Venturing Out with Arlene Dickinson and Jann Arden

Arlene Dickinson is getting all the secrets behind some of Canada's biggest entrepreneurs. This episode she speaks to longtime friend Jann Arden about branding in the music industry.

Episode 1: Arlene sits down with the singer-songwriter, author, restaurateur and philanthropist

Venturing Out with Arlene Dickinson is a seven-episode podcast that speaks to business movers and shakers about their success. (CBC)

CBC Calgary presents Venturing Out with Arlene Dickinson. It's a seven-part series of candid conversations between Arlene 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.

Jann Arden and Arlene Dickinson are longtime friends. In this first Venturing Out episode, they sit down to compare notes on what it's like to fail and get back up again — and there is no topic off limits.

We'll also find out what books they read, and how much sleep they get and whether or not there is such a thing as work-life balance. 

Jann Arden hit it big with her Living Under June album in 1994, but she says it's taken a lot of work to maintain her brand. (Bruce Allan Talent)

This interview has been edited for length and clarity.

Q: One of the reasons I was really keen to speak with you is that I don't think people think about musicians and artists as entrepreneurs. And I think you are exactly that, because in order to build your career you have to be entrepreneurial, right? So do you think about yourself as an entrepreneur?

Arlene Dickinson talked to Jann Arden for her Venturing Out Podcast from CBC Calgary. (Jann Arden)

A: Yes, I do. I mean, I don't think I had a word for it 25 years ago, or 30 years ago. But what I always tell young singers who are coming up through the ranks — asking how do I become a singer — I'm like, stay in school, learn about numbers and make sure you have your head screwed on straight, because if you choose a career in music, five per cent of it is going to actually be singing, maybe less. 

And 95 per cent of it is going to be manoeuvring your way through a maze of business decisions, contractual obligations and fiduciary responsibilities to a record company, or to whomever. And I learnt that the hard way as I came through the gauntlet, the fire — baptism by fire.

Q: Isn't that what everybody in business is? Baptism by fire? But when you say that, I think about how in a creative world how business can be a bad influence on your creativity. There's some aspect of that where you have to make a business decision that may actually have impact on your creative choices or where you're going. So do you feel that? 

A: I think I'm in a very fortunate position in my career now. I've been with Universal now for 25 years. I'm about to start my 15th record at the end of this month. I have a manager named Bruce Allen. Bruce Allen is infamous in this country. He's looked after Bryan Adams for 35 years, Michael Bublé  is one of the biggest stars in the world, Bob Rock is one of the world's greatest producers, ... and Dave Pierce, who is an unbelievable composer. I do not make business decisions, Bruce does.

He will ask me, they will negotiate with me and say, 'I think you should do this, this and this', but ultimately it's up to me. But I always feel very confident that I'm not the person having to renegotiate my publishing deal with Universal, I'm not the person routing my tour. So that's where delegating comes in big time for me.

So I am, I'm a creative person. My strengths lie in creativity and I really put a good team around me. 

Q: It's a hard lesson. It took me a long time to learn that lesson. As you say that I think what is that ... most entrepreneurs have to do everything on their own, right?

A: That's how it starts! You have an idea and you're on your own.

Jann Arden says being a professional singer is about 5 per cent singing and 95 per cent of manoeuvring your way through a maze of business decisions, contractual obligations and fiduciary responsibilities. (Larry MacDougal/Canadian Press)

Q: And not only do you think you have to do it on your own, you don't think anybody else can do it as well as you did it at the beginning (laughs). You're the only one that can do it!

A: And in a lot of ways that's true! When I started out I had a management company that was ill prepared for my success on Insensitive. You know, I had been working with them in a development situation, you know, from the time I was in my mid-20s, and they were fantastic. 

Now we got to the part with the record deal. Insensitive takes off all over the world. We were ill-prepared. So that came to a crashing halt, because it was accounting, it was, you know, paying taxes on cheques that we were receiving. It just went to hell. I was depressed. I had to hire somebody else. I started my own management company. That was another phase were I wasn't growing my business at all. I'd gotten Insensitive, now I'm at status quo. Now I'm working with people that really didn't have the skill set to take me from that point to keep growing my business. So for 10 years I was in a holding pattern. I just did exactly what I needed to do just to stay where I was.

Q: You just said something that triggered a whole bunch of emotions in me. You said, 'You know I was depressed.' I have spoken to so many entrepreneurs, and people who on the surface look so successful, and have done so much with their careers and yet ... there is something about never feeling like it is enough. There's something about kind of always feeling like...

A: Well, you're probably a Type A personality so you're driven.

Q: Is that what it is?

A: I don't know if you ever get to the top of the mountain. I find that entrepreneurs get up the mountain, they get to the top of the mountain and they are like…

Q: They can only see the next mountain!

A: And there's a cloud, how can I get, how can I get a parachute to.… So and that's the beauty of ideas is that ... people always say, 'You're so lucky you've made it', and I'm like, 'oh no. No. No. No.' The day I signed on the dotted line with Universal. The work has never stopped. I have to not only maintain, but, you know, the idea of branding a career and being a creative person, and being a business person, I always have to be moving forward. Some people have the stomach for it. I've seen a lot of my contemporaries drop off over the years. It's pretty rare now to see a music career go into the 25-, 30-, 35-, 40-year mark.

To find out what are some of Arlene's and Jann's biggest regrets, when it comes to business, go to the full podcast page here.

New episodes of Venturing Out with Arlene Dickinson will be available every Tuesday, starting July 18, 2017. Next week she will be speaking to Dino Trevisani, the president of IBM Canada.

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