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Soon after Ron White opened his first shoe store in 1993, Canadian talk show host du jour Dini Petty became a regular customer.

When Mr. White organized a drive to donate customers' old shoes to charity, Ms. Petty stepped up. "Why don't you put my shoes in the window, create some excitement and some buzz?" she said. Her suggestion prompted Mr White to come up with the tagline: 'Follow in the footsteps of your favourite celebrity,' and a marketing approach that embraced celebrity was born.

Twenty years later, Mr. White, CEO of Ron White Shoes, has 50 employees and runs five stores in the greater Toronto area, an online store and a wholesale business that carries 20 different shoe brands, including his own lines.

He's given away products backstage at the Emmys, hangs out with Matt Damon and his wife, as well as Kevin Spacey, when they are in town and frequents celebrity parties. Recently, he hobnobbed at David Foster's house, where he chatted with Yolanda Foster about her wearing his shoes on The Real Housewives of Beverly Hills.

Pushing the celebrity angle is a marketing approach for many small business owners, especially those producing consumer-facing goods and services. However, short-lived plugs like photos, tweets and quotes don't always directly bolstering sales – they certainly don't for Mr. White.

Successful companies budget their investment, stay authentic and bask in the sometimes subtle side benefits of being in the spotlight which, like celebrity itself, can be fleeting.

While working with celebrities has evolved into a routine part of Mr. White's marketing strategy, he's not naïve about his efforts' return on investment. His high-end, comfort-driven shoes appeal to a mature buyer too busy to notice movie and pop stars. "My customer, who is usually 35-plus, makes up her own mind. If I was dealing with under 30s, it'd be different."

But being connected with big names, particularly early on, gave Mr. White confidence to try new things, like design his own shoes, and feel good about his brand. Meanwhile, his wholesale buyers perk up when they hear household names.

For Toronto social reading site Wattpad, which enables users to post original work and readers to interact with the writer and the content, household names mean a lot.

"I think it's very important to have celebrities on board for us," says Candice Faktor, general manager of the company, which dates back to 2006 and now has 60 employees, 20 million registered users and 30 million stories on its site. "But it's even more important to have our platform create celebrities."

Ms. Factor invests considerable time networking face-to-face in Los Angeles and at events that big-name writers attend. In early 2012, one of Wattpad's owners was introduced to Margaret Atwood, who immediately wanted to hear more about the site. Through regular conversations with Ms. Atwood, staff worked with her on a number of projects, including a serialized zombie story and a digital poetry contest called the Attys, which Ms. Atwood judged.

Now team members meet with the Canadian icon regularly to develop new projects and get her feedback on the site. "We feel so lucky that she really gets us. She's just been huge for us," says Ms. Faktor.

She feels the best celebrity relationships are those that develop somewhat naturally – a celebrity truly likes a product and wants to talk about it and use it. Better still, the relationship between the two sides actually benefits both in some way.

Writers like blogger and sci fit writer Cory Doctorow, author of Down and Out in the Magic Kingdom, and irish novelist Marian Keyes, author of This Charming Man, post original content on Wattpad because it helps them find new readers who will, in turn, buy books. (At this stage of her career, Ms. Atwood is all about giving back and advocating for technology bolstering the writing profession.) Ms. Faktor refuses to pay famous writers for endorsements, or for their work on the free site.

Hilda Kinross, national practice leader in marketing and communications for Hill + Knowlton, agrees the best connections between a celebrity and a product tend to happen organically. "There have been brands that have suddenly found themselves on the map because a celebrity has been spotted wearing their gear. But that is a more authentic, organic integration of brand and celebrity. And those are the ones that generally work best."

When it's authentic, you often don't have to approach a celebrity: they come to you. For example, when Katie Couric tweeted a picture of herself wearing Ron White shoes, Mr. White retweeted. But he never posts celebrity shots away from the red carpet and blindsides a big name into endorsing his products. "I'm waiting. If a celebrity loves something, they'll talk about it. If they talk about it, I'll add to the conversation, but I won't start the conversation," says Mr. White.

Since most celebrities get paid to endorse products, and just about everyone has their own perfume and fashion line, big names are sensitive about being put out there as a marketing tool.

"If you use and abuse a relationship, you'll get cut off," says Mr. White. He says sitting back and being responsive works best.

That's what sisters Cori and Bobbi Windsor have discovered too. The pair founded yoga clothing company TerraFrog Clothing Corp. in Sherwood Park, Alta., in 2007, and over the years, have sent products to celebrities, including Heartland's Michelle Morgan.

The duo, whose company has four employees and sells pants, hoodies and tanks online and to 25 retailers across the country, paid an LA gifting company to send hoodies to five celebrities in early 2012.

But when Reese Witherspoon was photographed in the hoodie, Cori Windsor felt she could not be sure it was really a TerraFrog product – the zipper looked wrong in the snapshot – and decided not to advertise the celeb connection. "The gifting company was mad at me, that I could not confirm it and refused to promote it. I'm not going to say it if I'm not sure. What if I was wrong?"

Then, a few months later, Ernest Borgnine's daughter Nancee called out of the blue, asking the pair to give away product at her fall Emmy party. The Windsors – who spent about $2,000 in total for the event – ended up taking lots of photos, giving away a table full of clothes, and garnering a lot of coverage in the Canadian media. As well, Ms. Windsor struck up a friendship with Nya Crenshaw, girlfriend of actor Eriq La Salle (formerly of ER and now a director), who ended up giving a tank to Michelle Obama a few months later.

"We had an increase in retail enquiries, our old retailers got fired up, our online sales increased and it gave us confidence in ourselves," says Ms. Windsor of the results of that single event.

But with a tight budget and a product line aimed at real women, not bone-thin actresses, investing a whole lot more in attending more celebrity parties – for which the company now had numerous invitations – hasn't made sense since. "If we go again, it's not going to get the same press buzz," says Ms. Windsor.

Mr. White says he's also taking a step back from certain celebrity networking opportunities. It's costly to attend events, hire staff, stay over and give away products.

The likes of shows like Dancing with the Stars demand $20,000 just for the right to show up backstage with swag. Big companies pay for tweets and endorsements. It's seldom always worth it for a small company.

Meanwhile, giving away product and particularly paying for endorsements comes with an unpleasant side effect. "If you stop paying them, then what?" says Ms. Faktor.

A celebrity who truly loves your product will keep using and, every once in awhile, mention it in an interview or be photographed with it. When the gig is just for money, the promotion stops when the money stops.

But even if getting yourself in front of celebrities is worth it for your company because there's resonance with certain writers, actors, musicians or other big names, you still can't predict when that high profile mention will come. One minute, it's quiet. The next you're in People magazine and friends and local media won't stop calling.

Best diversify your marketing strategy and make sure your work with celebrities is underpinned by careful thought and a reasonable budget. Says Ms. Kinross: "I can certainly understand the attraction around aligning your company with a celebrity – even from a personal storytelling point of view, it can be exciting and kind of glamorous. But it needs to remain an analytical business decision."

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