I don't know about "breaking the law intentionally" but here are some examples of things startups have done that other people have thought were illegal. In some of the cases people have thought that so strongly that they've filed lawsuits.

Groupon selling coupons for alcohol in Massachusetts: http://articles.boston.com/2011-03-18/business/29351154_1_gr... (here are some other suits: http://www.portfolio.com/business-news/2011/03/29/groupon-fa...)

Facebook not living up to privacy promises: http://online.wsj.com/article/BT-CO-20111129-710865.html

YouTube/Google not paying royalties/failing to control copyright infringement: http://paidcontent.org/article/419-music-publishers-settle-w...

AirBNB's operations in New York: http://www.betabeat.com/2011/05/31/airbnb-takes-manhattan-wi...

If I remember correctly, Uber is also facing legal action about the legality of their car service.

Somewhat bullshit legal action, though. All they need to do is move their company out of San Francisco and then the City can't do anything about it. Cars for people in California can arranged from anywhere in the world with phone lines and intarwebs, and I doubt the City of San Francisco has much jurisdiction over people in, say, Russia.

Facebook is a startup?

Isn't it one until at least the first major exit event happens, like, until an IPO, or something?

Almost all startups, small companies, and even large companies that I've worked at have had some level of software piracy in their organization. Of course, I could just be unlucky in where I've worked, but it's always been rationalized away in some capacity ("once we start making money, we'll buy legitimate licenses").

There was a big discussion a week or so back about Dwolla's operations not being legal in California.

Facebook, CareerIQ, and I am sure you can find a few more.

Straight from wikipedia - http://en.wikipedia.org/wiki/Zynga

Scam ads

Through 2009 Zynga made money from lead generation advertising schemes, whereby game participants would earn game points by signing up for featured credit cards or video-rental services. These were criticized as being less cost-effective than simply buying game points, and in some cases, being outright scams that would download unwanted software or unwittingly sign up for a recurring subscription.[38] One ad signed up players for subscriptions to expensive and unwanted text-messaging services.[39]

On October 31, 2009, Michael Arrington of TechCrunch said that Zynga intentionally worked with scam advertisers, and that lead generation made up a third of Zynga's revenue.[64] Arrington also alleged that Facebook was complicit in this.[65] On November 2, 2009, CEO Mark Pincus announced a reform in its offers: Tatto Media, a major offer provider that enrolled users into recurring cell phone subscriptions, would be banned, all mobile offers would be removed, and offer providers would be required to pre-screen offers.[66]

Arrington continued to question Pincus' role in the scams, republishing a video of a speech by Pincus.[67] In the speech, Pincus said:

"So I funded [Zynga] myself but I did every horrible thing in the book to, just to get revenues right away. I mean we gave our users poker chips if they downloaded this Zwinky toolbar which was like, I don't know, I downloaded it once and couldn’t get rid of it. laughs We did anything possible just to just get revenues so that we could grow and be a real business." —Mark Pincus, Speech from Startup@Berkeley

In response, Pincus noted that after offering the Zwinky toolbar, his team of ten decided to remove it since it was a "painful experience".[68]

Several days after the Techcrunch story, Zynga's most recent Facebook game FishVille, was temporarily taken offline by Facebook on claim of advertising violations. According to Zynga, Fishville had 875,000 users within two days of launch. A release from Facebook on its reasons for taking the game offline read that "FishVille will remain suspended until Facebook is satisfied that Zynga demonstrates compliance with Facebook restrictions – as well as Zynga’s own restrictions – on the ads it offers users."[69] FishVille was later un-suspended at midnight November 9–10.[70]

Several suits were filed against Zynga for promoting such offers,[71][72] including the class-action lawsuit Swift v. Zynga in the United States District Court for the Northern District of California for violation of the Unfair competition law and the Consumers Legal Remedies Act, after the lead plaintiff's credit card was billed more than $200 for offers she completed to receive YoVille currency.[73][74][75]

Pincus later said that he had been too eager to increase company revenues through advertising, and that operating in reactive mode by taking down ads only after receiving complaints had not worked. The company removed all ads for a time, relying only on direct purchase of game currency, then began reintroducing third party ads only after they had been screened.[38]

You are debating against rocks. The reason I say this is because once people decide some one is wrong. They are wrong for life. Nothing you write here will convince people that this peddler is right in doing what he is doing.

Being right is not always synonymous with legal.

Society is so unfair, when some uses unfair means to game the system and make lots money, he is termed 'intelligent'. Because big money is glamorous. Here we are a guy at the subway making same kind of average money your average developer might make, now suddenly hell breaks loose. 'How dare he?', I mean the reactions are basically 'How dare this guy? without any college education without learning and reading? make the same average amount of money as I do?' So obviously they end up with 'All this is illegal so it doesn't matter'.

Go check your life, you will find you are doing N number of things every day which might not be complying 100% with the law. Yet you can do it without harming any one.

The problem here and reason with many problem here is clear. No body likes the idea that a poor un educated guy is making the same money as they are. Doing less intellectual work. And yet here they are, after all those high aspirations and that intellectual work still the same as a subway peddler. So what really is the difference between them and a candy peddler in the subway.

Its this thing that is really giving all the invisible pain. Not the illegality of the selling candy in the subway.

If only the number were not $50,000 and way lesser than that, you would see a totally different thread.

Some time back people here were angry with a VC for a making a comment on the 'Google Chef' who got rich in an IPO. The same situation here.

Subway candy peddler is to these hackers what the 'Google Chef' was to a VC.