I'm a pirate

What do Steve Jobs and Blackbeard have in common?

Sup nerds

For the last week, I’ve been obsessively reading about pirates.

And I think I know why. It’s because deep down I’ve always known I’m a motherfucking pirate. To be an entrepreneur is to be a pirate.

“Why join the Navy when you can become a pirate?”

Steve Jobs

Last week, I finished up The Pirate Organization: Lessons from the Fringes of Capitalism. The big takeaway was pirates don’t just dominate the seas, pirates thrive wherever there is a new technology and almost no rules.

If you want to win online, you should learn the ways of the pirates.


The 17th century is the golden time of seafaring pirates.

Blackbeard had 300 men sailing the seas. Bartholomew Roberts had 4 ships and 500 men. And Captain Morgan sails the seas with a fleet of 30 ships and 2,000 men. He was the big dog, that’s why he got the rum named after him.

Pirates rule the seas until the 19th century and then you stop hearing about them. That’s because there’s up until then, there’s good pirate tech (boats/guns), but no communication infrastructure to uphold peace. Then comes radio, phones, and planes, so traveling by boat becomes safer and less common—unless you’re a WASP from New Hampshire.

This is when the pirates shift from seafaring to mostly land-faring.

Fastforward to the 1960s: radio is common and rock n’ roll is born. But the UK banned BBC and all UK stations from playing rock (because they’re pretentious British twats of course). So some smart, definitely drunk British lads on boats and sea forts started “pirate radio stations” to play rock n’ roll 24/7 which was legal because they weren’t technically on UK land—which is the most rock n’ roll pirate shit I’ve ever heard.

Meanwhile in California, 2 young pirates Steve Jobs and Steve Wozniak are wreaking havoc in the new lawless land of computing. Jobs and Woz go around campuses selling “Blue Boxes” that let kids hack telephones to make long-distance calls for free. They start building computers at Apple and in their free time hang with other nerds and pirates at the Homebrew Computing Club hacking into software to get access for free.

Steve Jobs Pirate Flag Apple

Steve Jobs and the Homebrew Computing Club

Then comes the consumer internet and all hell breaks loose.

Pirate Bezos starts Amazon. Google is founded. Oh and of course there were loads of pirates doing everything from downloading music, movies, and porn to pirate-bloggers sailing RSS feeds to pirates profiting on penis pills (my new side hustle). Then the 2000s hit and we start sailing the technology sea at like 100 knots/hour. Pirates are born everyday.

You have the invention of the iPhone in 2007.

With that comes pirates jailbreaking phones, selling iPhone wallpapers, making underwater iPhone cases, and loading up the App Store with fun meaningless games. Remember the Flappy Bird creator who was making $50,000/day but got stressed out and shut it down? RIP Flappy Bird.

Anyways, then in 2009, Bitcoin comes along. 

No one gets rich for a while so no one cares. For a solid decade, the only thing crypto is used for is crime, most famously by Silk Road founder Ross Ulbright who literally called himself The Dread Pirate Roberts.

And meanwhile, social media starts to be a thing.

You have Facebook in 2004, YouTube in 2005, and Twitter in 2006. But the creator economy starts slow. Facebook is for talking to friends, YouTube is for cat videos, and Twitter is for tweeting about your breakfast. Instagram comes along in 2010, Snapchat in 2011, and Vine in 2012 and the creator economy starts moving exponentially faster. Young pirates and hustlers catch on fast.

E-commerce dudes combine Facebook ads and dropshipping to make millions. YouTubers start getting mansion rich. Bloggers like Tim Ferriss and Ryan Holiday use Twitter to get internet-famous. The dude behind Instagram page @FuckJerry realizes no one was posting memes on Instagram and then builds a 7-figure network of meme pages. The MagCon boys blow up on Vine.

Fastforward a few years.

TikTok comes along and births a new generation of influencers with no clothes and lots of dance moves. Everyone now has a podcast and an OnlyFans. Meanwhile MrBeast has become so rich he’s now curing the blind and feeding Africa. And oh yeah, the richest dude in the world buys Twitter to free speech.

So here we are today and much of the social media seas are already sailed—so the only questions you have to ask yourself are:

Where can I sail uncharted seas?

Where can I find treasure?

Where can I be a motherfucking pirate?

The Vision Pro is here and it’s the most cyberpunk thing ever.

That’s why I went pirate and launched a 2nd newsletter on spatial computing.

If you want 20/20 Vision on spatial computing news, cool apps, and dank memes, subscribe here:


The Vision Pro memes too good this week:

Thanks for reading, nerds.

Let’s blow up the internet together.

Jason Levin