Tonight: O'Leary behind bars in Redemption, Inc

It is a sight to put a smile on the face of anyone ever given the bum’s rush out of the Dragon’s Den: Kevin O’Leary, the belligerent, bald-headed bully dragon, behind bars.

The venture capitalist didn’t pull off a ponzi scheme or abscond with his O’Leary Fund assets. He trades in his designer duds for an orange jumpsuit and spends over 12 hours in a cell as part of the opening episode of Redemption Inc. The Apprentice-meets-Alcatraz reality series premieres Monday at 9 p.m. on CBC.

The show takes 10 actual ex-cons and puts them through a series of business challenges. In the end, one will gain redemption in the form of a business partnership with O’Leary, who will stake $100,000 of his own money on the start up.

Some of the participants have spent up to seven years in prison. “My perceptions have completely changed as a result of doing this show,” says O’Leary. “It’s amazing to see how resourceful these people are, how great they are as entrepreneurs.”

There were restrictions on as to who could apply. Conrad Black and Garth Drabinsky will have to wait until the celebrity edition. Other ex-cons just seemed inappropriate. “We didn’t want to bring in anybody that had done a crime against women or children,” says O’Leary, “but there’s many other crimes out there like drug trafficking or financial fraud or bank theft.”

It was trafficking that tripped up Brian O’Dea before he found redemption. At the height of his career as a drug smuggler, he ran a trucking company, operated two 100-foot fishing vessels. He had a workforce of 120.

A heart attack at 40 sobered him up and he walked away from the drug business. Three years later, U.S. authorities caught up with him working as a drug and alcohol counsellor. He pled guilty to trafficking charges and spent 10 years in jail.

Now he’s a key advisor with O’Leary on this venture, helping him assess the participant’s progress.

True to his money-means-everything rep, O’Leary takes a bottom line approach to why Canada should rehabilitate more ex-cons. “If you go to prison, if you get a record,” he says. “It doesn’t matter what you did, when you get out you can’t borrow money, you can’t get a job, you can’t get a credit card, you can’t buy a car. Anybody that looks at your resume and does a background check, you never hear from them again. You are invisible, you are tainted meat.”

The Montreal native says, with no legitimate means of support, many ex-cons are back in jail within two years. “It costs us as a society $250,000 a year to keep these people in prison,” he says. “It’s insane. I look at that as a taxpayer saying, ‘This is broken. How can I fix it?’”

One thing O’Leary knows for sure—he’s never going back to prison again. “I’ll remember every minute of it,” he says. “You can’t sleep, they don’t turn the lights off. There’s sensory deprivation. There are no newspapers, there’s no music, you can’t talk to anybody and there’s just a cold slab of concrete there. That’s it.”

Giving up 12 whole hours had to screw up O’Leary’s busy schedule. He claims he only spends 30% of his time on his TV ventures, but the man has four TV shows on the go. Besides the Den, there’s his regular CBC News Network gig on the The Lang and O’Leary Exchange plus the Mark Burnett-produced Dragon’s Den clone Shark Tank on ABC.

So—no matter how much glee it brings Dragon Den rejects--no more hard time for O’Leary. “When he came out the next morning,” says O’Dea, “he said, ‘I’m never doing that again!’ I said, ‘That’s what they all say.’”