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Q&A: Daniel Debow, the $292-million man that hit the jackpot—twice

He made his first splash with Workbrain before recently selling Rypple, a social media program based a shockingly simple idea: people like feedback

Daniel Debow

(Image: Mark Peckmezian)

Rypple purports to bring the performance review into the social media age. Employees can receive recognition on a Facebook-style wall and ask for feedback via private messages. What was wrong with the traditional, pen-and-paper performance review?
What was right with it? It’s slow, inefficient and way too formal. Rypple makes feedback fun and social, and it reaches an employee right away, rather than six months after the fact. It uses real lang­uage, too. No one says, “You exhibited the com­petencies of leadership and decisiveness.” They say, “You were a rock star. You kicked ass on that deal.”

Rypple users can give each other badges that say “You’re #1!” and “Thumbs up,” which seems goofy. Do people really crave that kind of hyper-positivity at work?
Yes! People aren’t robots. Recognition means a lot. People care a lot about money, of course, but once they reach a certain compensation level, salary ceases to be a significant motivator. Coaching, recognition and relationships with management matter more.

In 2007, you sold Workbrain, a workforce management company, for $227 million, and you just sold Rypple for $65 million. What do you know that the rest of us don’t?
Nothing. I’m just willing to take some crazy risks and fail a lot along the way.

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The Chase: a young couple finds a place to party in the west end

The BuyersThe Buyers: Joel McConvey, a 33-year-old freelance writer and producer, and Amy Butoiske, the 33-year-old manager of the Worldwide Short Film Festival.

The Story: McConvey and Butoiske, who lived in a small apartment at Bloor and Ossington, never thought they’d be able to afford a house in Toronto. Then, about a year ago, McConvey finished work on The National Parks Project, a popular documentary series, and the couple found themselves with a windfall (he got paid, unusually, for all 13 episodes at once). “We thought, ‘Who knows when this will happen again? Let’s put the money into a good investment,’ ” McConvey says. The couple loved their neighbourhood, with its cool bars and restaurants, and hoped they could find something nearby. They wanted a place big enough for McConvey to have an office (he works from home) and with a good-sized backyard for hosting summer barbecues. The couple set a budget of $465,000 and started their first-ever house hunt.

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The weirdest mayoralty ever—the inside story of Rob Ford’s city hall

Loyal councillors have defied him. His approval ratings have plummeted. And his powerful Conservative backers are nervous. How did it all go so wrong? The strange story of Rob Ford’s city hall

The Incredible Shrinking Mayor

On Newstalk 1010, the sly strains of the Hollies hit “He Ain’t Heavy, He’s My Brother” offered the first clue. Then morning host Jerry Agar burst on the air with a surprise announcement: Rob Ford and his councillor sibling Doug were taking over the station’s Sunday afternoon talk-fest, The City. For the once-staid CFRB, landing the boisterous brother act that Margaret Atwood had puckishly dubbed the “twin Ford mayors” was clearly a coup, but that didn’t answer the more obvious question: why on earth would the Fords want to spend two more hours a week in front of an open microphone when they were hardly suffering from a lack of media exposure?

Rob Ford, after all, ranks as one of the most compelling and exhaustively chronicled figures in Canadian politics, adored and despised with equal gusto. His every pronouncement seems to turn into front-page fodder, his every grimace and belly scratch catalogued by rapt photographers. And who could forget the YouTube footage of comedian Mary Walsh arriving in his driveway, decked out with a velvet breastplate and a plastic sword?

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Jan Wong: Why the LCBO—the antiquated, paternalistic monopoly that’s deliberately gouging us—has got to go

Body Politics

On a recent Sunday afternoon, I stopped by the LCBO’s flagship Summerhill store.
A glorious 35,000 square feet of creamy Italian porcelain floors and sparkling lights, the refurbished Canadian Pacific Railway station is adjacent to a cluster of gourmet shops that affluent shoppers call “The Five Thieves.” Here you pay dearly for ready-to-heat osso buco or a square of chocolate cake sprinkled with edible gold leaf. Despite its prime location, this outlet, the LCBO’s largest, is no pricier than any other location in the province. You pay the same fixed $12.60 for a 2009 Louis Bernard Côtes du Rhône here as you would at Scarborough’s lowly Cedarbrae Mall.

Nice, huh? But wait—you and I are paying for those pot lights, the Martha Stewart–style test kitchen (used for cooking demos and wine appreciation classes) and the standalone tasting bar, not to mention the lease on this prime piece of real estate. We all pay—whether we’re teetotalers or boozehounds—because higher overhead reduces the annual dividend the LCBO remits to the province. That in turn means less money for everything from social services to infrastructure.

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Editor’s Letter (May 2012): the city is in the midst of a cultural renaissance—except at city hall

Sarah FulfordThe spectacle at city hall has become a common obsession, even among people who never before cared much about municipal politics. It’s part comedy, party tragedy, and overall the weirdest show in town. The carnival-like atmosphere reached its apex when Rob Ford jumped on a giant scale and turned his weight problem into a public exhibit. David Miller, for better or for worse, was at least sensible enough to drop his extra pounds before discussing it with the world. In our cover story this month (“The Incredible Shrinking Mayor”), the writer, Marci McDonald, makes the case that beneath all the Ford family buffoonery is something quite dark. And also sad. The portrait that emerges from her sweeping narrative is of a man who would rather be coaching football than running the city. In fact, he’s a failed football player and reluctant mayor, much like George W. Bush was a reluctant president who really wanted to be baseball commissioner. And it’s no fun to watch someone ill-suited to his job struggle on a daily basis, particularly when the stakes are so high.

If you closely follow the day-to-day skirmishes at city hall—over subways, the waterfront, bike lanes, labour unrest—you might start believing that Toronto is hopelessly debilitated, which just isn’t the case. This is, I believe, a great moment for Toronto. The city is more energetic, creative and prosperous today than maybe ever before. In a recent issue of Toronto Life, we ran a profile of the city councillor Kristyn Wong-Tam, who said something that stuck with me: “Right now city hall is completely out of touch with the urbanism and energy that I feel in our neighbourhoods. We’re in a period of cultural renaissance and transformation.”

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Dear Urban Diplomat: do you need to give a standing ovation in Toronto even when one isn’t deserved?

Dear Urban Diplomat

(Image: Alfred Cunningham)

Dear Urban Diplomat,
I just moved to Toronto from London, England, and I’ve noticed that nearly every theatre production here gets a standing ovation. I saw a supreme stinker at the Elgin last week and everyone leapt to their feet. I remained seated and got the evil eye from my new Toronto friends. Is it customary here to stand even if you don’t mean it?
—Pleased to be Seated, Cedarvale

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Tony Keller: why the obvious fix for the country’s collective pension problem is being ignored

Work Till You DieLast fall, the Royal Bank of Canada—with $27 billion in annual revenue, $752 billion in assets and 74,000 employees, the biggest and most prudent bank in the world’s safest banking system—announced that new employees would no longer be eligible to receive what is probably the company’s most important workplace benefit: the comprehensive retirement insurance plan. It insures the Royal’s Canadian employees, or at least those hired before January 1, 2012, against all sorts of risks. The risk of reaching retirement age at a time when stock markets are down, or interest rates are low. The risk of outliving one’s retirement savings. Inflation risk. Risks you’ve probably never even heard of, like reinvestment risk and liquidity risk. Even the risk of earning below market returns.

This generous program wasn’t unique to the Royal. Many employers, particularly big companies, once offered similar plans. Some still do, though their numbers are dwindling. You may be wondering, “Why have I never heard of retirement insurance?” You have. It’s called a pension.

We’re heading for a pension crisis. The federal government says so. The opposition says so. Most provinces say so. The library shelves of the land groan beneath the weight of studies. The first class of baby boomers hit 65 this year, and we’re still not ready. The economist Michael Wolfson, formerly the assistant chief statistician of Canada and now at the University of Ottawa, estimates that half of all Canadians born between 1945 and 1970 who have average career earnings between $35,000 and $80,000 are facing a drop of at least 25 per cent in their post-retirement standard of living. Which is perhaps not surprising given that most of us don’t have a pension plan.

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Memoir: two young protesters find love among the tents at Occupy Toronto

Memoir: Your Tent Or Mine?I’m a 28-year-old film editor, and I don’t want for much. I live in a spacious apartment on a quiet street off Queen West. I rarely have trouble finding meaningful and well-paying employment. But after following the Occupy Wall Street protest in New York, I was inspired to step outside my comfort zone.

On Saturday, October 15, when a group of people set up tents in St. James Park, I decided to stop by and show my support. By the time I got there, the sun had begun to go down and a general assembly was underway. There were hundreds of people of various ages and ethnicities, income and education levels, all energized and eager to have their voices heard. At the end of the assembly, a smaller facilitation meeting was organized in the park’s gazebo to discuss the process of working together as a group. There were about a dozen of us. As the sky darkened and the floodlights lit up the gazebo, we began introducing ourselves. Almost immediately, a familiar voice spoke.

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Who Worships Where: an agnostic assessment of Toronto’s most formidable flocks

Who Worships Where: An agnostic assessment of Toronto’s most formidable flocks
Religious attendance might be in free fall across the city, but over the years a handful of Toronto congregations have managed to stockpile both money and influence. We look at the places where power brokers still kneel before something far mightier than themselves. Check out our profiles of five Toronto power congregations »

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The Chase: one couple’s search for suburban comforts in the urban wilds

The BuyersThe Buyers: Karie Whetter, a 32-year-old marketing account director, and Paul Cussons, a 35-year-old account executive.

The Story: Whetter and Cussons met and started dating in mid-2010. The relationship quickly flourished, and just over a year later they were already talking about moving in together. Renting was out of the question—they had each been saving for a down payment before they met, and so they decided to pool their resources and take the ownership plunge together. Whetter and Cussons both worked in Mississauga, but neither of them wanted to live there. Most of their friends had recently moved to Toronto, and they wanted to do the same. The couple set their sights on the city’s west end—just on the cusp of Etobicoke—which was still relatively close to work. The area also had housing stock that offered some of the suburban-style conveniences they wanted—a garage, a driveway and a big backyard for Whetter’s two huskies, Bukka and Shade. So they decided on a budget of $700,000 and started their search.

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Reason to Love Toronto: because Regent Park’s The Citadel dance theatre is now a reality

Reason to Love Toronto: because we like to bet on long shots

(Image: Dave Gillespie)

At Dundas and Parliament is a gleaming 60-seat dance theatre called The Citadel. It’s the best thing to happen to Regent Park since the colossal $1-billion neighbourhood revitalization began in 2006, and it almost didn’t happen at all. In 2007, when Bill Coleman and Laurence Lemieux, the husband-and-wife founders of the dance troupe Coleman Lemieux and Compagnie, bought a former Salvation Army soup kitchen, their enthusiasm blinded them to the fact that they couldn’t afford it. The building cost $750,000 and needed at least $300,000 in renos; they were earning $30,000 a year combined. They begged and borrowed enough for a down payment, and maxed out 11 credit cards to cover their living expenses. AmEx was hassling them daily by the time Mitch Cohen, the head of Regent Park redeveloper Daniels Corporation, heard their tale. He’s a sucker for a feel-good story, but also a businessman who realized that the presence of a renowned dance company could persuade prospective buyers that the area would gentrify. He connected them to his tradespeople, and $300,000 in aid started rolling in: windows from Toro Aluminum, engineering design from SNC Lavalin and more; Diamond Schmitt supplied architectural designs pro bono, and an investment banker named David Banks and media-shy arts patrons Gretchen and Donald Ross chipped in much-needed cash. Now, The Citadel is open, and professional dancers and area kids (who get free classes on Saturdays) have a beautiful, high-quality performance space in which to hone their craft. And while finances are still shaky, the venue is booked into the summer, a sign that Coleman and Lemieux’s flying leap might just work out, after all.

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Get a sneak peek at our May cover story: Rob Ford and the weirdest mayoralty in Toronto history

The incredible shrinking mayor

Below is an excerpt from our May cover story, “The Incredible Shrinking Mayor” by Marci McDonald. The full text is now available online. Click here for more »

On Newstalk 1010, the sly strains of the Hollies hit “He Ain’t Heavy, He’s My Brother” offered the first clue. Then morning host Jerry Agar burst on the air with a surprise announcement: Rob Ford and his councillor sibling Doug were taking over the station’s Sunday afternoon talk-fest, The City. For the once-staid CFRB, landing the boisterous brother act that Margaret Atwood had puckishly dubbed the “twin Ford mayors” was clearly a coup, but that didn’t answer the more obvious question: why on earth would the Fords want to spend two more hours a week in front of an open microphone when they were hardly suffering from a lack of media exposure?

Rob Ford, after all, ranks as one of the most compelling and exhaustively chronicled figures in Canadian politics, adored and despised with equal gusto. His every pronouncement seems to turn into front-page fodder, his every grimace and belly scratch catalogued by rapt photographers. And who could forget the YouTube footage of comedian Mary Walsh arriving in his driveway, decked out with a velvet breastplate and a plastic sword?

But by the time Agar announced the show’s February 26 debut, the mayor was none too keen on his press clips, which aptly mirrored his increasingly bleak political fate. Ever since the new year, a small band of independent councillors had been leading an open revolt, dealing him a series of humiliating defeats, first on his budget, then on his cherished subway-building agenda. No matter how he tried to spin it, one conclusion was unavoidable: the mayor was increasingly isolated on his own council.

In Conservative backrooms across the city, there was undisguised consternation. Ford’s predecessors, David Miller and Mel Lastman, would never have allowed themselves to lose such key power struggles, especially so early in their first terms. Ford was becoming an embarrassment—one who could do lasting damage to the party as a whole. “There are only so many votes you can lose,” says a prominent Tory advisor who asked for anonymity, “and then you end up becoming sort of neutered.”

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Memoir: I’m usually loyal to a fault—so why do I always betray my hairdressers?

It’s time I faced the truth about my philandering ways

Memoir: My Cheating Hair Janet opens the door to her house, already wearing her powdery white latex gloves, left over from her mother’s kidney dialysis.

“Did you bring the foils?” she asks.

“Yeah, I cut some at home.”

“We should get the ones from the beauty supply store for next time,” she says. “They’re thinner and easier to work with.”

I put down my bag of contraband hair products, procured from my sister, a professional stylist, and pick up a glass of wine. Our friend M. is already here, with a towel around her shoulders. Her hair is swirled around her head in a muddy paste. (M. has asked for anonymity out of respect for her former colourist.) She checks her watch; eight more minutes to go.

“Shall we start?” Janet says to me, snapping her gloves. I pull out assorted bleaches, toners and potions, along with my sister’s handwritten instructions. One sentence is underlined: “No more than 10 minutes under dryer,” it reads, “or hair may fall out.” We mix up a nasty-smelling brew that turns a purple colour—a horrible Easter pastel that, when slathered on my hair and blasted with heat, will result in lustrous streaks of blond.

Homemade highlights.

I was tired of spending $120 and long afternoons in a salon chair. Everything else today is high-speed; I eagerly await the blond app. In the meantime, our colour cabals have become a pleasant ritual. We save a pile of money, while also enjoying a nice sauvignon blanc. And so far no one has run screaming from the results. Our DIY salon intervention is working out well.

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Dear Urban Diplomat: don’t I have the right to use the washroom at a Maple Leafs game as often as I need to?

Dear Urban Diplomat

(Image: Mark Watmough)

Dear Urban Diplomat,
I went to a Leafs game recently and, after downing a litre-sized beer, found I had go to the bathroom a few times (I waited for stops in play). Every time, I was given the stink-eye by a woman who refused to move her legs. The last time, while I was practically straddling her to get by, she snarkily suggested I invest in a pair of adult diapers. Was I in the wrong? I was only responding to a biological need.
—Pissed Off, ETOBICOKE

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The Moment: when Karen Stintz went rogue and defeated Rob Ford on the transit vote

The Moment: Stintz Goes Rogue

(Image: Christopher Wahl)

February 8, 12:33 p.m. When Karen Stintz called for a special meeting of council to resuscitate the transit plan that Rob Ford had spent considerable political capital trying to scrap, she was risking career suicide. After seven years of being sidelined by David Miller’s administration, Stintz, as chair of the TTC, was finally in a position of power. Ford expected her to be his voice on the commission, and he wanted a subway—even though his plan would reach less of the city and cost about a billion dollars more than Stintz’s light-rail alternative. Remarkably, her motion passed, 25-18. The councillor gamely insisted that the plan would be a win for everyone, including the mayor. Nobody believed that last part. It was a humiliating defeat for Ford. The apoplectic mayor dismissed the vote as irrelevant (it wasn’t), accused Stintz of backstabbing and axed Gary Webster, the TTC’s chief general manager. “Here comes Mayor Stintz,” someone quipped as she approached the cameras outside council chambers. Stintz cracked a smile and launched into her talking points, basking in the prophecy.

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