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...