The Business Pundit is at it again. This time the popular site put out a list of the top 25 businessmen who broke the rules and won. The theory in business is if you risk big, you win big. Here are some of the people who risked the most and won as a result.

The top 5 on the list were:

1. Jack Welch

Named “Manager of the Century” by Fortune Magazine in 1999, Jack Welch is perhaps most famous for streamlining GE, reducing management from 29 levels to only six, closing businesses, and firing a significant percentage of his subordinates. Despite his strong, seemingly brash tactics (he was nicknamed “Neutron Jack” for firing so many employees), he brought the value of GE up from $12 billion to $280 billion, the largest increase for any company under any CEO. He also championed the notion of informality, which he brought to GE.

2. Steve Jobs

Co-founder of Apple and chairman of Pixar, Steve Jobs towers over Silicon Valley as a renegade and artist as much as a business manager. Fortune magazine calls him a “global cultural guru,” responsible for changing the way the world works and plays. Yet, he has been criticized for his superior attitude, taking credit away from his subordinates, micro-managing his business, firing employees in fits of anger, and any number of minor infractions, such as parking his Mercedes in handicapped spaces. His net worth is estimated to be over $20 billion.

3. Sir Richard Branson

In 1972, at the age of 22, Richard Branson had recently opened his first Virgin record store in London and signed his first artist, Mike Oldfield, to Virgin records. Oldfield’s “Tubular Bells” was released the next year and would sell millions of records, becoming a classic document of electronic experimental music. Five years later, Branson signed the Sex Pistols, a leading pillar of the British punk rock scene who had been rejected by every other record label in England. In addition to his groundbreaking Virgin record label, record stores, and competitive airline, Branson is famous for his world record-breaking attempts, earning him respect as a daredevil as much as a business mogul. A charismatic and like able persona, he has appeared on a number of the world’s most popular television shows, including Friends and Baywatch. He also has a space plane. If nothing else, Branson has proved that a man can be one of the richest, most successful people in the world and still be cool.

4. Sam Walton

At the end of his autobiography, Made in America, Sam Walton wrote that the most important rule in business is to break all the rules. He has also said, “I always prided myself on breaking everybody else’s rules, and I always favored the mavericks who challenged my rules.” His innovative and daring approach to business established the worldwide Wal-Mart chain, which replaced Exxon as the largest corporation in the world in 2002.

5. Bill Gates

It is common knowledge that the richest man in the world is a college dropout. Instead of completing his education at the prestigious Harvard University, Bill Gates decided to take a risk and devote himself fully to a little business called “Microsoft” he co-founded with a classmate, Paul Allen. Not content with the prevailing open-source practices of software development, Gates decided to buck the system by demanding a closed-source ethic. By changing the rules of software development, he established the software industry as we know it today.

Rounding out the list were:

6. Donald Trump
7. Henry Ford
8. Ray Kroc
9. Jim Buckmaster
10. Li Ka Shing
11. Rupert Murdoch
12. Kerry Packer
13. Paris Hilton
14. Andrew Carnegie
15. Boris Berezovsky
16. Arkadi Kuhlmann
17. Chris Albrecht
18. Michael Dell
19. Roman Abramovich
20. Jeff Bezos
21. Sergey Brin and Larry Page
22. Ingvar Kamprad & Family
23. George Soros
24. Steve Wynn
25. Chad Meredith Hurley

What do you think of the list? Who would make your Top 5?