Sales Consulting

What Can Sales Leaders Learn from the Wolf of Wall Street?


Wolf of Wall Street Sales Training & Lessons

Does Hollywood paint a realistic picture of business? In short, probably not. However, that doesn’t mean that real-life business lessons can’t be learned from the movies.

Take this year’s Oscars best picture award finalist, The Wolf of Wall Street, based on the true story of the rise and fall of stockbroker Jordan Belfort (played by Leonardo DiCaprio). Despite the fact that this humor- and drama-filled flick casts the financial sales profession in a negative light, the surreal plotline does highlight at least two valuable lessons for sales leaders.  


Never underestimate the power of quality training in building a high-performing team. For those who saw the movie, you know the atmosphere at Belfort’s brokerage firm was ludicrous. However, outside of the lavish spending habits and outrageous parties, Belfort created a competitive and energized environment through training and constant, visible motivation.

Jordan Belfort truly understood the importance of training in a highly structured sales approach. He successfully transformed uneducated and unqualified people into results-driven performers with his simple, but consistently applied methodology. We can all question the ethics of Belfort’s model, but his focus on training and ongoing reinforcement of that approach was key to ensuring his less experienced hires were successful.

The takeaway? Investing in the development of your sales team provides the foundation for business growth. 


There’s one memorable scene in the movie when Jordan teaches his sales team one of the most important lessons in sales: focus on establishing a need for your product/service. We’ve all heard this classic piece of wisdom in our careers and have no doubt communicated this to our reps on countless occasions. But, the simplicity of how one scene makes this point is worth noting. 

In this scene, DiCaprio’s character Jordan is sitting at a table with his hometown buddies, a group of inexperienced misfits, whom he hopes to turn into penny stock sales pros. In an attempt to teach them their first sales lesson, Jordan pulls out a pen and going around the table, thrusts it in their faces, one by one, with the instruction: “Sell me this pen!”

As each one takes the pen from him, they fumble through an attempted sales pitch: “This is the best pen ever made…”, “Let me tell you about why you’d want this pen…”, and so on. After each one, Jordan shakes his head and snatches the pen back. Finally Jordan hands the pen to his friend Brad, who he believes is a natural sales person.

Jordan (DiCaprio): “Brad, show ‘em how it’s done. Sell me that pen.” 

Brad: “Why don’t you do me a favor and write your name down on that napkin for me.”

Jordan: “I don’t have a pen.”

Brad: “Exactly! Supply and demand, my friend!”  

The takeaway? Continue to remind your teams of the pitfalls of emphasizing only the features of your products and services. But frankly, most people don’t care. Effective sales is about framing things around your customer’s needs and issues. You must clearly define the business issue or problem to solve before you can convince someone to buy.

Hollywood is often chastised for painting an exaggerated view of business. While this perception may be true, sometimes movies can be as insightful as the most respected Ivy League professor. In our client sales training sessions, we regularly use short movie and television excerpts to bring a key learning points.

This approach, however, doesn’t need to be reserved for formal training. In your next Monday Morning Meeting or sales manager review session, think about creative ways to use movie or TV clips to communicate some of the messages you’d like to share with your leaders and teams. Once you start looking, you’ll be surprised by all the different and fun examples of selling (good and bad!) you can find in today’s popular media.

About The Author

Author photo Researcher, consultant, and sales leader, Brian uses a data-driven approach to drive sales effectiveness. His clients include leading sales organizations in financial services, technology, healthcare, and professional services. Using insight from academics and change management, Brian helps senior leaders and sales enablement teams understand and succeed in today’s more demanding market. His research has been published in Harvard Business Review and other outlets.

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