Two Blokes Trading

What Billionaire Traders Don't Want You To Know | Gregory Zuckerman Interview


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Short Description

What Billionaire Traders Don’t Want You To Know, Gregory Zuckerman Interview takes you behind the curtain with one of journalism’s most revered finance reporters, Gregory Zuckerman. In this episode, Zuckerman shares the psychology and secrets of billionaire traders, from why unchecked power and “yes‑men” can lead to failure, to how he manages the tension between breaking billion‑dollar stories and maintaining integrity. He also reveals an intriguing perspective on the role of AI in journalism: how, even when only 30 percent of AI’s suggestions are useful, those contributions can sharpen clarity and strengthen storytelling.

Listen as Zuckerman recounts his decade‑spanning investigative career: uncovering Wall Street scandals like the London Whale, chronicling John Paulson’s record‑breaking subprime trade (The Greatest Trade Ever), exploring the rise of quantitative investing (“The Man Who Solved the Market”), and tracing the high‑stakes race for a COVID‑19 vaccine (A Shot to Save the World). In an industry where timing matters but accuracy is paramount, he explains why thoughtful skepticism and human connection remain essential.


This episode is essential for traders and market observers who want to understand not just the how of investing strategies, but the who, and what they fear.


What You’ll Learn in This Episode

In this interview, you’ll discover the hidden forces that shape elite investing and financial journalism. Gregory Zuckerman demystifies the often unseen vulnerabilities of billionaire traders— how isolation and surrounded by agreement, even the most successful investors become prone to mistakes. He offers a rare window into how high-stakes stories are researched and verified, emphasizing that accuracy must always trump urgency.


You’ll explore the surprising but growing role of AI in journalism. Zuckerman shares how AI tools—though imperfect—enhance the writing process by highlighting weak phrasing, redundant passages, and clarity issues. Learn why combining human judgment with machine insights—“man + machine”—remains the most powerful tool in storytelling and reporting.


Drawing on scoops from John Paulson’s subprime trade to Jim Simons’s quant revolution and the COVID‑19 vaccine saga, he demonstrates how curiosity, persistence, and access to sources underpin the most impactful stories. Whether you're a retail trader seeking competitive edges or an aspiring journalist, this episode delivers actionable insights into strategy, ethics, and the evolving dynamics between humans and technology in finance.


Jonathan Farrelly – Host

Jonathan began his trading journey over 15 years ago, learning from top institutional traders. Over the last nine years, he has educated thousands of retail traders on how to navigate markets effectively. Jonathan's ethos centers on transparency, with the goal of helping both new and experienced traders succeed.


About Gregory Zuckerman

Gregory S. Zuckerman is a Special Writer at The Wall Street Journal with more than 25 years of experience covering finance, energy, biotechnology, and investing. A three-time Gerald Loeb Award winner, he is the author of acclaimed books including The Greatest Trade Ever, The Frackers, The Man Who Solved the Market, A Shot to Save the World, and two inspiring titles for young readers co-authored with his sons, Rising Above and Rising Above: Inspiring Women in Sports

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Two Blokes TradingBy Jonathan (Two Blokes Trading)

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