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Chat With TradersConversations with talented traders Author: Kevin Avery
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326 · Jason Berry - This Market Wizard Only Had 5 Losing Months in 14 Years... Here's How
Episode 326
Wednesday, 24 June, 2026
Jason Berry co-founded Positive Equity in 2008. Built alongside partners and traders who raised the bar, the firm operates trading floors in Ireland and Croatia. Over a 14-year stretch of verified clearing statements, his small losses, long career approach resulted in only five losing months.Most people think trading success comes from predicting markets. In reality, Jason's multi-decade longevity proves that true consistency comes from deep discipline, strict risk control, and surviving long enough for compounding to work, earning him a featured chapter in Jack Schwager's book, Market Wizards: The Next Generation.In this conversation, Jason pulls back the curtain on his journey from a remote Northern California commune to the chaotic trading floors of London and Dublin. He breaks down the realities of managing a decaying edge, his framework for identifying raw talent in trainees, and why surrounding yourself with a team of disciplined professionals is the ultimate source of career longevity.In this episode, we explore:· How Jason transitioned from an isolated childhood to the chaotic London trading floors· The hidden edges of the open outcry era and the nature of "elbow trades"· What Jack Schwager and the Market Wizards team look for when verifying a trader's record· The structural reality of Jason's risk-reward framework· Why summer vacations can cause traders to become rusty and lose touch with the market tape· How to spot decaying market edges through the P&L before they do catastrophic damage· The core personality traits and tells that separate successful trainees from those who fail· Jason’s outlook on which traders will survive the next decade of AI and machine learning About Jason Berry:Jason is a professional futures trader, co-founder of Positive Equity, and a featured market wizard in the book, Market Wizards: The Next Generation. Over a career spanning nearly 30 years, Jason has documented a legendary track record of consistency and durability. He has trained well over 200 traders, expanding his operations from Dublin to Croatia while championing a team-driven approach to market mastery. Links + Resources:X (Twitter): https://x.com/JasonHBerryLinkedIn: https://www.linkedin.com/in/jasonhberry 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 He Only Had 5 Losing Months In 14 Years 03:09 Introduction To Trading 09:33 Using Elbow Trades As An Edge 16:22 What Your Risk-Reward Looks Like 20:34 Can You Make A "Mr. Consistency" System? 25:29 What You Possess That Others May Also Have 30:23 Why You Get Rusty When Taking A Summer Vacation 35:56 How Important It Is To Constantly Innovate 38:51 What Traits You Can See In Your Trainees 45:10 The Single Greatest Rule In Trading 51:35 How Do You Scale Positions? 55:54 Which Traders Do You Think Will Survive The Next Decade? 59:45 Trading Euro Stocks 01:03:05 What The Next 30 Years Look Like For You 01:08:30 Have You Had Your Trainees Outperform You? 01:09:34 What Your Advice Is To Traders 01:14:11 Where Can You Find Jason Berry 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
