In this powerful episode of Risk On, we step into the dramatic and often jaw-dropping life of Jesse Livermore – the man who shorted the 1907 and 1929 stock market crashes and walked away with millions, only to lose it all multiple times. Known as the “Boy Plunger” and the “Great Bear of Wall Street,” Livermore's career is a gripping tale of triumph, tragedy, and timeless trading wisdom.
We break down:
Livermore’s legendary trades during the 1907 Panic and the 1929 Crash
The trading principles that made him millions – and the lapses that cost him everything
Why Reminiscences of a Stock Operator is still required reading for traders
How Livermore might approach today’s algorithm-driven markets
Practical takeaways for swing and intraday traders, blending Livermore’s wisdom with modern tools
Packed with quotes, dramatic storytelling, and insights for traders of all experience levels, this episode is both a tribute and a tactical guide. Whether you’re trading from your laptop or managing institutional capital, Livermore’s rules on trend-following, risk control, and patience remain essential.
📘 Episode Highlights:
1907: Short-selling through chaos – how Livermore made millions during a panic
1929: The ultimate contrarian play – how he foresaw the biggest crash in history
How he read the "tape" before indicators even existed
What Livermore would do with Level II, algos, and order flow today
How to apply his principles in real trades right now.
🔔 Subscribe now and don’t miss next week’s episode, where we unpack the Comparison Trap and the impact of Social Media and the Illusion of Trader Success.
📚 References (Alphabetical):
Lefèvre, E. (1923). Reminiscences of a Stock Operator. George H. Doran Company.
O’Neil, W. J. (2002). How to Make Money in Stocks. McGraw-Hill.
Seykota, E., Schwager, J. D. (1992). Market Wizards: Interviews with Top Traders. Wiley.
Smitten, R. (2001). Jesse Livermore: World's Greatest Stock Trader. Wiley.
TraderLion. (2021). Jesse Livermore's Trading Rules. www.traderlion.com
Tudor Jones, P. (2004). Paul Tudor Jones Interview – Market Wizards Series.
Unknown Author. (n.d.). The Wisdom of Jesse Livermore. Various collected quotes and archives.
Wikipedia contributors. (2024). Jesse Livermore. Wikipedia.
