The Pros and Cons of Business

He’s a venture capitalist known to crack the core of a begging entrepreneur with a swift and slicing speech; an established brand-builder in the industries of education, computer software and finance, and an overconfident capitalist that once went head-to-head with the berating and uncompromising nature of the late Steve Jobs. He respects his money just as much as he loves the freedom that comes with it, and will never yield to what won’t generate profit.

As co-host of CBC’s The Lang and O’Leary Exchange and unassailable personality on business reality shows Dragons’ Den and its American adaptation Shark Tank, Kevin O’Leary is now offering a start-up investment of $100,000 to the frontrunner of his latest venture, Redemption Inc. The prime-time series judges 10 Canadian ex-convicts on their potential to become legitimate entrepreneurs in challenging business settings. The former offenders are given an unexpected second chance, either by earning O’Leary’s generous cheque to start a lawful business, or accepting an ‘exit package,’ which includes anything from life coaching and scholarships to vacations and computer equipment. “Trust is something you build over time,” says O’Leary. “These aren’t some strange foreign aliens, these are your sisters, brothers, uncles, cousins – they are people who made a mistake. Every family has somebody like this in them.”

Solely for the drama or tragedy of it, the premiere episode of Redemption Inc. has policemen handcuffing a bewildered O’Leary, who is then forced to swap his business suit for a ratty orange jumpsuit and thrown behind bars. The pseudo arrest gave O’Leary a bitter taste of his worst nightmare. “The idea of being incarcerated is just sheer terror to me. [Your freedom being taken away], and all your decision-making removed from you is a horrible thing, and so, you know, I didn’t like it, and it was very sobering and very disturbing for me and disorienting. Freedom is everything.”

Not your typical storyline for a television show, O’Leary was doubtful when Jasper James first brought the concept to his attention. As the co-founder of a global investment firm with $1.5 billion in holdings, he turned to him and said, “Are you out of your mind? I can’t get involved with ex-cons; I’m chairman of O’Leary Funds.” After a clarifying conversation with the British producer, O’Leary tuned into the reality of a world where many ex-offenders may not become taxpayers due to society’s inability to trust them with a job. “It’s incredibly unfair to incarcerate them, make them pay their price and then not give them a second chance. I got involved because I would like to fix this problem; I would like to get some percentage of the people that come out [of prison] jobs so they don’t go back in. It saves us hundreds of millions of dollars in taxpayers’ money.” More than that, O’Leary speculates that with offenders having no means to support themselves, they return to a wayward life. According to Statistics Canada, 62 per cent of men and 48 per cent of females have prior convictions when committing a crime. While O’Leary isn’t blind to the concept of repeat offenders, he remains steadfast on one’s ability to rehabilitate. “Not everyone is like that.”

Take Brian O’Dea as an example. A former drug smuggler and user who came close to death’s door, he became a venture capitalist, author and television producer after serving time in jail. He’s never looked back. Now a fixture on Redemption Inc., O’Dea analyzes the participants’ leadership and teamwork skills and reports his findings to O’Leary. The selected candidates’ offences range from drug trafficking and theft, to armed robbery and securities trading – enterprises that hit at the heart of entrepreneurship. Offences don’t include violent crimes such as murder or child-related felonies. “I don’t approve of their business. I don’t believe in breaking the law, but they are running a business that involves logistics, transportation, produce costs and marketing. It’s a real business and if it was a different product, they wouldn’t be in jail.” According to O’Leary, the keys to entrepreneurial success include one’s ability to take risks and deal with the outcome, the aptitude to articulate an intended vision, and the gift to execute a business plan. “Entrepreneurs have huge amounts of sacrifice in their lives, huge decisions about the balance of their lifestyle and time – and they are willing to take them. That’s the only way you are going to be successful.”

In his cathartic book, Cold Hard Truth: On Business, Money and Life, O’Leary describes the difference between making money and creating wealth. While enrolled as a student at the University of Waterloo, he capitalized on one of his hobbies by running a shuffleboard business with his roommate at a local pub. When the owner of the watering hole noticed their profits rising, she demanded a cut of the winnings. “We were making good money playing shuffleboard, but we weren’t becoming wealthy. The bar owner, however, had just discovered another way for her existing business to generate more revenue,” he wrote.

A moneyed O’Leary candidly admits that, as anyone, there was a time when breaking the law was a welcome temptation. In fact, before the multi-millionaire could pave his road with gold, he walked along a path of self-destruction. “I was failing in school and I was sort of with the wrong crowd … I started to explore some illicit things.” More party animal than pupil, it wasn’t until his last year of high school and crashing his family’s car when his stepfather George Kanawaty approached him with questions about his future that a spark ignited in O’Leary. He adapted to the lesson wholeheartedly, one that required him to keep asking himself for more out of life. “Everybody has the potential to be a criminal; everybody has that weakness in them. I just feel that I’m very passionate about redemption because I found something in society that I think is broken and I want to be part of the solution; I want to fix it.” While he can’t reveal the winner of Redemption Inc. just yet, the intuitive O’Leary admits that he was stumped by the outcome. “As you watch the show, different talents start to appear … my assessment, initially, was wrong about them. The outcome is quite unusual.”

www.cbc.ca/redemptioninc