A dead dream turned up in the basement last weekend.
Buried at the bottom of storage closet was a long forgotton box. Inside the box was the daily cartoon strip I drew for the school paper back in my university days.
Instead of going to class, I doodled. And instead of reading textbooks, I studied the collective works of Garry Trudeau, Bill Watterson and Berkley Breathed.
The strip was badly drawn and rarely clever. But sometimes I’d get in a shot at the sorority sisters and fraternity brothers who gave the Harvard of the North its well deserved reputation.
A few of my strips got taped to office doors, pinned to bulletin boards and were the target of angry letters to the editor.
For a time, I dreamed of becoming a full-time cartoonist. I’d create the next Calvin and Hobbs, Doonesbury or Bloom County. I'd be happy, rich and famous.
But once I left the ivory tower, I quickly came to realize I wasn’t prepared to invest the time, pay the price and make the sacrifice on what was at best the longest of shots. I'd never be a great or successful cartoonist.
It’s the same conclusion that Kevin O’Leary reached with help from his stepfather George Kanawaty.
Before he was a successful entrepreneur, chair of his self-named investment fund company and media personality, O’Leary was a struggling teenager in search of direction back in the early 1970s. He harbored ambitions of being a photographer.
“In my last year of high school, George sat me down for the Talk About My Future,” says O’Leary. His stepfather asked O’Leary what he was willing to do in order to be a photographer. Was he willing to pay the price?
“How much money do you think you’d need to make, every year, to be happy,” Kanawaty asked his stepson. O’Leary said $20,000.
Most photographers don’t make that much, Kanawaty said. Which meant O’Leary would need a full-time job with photography gigs on the side. He’d have to put up with jobs he didn’t enjoy to continue doing what he loved.
Yet even at that early age, O’Leary knew he couldn’t work for someone else. He was meant to be an employer and not an employee. “What was I willing to do to make money while I honed my craft? Lay bricks? Work in retail? Clean garbage trucks? Plant trees? I’d done all those jobs. The idea of spending the rest of my life subsidizing a passion felt impossible, and because I had no postsecondary education, those were about the only jobs for which I was qualified. Without the drive to work at other jobs to support that passion, I had no chance of becoming a wealthy photographer.”
So O’Leary put that dream to rest, went to the University of Waterloo and got an MBA at Western. He credits his MBA with giving him a head start, some much needed discipline and a rolodex of classmate contacts that proved equal to the cost of tuition.
After graduation, O’Leary launched Special Events Television. The feather in the company’s cap was Don Cherry’s Grapevine, a half-hour program that premiered on CHCH-TV. Cherry followed a few golden rules for TV that O’Leary clearly took to heart. Never be boring. Never be small. Always be the antagonist because the good guy’s not interesting. And always get in the first and last words.
O’Leary sold his stake in the production company and got into the computer software business in the early 1980s. He started the company out of his basement with a $10,000 loan from his mother. The company took off, licensing software for pennies and bundling with printers which sold in the millions. The company sold its products in big box stores and retail giants like Wal-Mart, stayed flexible on pricing and put a heavy emphasis on product testing and package design.
The company was stamping so many CD-ROMs that one of the production runs delayed by four days the release of Michael Jackson’s album Bad. “Bad went on to sell about eight million copies that year, which should give you some idea of how big we were, and how fast we were growing,” O’Leary says.
A few years later, he sold the educational software giant for more than $3 billion.
O’Leary then looked at buying Report on Business Television. Instead of making a deal, the CEO put O’Leary in front of the camera and a star was born. O’Leary now co-stars on Lang & O’Leary Exchange, Dragon’s Den – the number one Canadian produced TV show – and Shark Tank south of the border. He’s also chairman of O’Leary Funds, a money management firm.
“Whether I’m wearing the scales of a Dragon or the fins of a Shark, my message is consistent and clear: I want to go to bed richer than when I woke up,” says O’Leary. “By reinforcing that idea on my television shows, in books, on the radio and in newspapers and magazines, I’ve made making money my brand.”
According to O’Leary, entrepreneurs are the superheroes of capitalism. “Entrepreneurs do something governments can’t do: we inspire the next generation of wealth builders.”
And he adds that the only thing money truly buys you is freedom. “Freedom is a gift I’m grateful for every day. It is the result of a single-minded pursuit of the only thing that matters in business: money. I took great risks and made some hefty sacrifices to get here, and I’ll do whatever it takes to stay here. Because let me tell you, here is a very nice place.”
O’Leary’s book reads exactly like he talks on Dragon’s Den. He doesn't pull any punches. He’s also a consummate marketer so it’s no surprise he does a masterful job of telling his life story with the right mix of swagger and humility. You’ll gain a deeper appreciation for his business acumen, drive and determination. And if you’re an aspiring entrepreneur or someone who’s debating whether to pursue your passion, you’ll get some invaluable advice and cold hard truth for the bargain price of just $29.95.