Dragons' Den stars  Arlene Dickinson, Jim Treliving, Kevin O'leary, W. Brett Wilson, Robert Herjavec

Led by Robert Herjavec and Kevin O’Leary, books from Dragon’s Den stars have landed on many a national bestseller list. (Gluekit)

Features | From Pivot Magazine

The wisdom of Dragons

For a bracing, sometimes terrifying lesson in what it takes to be an entrepreneur, you could read all the bestsellers by the stars of Dragons’ Den. Or you could just read this.

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Canada’s Dragons—the soaring capitalist ones, that is—began spewing literary fire in 2010, in the chaotic wake of the Great Recession and four years after they first gathered in their CBC lair. Led by Robert Herjavec and Kevin O’Leary—both now departed from Dragons’ Den but still visible on the American equivalent, Shark Tank—Dragon books immediately landed on national bestseller lists. And, despite pauses over the years since—these authors are very busy people indeed—the books have kept on coming, no doubt reliable profit centres for their publishers. Arlene Dickinson, the most prominent and popular current Dragon, is applying the finishing touches to her third volume, slated for January publication. Canadians still love their Dragons, past and present, and still seek their entrepreneurial wisdom. 

The Dragons are celebrities, albeit in a modest Canadian way, but they aren’t (quite) famous for being famous—they are successful entrepreneurs first. The combination is what makes their books such hot sellers. If few of us, in a celebrity-obsessed culture, can imagine actually being Kim Kardashian, we can envisage being a middle-aged, balding curmudgeon with a sharp eye for the bottom line, like Kevin O’Leary—if only we can grasp, internalize and power forward with his business advice.  

Not counting a few outliers, most notably David Chilton’s Wealthy Barber phenomenon, which rocketed him to fame decades before the Dragons’ books took flight, five current and former Dragons have taken the literary plunge. They are O’Leary (three volumes of the Cold Hard Truth series), Herjavec (Driven, The Will to Win, You Don’t Have to Be a Shark) and W. Brett Wilson (Redefining Success) among the former participants in the show. Among the current cast, Dickinson, one of only four female Dragons ever (out of a total of 14), has penned Persuasion and All In, while Jim Treliving, the last original Dragon, wrote Decisions.  

So what do they have to tell their legions of readers? Spread across what has become a substantial body of writing, there are dozens of solid, if not always easy to master, pieces of practical advice—we’ll get to those. Taken as a whole, they comprise a kind of literary Great Course in the skills required and pitfalls lurking for a budding entrepreneur, as well as revelations about how would-be investors do, and should, think. And there is one adamantine conclusion held by every Dragon: you have to be born to the life. If it’s not in your psychological DNA, think twice, and then think again. Unless you’re “crazy” to get started on your entrepreneurial career, writes Herjavec, it’s not for you. You have to have the drive to turn a vision into reality, the urge to lay it all on the line for freedom and success, Dickinson says, and to do it 24/7 for 51 weeks a year, adds Wilson, who rather surprisingly admits to slacking off for seven days annually. The key necessity is passion, passion, passion. 

Entrepreneurs have to be performers in order to communicate their passion and sell themselves to investors and customers.

There are individual differences, of course, deriving from personalities (and personality clashes), and the Dragons’ different roads to success. Dickinson, 61, rose to wealth and celebrity status through her marketing firm, Venture Communications, meaning her primary product has always been herself. Her immensely popular first book, Persuasion, is all about selling one’s self as the essential skill for a would-be entrepreneur. Herjavec, 55, may have mastered a sellable product outside himself—Internet security systems—but he still agrees with Dickinson. Entrepreneurs have to be performers in order to communicate their passion and sell themselves to investors and customers, or it won’t matter at all what product they have on hand.  

You won’t hear that kind of talk directly from Boston Pizza magnate Treliving, 77, a former RCMP officer and cautious prairie boy to his core, the child of a man who refused to accept that anyone really owned their own home while there was still money left on the mortgage. But though Treliving doesn’t come right out and say it in Decisions, between the lines it’s clear he’s in complete agreement. Even Wilson, 61, whose book is a sobering account of the price that business success, let alone failure, can exact, tells his readers that scaling the heights turns on the seller, not on what’s for sale.  

Then there’s O’Leary, who, at 64 and four years departed from the show, remains the brightest Dragon star of them all. As befits a financial guy—his current incarnation now that he is out of politics after running for the federal Conservative leadership last year—O’Leary is focused on dollars and cents. Money has no sense of right and wrong, little patience for more than figures in black ink, and no time at all for a sob story; tears, in fact, irritate O’Leary like little else. Often there’s a bracing clarity to his stories of pathetic pitchers (the would-be entrepreneurs who appear before him) and readers can only nod along, however reluctantly. His reputation is a misreading of his essential kindliness, O’Leary claims with a certain charming chutzpah: it’s a far, far better thing to tell losers the brutal truth before they lose even more. His message is clear and consistent—never confuse money and emotion, and measure success by one simple question: “Did I go to bed richer than when I woke up?”  

O’Leary, who opens his first book with an airport washroom encounter with a viewer who calls him an “a—hole” for being mean to Dragons’ Den contestants, has no choice but to devote pages to discussing his public persona. But the other Dragons are happy to share their “We Need to Talk About Kevin” thoughts, too. With one notable exception, that is. W. Brett Wilson, often portrayed by other Dragons as the anti-O’Leary—in the sense they tend to think him too soft-hearted—has virtually nothing to say about his opposite number. (The latter does not return the favour, at one point declaring Wilson was suckered into an unwise investment in an acrobatic troupe by the spokeswoman’s tears—the same tears that so annoyed O’Leary. The Saskatchewan entrepreneur probably made zilch from the deal, O’Leary snarks, although he did manage to cement his reputation as a “knight in shining armour.”) 

Not only are entrepreneurs born, not made, the only real product they have to sell is themselves.

Wilson, whose book is about “redefining” success (as a social good, at least in part), is the true outlier among the literary Dragons. The others, who position themselves in the middle of a spectrum between Ebenezer Scrooge and Daddy Warbucks, have essentially stylistic disagreements with O’Leary. (The bottom line rules, yes, but you don’t have to refer to a poorly conceived jewellery business as “I’m Really Small Cockroach Jewellery Incorporated” as O’Leary once did.)  

Herjavec is O’Leary’s only real rival for celebrity in Canada, and probably eclipses him in America, now that Herjavec is entering into the famous-for-being-famous stage of his career. He divorced his wife of almost 26 years in 2016, has performed on Dancing With the Stars, married his glamorous younger partner from the show (Kym Johnson), had twins with her in April, and has reportedly sued and been sued by an earlier girlfriend amid a swirl of sexual assault claims and denials. For whatever reason—pure competitiveness, perhaps—Herjavec is the only Dragon/Shark to repeatedly compare and contrast himself with O’Leary. Entrepreneurship is really about passion, he writes (from the vantage point of his estimated $200 million), and the drama of the TV shows will only seem to be about money “if the only Dragon or Shark you pay attention to is Kevin O’Leary.” Dickinson, in counterpoint to O’Leary, likes a good story—even a sentimental one—while Treliving name-checks his fellow Dragon when proclaiming success is not measured by fortune, but by health, family and contribution to the community.  

Those are the sort of differences to be expected from strong personalities who often find themselves in competition in the Den, and completely overshadowed by their essential unity. Not only are entrepreneurs born, not made, the only real product they have to sell is themselves. And for readers of Dragon lit, that convincing unanimity may provide the books’ ultimate value, for the Dragons do not shy away from laying out the costs, as well as the prizes, of the entrepreneurial life. 

“If you’re not passionate about the business you’re going into, you’re likely never going to succeed.”

First, though, are you up for it at all? O’Leary provides a helpful checklist for those wondering if they have what it takes, tongue-in-cheek in wording but serious in intent. Do you need to sleep? (Herjavec notes his ability to get by on four hours a night was hugely helpful in building his business.) Are you anxious if you have no idea how much money you’ll make this year? Or the next? Are you all right with being interrupted when working on something? Do you like the people you work with and hate the thought of staff turnover? Do you envisage a lot of “me time” in your life? Family time? Does the adrenalin flowing through you when you’re awaiting the outcome of a risky decision make you sick? Answer “yes” to any of those, and you should reconsider quitting your day job; answer “yes” to the majority, there’s nothing to consider: entrepreneurship is not for you. “If you’re not passionate about the business you’re going into,” writes Wilson, who was deeply so and ended up both financially successful and personally regretful of his passion, “you’re likely never going to succeed.”  

Say you pass the O’Leary stress test. You have Herjavec’s drive, Dickinson’s willingness to go all in, and the passion Treliving and Wilson write about. What then? The good news is that the vistas open wide, and the Dragons have solid advice to offer. Since the entrepreneur is the product, exactly what better mousetrap you might use to open investors’ wallets is almost immaterial. This point is never more evident than when cast in the negative. O’Leary’s self-described kindness is meant to stop would-be entrepreneurs from drowning in debt for a hopeless cause; Treliving declares himself “angry” when he listens to pitchers describing how they plundered their kids’ RESPs for something that will never make money, and Dickinson makes it plain: be a serial entrepreneur, don’t fall into the sunk-cost fallacy and rack up more debt in pursuit of money already gone forever, and do not despair that you will never have another idea.  

So pick your poison. Your idea doesn’t have to be completely original, Herjavec says, as long as it offers unique benefits. It has to be something your competitors can’t easily and quickly duplicate—meaning some key part or aspect should be patentable. Then, the Dragons add in Greek chorus, research it into the ground. Know everything about it and be convinced it has a future. Picture in detail what you will actually be doing, adds Treliving, what making or importing, marketing and selling this item or service will mean to your daily life for years to come. Can you stand the prospect?  

Then it’s on to the money moment, including the pitch. Pitchers must engage the Dragons’ attention quickly, which doubles their chances of success, says Herjavec; keep it simple, says O’Leary—if you can’t explain your business to an eight-year-old, a venture capitalist’s eyes will also glaze over; emphasize the benefits to investors, and try to move your monologue into a dialogue, advises Dickinson; stay pleasant, they all add—rude and arrogant pitchers, like O’Leary’s despised snivellers, are doomed (the Dragons have the money and the right to arrogance, says everyone in so many words, save O’Leary, who spells it out); demonstrate that you’ve identified a real need you are planning to fill, says Wilson; be delusion-free, Herjevac insists—anything that sounds like, “My product is so great it will sell itself” won’t get the chance to prove it; above all, have detailed and believable financials.  

The winners on Dragons’ Den all evaluate their financials soundly and outline them persuasively, says Treliving. They lay out sales records or plausible projections based on market research, several Dragons note, and they have information on their profit margins, on the best place for production based on costs, the market percentage they can reasonably aim for. They are honest and transparent about debt, and any other past setbacks.  

So, you have the mindset and, just as important, have convinced the people with money that you do—that is, have sold yourself—and, almost incidentally, also have that need-filling product. That still doesn’t mean you are on the cusp of wealth—far more start-ups fail than succeed. But, the Dragons agree, you have a shot, and they have much more practical advice to offer: on maintaining deep social and community engagement, for that’s where potential backers will be found (Treliving); or reducing social ties and marrying late (Dickinson); on holding back on too-rapid expansion (Herjavec); on hiring, managing and firing employees (Dickinson again); on how to make sound decisions and deal with your own inevitable second-guessing (Treliving again); on the perils of being surrounded suddenly by yes-men after all the naysayers of the early years; on sharing the wealth or, more simply, revelling in it (O’Leary, of course). 

If you can’t leave work behind, try to incorporate family and friends within your work.

The Dragons don’t dwell on the price of failure, unsurprisingly, but they do write, to a greater or lesser degree, about the cost of success, particularly in terms of a major contemporary social issue, the elusive work-life balance we are all supposed to be striving for. Sometimes, it’s the briefest flick: the balance is a myth, Treliving declares, because the all-consuming work has to come first, and thus his first two marriages failed.  

Herjavec was dismissive of the clash of work and personal life as a real issue in his first book. Like the other Dragons, he allowed no doubting the notion that entrepreneurs cannot let go of their business demands on any consistent basis, but blandly asserted that success ultimately made up for all the time away from his wife and children. Not in his case, as it turned out—six years later, Herjavec was writing about the “overwhelming pain and sense of loss” his divorce had brought him. Wilson writes about his passion and commitment to his work, and his lack of those qualities elsewhere in his life: “I literally walked away from my marriage… ignored my health and… my children.” The elusive balance has to be fashioned in some way, says Wilson, and he found it in socially conscious investing. Over his three seasons, Wilson was the Dragons’ leading dealmaker, he says, making twice as many investments as any other, and basing his judgments on the moral qualities of both applicant and project. 

If Wilson writes with the rawest emotion, Dickinson provides the most wide-ranging discussion of family life in the entrepreneurial pressure cooker. In part that’s probably because she is a woman—certainly she is the woman, for eight seasons alone among the boys in the Den—and has likely had the job thrust upon her by reader expectation. She too believes the balance is a myth. Cancelling meetings or trips with friends, missing kids’ hockey games and failing to show up for family gatherings are all inevitable entrepreneurs’ sins. Those drawn to the life have to shake off the guilt, because they are artists, as prone to obsessive immersion in their work and dark periods of doubt about their creative pursuits as any painter.   

Live your life in changing “chapters,” Dickinson suggests, with some chapters having more time for private life than others. And, if you can’t leave work behind, try to incorporate family and friends within your work. That sounds more than a little hazy, although not as contradictory as Dickinson’s statement that she’s learned to be present in the moment, whatever she is doing. If she’s with her children, she says, she turns off the cellphone, something she had just spent pages arguing was impossible. Maybe, regrets and work-arounds notwithstanding, that’s just the way it has to be—for entrepreneurs, the balance will always be hauntingly just out of reach. It’s a sobering, useful lesson for readers, even those who are prepared to do the 24/7 and are either dedicated to a loner life or serenely convinced they—and their closest relationships—can beat the odds. 

And maybe they can. Consider the group’s anti-hero. O’Leary doesn’t even acknowledge the concept of work-life balance. For him, all true entrepreneurs will at some point realize that they’ve just spent weeks in airplanes or days without sleep, and haven’t seen their families since who remembers when. And realize, too, that they’ve “never been happier.” Perhaps happy entrepreneurs make for happy families. O’Leary, after all, though his marriage has had its ups and downs, is the only literary Dragon never to divorce.  

DRAGON’S DIS: We need to talk about Kevin 

Everyone has something to say about the abrasive Kevin O’Leary, except W. Brett Wilson, who wasn’t always pleased with his fellow Dragon (but rarely calls him out by name). Even O’Leary has comments on O’Leary, though he’d rather tell readers how soft a touch Wilson is. 

“Anyone who seeks profit at Kevin’s expense is greedy, and anyone whose business plan exhibits a flaw is a cockroach and will be crushed like one. I find his approach to life and his single-minded attitudes toward money offensive.” —Robert Herjavec, The Will to Win 

“I’ve never looked at success through the lens of money. Apologies to Kevin O’Leary, my fellow Dragon, but you’re wrong about this one, buddy.” —Jim Treliving, Decisions 

“Kevin likes to say that money has no emotions. What he misses is the point that money is the driver of so many emotions.” —Arlene Dickinson, Persuasion 

“For some reason, pitchers feel I need to know their medical history, their family’s troubles, their dead dog’s name… I blame this trend on some of my more sentimental colleagues.” —Kevin O’Leary, Cold Hard Truth: On Business, Money and Life