Chat With Traders

320 · Stefan Stadie - Sports Betting and Prediction Markets - Through a Trading Lens

Stefan Stadie is a professional sports trader at Kero Sports whose work sits at the intersection of equities, sports betting, and prediction markets. After starting his trading journey in equities, Stefan evolved toward a more process-driven approach focused on price, liquidity, and market behavior. Today, his edge comes less from predicting outcomes and more from identifying mispricing, capturing inefficiencies, and operating across multiple markets in real time. In this conversation, Stefan shares how the same principles—crowd psychology, liquidity, and price discovery—show up across different environments, from stocks to sports to decentralized prediction markets. He also walks through his transition into arbitrage and market making, how he approaches risk, and what it takes to stay disciplined when operating in fast-moving, competitive markets. This episode offers a different lens on trading—one that challenges traditional thinking around prediction, edge, and where opportunity actually comes from. In this episode, we explore: ·        Why trading principles can transfer across completely different markets ·        The role of liquidity and crowd behavior in shaping price ·        Moving from directional trading to arbitrage and market making ·        How mispricing creates opportunity across fragmented markets ·        The reality of being limited or banned by sportsbooks ·        Differences between traditional financial markets and emerging prediction markets ·        Managing psychology and discipline in fast-moving environments ·        Why focusing on price—not opinion—can change your approach to trading About Stefan Stadie: Stefan is a professional sports trader at Kero Sports, specializing in market structure, arbitrage, and market making. He also trades equities and participates in prediction markets, applying a consistent framework centered on liquidity, psychology, and price discovery across different trading environments.   Links + Resources: ·        X (Twitter):  https://x.com/BronzeBeardd   Sponsor of Chat With Traders Podcast:  ●       Trade The Pool:  http://www.tradethepool.com   Time Stamps: Please note: Exact times will vary depending on current ads.  00:00 Introduction 04:39 Early life, education and entry into oil & gas06:18 2020 oil crash and negative crude prices08:14 Early trading career, swing trades and going full-time09:18 Trading mistakes, position sizing and risk management11:33 Trading during the COVID crash and learning resources12:41 Transition to short selling and strategy shift14:14 Liquidity events and shorting tactics16:53 Entry into predictive markets and sports betting18:23 Arbitrage strategies and OddsJam scanner21:38 Bans from retail sportsbooks and joining Kiro Sports26:37 Polymarket, peer-to-peer exchanges and crypto betting29:04 How prices are set and market-making basics35:32 Market-making tactics, spreads and target returns40:31 Directional positions and daily activity in predictive markets41:43 Parlays, selling parlays and house edge44:10 Growth, regulation and insider-risk in prediction markets49:20 Comparisons with financial markets: liquidity, edge and crowds01:01:54 Gamification, responsible use, psychology and advice for newcomers01:10:00 Closing remarks and contact information   Trading Disclaimer:  Trading in the financial markets involves a risk of loss. Podcast episodes and other content produced by Chat With Traders are for informational or educational purposes only and do not constitute trading or investment recommendations or advice. Learn more about your ad choices. Visit megaphone.fm/adchoices

319 · Sam Gaer - From the Copper Pits to Crypto Derivatives: How Trading Edge Evolves

Sam Gaer’s career spans several major shifts in market structure — from the open-outcry pits of COMEX to high-frequency trading and now crypto derivatives. Sam began his career as a teenage runner on the COMEX floor during the gold boom of the early 1980s before becoming a copper pit trader himself. While most traders relied purely on instinct, Sam was already experimenting with technology — building early pricing tools that helped identify inefficiencies in spread markets. His path eventually led beyond the trading floor into exchange technology and market infrastructure, including building trading software that was later acquired by the New York Mercantile Exchange. In recent years, Sam has focused on crypto markets, where he applies traditional derivatives frameworks to volatility, options, and digital asset trading. In this episode, Sam shares insights from decades of experience across multiple market regimes and discusses how trading edge evolves as markets and technology continue to change. In this episode, we explore: · Getting introduced to markets as a teenager · Life inside the COMEX copper trading pits · Early use of computers to price commodity spreads · Inefficiencies in open-outcry markets · Building exchange technology and selling Trading Gear to NYMEX · The transition from pit trading to electronic markets · Market structure lessons from traditional derivatives markets · Why Sam shifted his focus to crypto markets · Opportunities in crypto options and derivatives · Convexity, volatility, and institutional trading frameworks in digital assets About the guest: Sam Gaer, Chief Investment Officer of the Directional Strategy at Monarq Asset Management, has more than three decades of experience across derivatives trading, exchange technology, and quantitative strategy development. He previously served as Chief Information Officer of the New York Mercantile Exchange (NYMEX), where he helped modernize the exchange’s trading infrastructure. Earlier in his career, he was a floor trader on the COMEX commodities exchange and later founded Trading Gear, a technology firm whose trading software was acquired by NYMEX. Sam has also launched and managed quantitative trading strategies focused on derivatives and volatility markets, and today works on institutional trading approaches within digital asset markets. Links + Resources: · Website:  https://www.monarq-am.com · Email:  investors@monarq-am.com Sponsor of Chat With Traders Podcast:  Trade The Pool:  ⁠http://www.tradethepool.com Time Stamps: Please note: Exact times will vary depending on current ads. 00:00   Intro and Background 01:48   Early career: COMEX runner to copper pit trader06:40   Programming background and early trading automation16:19   TradingGear: pivot to exchange software and NYMEX sale / CIO role21:09   Trading style evolution: scalping to event-driven and electronic trading23:42   High frequency trading, FINRA experience and entrepreneurship25:09   Transition into crypto: Katana Financial and early crypto market making28:01   Crypto derivatives focus: options, convexity and strategies34:19   Recent crypto market decline: causes, liquidations and regulatory uncertainty39:51   Institutional adoption, ETFs (IBIT) and market-structure impacts42:57   Tokenization, real-world assets and digital asset treasuries (DATs) 56:17   Reflections on markets, challenges and use of AI 58:36   Closing remarks and contact information   Trading Disclaimer:  Trading in the financial markets involves a risk of loss. Podcast episodes and other content produced by Chat With Traders are for informational or educational purposes only and do not constitute trading or investment recommendations or advice. Learn more about your ad choices. Visit megaphone.fm/adchoices

318 · Dave Mabe - The Shift to Systematic Trading — Building Backtested Confidence

When Dave Mabe backtested his strategy, it outperformed his own discretionary trading — and changed how he approached everything. In this episode, we discuss gapping breakouts, expectancy, systematic trading, drawdowns, and the reality gap between backtests and live execution. A practical conversation for traders serious about building durable edge. In this episode, we explore: ·        How Dave got introduced to markets: From early exposure to investing through his family to actively seeking more control over his capital and moving from swing trading into day trading. ·        Why rules matter: The transition from discretionary decisions to systematic frameworks — and why trading without a process is a fast path to inconsistency. ·        Backtesting as a “superpower”: What backtesting really does for strategy development and confidence in your edge. ·        Reconciling backtests with real life: Practical realities of execution, slippage, and market structure — and how to build a feedback loop so your live results get closer to your imulations. ·        Drawdowns and mindset: How to handle periods where a strategy doesn’t behave as expected, and why many traders quit in drawdowns rather than at all-time highs. ·        Scaling a trading business: The difference between scaling size versus scaling breadth — and why uncorrelated strategies matter. ·        Practical first step for systematic traders: How to start adding structure to your trading with backtesting, even if you’re not a programmer.   About the guest:   Dave has been a professional trader and technologist for over two decades. As a former CTO of Trade-Ideas, he has unique experience at the intersection of algorithm design, real-time market data, and automated execution. Outside trading, he writes a popular daily newsletter on backtesting and systematic strategy development, and hosts the Line Your Own Pockets podcast focused on systematic approaches to markets. Links + Resources: · Link to Better Backtesting —Dave’s free multi-day email course on building strategies and improving them over time. · Trade-Ideas, Amibroker, RealTest — examples of backtesting and strategy development platforms discussed in context.   Sponsor of Chat With Traders Podcast:  Trade The Pool:  http://www.tradethepool.com Time Stamps: Please note: Exact times will vary depending on current ads. 00:00 Intro and Background 08:29 Stock Selection and Systematic Trading Rules 11:32   Position Sizing, Expectancy and Risk Management 16:50   Discovering Backtesting and First Backtests 18:40   Backtesting Principles, Sample Size and Common Pitfalls 20:34   Gradual Automation and Live Trading Implementation 22:17   Trading Journal and Reconciling Backtest vs Live 27:27   Scaling through Automation: More Trades, Better Results 29:26   Drawdowns, Psychology and Handling Setbacks 34:14   Tools, AI and Software for Backtesting and Coding 39:56   Common Trading Myths Debunked (Partials, Stops) 48:01   Getting Started: Practical Steps, Resources and Closing   Trading Disclaimer:   Trading in the financial markets involves a risk of loss. Podcast episodes and other content produced by Chat With Traders are for informational or educational purposes only and do not constitute trading or investment recommendations or advice. Learn more about your ad choices. Visit megaphone.fm/adchoices

317 · John Assaraf - The One That Shows Up — The Identity You Practice

In this episode, Ian sits down with John Assaraf, entrepreneur, behavioral neuroscience educator, and founder of NeuroGym, for a conversation about the invisible forces that shape performance — long after planning, analysis, and good intentions are in place. John shares his personal journey from a turbulent upbringing to building multiple multimillion-dollar businesses, and the pivotal moment at age 19 that reframed how he thought about success, identity, and commitment. From there, the discussion moves into the neuroscience behind habits, automatic behavior, fear, and why people often snap back to familiar results — even when they know what to do. This is not a trading tactics episode. It’s a conversation about execution, follow-through, and the human side of performance — in trading, business, health, and life. About the guest: John Assaraf is a serial entrepreneur who has built multiple multimillion-dollar companies, including helping scale a real estate organization to over $4 billion in annual sales and co-founding a technology company that later went public on the NASDAQ. He is the founder and CEO of NeuroGym, where he focuses on applying neuroscience to performance, habits, and behavior change. John is also the author of several New York Times bestselling books, translated into dozens of languages, and has been featured in films such as The Secret, where many people were first introduced to his work.   Links + Resources:  Free eBook: The Power of Visualization    Sponsor of Chat With Traders Podcast:  Trade The Pool:  http://www.tradethepool.com   Time Stamps: Please note: Exact times will vary depending on current ads.   00:00   Intro and Background 11:16   Mindset Shift: Interested vs. Committed 11:46   Behavioral Neuroscience and Goal Achievement 16:17   Conscious vs. Subconscious Mind 17:12   Creating Permanent Behavioral Changes 21:22   Emotional Regulation and Decision Making 25:30   Overcoming Self-Sabotage 35:20   AddressingFear in Decision Making 42:37   Inner Size: Exercising the Mind 44:27   Self-Sabotage and Financial Set Points 48:21   The Science of Goal Setting 50:17   Visualizing and Embodying Goals 54:40   How to reach John   Trading Disclaimer: Trading in the financial markets involves a risk of loss. Podcast episodes and other content produced by Chat With Traders are for informational or educational purposes only and do not constitute trading or investment recommendations or advice. Learn more about your ad choices. Visit megaphone.fm/adchoices

316 · The Turning Points That Shaped Great Traders

Over the years, we’ve recorded hundreds of conversations with traders across different markets, strategies, and generations. And while no two trading paths look the same, certain moments tend to repeat — not moments of big wins or dramatic calls, but quieter turning points. The moments where something shifts internally. Where progress depends less on the market… and more on how the trader evolves. In this special episode of Chat With Traders, we revisit excerpts from past conversations with traders who reached those inflection points — moments that reshaped how they thought about risk, discipline, accountability, and longevity. It’s a collection of turning points — the decisions, realizations, and hard lessons that changed the trajectory of a trading career. Links + Resources: Episode039     Tom Dante      Episode236     Lance BreitsteinEpisode249     Jack KelloggEpisode036     Peter BrandtEpisode255     Vincent BruzzeseEpisode212     Kristjan KullamägiEpisode286     Jason ShapiroEpisode260     Patrick PeterssonEpisode259     Lukas Frölich (The Short Bear)Episode163     John “Rambo” MoultonEpisode250     Sunny Harris Time Stamps: Please note: Exact times will vary depending on current ads.  00:00 – Intro and Background 01:10 — Tom Dante - A moment of accountability that forced change — and lit a competitive fire.02:35 — Lance Breitstein - Why the best traders bet exponentially when the odds are truly skewed.04:00 — Jack Kellogg - The cost of obsession, burnout, and relearning how to live after the grind.05:25 — Peter Brandt - Market tuition, mistakes, and committing fully to a process (Featured in Jack Schwager’s Market Wizards)06:55 — Vincent Bruzzese - How wealth mindset — not strategy — shapes risk and decision-making08:25 — Kristjan Kullamägi - Scaling up, earning the right to push risk, and long-term conviction 09:55 — Jason Shapiro - Contrarian trading, positioning over prediction, and embracing discomfort (Featured in Unknown Market Wizards)11:25 — Patrick Petersson - The lesson learned at absolute rock bottom — and the cost of not cutting losses.12:55 — Lukas Frölich (The Short Bear) - Running trading like a business — and how progress compounds quietly.14:25 — John “Rambo” Moulton - Detaching from money to trade with clarity and consistency15:55 — Sunny Harris - Taking control after realizing professionals can lose, too.17:30 — Closing reflections20:20 — Outro / End Sponsor of Chat With Traders Podcast:      Trade The Pool:  http://www.tradethepool.com Trading Disclaimer:  Trading in the financial markets involves a risk of loss. Podcast episodes and other content produced by Chat With Traders are for informational or educational purposes only and do not constitute trading or investment recommendations or advice. Learn more about your ad choices. Visit megaphone.fm/adchoices