Episode 230

The One Trade That Changed Everything: A Trader’s Confession - Smart Money Moves for Chaotic Markets 

In this episode veteran options trader and commentator Jon Najarian walks listeners through his path into options trading, revealing the pivotal moment that set his focus and the trade that taught him his biggest lessons in discipline and risk management. Najarian discusses how trade wars, government shutdowns and other macro events shape market behavior, and explains how options‑flow and retail order flow have altered dynamics over the past five years. He outlines the most common beginner mistakes (and corrective habits emphasized by Market Rebellion), shares his approach to trading volatility around earnings and Fed decisions, and describes when he favors defined‑risk structures versus directional plays. Najarian also covers the psychology of trading—managing fear and FOMO—and offers practical coaching tips. Finally, he weighs the benefits and risks of commission‑free/social trading, suggests how regulators should balance access with protection, highlights sectors he’s watching now, and gives long‑term skills and habits for listeners building multi‑decade trading plans.

Guest

Jon Najarian, ‘‘DRJ,” was a linebacker for the Chicago Bears before he turned to another kind of contact sport – trading on the Chicago Board Options Exchange. He became a member of the CBOE, NYSE, CME and CBOT and worked as a floor trader for some 25 years.

In 1990 he founded Mercury Trading, a market-making firm at the Chicago Board Options Exchange (CBOE), which he sold in 2004 to Citadel, one of the world’s largest hedge funds. In 2005 Jon co-founded optionMONSTER and tradeMONSTER. He partnered with private equity firm General Atlantic Partners in 2014 and they sold the firm to E*Trade for $750 million in September of 2016. Today, he is a professional investor, money manager and media analyst.

Jon has earned a reputation in the industry as an options trading expert and pioneer. He developed and patented trading applications and algorithms used to identify unusual activity in stock, options, and futures markets. optionMONSTER, the options news and education site he co-founded, was described by Securities Industry News as “content king of the options business.” For years, tradeMONSTER was consistently rated “Best for Options Traders” by Barron’s and was the first online broker to deploy streaming, desktop-like trading in a web browser.

Jon and Pete invest in and work with start-ups via Rebellion Partners, a venture consulting firm they launched in 2015. In 2016 Jon and Pete co-founded Market Rebellion, a company focused on educating the individual investor.

Formerly, Jon was a 16-year contributor to a variety of CNBC programs including Worldwide Exchange, The Halftime Report, Fast Money, and Power Lunch. Today, you can catch Jon on Fox Business and Market Rebellion’s exclusive, regularly scheduled shows on Market Rebellion TV.

Host

Olyasha Novozhylova @notbasicblonde_

NotBasicBlonde Podcast @nbbpodcast