CBC Calgary presents Venturing Out with Arlene Dickinson. It's a seven-part series of candid conversations between Dickinson and some of Canada's top entrepreneurs. They cover the highs, the lows and everything in between when it comes to starting and running a business in Canada. 


In this episode, Arlene chats with Terry O'Reilly, CBC host of Under The Influence, author and serial entrepreneur, about the importance of marketing when it comes to branding a business. Arlene and Terry also share tips about what is the best approach when it comes to  entrepreneurs using social media. 

This interview has been edited for length and clarity.

Q: There's lots of agencies that have been founded by creative people but they are usually run by business-type people. What made you different? I mean, you've built Pirate Radio and TV, you have Under the Influence, you have written books. You are a true creative entrepreneur. What made you different?

A: Good question. First of all, I was the world's worst employee, Arlene. I knew I wanted to be my own boss, I knew that. You know what it was? I think, and I know you'll agree with this, I think the most interesting companies in the world start with a fist slam. The founder says there has got to be a better way. And that is what happened to me.

So as a copywriter I would write a radio campaign or a television campaign, and then the next step would be to hire a production company and a director. And I would do that, in Toronto, in Vancouver, in New York, in Los Angeles, in Chicago, in Detroit, in Minneapolis, and I always faced the same problem. Which was, the director would run away with my script. They would throw out the marketing, concentrate on the humour, fight me on every beat, and I hated it. And I slammed my fist on my desk one day, and said there's got to be a better way.

That was the genesis of my company. I created the company I could not find. And that was a production company that protected ideas, that directed ideas from a writer's point of view.

Terry O'Reilly

Terry O'Reilly, CBC Host, author and serial entrepreneur (Debbie O'Reilly)

Q: Interesting. And I get the nucleus of saying there is a better way to do it and let's do this. But, how did you draw out the skill set? Years of working with creative types has taught me that there is a different process that goes on in your mind about whether processes are actually important. Let's start there. How did you tease that out of yourself? How did you keep your creativity but still balance it with a business sense?

Terry O'Reilly

A: When you're a creative person in an advertising agency, you are very well protected. They keep all the money issues away from you. They just want you to create with your feet up on your couch and generate ideas. So when I went out on my own, I really had almost no skill set to run a business. The financials, the going to the bank for a line of credit, all of those things, I did not know. So half of those I stumbled through, and learned the hard way. But the other great thing I had was I had a partner.

I went out first as O'Reilly Radio, just by myself, and that's where I did a lot of my stumbling and just going through the motions and learning, building the bridge as I was walking across it. When I started Pirates with another partner, he had that business ability. So he would run the business of the business, which would allow me to concentrate on the creativity, which was the product of the business.

So between the two of us, we were able to go forward. And then I started to take on some of the business skills, he started to take on some of the creativity, and then we really kind of meshed from that point on.

Terry O'Reilly

Don't count radio out, it's finding a new niche even in the internet age, says O'Reilly. (CBC)

Q: So you identified early on that you were better with a partner than you were alone?

A: At that stage, yes, no question.

Q: That makes good sense to me. I think about marketing in general, Terry, and I have listened to your podcast. I find them fantastic and informative and entertaining. You have managed to break through in a very crowded media environment. With all the media messages that are hitting us, if you're a small entrepreneur, or a small business getting started, how do you make that one that stands out? What made you able to stand out?

A: In business it was that I isolated that problem with production companies, so when Pirate eventually opened up its doors, we were inundated with business. Not because we were so good, although I do think we were good cause we were passionate. We were so inundated because so many other writers and art directors felt the same way, that they were fighting directors all the time. So that's what made us stand out.

The second part of that, Arlene, is we made radio sexy. So we started out as a radio company and then eventually became a radio and TV company. But what we did is that we made radio sexy. Radio in an advertising agency was always the bottom of the ladder. It was given to the juniors. Nobody cared about it. The studios were small dingy basements, and I hated that, too.

So my partner and I built a studio that was beautiful and had windows to the outside and were decorated like beautiful cottages in Muskoka. And instead of just handing menus out at lunch, we brought in five-star catering. We fed our staff breakfast every morning, we flipped pancakes — because the family that eats together stays together. So we created a whole new way to create radio.

On my radio show, I think maybe, if I do stand out, one of the reasons might be because I aim my show at the average Canadian — in other words, not at marketers. It's to the average Canadian that I'm talking to. And I really…one of my favourite emails I get, Arlene, and I get it often, is this… 'hate advertising, love your show.' Hate advertising, right?

Q: Right!

A: What I interpret that to mean is people don't hate advertising, in general, they hate advertising specifically when it's terrible. 

  • To find out what Arlene and Terry think is the best approach to using social media for their business, go to cbc.ca/listen

New episodes of Venturing Out with Arlene Dickinson are available every Tuesday. Next week, in the final episode, she will be speaking to Kirstine Stewart, chief strategy officer at Diply Canada.

Subscribe at Apple Podcasts or on your favourite podcast app, or listen on the free CBC Radio app for iOS and Android, or at cbc.ca/VenturingOut.