Trading Without Stress: Tom Basso’s Secrets on Systems, Risk, and Longevity offers an in-depth look into the mind and methodology of one of the most respected traders in the world, Tom Basso. Also known as “Mr. Serenity,” Tom has spent over 50 years in the markets developing a calm, logic-based, and system-driven trading approach. In this episode of Two Blokes Trading, we explore how he blends systematic trend following with volatility-based position sizing, all while maintaining a stress-free, balanced lifestyle.
Listeners will gain powerful insights into trading psychology, automated systems, and the often-overlooked importance of emotional discipline. From the evolution of AI-assisted trading to building retirement-friendly strategies, Tom walks us through his journey from managing hedge funds to trading on a cruise ship with a Starlink connection. Whether you’re a beginner or seasoned trader, Tom’s perspective on long-term consistency, diversification, and automation provides actionable takeaways to elevate your trading.
If you’re interested in topics like systematic trading, position sizing, risk management, and developing a mindset for success, this episode is a must-listen. Learn how to trade smarter, reduce stress, and build strategies that last.
💡 What You’ll Learn in This Episode:
In this episode, Tom Basso — legendary trend follower and original “Mr. Serenity” — shares the trading mindset and systematic processes that have allowed him to thrive in markets for over five decades. You’ll learn how to integrate trend following trading psychology with logical systems to trade more effectively and sustainably.
Tom explains how volatility-based position sizing allows traders to adjust automatically to market conditions, reducing risk and optimizing returns. He discusses how to leverage AI tools such as GPT and Co-Pilot to automate tasks even if you’re not a professional coder, showing that systematic trading is more accessible than ever before.
Crucially, Tom walks listeners through the emotional habits and mindset that underpin trading longevity. Rather than obsessing over every market tick, he advocates treating each trade as one of the next 1,000 — a practice that fosters objectivity and detachment. He also explores how diversification across timeframes — from short-term day trades to longer trend positions — can reduce drawdowns and improve consistency.
Whether you’re looking to automate your trading, reduce psychological pressure, or simply want to learn from a master who still trades from his mountain home or even at sea, Tom’s principles are deeply relevant. This episode is a blueprint for achieving success in today’s fast-moving markets — without sacrificing peace of mind.
Hosts
Jonathan Farrelly – Host
Jonathan started his trading journey over 16 years ago, learning from some of the best institutional traders in the world. Over the last 9 years Jonathan has taught 1000’s of retail traders how to successfully navigate the financial markets. Jonathan’s ethos has always been based on transparency with the goal to help new & experienced traders achieve their goals.
Tom Basso – Guest
Tom Basso is a veteran trend follower and former hedge fund manager known for his appearance in New Market Wizards by Jack Schwager. Often referred to as “Mr. Serenity,” Tom is admired for his calm demeanor, disciplined systems, and balanced approach to trading and life. Now retired from fund management, he continues to educate traders through EnjoyTheRide.World, where he promotes stress-free, systematic trading and a lifestyle-first philosophy.
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