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Young Lions founder Bobby Kimberly, right, meets with Owen Steinberg, co-owner of Harvest Kitchen, to discuss a music playlist he has curated for the restaurant in Toronto. (Galit Rodan for The Globe and Mail)

Of all the luxuries a home office affords, bed bugs were not one Bobby Kimberley expected. The Toronto marketing entrepreneur had to drop everything and get out of his Parkdale neighbourhood apartment this August, finding a temporary home – and workspace – with a friend across town.

As life often goes, this coincided with the busiest few weeks of Mr. Kimberley’s career. In September, he programmed a music festival, organized a musical Lake Ontario boat cruise, and masterminded an extravagant party themed on 2001: A Space Odyssey, along with a companion installation for the Toronto International Film Festival. By mid-October, Mr. Kimberley earned some time to breathe – but only after DJing a dance party with his business partner and girlfriend, Anna Wiesen, and overseeing a semi-surprise concert for client Red Bull with New Jersey-bred punk band Titus Andronicus.

Bed bugs couldn’t stop 32-year-old Mr. Kimberley’s business; he has learned to be nimble in his three years as an entrepreneur. He runs two companies: Young Lions Music Club, a community-focused music events and marketing company, and a creative agency, Young Offenders. Each plays off the other, as he taps his network of talented creatives to put on increasingly more entertaining and elaborate events – for himself and for brands – throughout Toronto.

Brand partnerships are an essential part of Mr. Kimberley’s business model. They’re also the reason he struck out on his own to in 2011, when the music PR company he helped run insisted it subsist on low-revenue campaigns for bands instead of seeking out new income streams, partnerships included.

He took the connections he’d developed at the firm, including with the lifestyle-marketing wing of Toyota’s Scion division, and started his own company, making a career out of brand relationships. Three years later, his plate is more than full.

Young Offenders masterminds Bobby Kimberley and Anna Wiesen get in character in one of the set pieces from their extravagant 2001: A Space Odyssey party in September.
Projects that seem certain to land never do, and then others ... just show up out of nowhere.
Bobby Kimberley

Today, in his temporary (but bed-bug-free) home office, Mr. Kimberley has found time to sit down for a coffee as he watches his French bulldog, Charles, gnaw at some stuffed toys. “I’m transitioning from the guy who does everything to somebody who can pull people in to do the things that I’m not good at, or not super interested in doing, in the day-to-day,” he says. “It’s really just been in the last couple months that I feel like I’m starting to run like as real, actual business.”

That business is, perhaps, the inevitable merger of Mr. Kimberley’s love of music and keen sense of opportunism. As a teenager growing up in Lindsay, Ont., near Peterborough, he organized local concerts for the sake of the town having concerts at all. At the University of Ottawa, he saw untapped event budgets as a chance to lure his favourite bands to campus, including Metric and Constantines – the latter of whose songs inspired both of Mr. Kimberley’s company names.

In 2007, just months after finishing school, he translated his event-planning experience into a lifestyle marketing job at Sony Music Entertainment in Toronto, pushing artists on the label’s roster into communities across Ontario. He was lured out of the tumultuous major-label system a year later to The MuseBox, the aforementioned music PR company. He increased sales more than 300 per cent during his first year there, he says, “but there was something inherently broken – the sales increase didn’t ever feel like it let the pressure off.” After three years, Mr. Kimberley left to start Young Lions Music Club.

He started off small: a Scion partnership with a Canadian Music Week event and a monthly dance party hosted by a who’s-who of musicians. There was “a lot of spreadsheeting,” he says, as he balanced bare-minimum survival costs with income opportunities: “I just kept my feet moving to try and close that gap.”

The “club” component of Young Lions came into play a few months later, in November of 2011, when Mr. Kimberley began to issue “club cards” to music fans for discounts for his events and at local businesses. (Disclosure: This reporter is a club member – along with 1,260 others.) Those members grew by hundreds as Young Lions events became bigger: New Year’s Eve parties, a lake cruise DJed by a member of The Smiths, a series of Stanley Kubrick film-themed parties. Many of his events feature performances by Dwayne Gretzky, a local indie supergroup specializing in covers, which he manages.

At the Big Shiny Dwayne concert this past April, Young Lions-managed band Dwayne Gretzky indulged the nostalgia of a sold-out crowd at Toronto’s Phoenix Concert Theatre with a set of only ‘90s hits. (Anna Wiesen)

Mr. Kimberley and Ms. Wiesen moonlight as the Summer Fling DJs at parties in and around Toronto.

After helping design a David Cronenberg tribute for TIFF in 2013, Mr. Kimberley realized the “music” component of his own brand was, on occasion, a misnomer. So he and Ms. Wiesen created Young Offenders – a separate, more broadly focused agency, to leverage the creative talent that helped put their elaborate parties together, from photographers to set designers and projection artists. Less than a year into its existence, Young Offenders’ is set to generate more revenue than Young Lions itself, Mr. Kimberley says.

Over time, his arsenal of brand partnerships steadily grew: Red Bull, Mill Street Brewery, Movember, Ubisoft. “He’s got a great vision, and a well-rounded sense of what’s cool,” says Steve Abrams, co-founder of Mill Street Brewery, who worked with Young Lions for its Strange Brew festival last year. Mr. Kimberley and Ms. Wiesen, he says, “have a passion about music, popular culture, being creative, seeing things from a different angle – and making it work on a budget.”

Mr. Kimberley and the Young Offenders team “speak the creative language of their generation,” says TIFF senior manager Paula Whitmore, “but can manipulate their ideas quickly and easily to fit in almost any setting – from high tech street level promotion to high art luxury gala. They understand the importance of the experience, which makes their events and activations that much more influential.”

The growth of Mr. Kimberley’s partnerships and events has pressed him to expand his would-be office for the first time. A former intern manages the club community; a new employee is handling a burgeoning event partnership with the Eaton Chelsea Hotel, Canada’s largest; and, for the first time, Mr. Kimberley has hired a production manager, to oversee a replication of his 2001: A Space Odyssey party in Kitchener, Ont., just this past weekend.

After the success of Young Lions Music Club, Mr. Kimberley launched Young Offenders as a creative agency to organize events beyond just the music world. (Galit Rodan for The Globe and Mail)

Delegation, he says, has taken some getting used to. “When you’ve controlled a project 100 per cent to date, trying to hand that off is a really difficult thing.” But he recognizes that by bringing people – the word “staff” doesn’t come up, but it’s implied – in early in the ideation and development process, “I’ll be able to become less stressed over all.”

Simon Parker, a professor and director of Ivey Business School’s Entrepreneurship Cross-Enterprise Centre at the University of Western Ontario in London, Ont., says delegation is something entrepreneurs like Mr. Kimberley should learn to get used to early on. Because if he’s already feeling these growing pains, they’re only going to get worse. “As [the business] grows beyond a certain point,” Prof. Parker says, “it’s not going to be possible to do more” on his own. If Mr. Kimberley wants to keep his mind on the big picture, “He’ll have to have a dedicated person who looks after the day-to-day as he gets on to selling and strategizing.”

It’s a real possibility. Mr. Kimberley has rarely been able to predict what comes next for his businesses. Much like life handed him a bed-bug infestation, it can hand him any number of unexpected left turns. Every year, his projected revenue estimations are “way off” – not in how much, but from where. “Projects that seem certain to land never do, and then others – like Eaton Chelsea – just show up out of nowhere.”

But Mr. Kimberley, by this point, has learned to roll with the punches. So far, it’s paid off in spades.

'It’s really just been in the last couple months that I feel like I’m starting to run like as real, actual business,' Mr. Kimberley says. (Galit Rodan for The Globe and Mail)
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