A Valuable Business Lesson from "The Princess Bride"

One of my all-time favorite films to watch repeatedly is Rob Reiner’s “The Princess Bride.” An endearing, funny and surprisingly poignant tale of action, adventure, loyalty, life purpose, and of course…”tru wuv.” And the characters are so memorable—Wallace Shawn as Vizzini (“INCONCEIVABLE!”); Mandy Patinkin as Inigo Montoya (“Hello. My name is Inigo Montoya. You killed my father. Prepare to die!”); Christopher Guest as the cold and heartless Count Rugen (“Do remember, this is for posterity.”); and Cary Elwes as the dashing Westley (“As you wish.”). I could of course go on and on. But, would you believe there’s also a valuable business lesson to be learned from this classic 1987 film? No? Well, humor me for a minute or so, and I’ll show you.

A key aspect of the story centered on the title character, Buttercup (played by Robin Wright in her debut feature film role), believing that her true love Westley was caught and killed by the Dread Pirate Roberts. Later she is reunited with Westley only to find out that HE is the Dread Pirate Roberts. But, she’s confused. How can that be since the Dread Pirate Roberts has been terrorizing the seas for years before they were even born. Westley explains to her that he was indeed captured by the Dread Pirate Roberts, but in fact, his captor was not the REAL Dread Pirate Roberts. He was just using the name, and passed the name on to Westley. In fact, the person who proceeded Westley’s captor was not the real Dread Pirate Roberts either. HE was in fact given the name by someone before him. Turns out, the original Dread Pirate Roberts had retired many, many years ago a very wealthy man, but just passed on the name and “legend.” All that really mattered was the name and the fear that was associated with it.


Here’s the lesson: are you building a business that will survive you and maintain the reputation you’ve built? Even if you have a studio or company named after yourself, long after you’re gone, the brand you’ve built for yourself should live on, e.g. I suspect that years after Vera Wang is dead, her company name will still stand for couture fashion and impeccable quality.

Here are some tips on creating a “Dread Pirate Roberts” Business:

  • Train your people: in “The Princess Bride,” each DPR taught his succeeding protegé all the tricks of the trade, then stayed on long enough to ensure the training stuck. Likewise, train your team members well, and if at all possible, identify a successor.
  • Live your brand: it was key in the movie that Westley lived up to the DPR “brand.” Whenever he was out in public in front of his crew, he needed to be dastardly, cruel, etc. Likewise, whenever you’re out in public representing your company, everything about you should support your brand. If you’ve created your brand as a stylish, couture wedding photographer/videographer, but when you go to conferences you dress like Homer Simpson, your brand is weakened.
  • Put Systems in Place: there’s no way the legend of the DPR could persist if there wasn’t a system in place to locate, train, and install each succeeding DPR. Likewise, you need to put systems in place to maintain great customer service, support, training, and improvement.

A true sign of a great movie is one that not only thoroughly entertains and stands the test of time, but also offers value business and economic lessons. 😉 Who knew?

9 thoughts on “A Valuable Business Lesson from "The Princess Bride"

  1. What a serendipitous blog post this morning Ron. I actually just watched The Princess bride last night after not seeing it in years, and I just finished The E Myth Revisited which talks all about building systems to be able to have your business run the same even if you’re not involved. Great post!

  2. Great advice Ron!

    Certainly pays to lay a solid foundation first. Thanks for the insight.

  3. I just realized I forgot to hit “Post Comment” this morning before I rushed off to respond on begtodiffer.com. Sorry for the poor etiquette and thanks for your comment. Brilliant insights on creating a “Dread Pirate Roberts” Business as a way of capturing sustainability, succession, and systematizing the brand.

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