Entrepreneurs: Pirates of the Digital Age

As I watched Captain Jack sail away on the Black Pearl at the end of the first Pirates of the Caribbean film, it hit me: “That’s us. That’s me. We’re all just pirates.”

If we ignore for a moment all the violent and illegal parts inherent in a life of piracy.

(Which we don’t condone at all, by the way. Violence and illegal stuff = bad. But drawing parallels between our lives as entrepreneurs and the lives of pirates = fun and interesting. And it makes us feel like badasses .)

So if it’s not the bad stuff that makes entrepreneurs like pirates, then what is it? What good reason do we have to want to draw parallels between the 2?

There’s actually a few reasons: The pirate’s code. The need for independence. The willingness to accept the risk. And the craving for reward.

Let’s begin our tale of the modern-day pirate in the dim light of the tavern.

Sharing Ideas: We Do It at the Bar, They Do It at the Tavern

Imagine your after-work gathering for a few drinks with colleagues taking place in a tavern instead of a bar and you’ve got yourself a nearly authentic picture of old-timey pirates planning their next treasure hunt. (Works best when you and your coworkers all dress up as pirates. You know, for authenticity. Or just for fun.)

After all, that’s usually when these talks of independence and a need for “something different” come to light, right?

to unwind and gossip over drinks and as the night grows darker and the grog renders you groggier, inevitably conversations take on a peculiar tone.

“You should do your own thing!” and “You should stop working for the man!” or “I want to do something I’m really passionate about.”

There begins the talk of secession from your current daily grind, often with your favorite coworkers in tow. To try something new. To go hunting for a different kind of treasure.

Is that not exactly what pirates do? Do they not also plan their secession—but for them, it’s from society—so they can go hunting for something more? Do they not also gather at the tavern to share ideas, to talk recruiting, to talk strategy?

Risk & Reward: They Risk Imprisonment, We Risk Our Livelihood

Whether you’re an entrepreneur in the digital age or a pirate of old, there’s going to be a risk. (At least one of us won’t be sent to the gallows if we fail.)

The odds of running a successful venture for an entrepreneur sits at, odds that—for normal people—seem pretty scary.

But the odds are just high enough that it makes pirate-minded entrepreneurs say, “So there is a chance of success!” Yo ho, yo ho.

Back at the tavern, inevitably our talks to will turn to risk and reward. Inevitably we come head-to-head with the big decision.

Because no matter how exciting, how adventurous it all seems, as digital pirates, we realize there’s a moment where we’re either in, or we’re out. We’ve got to decide: is the risk worth the reward?

Is the opportunity to make it on our own worth quitting our jobs? Worth giving up comfort? Is it even worth losing all of our money?

It’s why we become entrepreneurs, and it’s why they became pirates: the risk outweighs the reward. Setting sail alone (or with a motley crew) seemed better than joining the navy and getting low pay and grunt work in return.

And setting sail alone as an entrepreneur seems better than working hard for someone else’s dream instead of your own.

Raising Capital: We Need Funds, They Need Ships

And we both need the supplies and the manpower.

And we both start with the number one resource of all: a good idea. They call it a treasure map, we call it a business plan.

Don’t have a business plan, the supplies, or the manpower? Then back to the tavern it is. Talk it out. Ask yourself and your crew: do we have a good enough idea? Can we draw out a treasure map that works?

You’ve got to ask yourself these questions, because—although I love the entrepreneur’s life and welcome like-minded pirates to hop onboard for the journey—I still must warn you that you must join for the right reasons and not lose yourself along the way.

Because you will get lost, and you will hit stormy weather. Your idea must be so good that it carries you through bumpy waters and has you inspired enough to live another day.

And We Both Have a Code

Democracy. Camaraderie. But most of all, independence.

When you think of it that way, clearly all us entrepreneurs are just pirates in cleaner clothing. I’ll cheer a hearty “yo ho, yo ho” and a bottle of rum to that. It’s definitely a pirate’s life for me—what about you?

Since I could go on forever about how cool pirates are (and how often people get the facts wrong), I’ll point you in the direction of this handy resource on pirate myths and facts.

If you’re a new age pirate like your friends at Idea180, check out this start-up resource page we’ve put together for the brave entrepreneurs of South Florida.

Special thanks to the editor of this piece, Maison Piedfort for cleaning up the mess and giving this post a real shot.