Copyright and taxi-medallion laws are grossly immoral examples of regulatory capture that impoverish and endanger the public in order to provide a much smaller benefit to a small number of "exploiters." YouTube, BitTorrent, and Uber Cab were able to improve this situation, making them very popular despite greatly angering the exploiters. Similarly for, say, marijuana sellers. Doing illegal things that are nevertheless ethically upright and very popular may pay off for a business, as it did in those cases. Or it may not.

It's less likely to pay off when the illegal things are instead unethical, unpopular, and harmful to the public, at least if you get caught—and when they involve betraying the people closest to you, you're probably going to get caught.