The Princess Bride Guide to Entrepreneurship

Last night I went to what might have been the most fun show I have ever attended: the 27^th anniversary showing of the movie The Princess Bride. The event was done as a “quote along” where the audience shouts out the lines along with the movie. While I should probably pretend that I am impressed by more erudite fare, the truth is that The Princess Bride is my all time most favorite film. I have seen it at least 25 times and probably more. I was one of those 1400 or so idiots at San Francisco’s Castro Theater last night who can actually quote along with the movie. And furthermore, at last night’s show the male lead, Cary Elwes, showed up to talk about his experience starring in the role of Westley. Be still my heart.

The most famous line from The Princess Bride is probably this one, spoken by Inigo Montoya (played by a very young Mandy Patinkin), “Hello. My name is Inigo Montoya. You killed my father. Prepare to die.”

httpv://youtu.be/kRAI9_MkmBM

I’m guessing that even the 3 of you readers who haven’t seen the movie know that particular line. But what struck me as I sat there shouting out “Inconceivable!” with my theater-provided props (awesome inflatable sword included), is that there are many lines from the movie that could be right out of a Silicon Valley start-up advice book.   So I decided that, in the interests of advancing the field of business, I would bring to you The Princess Bride Guide to Entrepreneurship.

Buttercup: We’ll never survive.

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

This exchange takes place when Buttercup, the princess, and her love interest, Westley (aka the Man in Black) is leading them into the Fire Swamp to escape certain capture. The Fire Swamp, is full of treacherous dangers like quicksand and Rodents of Unusual Size; everywhere you turn there is a daunting risk to overcome.   I can’t imagine a metaphor more appropriate to the start-up world, where entrepreneurs must venture into entirely uncharted territory where the odds are against success. As entrepreneurs bring their crazy new ideas out into the open, all too often they hear, “This can’t be done; it’s never been done; you’ll never make it.” Thank goodness that successful entrepreneurs have the capacity to ignore these admonitions, or nothing new would ever be created and our healthcare system would still be largely leech-based.   Being able to conceive of what’s never been done, convince yourself that you are the one to do it and sell that story to others while avoiding the quicksand – that is the essence of entrepreneurship.

Inigo Montoya (the Spaniard): I must know…

Man in Black (aka Westley): Get used to disappointment.

On the other hand, just because one can conceive of an idea doesn’t mean you can see all the pitfalls that stand in its way or that it will be a straight line to success. The trick is having the confidence to acknowledge the challenges, respond appropriately and keep moving forward. Disappointment is one of the major currencies of new business creation. People won’t want what you developed; others won’t fund it; the original concept may not be quite right; the timeline you envisioned may not be possible; people may not do what you want them to do when you want them to do it. Getting used to disappointment is an essential skill of entrepreneurs. The successful ones get used to it but don’t let it ruin them. Thus the creation of the word “pivot.”

Westley: As you wish!

This is Westley’s signature line in the movie, and something he often says to his primary target audience, Buttercup, the love of his life. It is a great reminder to listen well to one’s customers and to build products that they actually want. The best entrepreneurs start by finding out what the market actually wants—the problem they want to solve—and then building solutions that meet their desires.

Westley: We are men of action, lies do not become us.

All too often, the stress of starting up a new company can make people a little blind to reality. Sometimes, when those previously mentioned disappointments come, it is somewhat easier to tell yourself a little white lie than to really hear the feedback. Damn the torpedoes (and the skeptics) you might say; full speed ahead! But what lean startup principles have taught us and what great entrepreneurs know is that you have to hear the hard stuff—you can’t lie to yourself in the face of those disappointments. Discerning when to listen to the skeptics and learn from them is an essential skill. Being so in love with your own idea that you can’t hear the truth about your somewhat ugly baby is a sure path to oblivion. Action, yes, but not at the expense of admitting you need a course correction.

Inigo Montoya: You know, Fezzik, you finally did something right.

Fezzik: Don’t worry, I won’t let it go to my head.

When things go right in a new venture, there is a lot of high fiving. But then you must get back to work and remain humble even when you are flying high. One thing I know for sure is that when egos grow too large, they can block the path to the ears, thus making it easy to stop hearing your critics or notice your competitors’ gains. When things go right, celebrate for a moment and then get back to the task at hand with the same openness of spirit that got you there. The minute you start patting yourself on the back and thinking you are the smartest person in the room, the easier it is to blindly end up in the Pit of Despair.

Miracle Max: You rush a miracle man, you get rotten miracles.

Silicon Valley places such a premium on being first to market that we sometimes fool ourselves into thinking that speed is the same as success. The entire process of creating a company and getting it from concept to cash in your pocket is quite the miracle, given the many traps along the way. Sometimes it takes time to reach the Promised Land. Short cuts can get you to a decent minimum viable product or to an irreversible path to nowhere. It is utterly essential to know when speed kills and when patience pays. This is especially true in the cultivation of one’s first customers and even truer during those long years it takes to build enough value to maximize your exit. I am always made nervous by those entrepreneurs who tell me their plan is to get the product built and that its sudden magnificence will bring buyers to their knees even before they have sold dollar one.   What’s the hurry? If what you have is so great, let the miracle mature enough to maximize its value. In healthcare we have learned this can take 10 years and sometimes even more. Trying to rush the process beyond its natural pace can make for some rotten miracles.

In addition to a hilariously fun story, The Princess Bride offers us some great lessons in entrepreneurship.   Make sure to heed them and have fun storming the castle!