.Applying portfolio thinking to careers, creative projects, and opportunities that change with each stage of life.Weighing retirement saving against other opportunities, and why Jack Raines treats expensive debt as a constraint on taking risks.Escaping the "someday" trap while giving long-term venture investments time to develop.Combining steady income and index funds with independent bets, while treating status as a tool rather than a goal.Why Jack Raines believes investors learn about risk through experience, with stakes they can afford to recover from.Timestamps:00:00 Jack Raines on the lessons of losing money04:57 Inside the SPAC trades and the $157,000 loss15:16 Separating market hype from downside math22:18 Building a life with portfolio principles29:45 Retirement saving, trading obsession, and the cost of time36:56 Debt, freedom, and the trap of waiting for someday44:33 Venture investing: acting quickly and waiting patiently51:03 Using status without making it the goal56:08 The investing lesson experience has to teachLearn more about the Excess Returns podcast network:https://excessreturns.coNo information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.