Bootstrapping from The Man In Black

“…a man who can do that can plan my castle onslaught any day!”

I have written a lot recently on the entrepreneurial art of the bootstrap. From the history of the term to some recent accomplishments, but I am not sure that I ever succinctly defined it? Bootstrapping is about making use of what is available to you to overcome a challenge. That definition covers a variety of uses across disciplines like statistics, biology, and finance.

Bootstrapping also implies personal growth, perseverance, hardwork, and ingenuity — at least when used in reference to an individual or business. This specific definition is put on full display in the epic castle onslaught scene from The Princess Bride. As with any reference to that classic movie, it comes with some great quotes and comedy.

The Princess Bride

For those who have never seen this movie, seriously!? Take an hour and a half of your life and experience it. The humor, the quotes, the celebrities — it is worth it and then some.

But again, for those who either haven’t seen the film or who haven’t enjoyed it in a while — the castle onslaught scene begins the climatic final third of the movie. Our heroes, the overly narrative Inigo Montoya and the ‘mostly dead’ Man in Black (Westley), have arrived at a well guarded castle in order to rescue the fair Princess Buttercup and seek revenge on the vile six-fingered man (Rugen). They are accompanied by the optimistic and slow-witted giant, Fezzik as our scene begins:

Scene: Atop a battlement overlooking the gate Fezzik: Inigo, there’s more than thirty!

Inigo: What’s the difference? We’ve got him. Lifts Westley’s head. Help me here. We’ll have to force-feed him.

Fezzik: Has it been fifteen minutes?

Inigo: We can’t wait. The wedding’s in half an hour. We must strike in the hustle and the bustle beforehand. Tilt his head back. Open his mouth.

Inigo kisses the pill and pushes it into Westley’s mouth.

Fezzik: How long do we have to wait, before if we know the miracle works?

Inigo: Your guess is as good as mine.

Westley: I beat you each apart! I’ll take you both together!

Fezzik: Clapping hand over Westley’s mouth. I guess not very long.

Westley: Why won’t my arms move?

Fezzik: You’ve been mostly dead all day.

Inigo: We had Miracle Max make a pill to bring you back.

Westley: Who are you? Are we enemies? Why am I on this wall? Where’s Buttercup?

Inigo: Let me explain. No, there is too much. Let me sum up. Buttercup is marry Humperdinck in little less than half an hour, so all we have to do is get in, break up the wedding, steal the princess, make our escape. After I kill Count Rugen.

Westley: Tapping thumb against chest. That doesn’t leave much time for dilly-dallying.

Fezzik: You just wiggled your finger! That’s wonderful!

The normally verbose Inigo does an excellent job of summing up the situation. Westley — aka The Man In Black — aka The Dread Pirate Roberts quickly begins to assess their situation. As any good bootstrapper, he is keenly aware of the urgency of their situation and the value of time. The scene continues:

Westley: I’ve always been a quick healer. What are our liabilities?

Inigo: There is but one working castle gate. They look. And it is guarded by… sixty men.

Westley: And our assets?

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

Westley: That’s it? Impossible. If I had a month to plan, maybe I could come up with something, but this… Shakes head.

Fezzik: You just shook your head! That doesn’t make you happy?

Westley may seem a little defeatist at first, but then originally bootstrapping defined an impossible situation. It only transformed into its more aspirational meaning at the start of the 20th century. More importantly, this scene emphasizes the rationality and realism of the bootstrapper. Okay, that is a stretch for a fantasy/fairy tale but go with me here.

Bootstrappers keep their day job. They don’t raise multi-million dollar venture rounds. They control their investment and keep their options open. They maintain low burn rates and recognize the value or time and prioritization. Most importantly recognize the need to think outside the box, to innovate, and to overcome. As Westley shows:

Westley: Turns to Fezzik. My brains, his steel, and your strength, against sixty men, and you think a little head jiggle is supposed to make me happy? Hmmmm? Fezzik smiles. I mean, if we only had a wheelbarrow, that would be something.

Inigo: Where did we put that wheelbarrow the Albino had?

Fezzik: Over the Albino, I think.

Westley: Why didn’t you list that among our assets in the first place? What I wouldn’t give for a holocaust cloak.

Inigo: There we cannot help you.

Fezzik: Pulling the cloak out of his shirt. Would this do?

Inigo: Where did you get that?

Fezzik: At Miracle Max’s. It fit so nice, he said I could keep it.

Westley: All right, all right. Come on, help me up. They lift him. Now I’ll need a sword eventually.

Inigo: Why? You can’t even lift one.

Westley: True, but that’s hardly common knowledge, is it? His head falls, Fezzik lifts it. Thank you. Now, there may be problems once we’re inside.

Inigo: I’ll say. How do I find the Count? Once I do, how do I find you again? Once I find you again, how do I escape?

Fezzik: Turning Westley’s head away. Don’t pester him. He’s had a hard day.

Inigo: Right. Right. Sorry. They creepdown the wall.

Fezzik: Inigo?

Inigo: What?

Fezzik: I hope we win.

Our final lesson from the scene comes from the giant and it is not his endearing optimism. Bootstrapping is an iterative process. Constrained resources require step-by-step development and process. Bootstrappers rarely have five year plans. They see the big picture. They have big dreams. But they know all too well that their journey of a thousand miles is built one step at a time.

This scene from the Princess Bride is a near perfect synopsis of the art of bootstrapping. Admittedly, their eventual plan is a bit ludicrous and silly but as fairy tales go — it is ultimately effective. This gives us one final lesson to draw on. Bootstrappers are rarely concerned with anything other than outcomes. The plan doesn’t need to look good or even make a whole lot of sense. It simply needs to work.

Thanks for reading and the best of luck in your bootstrapping endeavors!