Arlene Dickinson on family, career and business success

Roberto Caruso

It’s early summer, close to noon, but Kevin O’Leary and Arlene Dickinson are in bed, teasing one another with the ease of long-time lovers. “You’re such a snuggler,” he coos, clasping her hand. She cuddles closer, murmuring, “Could you tell me a story?”

For fans of Dragons’ Den, the hit CBC show, the scene has the improbable narrative appeal of a man-bites-dog tale. On air, these two multi-millionaire business titans are more frequently at each other’s throats. Entrepreneurs who come on the show looking for financial backing often witness fireworks instead, as the pair argue over the right way to do business. Where Kevin is gleefully Machiavellian and cutting, with a cold eye firmly fixed on the bottom line, Arlene is the kindly den mother: visibly moved by a contestant’s hard-luck story, protective when she feels another dragon is being too harsh, stern when she feels an entrepreneur is out of line.

So what are they doing in bed together? On this particular day on the set — a cavernous affair, far larger than it appears on television — a teen entrepreneur with a new idea about bed linens has invited the pair to sample his wares. “Come on, Arlene, you’re the hot one,” the kid urges. “She’s the cold one, trust me,” Kevin grumbles en route to the bed. Arlene rolls her eyes but laughs easily, saying, “Oh, come on, Kevin, I’ll show you what to do.” For the next 10 minutes or so, and much to the amusement of their three fellow dragons, the pair lounge on top of the covers, bantering and putting the young entrepreneur through his paces: “What’s the market for this product? What were your sales this year?”

Later, in her pale green dressing room, Arlene pulls a bathrobe over her TV outfit to keep it clean, then sinks into an armchair and surveys the clutter: samples of products that have been pitched on the show, boxes stacked up on a makeup chair, papers. “I’m starting to feel like a doll, not like a real person,” she says quietly. “People are doing your hair and makeup, they’re feeding you, they treat you really well, but...This becomes your reality, and it’s so not reality. I’m very mindful of the fact that even a small bit of fame can eat you alive and make you lose touch with who you really are.”

Arlene’s uneasy relationship with her own celebrity, which she calls “a gnat’s version of what a real star experiences,” is likely part of what makes people feel they can relate to her. She seems 100-percent genuine, not stuck-up or into herself. In restaurants and on the street, she’s stopped by people who want to have their photo taken with her or pitch an idea or just see what she’s really like. She’s unfailingly gracious and warm, even when people are interrupting a private moment, and yet there’s some discomfort too. In her dressing room, Arlene says, “A lot of people attribute magical skills and knowledge to those who’ve been elevated in some way, whether it’s being on TV or having an impressive title. It’s such crap, and it’s really important to keep reminding yourself of that fact. I’m so grateful this didn’t happen to me in my 30s. I don’t think I could have handled it—it probably would’ve gone to my head. But at age 55, when young guys come up and tell me they love me, I know it doesn’t mean anything. If I weren’t on TV, they wouldn’t even notice me.”

Well, maybe. But maybe not. Arlene is dynamic and energetic, the kind of person who brings a gust of air into a room and attracts notice without trying. There’s her style—that trademark streak in her hair, the funky wardrobe—and her warmth: Arlene is a hugger, a laugher, the person at the party who falls into a deep conversation on the sidelines with the caterer, whom she genuinely finds fascinating. And she has the most compelling brand of charisma, the kind that arises from contradiction: in her case, the clash between her toughness and her vulnerability, her success and her self-doubt, her present and her past.

I first met Arlene a year ago, at our mutual publisher’s request: Could I help Arlene shape the manuscript for Persuasion: A New Approach to Changing Minds? I’d never watched a full episode of Dragons’ Den, yet I knew who she was, the only female entrepreneur on the show, and a CEO. I was intrigued by what little I knew of her personal story: She’d risen like a phoenix from the ashes of a traumatic divorce, after which her kids wound up living with her ex. How did she manage to get her life and children back?

I was curious to know, but also, after years of interviewing celebrities, wary; most are either so guarded, or so prone to preening, that it’s impossible to imagine working with them. But when I met Arlene in the hip downtown-Toronto office of her Calgary-based marketing agency, Venture Communications, one of the very first things she said was, “Professionally, I am very confident. Personally, I am the opposite. And my problem with this book is that I’m really wondering why anyone would even care what I have to say.” The logos of current clients lined the wall outside her office — heavyweights like the Mayo Clinic, Travel Alberta and Toyota — and inside, on a desk in the corner, sat a Gemini Award. The incongruity between her accomplishments and her lack of self-confidence was not lost on her. “Yeah, I know how it looks,” she laughed, “but the person who’s hardest to persuade of your own self-worth is always yourself.” And that, as it turned out, wasn’t just the theme of her book. It’s been the theme of her life.

Arlene was born in South Africa, the youngest of three girls, and her family emigrated before she was three years old and settled in Calgary. Her parents’ marriage was not happy, and poverty didn’t improve it. “By the time we landed in Canada, my parents had only $50 to their name. They’d given up everything to come here, and we lived a very hand-to-mouth existence,” Arlene recalls. Her father got a job teaching electronics at a local college and walked to work to save the 15-cent bus fare; Arlene didn’t get her first brand-new dress until she was in her teens. At one point, her mother had to trade one of her most prized possessions, a diamond ring from her father, to purchase an old clunker of a car. In the typical rags-to-riches story, being poor is often made to sound cozy, drawing families closer and ‘making them value the important things in life.’ Arlene, however, remembers her parents’ heated arguments about money, and her own response: “to stay under the radar as much as possible.” Even this much had to be pried out of her, and she qualifies it by stating that her parents did the best they could. Although she frequently and fondly speaks about her father, who passed away years ago, she rarely talks about her childhood, saying, “Either I have a terrible memory or I’ve blocked a lot of it out.” When she was 13, her parents split up, which made her feel like an outlier in her tight-knit church community — she was raised a Mormon — and at school. “No one else in my class came from ‘a broken home.’

I remember being teased about it, and the message I took was that I was broken, too. My main memory of high school is just of trying to escape notice. I’d be surprised if many of my classmates even remembered me.” Only 16 when she graduated, she felt she “had to get away from the drama at home and didn’t feel smart enough to go to university,” despite having accelerated two grades in one year in primary school. So she moved out on her own and got a job instead. “That broke my father’s heart. He was a teacher, education was his reason for living, and I remember him telling me I’d be barefoot and pregnant the rest of my life if I didn’t have a degree.”

But that prospect didn’t upset Arlene, whose sole ambition in life was to create the happy family she’d yearned for as a child. “There’s a lot I really admire about the Mormon religion, but it was very patriarchal. Women of my generation were very much encouraged to marry young and to believe that our role in life was to raise children. Having a career didn’t even cross my mind as an option.” But she always worked — in the kinds of jobs you can get with a high-school diploma: secretary, sales clerk, bill collector. At 19, she married her best friend’s older brother; just weeks after her 21st birthday, the first baby came, and then, in rapid succession, three more. They couldn’t afford a place in Calgary, so they built a house in Carstairs, a small town about 50 km away. “We had no money and had to do a lot of it ourselves, everything from hanging wallpaper to shingling the roof — I acted as my own general contractor when I was seven months pregnant!” She was also growing and canning vegetables, baking bread, doing endless loads of laundry and, when her husband decided to go back to school to become a teacher, working full-time to support her family.

She had the life she thought she’d always wanted. But she was miserable in her marriage. She felt unloved. “I persuaded myself I was stupid, and also that I was unattractive and pretty much worthless,” she said early one Saturday morning, while nursing a cup of tea in her Toronto home. Arlene was in sweatpants, with no makeup, and her fiancé, David Downer, was lounging on the couch watching TV. He is a sales entrepreneur, casual and laid-back; they met at a Dragons’ Den launch party several years ago, and he is clearly gaga over her, equal parts protective and proud. All around, there’s proof of Arlene’s competence and success: the non-stop BlackBerry messages from clients, staff and others, the pressure of the day’s appointments and a charity event that evening. Yet, talking about her life before the divorce, she seems still to half believe her old version of herself: “uninteresting, not smart, not worthy,” she explains in the straightforward, factual manner of a woman who doesn’t want to be argued with or pitied. “Part of it was how my husband treated me, part of it was feeling I couldn’t live up to the Mormon standard, and part of it was simply that growing up, I’d always felt inadequate.” She’d been so surprised — and grateful — that anyone wanted to marry her that she didn’t think to question her own motives and didn’t listen when her parents suggested that she was too young to know her own mind.

Then, at 30, a turning point that wound up shaping the rest of her life: She had an affair. “Flowers, jewellery, money — they don’t mean anything . But if somebody is kind, stops and listens, that is more compelling to me than anything. I didn’t understand how unhappy I was in my marriage until this other man was nice to me. I was so hungry for any scrap of affection and validation.” None of which, she adds, excuses what she did: “It was a terrible choice, not just in retrospect but at the time — living a lie, telling lies, makes you feel horrible. I wish I’d had the courage to do the right thing and exit my marriage in a better way.” The price she paid, once her husband found out, was high: She was excommunicated from her church after a very humiliating interrogation by church officials who demanded intimate details of her affair. “I didn’t understand that I didn’t have to answer, that I had a choice,” she remembers, wonderingly. “I was in many ways young for my age.”

But the most devastating consequence of her affair was losing primary custody of her children. Her ex got the Carstairs house in the settlement and she didn’t fight it because “I just felt so guilty about what I’d done.” She wound up sleeping on her father’s couch in Calgary. Then the family court judge who ruled on her case told her that if she wanted her kids back full-time, she had to prove she could support them and make a home for them. “I only got to see them on weekends, which was torture,” she remembers, tearing up. “And at that time the mother always got the kids, so it was hard to explain.” Nevertheless, in an improbable twist of fate, within a year she was a partner at Venture, then a small marketing agency in its infancy. She accomplished this without going back to school or retraining.

How did she do it? “The short answer is that I learned how to be persuasive without being aggressive, and I convinced key people to back me and give me a chance,” says Arlene, rising to put her teacup in the dishwasher. “Plus, I worked like a dog!” The long answer, which she lays out in her book, involves her three core business principles: honesty, authenticity and ensuring reciprocity. What this means in practice is admitting when you don’t know something. Listening more — way, way more — than you talk. Paying attention rather than planning what you’re going to say next. Not trying to fit a preconceived business mold and not trying to be what you think others want you to be. Asking yourself what you can deliver in every situation, rather than simply what you can get out of it. “I know it sounds simple,” Arlene says. “But many people think success is much more difficult to attain than it actually is. The biggest obstacles are usually internal, not external.”

So how did she overcome her own biggest barrier, her lack of confidence? “By giving myself permission to make mistakes and learning to look for the potential in a situation rather than focusing on the problems,” she says; then she flashes a huge smile. “But let’s face it, I had the best motivator in the world: I wanted to get my kids back.” And eventually, as with most other things Arlene sets her mind to, she succeeded. “My kids and grandkids are everything to me,” she explains simply. “Anything I’ve achieved in life is because of them.” It’s July, and Toronto is in the death grip of a sickening heat wave. Arlene is spending a lot of time at her cottage, golfing with her fiancé, or at home, doing glamorous things such as watching old episodes of Modern Family. She needs low-key downtime, because she is busier than ever, getting ready to launch a mutual fund in the fall. Her new cause: “Financial literacy for women. A lot of women find themselves alone at some point, whether because they’re single, divorced or widowed, and a lot of them have been convinced they can’t manage their own finances, which is ridiculous. My goal with the mutual fund is to strip away all the jargon and help women see this isn’t rocket science. It really is possible to manage your financial future.”

Typically, even with her book at the printer, she’s still second-guessing herself. “Maybe it will help some people, seeing that someone like me was able to be successful. Or maybe people will just think, ‘Why did she write a book?’” A third possibility, that the book might, like most things she does, meet with approval and find a wide audience, seems not to have occurred to her, though she does allow, “That would be nice.” But a touch of self-doubt is not all bad. “The minute you’re complacent in business, it’s all over,” Arlene explains. “CBC is always auditioning new dragons, in case one of us gets hit by a bus or is viewed as a drag on the ticket. You can use that knowledge to push yourself harder and stay humble. It’s impossible to think you’re God’s gift when you know your replacement is waiting in the wings.” That, it turns out, is the key not only to her drive, but to her appeal: Arlene doesn’t understand just how irreplaceable she is.

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Persuasion: A New Approach to Changing Minds , by Arlene Dickinson, $33, is available now at Indigo.