“But the real payoff is the pirate life itself!” The argument for doing the insane startup work is the slim potential the team sells for $100M or more, but really, you’re in it because you love risk. You love the lifestyle! You love the sailing around the world and visiting exotic new ports of call and the rum and the wenches and oh wait we’re not actually talking about pirates you idiot.

Real pirates tended to be out-of-work privateers who had nowhere else to go, criminals trying to escape the law, or the desperately poor; their careers at sea rarely lasted more than a few years and usually ended in death. The number who retired comfortably in their mid-30s to start investment funds to back new up-and-coming pirates is roughly zero. But in Arrington’s “fantasy pirate world,” they’re all Jack Sparrow.

There may well be an “entrepreneur lifestyle” which roughly corresponds to the pirate lifestyle. I know a serial entrepreneur who seems to always be traveling to meet with high-power executives and VCs, to make deals over lunch and dinner and wine and bocce, and I don’t doubt for a minute that he puts in 80+ hour weeks or that it isn’t genuinely hard work. But the lifestyle that people are “crying and whining about” is, ultimately, not the entrepreneur lifestyle. It’s the first-hire lifestyle. Arrington may genuinely believe that all hard work is roughly identical, but it isn’t. The hard work he put in building TechCrunch was finding and managing employees, writing, and a lot of meetings with Internet movers and shakers. Surely that is hard work, but it’s no more comparable to an 80+ hour week of sitting at (or under) a desk coding until you have RSI than it is to tomato farming.

What brought on Arrington’s righteous anger was the complaints that people like, well, me had about Zynga reneging on stock options. He thinks that’s just whining. Bullshit. Zynga is whining. And let’s not pretend that Zynga is a Google or Twitter or a JWZ-era Netscape—or even a TechCrunch. They’re a Skinner box. I won’t go so far as to say that Mark Pincus should be first against the wall when the revolution comes, but he should be sleeping under a desk.

Pincus started—started—where Uncle Mike is now: as a venture capitalist. The material wealth both of them enjoy came from work very far removed from first-hire engineering. Arrington may fancy himself a pirate, but he hasn’t ever had to worry about scurvy.

[Too brilliant for me not to quote so heavily. It’s worth reading the entire piece. There’s another confusion taking place as well. The one where someone writes code or has an idea they’re so passionate about that they can’t stop doing it. That happens as well, but it’s only slightly more common than winning the lottery, hitting it big with a startup, or becoming a rock star considering how hard it is to maintain that level of intensity over any length of time.]
Source: Coyote Tracks