How To Build An Industry: Heather Ostertag

I would guess that there are very few of us that can claim membership to an elite group whose members including Canada: Bryan Adams, Leonard Cohen, Celine Dion, David Foster, Sarah McLachlan, Neil young. In Britain the membership including: Sir Tom Jones, Bob Geldof, Bono, Sir Elton John, Sir Mick Jagger and Sir Paul McCartney. Or in the States: B.B King, Bob Dylan, Aretha Franklin, Frank Sinatra, Barbara Streisand and Stevie Wonder. Well, my guess today is in fact one of the members of this elite group, and in Canada it is called the “Order of Canada” which recognizes outstanding contribution to our country. The equivalent in Great Britain is knighthood and in the United States it’s the presidential level of freedom. Heather Ostertag indeed deserved her “Order of Canada,” and in her case not as an individual artist but in the recognition of her contribution to the entire music industry. As the leader, Executive Director, and then President and then President CEO of factor, and not for profit organization that dedicates itself to the growth and development of Canadian independent recording, Heather grew the budget from 200,000 to 20,000,000. And in her leadership of 20 years, she had not only did this massive financial growth, but she built an infrastructure that would allow artists to be discovered and put on the stage from coast to coast to coast. Indeed she is the epidemy of a woman who leads, but membership to these elite groups does not protect you. And in fact, in Heather’s case, it didn’t protect her from having a gun literally put to her head, nor metaphorically a significant kick in the gut. Take a listen to my interview with this outstanding woman, and find the story of how she built the Canadian music scene and then what happened.

Tune In - Women Who Lead

Lesley:  Well, as mentioned in my introduction to my incredible guest today, she is indeed the recipient of the Order of Canada, which recognizes outstanding achievement, dedication to the community and service to the nation. And if you want to know the equivalent in other countries, it’s the equivalent of a Knighthood in Great Britain and it is the equivalent of the Presidential Medal of Freedom and the congressional gold medal, all the highest forms of recognition to citizens who have done an outstanding contribution to their country. And so, it is with great honor that I welcome Heather Ostertag, who is indeed well deserving of this recognition by our country. And Heather’s recognition came from her contribution to growing the music industry in this country, a very complex industry indeed. And so my very first question to my honored guest is, what would you say was the leadership strategy that you used to build the music industry in our country?

Heather: I think its other kind words, Lesley. I would say that my strategy was to prevent to the industry a recognition of what their needs were, and responding to that in a way that they could see by coming together, and working together, and collaborates it and staring their objectives would be met, while building something bigger than anyone of the provincial or territorial music industry associates could do by themselves.


Lesley: So how would you describe the industry when you started out initiating this industry development?


Heather: It was extremely fractured. They were really Toronto, Montreal and Vancouver where there are three hotspots. They continue to be but what has happened is where there was no support and there were artists trying to do things on their own. They were able to build associations coast to coast to coast that have actually allowed artists to come out from other parts of the country that may not have been able to get there as quickly as they did because there was no local support, there was no information. I can remember back in the very early days the Alberta Music Association telling Venard Matt she was too unattractive to succeed. You know, you had people like that, they were doing things that were like “wow really?”


Lesley:  So here we have not only goes that have well-achieved status in international music being told that they weren’t going to get anywhere. You also have those that would never get discovered if it hadn’t been for the type of collaboration that you’re talking about.


Heather: Yeah. And when you look Canada and Canadian artists in the early days there was a lot of “The money should go to… money shouldn’t go to Toronto, it should be here, here and here.” And one of the questions that I would ask people was, “Okay, so we have got Sarah McLachlan, who was an East Coast artist then they signed to a label in British Colombia but recording in Alberta, why does that matter?” The most important thing is that there is a talent, it’s being recognized and it’s being exposed to the universe.


Lesley:  So, prior to you taking on this massive movement, what would’ve happened to the Sarah McLachlan of the world? Would there have been a lot of infighting and questioning about where her appropriate location would be?


Heather: There was a lot of fighting and everybody wanting a piece of the pie, and that was coming from their not being a co-piece of strategy that was inviting and engaging coast to coast to coast. The accusations that were coming at the organization were true in the sense that the money was going to Toronto, Montreal and Vancouver, but that’s where there were companies situation. Now there are companies across the country, they’re accessing it and that argument probably will never go away but it’s certainly been defused.


Lesley:  So, you know, as we know musicians are a very independent lot, I mean, they’re artists in the true sense. So I’m intrigued by your approach to collaboration that you used to bring these highly independent players together.


Heather: It was a matter of talking to them authentically and really hearing the challenges. Like all of the provinces in Canada the music that’s coming from this province and territory is unique and distinct. It doesn’t make it that, it doesn’t make it long, just makes it unique. And in acknowledging that and acknowledging the unique challenges that come with each part of the country and finding ways to talk about it and honor it, you have enable to gather and gain a respect and trust of the associations. And while we’ve had many battles over the years and agreed to disagree on many things, the one thing we always agreed on is we’ve got amazing talents in this country. And that was kind of the battle. And when you would see for example in their blanking now that came other Manitoba the number of years ago. I’m sorry I’m blanking here and that’s probably not good for the interview.


Lesley:  Just keep going because it’s going to come back to you.


Heather: Um, when we succeeded it really inspired a lot of people across the country to see that it can happen. There is an opportunity; it doesn’t have to come from Toronto. Yes, Manitoba can produce talents, Alberta can, so can Saskatoon and it’s continuing and continuing. And I’d like to think that there’s lots of an issue about where an artist is coming from and more about how can we expose them to the universe.


Lesley:  Well I know that through the work that you did…


Heather: It was the crash test dummies.


Lesley:  Sorry?


Heather: It was a crash test dummies.


Lesley:  Oh, see now? You didn’t have to worry. It was going to pop back your instrumental, their arrival on the scene was so many hits on your side. It would be hard to remember them all but crash test dummies they are in play that’s for sure. But I do know that I would not have been exposed to some of the aboriginal music that you were instrumental in bringing to the fore. And so, how do you go about helping these associations uncover the enormous talent does in this country?


Heather: We have systems in placed with, um, I had started up where we had a peer assessment for deciding who would get the funding. And one of the fundamental things that really helped to garner trust than what we were doing is we started up where the music, the instrumentals were sent out across the country. And they made the decision that’s who should get the money. And what that afforded them to do and I saw that certain parts of the country that when a new association would come on board, you would see there was a very hard level of cruel that was going on with them because they didn’t have the singers that… But overtime you saw their decisions becoming more sophisticated. They became more aware of what is put to succeed. They were exposed to marketing and promotion plans, budget, everything. So it helped to educate them while they were taking on the responsibility of making the decisions.


Lesley:  So, peer decision making, how did you facilitate that? How did you help them?


Heather: We had some rules, some policies around it that you have a minimum number of people, and of course there have to be nobody involved in the process that was involved in a project. And we had some guidelines, and we continued to develop them in conversation with the association from the people running the theory and it was in the honor system.


Lesley:  So there’s a great deal of trust building that I hear in your strategy.


Heather: Huge. I can remember our very first meeting and people were terrified to talk, and then you couldn’t shut them up after. It became a community, it became an extended family. And we would spend almost as much time discussing the business of the organization, as we did discussing what each of the association was up to what they were doing, how they were doing, and what the results were and what information could be taken away for other associations to develop for themselves.


Lesley:  So it was really about building the individual elements but as a part of a full community so that they saw themselves as a Canadian music industry and also saw themselves as representing distinct cultural dynamics that their part of the country would by definition bring to the table with their music.

Heather: Yeah. And I mean we had it. We would bring them… There was a strategy going where we bring everybody together for a meeting and now would be around a key music industry of them whether be Canadian music leagues, country music leagues, whatever these music associations… And so it allowed them to come together and be part of something that their own budget couldn’t afford for them to be part of without the support and the financial backing that we gave them.


Lesley:  So, it was celebrating music as much as anything. I mean there’s nothing like seeing a Canadian artist perform for the first time, and there’s a national pride in that aside from wherever in the country that they came from, and to be part of those celebrations is huge.


Heather: Absolutely and it was affording an opportunity. So, wouldn’t you have for example the Northwest Territories with their very isolated being able to go to the East Coast and see what’s going on there?


Lesley:  Oh my gosh, because during your time of building the Canadian music industry, you clearly put the East Coast music into a limelight that shone. I mean, it’s got its own sound and it’s gone international in how it’s been able to be exposed. This is what coming together and celebrating one supporting one another actually does.


Heather: Absolutely. I’m really proud of the work that I did with the East Coast Music Association. They’ve gone on to give me a number of honors. They made me an honorary life on director, an honorary life on membership. They made this and that award and all of that, but they really have to give themselves credit because it wasn’t always easy. It hasn’t been easy all along but they stayed the course, they’ve honored who they are and they keep staying with it and working hard. And you’re right, it is international medal. You know, they don’t need anything from me. I said on the sidelines and I know they’re proud of what they’re doing and they should be as well.


Lesley: So what would be the type of obstacles that the music industry in Canada would face against other music industries in the world? What are some of the obstacles that you’ve had to help them overcome?


Heather: Well, one of the first ones obviously is money, you know, they hate funding. It’s expensive to get across this country. And ironically something that people think helps Canadians and it may on a one hand, but it doesn’t necessarily serve the Canadian well in the international market and that’s Camcon.


Lesley:  What is it?


Heather: …which is the CRTC Rule that Canadian artists must be played 35 percent of radio airplay. And while that sounds wonderful on the one hand, and it’s great that we’ve got a government that stands behind supporting our Canadian talent. The downside to it is tearful. One, broadcasters predominantly tend to treat that as a maxima. So if you think about it, 100 percent of Canadian artists are required to re compete for 35 percent of domestic airtime. The other thing is, is in the international market where they recognize that we’ve got Camcon. I think this is a God-given beautiful gift. They tend to be dismissive about domestic success.


Lesley:  Isn’t that an interesting conundrum? And so, was part of the work that you did try to breakdown some of those barriers with the broadcasters?


Heather: I work very closely with radio to talk to them about what was happening, because part of the money that the organization distributed came from broadcasters. And I wanted them to have an understanding and the passion for what their money was doing and how it was helping and what we could do to support in the local communities, but when it came to Camcon that is a really sensitive topic with radio and factor was nonpolitical and non-alliance. So I couldn’t really get into the subject with them because with most people nobody likes to be legislated. They have to do something.


Lesley:  Yes exactly.


Heather: And so, at that very level there is an attitude, not with everybody but there is out there and there is a friction. And a lot of the music organizations in the music industry that push hard for more and more and that’s their responsibility, radio pushes back. So, it’s an interesting situation would we be where we are without Camcon, who knows? But is it helping, who knows? It’s there and it’s a multi edged sword, it’s not just a double.


Lesley:  No. I can actually see that and I think that we that in other Canadian industries but it’s not as highly profiled as Canadian content is in radio broadcasting. So now I want to turn to the fact that you are a fundraiser extraordinary. You’ve done it in the music industry. You’ve done it in all kinds of other forms of philanthropy. And I’d like to ask you what is your number one rule for going into negotiation, where you know that you’re going to be up against a no or probably not? And how do you navigate? Because you’ve got some pretty good examples of where you walked out of the room and everybody were shocked with what you came out with.


Heather: I will always have information at my fingertips in the sense of I know what I’m speaking to. And I always believe that the negotiation is one where both parties walk away feeling they’ve won. And I also tried to always prevent argument the rationale for why they should give what I’m asking for from a place of how it accommodates their goals and objectives.


Lesley:  So the whole getting to yes kind of contract that really allows a negotiated agreement to be seen by both sides as you saw a win-win. What was your toughest negotiation?


Heather: Probably the last contract I negotiated with Canadian heritage under mister Harper did not seem to be that committed to wanting to do a great deal for the Canadian Music Industry. And I walked into the last meeting and it was whole before I could even open my mouth by the operatives that there was no money. There was a crisis with the automotive industry. There was a crisis with healthcare and there was no money to be handheld to musicians. And I turned it around and pointed out to him that we needed that money to continue to develop new artist. But in actual fact the amount of tax dollars being collected from the paying music industry far exceeded the number of investment dollars that they were actually providing, and I was there with a 5-year deal. And I remember the senior bureaucrats and the terror factory of the claim. Going out of the meaning I can’t remember what he said. I went into that zone of mine which is, “I’ve got to get this out there, I’ve got to say it, I’ve got to do this.” And then they’re going, “Oh my God you’re good.” And it was just…I said what needed to be said.


Lesley:  But you also believed a 100 percent in what you were saying.


Heather: Oh absolutely. I came on it. I can’t get out there and say it if I don’t believe that I suck at that. And I made a policy really long time ago that I was never going to get out and say anything in public. That wasn’t true. Now that’s created some challenge for me sometimes, but I work hard to find a way to say something up then check and it lets me sleep night.


Lesley:  Absolutely. And I want to get to… like the name of this show is Women Who Lead. And I’d like to understand, what is the nature of women in the music industry? Is it harder for women in the industry; is it harder for those of you who are supporting the industry by being a woman? Is it easier; is it different, what is it?


Heather: I think like everything is difficult for women, but I think it’s women doing it to women. I don’t think the majority of men are out there trying to stop women. I think we do that to each other. We haven’t learned how to share and support each other in a constructive way. We tend to compete with each other, and in doing that we stop things from happening. We end up distracted from what we really shouldn’t focus on, and it doesn’t serve any of us well at the end of the day. I would like to see where women who can learn to trust each other and believe that we actually can, should and are happy to be there and be a stand for each other to succeed.


Lesley:  Absolutely. And I want to ask a question, what was it like to be in the kind of role you were in in a male dominated infrastructure? So how would you describe that?


Heather: It was a lot of men that were dominating things, and there were moments where I wanted to tell them that they don’t stand but I chose not to. I chose to not give them that power over me. And when I was faced with situation where it was extremely inappropriate rather than calling them out, and say, “Oh you are such and such or whatever.” I would always resort to, “Excuse me, I’m confused here. Why do you think that’s appropriate?” No, it would cause them to have ten steps back from it, it wasn’t busting them.


Lesley:  No.


Heather: Because I think when you attack you don’t necessarily end up with a kind of result that you’re looking for. And for me personally, I’m not interested in taking somebody down because they misunderstood something or whatever. My experience was when I would stand in that place of I’m confused… that was usually they got the message and not ended it.


Lesley:  And I think confusion is an authentic reality. Because I get confused when people come at me in a certain way and I don’t understand where they’re coming from. And I think it’s not a tactic, it’s not a strategy, it’s an authentic description of the circumstance that you’re in.


Heather: Yeah no. And it came from just an automatically action the first time I get it and it worked. So it was a mental… And that’s when I continued to operate with. And from then on I don’t want to spend my time fighting with people. I trust that the universe is bringing to me what it’s supposed to the way it’s supposed to, and if I did that over somebody I don’t think they’re moving forward.


Lesley:  And so, what’s one battle that you really had to get over and trust that it was the best thing that happened for you even though at the time it didn’t feel that way?


Heather: And it wasn’t much the word “battle” but it was talent, and that was when I was fired from factor. There were four members that were angry about the way it was done. And because that they’ve been worrying of the package, and they thought that they could just put it on to me to fight their fight and their dissatisfaction about their peers and their peer’s behavior. And I was just like, “No I’m not doing that.” And, it was interesting to watch because there was some politics around the way it happened, and I think there is what they need dismissal of an executive. You know you’re the President and CEO, you’re fired, of course there’s going to be issues, but I stay true to myself. I negotiated that I should be given a retirement party which was awesome for me because I got closure in that. And I actually came to recognize they did the right thing to firing me if I didn’t know how to quit. They wanted to go on a direction that’s their prerogative, but it’s really interesting to watch their discomfort when I thank them for firing me.


Lesley:  I would say it would be confusing, and so you said that you didn’t know how to quit. What was it about what was happening that was inside of you wanting to separate from the organization?


Heather: I was working on a strategy to do that. I hadn’t gotten to the place though where I was ready to actually go, because there was more… And as time goes on and when I started with the organization it had a 200,000 dollar a year budget, when I left it was 20 million dollars a year. And the more money there is the more politics, the more battles, the issues… Giving out money believe it or not is probably the hardest you can ever do. When you look at it, 80 percent of the people are going to be told “No, absolutely not. You’re not gaining a nickel.” Then on the other 20 percent that are getting something, they’re usually not getting all that they want so they’re not happy either. And even though you’re giving them money they don’t have a problem again complaining to you that they didn’t get everything they wanted.


Lesley:  So, you’re damned if you do and you’re damned if you don’t.


Heather: Absolutely. And I mean I had a gun tote on me, my life was threatened, all kinds of stupid stuff was happening. And when I step back and I was like, “Really, you really wanted to be in this environment?” But I was caught up and then have been in there for so long. I was on the hamster wheel.


Lesley:  But you were on the warrior hamster wheel, which is even a harder hamster wheel to get off because you’re constantly pushing for growth in an industry that in itself has lots of complexities. And my God, have a gun tote on you. I mean, yeah, I guess wake up, smell the gun powder, I mean this is pretty serious stuff.


Heather: Well, we had managing an organization with board members were receiving some of the funds which is really, really challenging to manage. And the government…and as went down and the time that we put in probably two to three weeks before I was let go. They had the governances audit on us. We passed with flying colors. That doesn’t happen because you’re playing nice with everybody. That happens because you’ve put some stretcher in place and you make sure it’s followed, and you can’t allow yourself to be concerned with a follow from a decision for an individual.


Lesley:  Fascinating. So that would have been so clean slate but that comes from good governance.

Heather: Absolutely and a lot of challenges.


Lesley:  I can’t even think about them. So, let’s roll the camera forward. You opened up your own organization (heatherostertagandassociates) and what are you doing now?


Heather: I’m working with different artists that the one in particular I’m really excited about Rovena. I’ve been working with her for a couple of years and we’re going to be launching her second CD this year, but we’re taking the time for her to actually find her authentic voice. The woman is incredible, beautiful inside and out. And she’s got some message for people out there that I think it’s going to knock Adele off the charts.


Lesley:  Adele off the charts. That’s a big statement men.


Heather: Look out, Adele.


Lesley:  Well you know what, if anybody is going to pull that off it’s you. And I think that’s because you are so obviously passionate about what you do but you’re smart at what you do. And the combination of the experience you had, the intellect that you take into your strategies, your collaboration of approach, but I think underneath of all of this is the authentic voice that you search for in yourself and in others. That’s a tall order for a leader to do.


Heather: I don’t know if it’s a tall order. It’s just it is who I am and I want to be able to look myself in the mirror, and it’s like there was some slices I could’ve made…the decisions I could’ve made differently when I have factor. But us I say to people, I made the decisions that I made. I know that for every decision you make there’s a consequence, but I have to be able to look at myself in the mirror at the end of the day. I never sold myself out. That’s when everything for me and the fact that I can say that. You can’t possibly please everybody all the time, it’s impossible.


Lesley:  It’s impossible. But you sure pleased the Canadian country by the recognition that it gave you to tell the story that Heather Ostertag has been an industry builder. And I think if the audience could re-listen to this interview and hear not just the language that you used to describe your approach, but the deeply held beliefs that you hold that allowed you to conquer so many obstacles and to find new chapters in your life. And so I’m going to ask this last question, what is the belief that you hold so near and dear and that guides you no matter what the warrior stage you’re in and allows you to pursue what you need to pursue?


Heather: I would say that is: don’t listen to my head, trust my gut, follow my instincts. And in doing that every time I listen to my head it goes sideways, it’s a mess. When I go with my instincts and I’ll declare things and I have no idea how that’s going to happen, but my new things say it’s going to and you do… Many times in many conversations were people, and they’ll go, “Well, you know what, I know it wasn’t the right thing to do.” “Then why did you do it?”


Lesley:  And the other thing that I’ve always admired about you is you tell it like it is. So I want to thank you for your candidness and telling us like it is. And as a Canadian who loves our music scene, I want to say thank you for what you’ve done to make it possible for me to listen to artists I would never have dared. And I want to say to people stay tuned could you spell out the name so that people know who the one that’s going to conquer the charts, Sis?


Heather: Roveena R-O-V-E-E-N-A.


Lesley:  Okay. Let’s get together when she hits those charts, babe, and how you did it.


Heather: Come to the Grammy’s with us.


Lesley:  Alright, I’m with you. Thanks for spending this time with me, Heather.


Heather: Well, my pleasure.


Well that was quite the story. I found as I spoke to Heather as she expressed the sense of authenticity being at the center core of her being that she presented it in who she is. You know, far too often I hear the authentic self in the pursuit of the authentic self-intellectualized, and frankly find a great deal of the literature on it gobbledygook in terms of how the journey is pursued. You know it’s in us, it’s telling us as it is. It is the true test when we look in the mirror. And it’s not what we see in the reflection of our body but we look through the eyes of the sou. And ask ourselves, “Can I live in my soul with what this decision was? Can I live in my soul with what I have done? And if I come to peace in that question, then whatever the consequences are I’m ready for them.” That takes a huge amount of guts. I have faced those reflections in the mirror many times in my life. And I can say without question that the toughest decisions that I had to make, I found peace in looking in the mirror. The consequences in some of those situations were massive. Now, the gut that Heather uses I sure am going to see if we comeback, it’s RoveenaR-O-V-E-N-A. Let’s keep a lookout for that name on the music scene and put some backing behind this voice, and see if not we can get heard to the top of the charts. You can find out more about Heather at And, as you always, you can find out more about me and this show by going to my website, and of course the women who lead radio show on facebook. Remember, this is your show; I am your host Lesley Southwick-Trask. See you next time.

Be the first to comment

Leave a Reply

Your email address will not be published.