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11 Content Lessons I Learned From The Princess Bride

That seems a little far-fetched. Seriously? The “Mawage. Mawage is wot bwings us togeder tooday” movie actually taught you something?


It taught me 11 somethings.

As I sat down and watched The Princess Bride with my 3-year-old son (I like to ingrain quirkiness early in my children), I realized that I was drawing parallels between what was happening in the movie and what I was dealing with at work. So I got out my moleskin (light brown, pliable is my preferred) and started writing down everything I was noticing. I couldn’t write fast enough; the lessons just kept coming and coming until finally I decided to only write down the ones that really struck a cord with me.

After 98 very enjoyable minutes, I ended up with this:


This is just the syllabus. A Sneak-peak of things to come…
(Subject to change. I may be updating this post as I find more pearls of wisdom in this classic movie).

Lesson 1: Find Some Common Ground

The main story of The Princess Bride is a little hard to believe. Pirates, to-the-death mind battles, a machine that sucks your life away, we need to suspend our belief long enough to discount the improbable nature of its plot (that includes the ROUSs). So how do they get us sucked into the story? By using a scenario we all are familiar with: being sick in bed. The movie opens with an experience we can all relate to. We all know what it’s like to lie in bed and feel crappy. And when we feel that way, we want distractions, we want to escape, and reading a fairy tale is just such an escape.

So when you’re creating content for your website, start with something familiar, something that connects you, in a very personal way, to your readers. I’d like to use Nifty Marketing as an example here. We open our website with a nerdy guy introducing himself. Which of us can’t relate to that image? I suppose there are a few good-looking, high school class presidents that don’t know what it’s like to be awkward and nervous when introducing themselves, but for most of us it’s a familiar emotion. It’s an experience that we can bond over. And it’s the perfect common ground to introduce the idea that Local Search is a necessary part of an online presence.

Lesson 2: It’s not what you say…

Westley loves Buttercup. He loved her from the moment he laid eyes on her. And every time he talks to her he says the same thing, “As You Wish”. Come to find out, what he was really saying was “I love you”. Which begs the question, how could he be telling her he loved her, if he never actually said the words? The Answer? It was in the way he said, “As you wish”. So even when she pushes him down the ravine, hoping he dies, those three words make her throw herself down after him.

So how does this apply to content? Crafting your Unique Selling Proposition is all about how you say it, not what you say. Why? Because, unless you invented your market, there are hundreds just like you offering the same service. You need to set yourself apart from them. Again, I’d like to use Nifty as my case (seeing as I have intimate knowledge of the how and why it was written the way it was). Our USP is “We make Local sexy”. It’s saying the same thing as everyone else, we do Local search marketing, but it makes us unique. No other Local SEO company states that they can make Local sexy. Its appeals to the reader, it makes them feel that their Local presence would be better, cooler, sexier than if they went with someone else. It sets us apart from the rest while still letting them know what it is that we do. In other words, it’s not the words we use, but the emotion we evoke.

Lesson 3: No matter how insane a problem may seem, there is always a way to tackle it.

The Cliffs of Insanity. Just the name makes me smile. There are so many classic moments in the movie from this scene. But the lesson to be learned comes from Westley. I doubt climbing that tall of a cliff by rope was an easy task (I had problems climbing the rope in gym class), climbing it without a rope seems impossible. The book sheds some light here, telling us that he was punching the cliff to create footholds, but even knowing how he did it doesn’t help me believe a normal person could accomplish the same goal.

Case study time: We were killing it for one of our clients. They had a 9% conversion rate on their site and they were happy. Very happy. Sadly, I wasn’t. I have so much fun with this client because they let me do what I want; I needed that number to triple. It seemed impossible. We had run conversion test after conversion test to try and get it up (and they had worked), but we weren’t seeing the numbers we (ok, I) wanted to see. So I said, “Let’s do one more conversion test”. Here’s the test:


I realize that a 27% conversion rate is crazy. It’s insane to think that number could ever happen. And we still haven’t hit it. But you know what? Last week we hit a 24% conversion rate. Let me state that one more time: we hit a 24% conversion rate. Insane? Yes. Totally awesome? Heck yeah.

Lesson 4: Be yourself.

Fezzick says very little in the movie. But what he does say is priceless: “People in masks are not to be trusted”. This line is by far the best one-liner from Fezzick. And it makes sense, if someone can’t show you who they are, why would you trust them?

It’s the same with your content. If your personality, your unique view of the world isn’t expressed in your writing, no one is going to trust it, let alone buy from you. Take Nifty Marketing for example. This site sounds like us. It’s like we wrote down our conversations here at work and posted it on the website. You get a sense of who we are, what our sense of humor is like, and whether or not we would be a good fit for what you are looking for. Now, we could have said, “We do Local Search” or left out the bit about Freelance Ninjas and Smoothie Makers. And while we may lose some clients because of our attitude, at least we’re honest with who we are.

One of my pet peeves when it comes to content is when someone wants to be someone else. I deal with it on a daily basis and I just want to scream, “That’s not you!” but no one listens. The name of the game here is to be unique and you are the only you in the universe. Your content needs to match you.

Lesson 5: Leave some mystery in your writing.

It’s so tempting to put everything upfront and say “Have at it”. But this scene is the perfect example of the lesson I learned. And yes, I agree with you, this is the corniest part of the movie (but that’s why I love it). The moment Inigo says “I am not left-handed”, I keel over with laughter every time. Here’s a man who is such an amazing swordfighter that he can fight with either his left or his right hand. He goes through the entire fight letting Westley think that he is stronger, faster, and better and then reveals his secret.

The same holds true for content. If you reveal everything at the beginning, nobody will read past the first sentence. You have to draw them in with a sense of mystery, let them think that they could leave at any time, and then blow their minds.

The fact that Westley does the same thing back to Inigo is just icing on the cake.

Lesson 6: Know when to focus on the group and when to focus on the one.

Fezzik is a great fighter. Before his little foray in kidnapping, he was one of the most famous fighters in the world, able to take on 10 men and win. So how did Westley get the best of him? He knew which tactics to employ. The problem for Fezzik was that he hadn’t fought just one man in such a long time that he was unable to change his tactics.

The same thing happens in our content. I’m guilty of it. Sometimes I focus on the group, wanting to please everyone with a single piece of content instead of creating highly targeted landing pages that would address their needs better. And, much like Fezzik, when we give up the one in favor of the group, we lose.

Lesson 7: Let them think they’re in control.

Westley knows when he puts the poison in the cup that Vizzini is going to die. He knows that no matter what Vizzini does, the battle of wits will end with his death. So why does Westley let Vizzini think he’s winning? To not let on that he knows the real outcome of the battle. And it was nice of him to let Vizzini die laughing.

I’ve mentioned this site before but David’s Tea is the perfect example of this lesson. I think I’m in control. I choose to click the bookmark. I choose which tea I want to see next. I am in control. Or so I think. But in reality the content is so good, so compelling that I often find my Friday night consumed with browsing that website (luckily, my wife enjoys the content as well). So am I really in control? Nope. And that’s the kind of content needed on the internet. The kind of content that says, “Hey, come hang out for a while”; 15 hours and a few hundred dollars later, you have no idea why you bought that peacock teapot other than the content said you needed it.

Lesson 8: Write what’s true for you.

Westley has the best lines in the movie. Seriously, “Life is pain. Anyone who says otherwise is selling something.” is my favorite quote from the show. Why? Because it rings true. When Westley says this line to Buttercup, we can feel his pain. Here is a man who has defied death, overcome legends, climbs insane cliffs, and saved the life of the woman he loves. All of this while thinking that she moved on after his death in less than an hour. So when he says life is pain, there is no doubt he knows what he is talking about.

Your content needs that “truthiness” (credit goes to the great Content Marketer Stephen Colbert for that word). When people read what you write on your website, on your Facebook page, even those few words on Twitter, they need to ring true. Let me give you an example from my own life: Writing Nifty’s content was an experiment in self-discovery for me. While I had to remain true to who we are as a company, I also was trying to be myself. There are lines (freelance ninjas and smoothie-makers) that scream “This was written by Lance!”. And whenever I ask people why they contacted us, what caused them to call or fill out our form, the answer almost always has something to do with the personality of our content. What I wrote rings true to who we are (I mean, just check out our About Us page…). You don’t have to be funny. You don’t have to be flippant. Be yourself and you’ll get business.

Lesson 9: Just because no one has, doesn’t mean you can’t.

Prince Humperdinck has Buttercup and Westley surrounded. Their only hope is the Fire Swamp where no one has come out alive. Faced with this choice, Westley decides to enter the Fire Swamp. Why? His logic is genius: “Nonsense! You’re only saying that because no one ever has.”. Just because nobody has done it, doesn’t mean it can’t be done.

This is the pure meaning of Content Marketing. To create something that nobody has. To stand in front of the mocking and doubting crowds and say, “Nonsense!”. It takes courage. It takes a slightly crazy mind. It takes ingenuity. And that is why, when someone does it right, amazing things happen. Westley and Buttercup survived the Fire Swamp because Westley wasn’t afraid to try. Yes, they failed a few times (sinking into the lightning sand had to be scary), but in the end they triumphed. Don’t be afraid to try something never done before with your content.

Lesson 10: Don’t use a big word, unless you’re going for the emotional sell.

I love the development of this scene. They use small words, garage, slime, filth, and then, Putrescence. It’s great. Especially the way the lady says it, ‘The Queen of Pu-tres-cence”. Wow.

And it works. Why? Because they gave enough contextual clues that even an 8-year-old who doesn’t know how to spell the word knows it’s not a good thing. We feel bad for Buttercup. This lady is demeaning her in front of a huge crowd. But it’s not until we hear that big word, the word that we don’t know the exact meaning of, that we really feel sorry for her.

So use big words in your content. They are a great way to express specific ideas. But make sure that you give enough contextual clues so that people will know what they mean, without having to go to

Lesson 11: Don’t be afraid to target a specific customer type.

I love Inigo. The book provides more insight into his character, and gives us an overview of his quest for revenge on Count Rugen. How he studied the sword for years, training under different masters, so when he found the six-fingered man he would be ready. He would look at him and say, “Hello. My Name is Inigo Montaya. You Killed My Father. Prepare to Die.” That’s my second favorite poem.

What does that have to do with content? Know who you want to go after, target them, do all that you can to slay them (and by that I mean get them to convert).

That’s the syllabus for the Princess Bride Content Course. Check back in the coming weeks for Lesson 1. I’d love to hear your thoughts in the comments.
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