326 · Jason Berry - This Market Wizard Only Had 5 Losing Months in 14 Years... Here's How

Chat With Traders

Kevin Avery

Business, Investing, Education

4.8 • 2.3K Ratings

🗓️ 24 June 2026

⏱️ 79 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

Transcript

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0:00.0	What would your trading look like if capital wasn't the constraint? That's the reality for most traders.
0:05.1	It's not skill holding them back, it's size. Trade the pool changes that. Step into the U.S. equity markets with up to $200,000 in buying power without committing your own capital. Full access to stocks and ETFs, longer short, executed with the precision and freedom serious traders expect.
0:22.6	Your performance is measured by one standard, disciplined risk management, and consistent execution.
0:27.7	Meet that standard and you operate at scale. No subscriptions, no ongoing obligations,
0:33.0	just a clear path forward. For those ready to trade beyond limitations, this is the next level.
0:39.7	Your team just added its 67th AITL and also your 67th security blind spot. The good news,
0:47.0	the Vantor agent works like a GRC engineer in the background, finding every app your team
0:52.0	uses, scoring the risk and drafting fixes for you.
0:55.6	Vanta is the platform used by over 16,000 fast-moving companies like Synthesia, Nandoz, and Granola,
1:02.7	who are shaping the future with AI and staying ahead of AI risk. Get started at vanta.com.
1:09.9	Trading in the financial markets involves a risk of loss.
1:12.7	Podcast episodes and other content produced by chat with traders are for informational or
1:17.0	educational purposes only and do not constitute trading or investment recommendations or advice.
1:22.5	And I find the rule in trading is that if it is difficult, it's the right decision,
1:26.8	whereas if it's easy, it's the right decision, whereas if it's easy,
1:27.7	it's the wrong decision.
1:28.9	I'm writing that down.
1:30.2	Generally speaking, the harder it is and more difficult it is to do is because you're
1:34.3	fighting the natural human emotion or the natural human choice.
1:38.4	And the natural human choice is to hold a loser and hope that it turns into a winner.
1:42.9	And the natural human choice for winners is to take the money off the table as soon as it's showing green.
1:48.0	I think one thing that stands out for me from when I started in the beginning, in the late 90s, early 2000s,
	...

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