There are no hard rules for how to be successful. Sure, we hear of people who work upwards of 20 hours a day to make it, while some people work only 6 hours a day and do fairly well. Hard work will always be there in some capacity, which means everyone has an opportunity to make it in their lives.

However, some people break the rules, either going the unconventional route, or breaking the law, in their fashion, and getting away with it. In an article on the Business Pundit blog titled 25 Businessmen Who Broke The Rules, some of the rules people broke include dropping out of college, making sex tapes, and generally behaving in ways that many people wouldn’t expect would make them rich, although infamy would easily have been expected. Some of the people have been linked indirectly to organized crime, but none have had the labels stick to them.

I’d rather go in a different direction and talk about someone who’s not on the list because he’s not alive now, but has probably ushered the most influence on America than anyone else. That person would be Joseph Kennedy Sr, the patriarch of the family that gave us a president, three senators, multiple congressmen and woman, and at least one governor that I can think of, as well as great political and philanthropic clout for over 70 years.

At one time Kennedy was the one of the richest men in the United States, worth over $185 million dollars during the depression in 1935. And just how did he build up all this money? Well, it could be his real estate dealings, which did amass a lot of money. However, he did two illegal things that really helped him get over. The first was forming what was called a “stock pool” at the time. This involved getting with a bunch of other folks and figuring out ways to pump up worthless stock so they could make quick money, then move on to something else. These days that will get you thrown into jail, but back then, it was considered a shrewd investment strategy. The other thing he did was run illegal alcohol during Prohibition, siding with many underworld figures in helping to import liquor from Canada.

Of course, there are many other foibles of the senior Kennedy, but he did end up rich, did end up quite philanthropic, and did send a heck of a lot of politicians to both state and federal positions who have fought for the rights of the everyday person, something the Kennedy’s were never going to be. Though I wouldn’t recommend doing things the way he did, it does show how out of the box thinking can help one achieve great success. So go ahead and break some rules today; just don’t get yourself caught!