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Investing and Business Lessons from The Princess Bride


If you have not at least watched the movie version of The Princess Bride, I suggest that you review your priorities in life.

“The Princess Bride was directed by Rob Reiner, who was in the midst of a dynamite run that also included This Is Spinal TapThe Sure ThingStand By MeWhen Harry Met SallyMisery and A Few Good Men; and written by William Goldman, who also wrote the book on which it was based. Goldman also wrote the screenplays for Butch Cassidy and the Sundance Kid and All The President’s Men.” “The film they made together goes something like this: in a fantasy kingdom, the evil Prince Humperdinck (Chris Sarandon) decides to marry simple farm girl Buttercup (Robin Wright), who is mourning the loss of her true love, Westley (Cary Elwes), following his untimely demise. When Westley reappears, he must save her from the evil prince and his henchman, Count Rugen (Christopher Guest), with the help of bad-guys-turned-good-guys Fezzik (Andre the Giant) and Inigo (Mandy Patinkin), while avoiding their still-a-bad-guy boss, Vizzini (Wallace Shawn). And this all takes place inside a modern-day frame, in which a kind grandfather (Peter Falk) reads the book to his sick grandson (teeny Fred Savage, before The Wonder Years).”

Also in the movie is Billy Crystal, who plays the part of Miracle Max. Mandy Patinkin has said this about working with Crystal: “He had in cataract contact lenses so he couldn’t really see.   He was making up 13th-century period jokes. The only injury I received on the entire movie was I bruised a rib holding in my laughter.” Variety tells this story about the movie: “Reiner had to walk away from the shooting because he couldn’t stop laughing, especially when Crystal said, ‘True love is the greatest thing in the world, except for a nice MLT — mutton, lettuce, and tomato sandwich, where the mutton is nice and lean and the tomatoes are ripe.’” Crystal told the makeup team that he wanted Miracle Max to look like a cross between former Yankees manager Casey Stengel and his grandmother. Crystal was filmed for three ten hour days in the making of this movie and never told the same joke twice.

True love is a great theme of the movie but so are innovation, duplicity and hubris. As the first of several asides, when the writer Goldman’s two daughters were asked what they would want in a story the first replied “A princess!” and the second said “A bride!”


Vizzini: “He didn’t fall? Inconceivable!”

Inigo: “You keep using that word. I do not think it means what you think it means.”

Vizzini is using the word “inconceivable” when he should be using the word “improbable.” This difference gets to the heart of what I wrote about in my recent blog post on Benoit Mandelbrot. When you are faced with situations like investing or making a business decision, you must take into account that the probability distribution of outcomes may not be a “Bell Curve.” For example, it may not be probable that Wesley survived the cutting of the rope as he tried to scale the cliff, but it is conceivable that he might do so.

In trying to understand the movie it is important to think about Goldman’s most famous statement. “The thing they’ll end up writing on my tombstone is the phrase ‘Nobody Knows Anything.’” Goldman explains the “nobody knows anything” idea in this way:

“I look at movies and I think what works and what doesn’t work, and it’s got nothing to do with quality. But there is something that they can’t figure out how to manufacture: word of mouth. That’s the great problem the studios have. If they could figure out how to manufacture that, they could all be relaxed about the world. But you can’t figure out why people say, “I want to see that,” and, “No, I don’t want to see that.” “No one has the least idea what is going to work,” he observes. “The minute people start acting like they know everything, we’re all in trouble. Nobody thought Taken would do $100m. Nobody thought Liam Neeson would make it as an action star at this stage in his career.” “When I was thirty, I got to work doctoring a show on Broadway for George Abbott, who was the most successful director in the history of American theatre. He said, “You can’t tell anything until you get hot bodies out there.” And I said, “What are hot bodies, Mr. Abbott?” He said, “People who don’t know your mother. People who want to come to the theatre and enjoy themselves or not and if they don’t, they’ll leave.” And that’s still true. They spend all this money hyping all these movies that open on Friday and they’ve gotten very skilful, but you still don’t know what’s going to work.”

The Guardian illustrates Goldman’s “nobody knows anything” principle with this example:

“In the late-60s, Goldman sold his first original screenplay – a little script called Butch Cassidy and the Sundance Kid – to 20th Century Fox for $400,000, a record at the time. Goldman, already a successful literary novelist who’d shown his gift for cinema by adapting Harper from a Ross McDonald book, felt the fee justified the eight years of research he’d put into the story, not to mention the script’s commercial potential. But film critics, particularly those from Goldman’s adopted home of New York, didn’t agree. Apparently resentful of his big payday, the New Yorker review appeared under the headline “The Bottom of the Pit”. Goldman and director George Roy Hill were in Manhattan the day the film was released. “When we got killed [by the critics], we were just crushed,” he recalls. “So George and I walked over to a theatre at 57th and 3rd and we asked to see the manager. He came out and when we asked how the film was doing, he said, ‘We’re selling out all the shows and the audiences love it.’ Still, we thought it might only be doing well in that theatre. So he volunteered to phone the manager at a theatre in Times Square – can you imagine anyone doing that today? – and he said the same thing. George turned to me and said: ‘Well, maybe it’s not a disaster after all.'” Butch went on to become the highest-grossing film of 1969 and won four Oscars, including Best Screenplay.

Predicting what people will do, particularly if it involves word of mouth is best discovered through experimentation rather than prediction. The best article on this topic is written by Duncan Watts and is entitled: “Is Justin Timberlake a Product of Cumulative Advantage?” As is usual, when I make a refence like this, a link to the article or book is in the Notes below.

A book entitled, The Princess Bride and Philosophy: Inconceivable! argues that Goldman is making a deeper point:


I’m somewhat skeptical of this interpretation, but I am making some unusual comments in this post myself. 


Miracle Max:  “There’s a big difference between mostly dead and all dead. Mostly dead, is slightly alive.” 

Miracle Max is talking about a danger associated with “Gambler’s Ruin.” To invest capital you must first have capital. Ed Torp describes the danger in this way:

“If you bet too much you’re likely to be wiped out…. You have to make sure that you don’t over-bet. Suppose you have a 5% edge over your opponent when tossing a coin. The optimal thing to do, if you want to get rich, is to bet 5% of your wealth on each toss — but never more. If you bet much more you can be ruined, even if you have a favorable situation. It’s a formula Bell Labs scientist John Kelly devised in the 1950s.”

To have a chance of outperforming a market index you must first stay in the game. In other words, if you have zero capital it is impossible to be an investor. For much the same reason Walter Schloss once said: “Remember it’s your money and generally it is harder to keep money than to make it. Once you lose a lot of money it is hard to make it back.”


Inigo:  “There is but one working castle gate. And it is guarded by sixty men.”

This seems like a reference to something Warren Buffett has said: “Capitalism is all about somebody coming in trying to take the castle. What you need is a castle with some form of durable competitive advantage, thus an economic castle with an economic moat around it to protect the corporate profits from its fierce competitors.” Unfortunately, someone eventually events a weapon like the cannon and the walls of the castle become a big cost burden rather than an asset.  I have written several blog posts on moats.  Prince Humperdinck’s castle looks impressive, but it is breached by the heroes with a few props, a clever ruse and bravery. As an aside, the castle used in the movie is Haddon Hall, a fortified country house rather than a real castle with an origin traceable to sometime before 1087. There is no actual moat at the castle, but remember that the film’s budget was tight. Changes to the book were made in the screenplay to reduce costs, such as changing the Zoo of Death into the Pit of Despair.  Creating a Zoo of Death is as you know very expensive.


Westley: “And our assets?”

Inigo:  “Your brains, Fezzik’s strength, my steel.”

Goldman is describing the innovation process in this scene that I wrote about last week. Inigo believes that Westley will invent an innovative solution that will enable them to beach the defenses of the castle. A wheelbarrow, a cloak and fire are used to great effect in in breaching the walls of the castle. The making of the movie itself is an example of innovation. “Reiner had a tough time marketing The Princess Bride because it was kind of genre-less. Swashbuckling comedy? Charming, witty fable? Tale of love and revenge? Nothing felt right. Reiner feared he had a “Wizard of Oz” on his hands – and “The Wizard of Oz” was a flop when it first hit theaters in 1939.” Of all the movies released in 1987, the Princess Bride ranked just 41st in domestic grosses, bringing in $30,857,814. ” As a reference point, the movie “Three Men and a Baby” brought in $167,780,960 that year. Elwes, who played Westley, explains in his book about the movie that “‘The Princess Bride really didn’t have an audience when it came out. It gained popularity in the VHS marketplace.”


Inigo: “I just work for Vizzini to pay the bills… not a lot of money in revenge.”

Mandy Patinkin who played Inigo has said that this is his favorite line from the movie. Inigo is expressing a view that is similar to Charlie Munger who once said: “Generally speaking, envy, resentment, revenge and self-pity are disastrous modes of thought.” A passage in the book The Princess Bride and Philosophy: Inconceivable! examines Inigo’s situation:


Patinkin said that when he stabbed Count Rugen in this scene he felt like he was killing the cancer that killed his father, and “for a moment, he was alive. And my fairy tale came true.”

A situation involving revenge in my own life happened when my five-year-old son opened a birthday gift from his grandfather, he discovered a water pistol.  He squealed with delight and headed for the nearest sink. I was not so pleased.  I turned to my father and said, “I’m surprised at you. Don’t you remember how we used to drive you crazy with water guns?” My father smiled and then replied, “I remember.” As another aside, “Revenge” is the name of the pirate ship of Dred Pirate Roberts. Also, there was a real and very famous pirate named Black Bart Roberts.



“Everyone had told her, since she became a princess-in-training, that she was very likely the most beautiful woman in the world. Now she was going to be the richest and the most powerful as well. Don’t expect too much from life, Buttercup told herself as she rode along. Learn to be satisfied with what you have.” 

This is a reference by Goldman to an idea that is central to a classic Charlie Munger quip: “The idea of caring that someone is making money faster is one of the deadly sins. Envy is a really stupid sin because it’s the only one you could never possibly have any fun at. There’s a lot of pain and no fun. Why would you want to get on that trolley?” Envy can lead to fear of missing out (FOMO)  which is what causes things like the Internet bubble. Warren Buffett tells the following joke about herd behavior that can be caused by envy:

A dead oil prospector arrives at the pearly gates and is told by St Peter that Heaven’s allocation for miners is full. The prospector leans through the gates and yells: “Oil discovered in Hell.” A stampede of men with picks and shovels streams out of Heaven. An impressed St Peter waves the prospector through. “No thanks,” says the prospector. “I’m going to check out that Hell rumor. Maybe there is some truth in it after all.”

As another aside, since Buttercup never actually married Prince Humperdink, she technically wasn’t a princess. But where is the fun in that?


Westley: “Ha! Your pig fiance is too late. A few more steps and we’ll be safe in the fire swamp.”.

Buttercup:  “We’ll never survive.”

Westley: “Nonsense. You’re only saying that because no one ever has.” 

Westley exhibits a classic missionary attitude in this scene and many others in the movie. Miracle Max is also a bit of a missionary in the movie since at one point he says: “I never worked for so little. Except once, and that was a very noble cause.” The writer Goldman himself exhibited missionary rather than a mercenary traits when he said in an interview: “You can only write what you give a shit about. You got to keep on doing that. If for example, you don’t like special effects movies, don’t try to write one because it will suck.”

I love the following story told by Goldman about the making of The Princess Bride that also demonstrates a missionary attitude. The new person in a role at a business too often feels like they must throw out any idea that could be attributed to their predecessor:

“Only one person per studio has anything resembling power, and that is the GG. The GG, you see, can make a picture happen. He (or she) is the one who releases the fifty million bucks—if your movie is aimed for Sundance. Triple that if it’s a special effects job. Anyway, the GG at Fox liked The Princess Bride.

Problem: he wasn’t sure it was a movie. So we struck a peculiar arrangement—they would buy the book, but they would not buy the screenplay unless they decided to move forward. In other words, we both owned half the pie. So even though

I was tired from finishing the abridgement, I went on nervous energy and did the screenplay immediately after.

The GG at Fox sent it to Richard Lester in London—Lester directed, among others, A Hard Day’s Night, the first wonderful Beatles film—and we met, worked, solved problems. The GG was thrilled, we were a go—

—then he got fired, and a new GG came in to replace him.

Here is what happens Out There when that happens: the old GG is stripped of his epaulets and his ability to get into Morton’s on Monday nights and off he goes, very rich—he had a deal in place for this inevitability—but disgraced.

And the new GG takes the throne with but one rule firmly writ in stone: nothing his predecessor had in motion must ever get made. Why? Say it gets made. Say it’s a hit. Who gets the credit? The old GG. And when the new GG, who can now get into Morton’s on Mondays, has to run the gauntlet there, he knows all his peers are sniggering: “That asshole, it wasn’t his picture.” Death.

So The Princess Bride was buried, conceivably forever. And I realized that I had let control of it go. Fox had the book. So what if I had the screenplay; they could commission another. They could change anything they wanted. So I did something of which I am genuinely proud. I bought the book back from the studio, with my own money. I think they were suspicious I had some deal or plan, but I didn’t. I just didn’t want some idiot destroying what I had come to realize was the most important thing I would ever be involved with. After a good bit of negotiating, it was again mine. I was the only idiot who could destroy it now.”

Goldman decided that Reiner was the right person to direct The Princess Bride based on his contributions to the movie This Is Spinal Tap. There is a Spinal Tap baseball hat in the bedroom of the sick grandchild, a cultural reference that Mark Knopfler made a condition for doing the movie’s soundtrack.


Vizzini: “But it’s so simple. All I have to do is divine from what I know of you: are you the sort of man who would put the poison into his own goblet or his enemy’s? Now, a clever man would put the poison into his own goblet, because he would know that only a great fool would reach for what he was given. I am not a great fool, so I can clearly not choose the  wine in front of you. But you must have known I was not a great fool, you would have counted on it, so I can clearly not choose the wine in front of me.” 

Vizzini is exhibiting what Keynes called a “Beauty Contest” attitude.  He would be would be a  terrible investor, since his approach is speculation.

“The Keynesian beauty contest is the view that much of investment is driven by expectations about what other investors think, rather than expectations about the fundamental profitability of a particular investment. John Maynard Keynes observed that investment strategies resembled a contest in a London newspaper of his day that featured pictures of a hundred or so young women. The winner of the contest was the newspaper reader who submitted a list of the top five women that most clearly matched the consensus of all other contest entries. A naïve strategy for an entrant would be to rely on his or her own concepts of beauty to establish rankings. Consequently, each contest entrant would try to second guess the other entrants’ reactions, and then sophisticated entrants would attempt to second guess the other entrants’ second guessing. And so on. Instead of judging the beauty of people, substitute alternative investments. Each potential entrant (investor) now ignores fundamental value (i.e., expected profitability based on expected revenues and costs), instead trying to predict “what the market will do.” The results are (a) that investment is extremely volatile because fundamental value becomes irrelevant, and (b) that the most successful investors are either lucky or masters at understanding mob psychology – strategic game playing.” Economicae: an illustrated encyclopaedia of economics

Keynes himself said:

‘It is not a case of choosing those [faces] which, to the best of one’s judgment, are really the prettiest, nor even those which average opinion genuinely thinks the prettiest. We have reached the third degree where we devote our intelligences to anticipating what average opinion expects the average opinion to be. And there are some, I believe, who practise the fourth, fifth and higher degrees.’ (Keynes, General Theory of Employment Interest and Money, 1936).


Westley: “Dread Pirate Roberts had grown so rich, he wanted to retire.” 

In my blog post on Dan Airely I quote him as saying: 

“Retirement is especially difficult because we not only don’t know exactly what we’re giving up, it’s also far away in the future.  That makes it very, very difficult to think about.  It’s called hyperbolic discounting — we just care less dramatically about the future so not only is it hard for us to understand what we are giving up, it’s also really, really delayed.” “If you think about the opportunity cost of money — if I spend a thousand dollars now on a new bicycle I know what I’m getting.  If I put it into my retirement account I don’t really know what I’ll get in the future.”

How much wealth must you save for retirement? What should your portfolio look like to achieve that and after you retire? These are topics worthy of a future blog post. I should note that on the succession planning issue, Westley served as an apprentice for a considerable period and was able to step into the Dred Pirate Role role quite effectively. Inigo inherits the title from Westley. In the first chapter of Buttercup’s Baby, the unfinished sequel to the novel, Goldman refers to “’Pierre,” who seems destined to be the next Dred Pirate Roberts. 


Vizzini: “You fell victim to one of the classic blunders—the most famous of which is, ‘Never get involved in a land war in Asia’—but only slightly less well-known is this: ‘Never go against a Sicilian when death is on the line’! Ha ha ha ha ha ha ha! Ha ha ha ha ha ha ha! Ha ha ha…[drops dead].”

My blog post on The Godfather is about one type of Sicilian wisdom. Speaking of Sicilians, Reiner at one point ran into mob boss John Gotti and his entourage outside a New York restaurant. One of the men with Gotti looked at Reiner and said, “You killed my father, prepare to die!” and then started laughing.

Vizzini, like many people with high intelligence, is a danger to himself and others since he mistakenly believed that his IQ was higher than it actually was and that his IQ was a substitute for good judgment.

As for the avoid land wars in Asia comment he is referring to advice Charlie Munger often gives about avoiding situations that are painful. When Munger jokes: “I just want to know where I will die so I can just not go there” he is humorously making a broader point about avoiding certain areas in investing and in life. Munger once gave a speech where he spoke about a famous Johnny Carson talk in which the comedian described all the ways one can be miserable. Munger said: “What Carson said was that he couldn’t tell the graduating class how to be happy, but he could tell them from personal experience how to guarantee misery. Carson’s prescriptions for sure misery included: 1) Ingesting chemicals in an effort to alter mood or perception; 2) Envy; and 3) Resentment. What Carson did was to approach the study of how to create X by turning the question backward, that is, by studying how to create non-X.” Invert!


Man in Black (Westly): “Life is pain, Highness. Anyone who says differently is selling something.” 

My blog post on how Charlie Munger deals with the inevitable adversity people encounter in life is one of my more popular pages on my blog. In it I quote Munger as saying: 

“Assume life will be really tough, and then ask if you can handle it. If the answer is yes, you’ve won.”

“Life will have terrible blows in it, horrible blows, unfair blows. And some people recover and others don’t. And there I think the attitude of Epictetus is the best. He said that every missed chance in life was an opportunity to behave well, every missed chance in life was an opportunity to learn something, and that your duty was not to be submerged in self-pity, but to utilize the terrible blow in constructive fashion. That is a very good idea.”

The people who step up when adversity arrives inspire me. Doing the right thing is a highly underrated part of life. It is a not only a test of character, but a chance to show what you have learned and who you are as a person.


Vizzini:  “I don’t guess. I think. I ponder. I deduce. Then I decide. But I never guess.”

What do you do when your are faced with a situation in which “no one knows anything” because you are dealing with complex adaptive systems? The best response to this is to do a lot of experiments using the very best data available and modern data science tools. There has never been a better time in history to do this work since the cost of running an experiment has never been lower. Rather than try to predict the unpredictable, it is a better idea to run experiments instead and then select the most favorable outcomes. A well-constructed trial and error process allows the experimenter to identify a favorable result from a test result and to exploit it when they actually see it. This topic will be part of my next blog post entitled: “Why is Data the New Oil?” 

Data is not a substitute for thinking. Bill Gates is one of the deepest thinkers I have ever known. He is interested in many things. For example, I ran into him once in an athletic club locker room and we ended up having a long talk very there about Mandelbrot sets. We completely lost track of time during that talk.  Bill’s “always thinking” character trait is not new. When Bill was a child, his mother Mary complained about him being slow to get into the car for a trip to a family event. When she asked Bill what he was doing, he responded by saying: “I’m thinking, mother. Don’t you ever think?” Bill’s father recalled that day in this way: “Imagine yourself in our place. I was in the most demanding years of my career. I was a dad, a husband, doing all the things parents in families do. My wife, Mary, was raising three kids, volunteering for the United Way, and doing a million other things. And your child asks you if you ever take time to think.”













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