A few weeks ago, I had the opportunity to hear from businessman Kevin O’Leary at a talk called “Rain Maker Lessons.” For those who don’t know who Kevin O’Leary is, he is a self-made millionaire, and stars on the hit television show Dragons’ Den. He is also featured on the Lang and O’Leary Exchange where he debates and discusses business and investment issues.

O’Leary told the audience of his first job working for somebody else. He was working at an ice cream shop and was ordered by his supervisor to get on his knees and clean some gum off the shop floor. He refused, and was subsequently fired. He vowed that day “never to work for someone else.” Since then, O’Leary has been self employed, struggling at times, but ultimately achieving a massive level of success, as he now manages O’Leary Funds Inc., a mutual fund with over $1 billion under management.

O’Leary had a few comments about Winnipeg that surprised me. He remarked that “Winnipeg is a wealthy, successful place,” and that “Winnipeggers hate debt.” He also explained how he felt Winnipeg was relatively unscathed by the economic crisis of 2008 due to our low overall debt levels.

During his talk, O’Leary made clear that he has a very well thought out and defined view of the business world. In his words, “I’ve been rich and I’ve been poor; rich is better.” His goal is “to go to bed with more money than when he woke up.” He also mentioned some lessons he has learned in business, chief among them the importance of focusing on your weakness, not your strengths. He believes it is important to “find a partner who is good at what you are weak at.”

As someone who has run numerous businesses, O’Leary was very clear that the path of a small business owner is a difficult one. To some, O’Leary’s suggestions for success in business may appear cold, but I feel there is no better authority on these issues then someone with the experience of creating wealth, and someone who had the responsibility of building a successful business. As O’Leary put it, the “difference between being an employee and an owner is that you will have to sacrifice people.” He explained that “business is war,” and that an owner must “be willing to sacrifice everything” in order to succeed.

All of this may seem negative and cause you to ask the question, “If being an entrepreneur is so difficult, why go down that path?” O’Leary has an answer for that: “Do it to set yourself free.” O’Leary no longer lives the stressful life of an entrepreneur. He is still involved in business of course, but he has attained a level of wealth and financial freedom that allows him to choose what he does with his life. By making sacrifices early on to attain wealth, O’Leary has, at a relatively young age, achieved a level of independence that most only dream of.

In his presentation, O’Leary described three attributes of success for an entrepreneur. First, “admit your weaknesses to yourself.” Second, develop communication skills. Third, “luck.” On this third point, O’Leary said that there is a special quality to those who succeed in business, a “spark in their eyes.” He quoted Napoleon, who said he liked “lucky generals.” Whether you call it “optimism, karma, sparks . . . it just feels right,” said O’Leary.

Near the end of his remarks, O’Leary said something that I found quite interesting. He said, “In almost every case of those who achieved the most success, their focus was not to be rich, but to be successful in business.” This is a variation on the saying, “Do what you love and the money will follow.” Whether you strive for success in business, or any other line of work, we can all learn from O’Leary’s experiences and determination, and we can all admire the success he has achieved.