In this interview, we sat down with Jason Shapiro, a true trading legend and one of the featured traders in Jack Schwager’s Unknown Market Wizards. Jason is a hedge fund manager with more than 30 years of market experience and an incredible track record—over 20 consecutive profitable years without a single losing one. Known for his contrarian approach, he shared powerful insights into how he developed his edge, the mindset shifts that transformed his trading, and the timeless lessons every trader can learn from his journey.
Watch on YouTube: https://www.youtube.com/watch?v=SRhvm7GQl6g
We’re also excited to announce that Jason Shapiro and The Crowded Market Reports have become official partners of Edgewonk. We’re proud to be working together and thank Jason and his team for their trust.
If you’d like to learn more about Jason’s work and his approach to the markets, visit https://crowdedmarketsreport.com and use code "ew15" to get a discount at checkout.
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How Jason Shapiro Found His Edge
Jason Shapiro developed his trading strategy by studying his own losing trades. After years of struggle, he went back through his journal to identify the trades that consistently made money over time. What stood out were trades with strong reward-to-risk ratios—even though many of them had low win rates. For Jason, the win rate became almost irrelevant; it was the size of the winners compared to the losers that truly defined profitability. His edge came from focusing on setups that offered large payoffs despite frequent small losses.
The Turning Point After 10 Years of Struggle
Jason Shapiro’s path to profitability wasn’t quick and it took him a full decade of losses and inconsistent results. He described years where he’d make 200% in one year, only to lose 90% of it the next. This boom-and-bust cycle finally pushed him to a breaking point. After ten years, he decided he was truly done with losing and committed fully to becoming a serious trader. That mindset shift, deciding to treat trading with full seriousness and discipline, is something many traders eventually have to reach before real progress begins.
Clear Risk Rules and Thesis-Based Exits
Jason Shapiro approaches every trade with a risk control process. Each position has a fixed size determined by the entry and stop-loss level and he always knows exactly how much he’s willing to lose before entering a trade. However, unlike many traders, Jason doesn’t use fixed profit targets. Instead, he stays in a trade as long as his thesis remains valid and exits only when the underlying reasons for the trade change. This way, his trades are guided by logic and evolving market conditions, not by arbitrary price levels.
Trade to Make Money, Not to Be Right
Jason Shapiro emphasized one of the most important mindset shifts in trading: your goal is to make money, not to be right. Many traders fall into the trap of wanting to prove themselves correct, arguing with the market, and repeating the same losing behaviors for years without change. Jason explained that he’d rather be wrong and make money than be right and go broke. True progress begins when traders can admit that their current approach isn’t working—because only then can they honestly reflect, adapt, and improve.
Your Methodology Must Fit Your Personality
According to Jason Shapiro, every trader needs a strategy that matches their own personality. You can study and learn from others, but you can’t trade someone else’s beliefs or instincts. Success comes from developing an approach that feels natural to you—one that aligns with how you think and react under pressure. While the lessons of trading are universal—learning from losses, risk management, reflecting, and improving—the actual methods must be personal. The traders who truly grow are those who get tired of losing, learn the hard lessons themselves, and then build a system that fits who they are.
Will AI Replace Traders?
When asked about the future of trading and the rise of AI, Jason Shapiro had a clear answer: retail traders don’t need AI to destroy themselves—history shows they’ve always been good at that on their own. Around 95% of traders fail, not because of technology, but because they don’t take trading seriously or fail to adapt. While AI may change how markets move and how edges are found, it won’t eliminate opportunity. The core challenge remains the same: developing discipline, self-awareness, and a process that works—traits that no algorithm can replace.
Jason Shapiro’s story is a reminder that lasting trading success comes from discipline, self-awareness, and a willingness to learn from failure. His journey shows that it’s not about being right—it’s about staying humble, managing risk, and continuously refining your edge.
