Jason Shapiro: Positioning Over Prediction

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 Breitstein
Episode249     Jack Kellogg
Episode036     Peter Brandt
Episode255     Vincent Bruzzese
Episode212     Kristjan Kullamägi
Episode286     Jason Shapiro
Episode260     Patrick Petersson
Episode259     Lukas Frölich (The Short Bear)
Episode163     John “Rambo” Moulton
Episode250     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-making
08:25 — 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 consistency
15:55 — Sunny Harris - Taking control after realizing professionals can lose, too.
17:30 — Closing reflections
20:20 — 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.

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