They're running a service called 'craiggers' that scrapes Craigslist listings and sells an API. It's clear trademark infringement. Why would we feel bad for them?

Alright, perhaps one can argue the name is too close.

But craiggers provides a very valuable service, namely showing pictures of items as you search. It made furniture searching so much easier.

I have zero sympathy for craigslist. They didn't get into their position through "years of hard work". They won the lottery (someone had to win it). They have done zero innovation (other than maybe anti-spam) for years and prevent others from innovating on top. Society wins if they are forced to open their data.

Maybe they had a rough childhood.

"Flying under the radar hoping we don't get caught and sued for something we know is wrong" should not be a part of any reasonable business plan.

But many startups do not have reasonable business plans. They have crazy business plans that everyone knows will fail, except sometimes they don't. Many startups have begun knowing they were going to be sued, knowing they were going to have legal and publicity problems. That's the nature of the disruptive business that everyone wants to be in these days.

>Many startups have begun knowing they were going to be sued

Name one startup that began knowing they were going to be sued and went on to a successful exit.

Parenthetically, the original Napster, the one that began knowing it would be sued, was sold about 3 years after its founding for less than $2.5 million as part of bankruptcy proceedings -- and I doubt that the owners took any significant dividends out of its before its sale: http://en.wikipedia.org/wiki/Napster#Current_status

I never made the argument that these companies were looking for successful exits. I'm not sure how you read that into my post. I were merely saying there are some companies that are started even when the founder knows there is a very low chance of defending the company legally. This article is one such point. One that comes to mind where the founder was actively looking to be sued was the OnLive Windows competitor.

Some do it to prove a point, some do it to prove that the market exists.

Grooveshark will probably have started out knowing they'd run in to trouble. Jury's still out on how that's going to end though.

OK... but I still don't feel bad for crazy, unreasonable business plans that fail.

It worked for AirBnB.