What Entrepreneurs Can Learn from The Pirates of the Caribbean

In honor of the new movie The Pirates of the Caribbean: Dead Men Tell No Tales coming out tomorrow, I decided to post my piece about Entrepreneurs and Pirates of the Caribbean. And I can’t wait to see Dead Men Tell No Tales! I’m so happy!

So here are some quotes from the classic first movie, The Pirates of the Caribbean: The Curse of the Black Pearl, that can help inspire you to be a better entrepreneur!

At the end of this post, I included video clips from YouTube of all my quotes I wrote about, if you want to jump ahead to watch them in all their cinematic glory. And be sure to check out The Pirates of the Caribbean: Dead Men Tell No Tales, in theaters May 26, 2017!

Seize opportunities when they arise

Remember the scene in Pirates of the Caribbean: The Curse of the Black Pearl, when Captain Jack Sparrow and Will Turner are going through the stash of treasure? Well, Will and Elizabeth share a “moment” let’s call it. But neither one of them say anything and Elizabeth turns away. Will didn’t tell her his true feelings!

And in his own swagger, Captain Jack Sparrow (with a crown on his head and treasure in his grasp), approaches Will and says, “If you were waiting for the opportune moment, that was it.”

As entrepreneurs, we must always snatch up opportunities or the “opportune” moment. Don’t let opportunities pass you by! Take the risk!

“The Opportune Moment.” Captain Jack Sparrow and Will Turner in The Pirates of The Caribbean: The Curse of The Black Pearl. (Image by: Oh My Disney.com)

Let them underestimate you

In the very first POTC, there was the classic scene between Commodore Norrington and Captain Jack Sparrow when Norrington temporarily captures Sparrow and this conversation happens:

Norrington: “No additional shot nor powder, a compass that doesn’t point north. [Looks at his sword] And I half expected it to be made of wood. You are without doubt the worst pirate I’ve ever heard of.”

Captain Jack Sparrow: “But you have heard of me.”

Even if you aren’t the “best” at what you’re doing right now, let the competition think that. Let others UNDERESTIMATE YOU. But know that you aren’t how others define you, you’re how you define you. Keep being the best you can be and working hard and anything you want is possible.

Also: a side note on that compass. It doesn’t point north because it has “powers” and points towards the object that the user most desires (not your “typical” north). But entrepreneurs can take comfort in the fact that not everyone is going to understand YOUR north, and that’s okay. It’s your compass, it’s your guide, and it’s your heart. Listen to it!

Your idea can be crazy and ingenious simultaneously

Again, it seems that POTC 1 always has some great quotes. Remember the scene when Will and Sparrow are walking under water in the boat?

Will Turner: “This is either madness…or brilliance.”

Captain Jack Sparrow: “It’s remarkable how often those two traits coincide.”

When you’re an entrepreneur, your business or tech idea may sound absolutely crazy to everyone else. But you know the brilliance of it. You understand that your idea could be the next big thing.

Define your Treasure and pursue it

You must know what your goals are if you’re an entrepreneur. Even if you don’t exactly know what is going to happen, at least you can have a road map.

Much like pirates looking for treasure, you have to have a blueprint of where you’re going.

Captain Jack Sparrow: “Well then, I confess. It is my intention to commandeer one of these ships; pick up a crew in Tortuga; raid, pillage, plunder…”

Captain Jack had a plan! Just make sure your plan isn’t breaking any actual laws and you’ll be good.

Break the Rules

Entrepreneurs are known troublemakers. They are not known to follow the conventional rules, they’re known for breaking them. So if someone is telling you that “this is the way it’s always been done”, don’t listen. Do it the way you want. Break the rules. The rules are just a “guideline” anyway. Who made them up anyway?

Elizabeth: “You have to take me to shore! According to the Code of the Order of the Brethren…”

Barbossa: “First, your return to shore was not part of our negotiations nor our agreement, so I must do nothing. And secondly, you must be a pirate for the Pirate’s Code to apply, and you’re not. And thirdly, the code is more what you call ‘guidelines’ than actual rules.”

You must make sacrifices

Often many entrepreneurs don’t put the full energy into what they are doing and their idea or business falls flat.

How far are you willing to go for your idea? What are you willing to sacrifice? Are you willing to work a 9–5 job and your idea on the side? You must fight for what you believe in and give it your all. That doesn’t mean sacrificing your mental or physical health, or your sanity. But you should be able to recognize what is important and what’s not, what you should focus your energy on or not. You must make some sacrifices. The end will be very rewarding. It’s worth it.

Captain Jack Sparrow: “This girl… how far are you willing to go to save her?”

Will Turner: “I would die for her.”

Captain Jack Sparrow: “Oh, good. No worries, then.”

Be obsessed with FREEDOM!

You’re tired of the 9–5. This is why you ultimately chose becoming an entrepreneur, for the freedom! Pirates and entrepreneurs might not be that different after all. You love seeking adventures, you love being independent, you love treasure, and you love your freedom. You love being able to call the shots. You love how your only limit is yourself.

All the late nights, early mornings, struggles, sweat, blood and tears have led to this: freedom. That’s why you do what you do. That’s why you chose this path.


In the scene where Captain Jack Sparrow and Elizabeth are stranded on the island at night at the bonfire, Captain Jack reveals to her what the Pearl really means to him.

Captain Jack Sparrow: “That’s what a ship is, you know. It’s not just a keel and a hull and a deck and sails, that’s what a ship needs but what a ship is… what the Black Pearl really is… is freedom.”