CM In Depth

The Era of the Artistpreneur

This article originally appeared in Canadian Musician’s 40th anniversary issue in March 2019.

By Andrew King

“I’m not a businessman; I’m a business, man.”

It’s been nearly 15 years since Jay-Z rapped those lyrics over the remix of Kanye West’s “Diamonds from Sierra Leone,” and while the line has been among my favourite bits of clever hip-hop braggadocio ever since, it has also proven prophetic for many in the music industry.

As Forbes asserted in the headline for an article from January 2018, “In The 21st Century, To Be A Musician Is To Be An Entrepreneur.” In the piece, Paul Pacifico, CEO of the Association of Independent Music (AIM), says: “Artists today are pretty much by definition music entrepreneurs and owner-operated companies, building their businesses and their brands. For them, technology has been the principle driver, reducing the barriers for entry in terms of lower costs and the democratization of industry supply chain resources, such as production equipment and support services.”

Of course, the vast majority of examples he cites are more of the sole proprietorship or small business type than Jay-Z’s massive entertainment and lifestyle empire. And though Mr. Pacifico’s statement sounds like one he has either memorized verbatim or carefully crafted in front of a computer screen, that makes it no less accurate. When I got started on a basic outline for this piece, the first call I made (to someone outside of the Canadian Musician office) was to Rick Barker. Now the president and CEO of his Nashville-based firm the Music Indus¬try Blueprint, Barker’s career is as long as it is diverse. Once the manager for global superstar Taylor Swift, he has since served as the social media mentor to finalists on American Idol, worked as a private consultant to com¬panies like Big Machine Label Group and Live Nation, and has managed American Idol winner Trent Harmon since 2017.

Barker has also become a popular podcaster and author and a sought-after consultant and speaker through his work under the Music Industry Blue¬print banner, all with the stated goal of “helping you navigate the new music business.”

[Pictured: Rick Barker]

I was initially running the idea by him to see if he’d be interested in collaborating in some capacity; five minutes later, I’d regretted not recording our call.

He acknowledged that those competing for a sustainable ca¬reer in music these days do in¬deed need to be entrepreneurs; the challenge, he says, is that most artists aren’t inherently entrepreneurial.

“What ‘thinking like an entrepreneur’ means is not being afraid to get punched in the mouth,” Barker asserts – “and I think most artists are so afraid of what everyone thinks. An entrepreneur doesn’t care; an entrepreneur just goes out and does.”

That’s not to pick on musicians or creative types in general. The fact is that successful entrepreneurs typically straddle the balance between left-brained and right-brained skills and personality traits.

Here are the 10 most important skills for today’s entrepreneurs according to Forbes (different article this time). How many do you associate with yourself or other artists you know, based on your personal experience?

  1. Curiosity
  2. Time management
  3. Strategic thinking
  4. Efficiency
  5. Resilience
  6. Communication
  7. Networking
  8. Finance
  9. Branding
  10. Sales

I got off the call with Rick freshly inspired and with a handful of ideas to develop. I hadn’t gotten far before he called back a day or two later with another idea I had to take him up on.

While he’s based in the U.S., Barker has developed close ties to the Canadian music business in recent years. He’s been a fixture of the last few editions of Canadian Music Week, coached participants on CTV’s The Launch, and established a professional relationship with a number of Canadian artists.

One of those artists is Chris Greenwood, much better known as Manafest, a genre-bending singer, songwriter, and rapper who combines elements of rock, rap, and pop in his signature sonic concoction. He has amassed four JUNO nods, multiple GMA Dove nominations, high-profile placements in popular film, TV, and gaming titles, and performed well over 1,000 shows across four continents.

Perhaps most impressively, though, is the fact that he’s sold over 300,000 albums as an independent artist – 15,000 of which were sold directly via Facebook ads in an aggressive 2018 campaign that has since been touted by Facebook itself as an example of the platform’s effectiveness. His page also has over 211,000 fans, which dwarfs those of some arena-touring CanCon staples.

[Pictured: Chris Greenwood, aka Manafest]

Greenwood now runs, featuring a wealth of courses and resources to help artists grow their fanbase, monetize their music, try new strategies for success, and maintain a positive mindset while doing it.

Bottom line, Barker calls Greenwood “one of the best entrepreneurs that [he knows],” and the two invited Canadian Musician to be a fly on the wall during a conversation on how artists can make 2019 their best year ever.

“It’s about thinking in a business mindset,” begins Greenwood. “Sometimes that’s hard to do as an artist because we just think, ‘Oh, I just want to make music.’ But an entrepreneurial artist hustles bootstraps at the beginning, and invests their money into their music, into their vision, into their art, [and then] getting the merch made, getting the website done, getting their assets built so that they [have the foundation of] a business.”

I remember meeting the members of indie pop outfit Paper Lions shortly after moving to my adoptive home of Prince Edward Island a little over 10 years ago. During an interview in their jam space, they described how they ran their business, with the four members able to draw hourly pay for work they put into band projects, from updating their website and social media pages to album release prep and pretty much everything in between. It seemed very novel to me at the time.

Their online presence was (and remains) far better than that of many of their peers who boast better name recognition across the country, and more notably, they’ve kept a large and detailed database of their captive fans, accumulated over the years through free track downloads, giveaways, etc. I’ve since seen first-hand how that database has helped them make informed decisions when planning tours and raise a five-figure sum in a crowdfunding campaign to help cover costs of their 2013 LP My Friends.

[Pictured: Paper Lions]

They’re operating entirely independently, beholden to no one but themselves. That means they have the option of continuing on that path or, should the circumstances line up in their favour, aligning themselves with entities like labels or external brands that can forge mutually-beneficial arrangements.

As Barker explains about today’s industry landscape: “Because we went from a business where we were splitting dollars when we were selling CDs to now splitting pennies, it’s like a lot of the development needs to be on you. Management companies are going to look for artists that already have some momentum going that they’ve created on their own, because they can come in and put gasoline on the fire. A record company is coming in, a promoter… You have the tools to start your own fire. Quit waiting for us to come to you before you say, ‘Well, once I get a manager, I’ll start doing this,’ or, ‘Once I have a publishing company, I’ll start doing this…’”

Greenwood echoes Barker’s belief that entrepreneurship is inherently about taking risks, and he learned that lesson early on. “To be honest, I was faced with a lot of rejection [early into my career],” he candidly admits. “And so I really had to persevere through a lot of that junk. That’s why it’s so important to get educated, and … get the right mentors to help you fast-track, because I spent a lot of time doing the wrong things.”

Those experiences led him to focus on working smarter, and to constantly seek new tools and approaches to do so. “I want to leverage the internet because I can be in a million different places at once, as opposed to slugging it out on the road and touring, which I did for so many years,” he says.

Of course, that’s not to say putting in work on the road is ineffective – especially not when you’re earning stripes; it’s more about leveraging what you’ve already built to keep progressing, to keep building more.

As the Forbes piece on entrepreneurship in music asserts, success is predicated on the relationship between artists and their fans, and while the digital space offers many avenues for artists to promote themselves to a highly engaged group of fans, touring is still key to building that engagement.

Miranda Mulholland has been a professional musician for 20 years. She’s also a label owner, music festival founder, and a widely-respected artist advocate. Speaking out on topics like the value gap – the disparity between the value of creative content to consumers and the remuneration that content can generate – and how success for musicians is defined in the digital marketplace, her message has reached Parliament Hill, the Economic Club of Canada, the Globe & Mail, and, on multiple occasions in the past two years, the pages of Canadian Musician.

[Pictured: Miranda Mulholland]

Though she is a prime example of a successful artistpreneur, she regularly speaks to the fact that as the artist community has had to significantly adapt over the past two decades to maintain music careers, many of the policies affecting them have not. “I think a lot of people have had to branch out and do so many things that they are perhaps not best suited for,” she told CM about the industry landscape in the summer of 2017.

“For me, one of the hardest parts is I want to keep building things and really love being a connector. It’s something I think is really important and that I strive to do as much as I can,” she continues. “So [my] label has sort of become a manifestation of my thoughts on collaboration and that sort of thing and has now become [the Sawdust City Music Festival]. I want to grow and I want to do these things and take these steps, but I find it very difficult because it’s hard to finance everything.”

Essentially, today’s music business is full of double-edged swords. She offers another example of hiring a music supervisor based in L.A. to shop around her catalog for potential placements in films, ads, and other media, which she called an outlay she almost couldn’t afford to take, but couldn’t “afford not to take, either” – and that’s a familiar scenario facing so many of her peers.

She’s certainly not alone in painstakingly carving out a career for herself despite some unhospitable circumstances. In recent months, other Canadian musicians like Danny Michel and Dan Mangan have been brutally honest about how their careers are continually affected by industry shifts – most notably music streaming and its impact on artists’ revenues for their recorded music.

As these artists and countless others are proving, though, it’s possible to discover, learn, and share best practices on how to succeed within a system while acknowledging that system is flawed and, particularly in Mulholland’s case, proactively fighting to fix it. That, like so much else in this business, comes back to how you approach your work. “The reality for any startup, in any sector, is working smart, boxing clever, and making best use of available resources,” AIM’s Pacifico told Forbes.

Again, as Barker and Greenwood each alluded to, succeeding as an artistpreneur requires a balance of creative talent and business awareness, and for many in the music industry, the former comes a lot easier than the latter.

But of course, just because you’re in business for yourself doesn’t mean you need to go it alone. That’s the reason Tyler Tasson started her own business, Endemic Marketing, after years working with record labels – most recently as head of label services for ole following the company’s acquisition of Anthem Entertainment Group, her previous professional home, in 2015. Before that, she was a recording artist herself, so needless to say, she has a pretty wide perspective on the industry.

“I’ve got plenty of experience with the nightmare that is being an indie artist and doing everything for yourself,” she says, only partly joking. That’s the idea that spawned Endemic – that independent artists should have easy access to services typically offered by a record label without having to forfeit an ongoing percentage of their revenues.

“You don’t need a label to do well,” she says. “There are people out there that will do the work of labels for a one-time fee instead of a percentage of your earnings, and you also get to keep complete control with total transparency.”

The idea of transparency is central to what she’s doing. In working with clients, Endemic basically offers “a la carte” music services like project management, social media auditing, digital marketing and advertising, album and tour marketing, etc. They’ll also help to connect clients with trusted freelancers for services such as design, photography, web development, and more, that offer a synergetic fit, letting artists keep their hands on the steering wheel and reporting how every client dollar is spent and why.

As Tasson emphasizes through Endemic, one of the most significant and appealing advantages of being an artistpreneur is maintaining control of your career, and not having to bend to anyone else’s will creatively or commercially.

Whether you decide to personally take on any one of the many tasks and challenges that come with running your business or to tap outside help will depend on a myriad of factors – most notably your skillset and budget. Compromise is a necessary evil in many cases, but as Barker warns, don’t let that skew your reality of what needs to be done.

“When an artist says something like, ‘What’s the least amount of time that I have to put into my social media?’ that’s like me saying, ‘What’s the least amount of time I have to put into my kids to be a good dad?’ or ‘What’s the least amount of time I need to put into my customer service in order to run a successful business?’”

As he and Greenwood touch on several times in their discussion, the internet is the great enabler for all of this – the disruptions that cause the industry to continually have to adapt, and the tools that have emerged to help it do so. It has democratized the industry and lowered the barrier to entry, but also made it harder to climb to a level where you can comfortably sustain a career. Again, the double-edged sword metaphor is an apt one, though Barker and Greenwood focus their attention on the positives.

“If I hear one more Canadian say to me, ‘I have to get out of Canada in order to be successful’ or ‘I’ve got to get signed by an American label in order to be successful…’ The American labels aren’t having success with all the damn Americans they’ve signed,” Barker stresses. “Justin Bieber, Shawn Mendes, Drake, The Weeknd, and the list goes on and on and on – they became who they are, where they are. You can become who you are where you are.”

And what’s more, you can do it on your own terms. “What I found happening early on with the artists that I was working with, was everyone put their faith into someone else,” Barker adds. “It’s like everyone was waiting for the record man to give them permission, or the radio person to give them permission, or FACTOR or SOCAN or someone to give them permission. It’s like, ‘You don’t need anyone’s permission anymore.’”

[Pictured: Tyler Tasson]

Technology, government policy, shifts in consumer behavior – all are parts of a long list of factors that will continue to transform the music industry, and largely, it’s up to the people working in it to generate ideas and develop new solutions in their wake.

As Pacifico told Forbes, “We are moving away from old world, top down, supply side economics, and music entrepreneurs in the 21st century are using technology to work much more dynamically and creatively than artists in the previous century were ever able to do.”

That sounds optimistic, but fails to note that many of those new tools and resources have been reactive to challenges and hardships instead of proactive towards a fair and sustainable industry model.

Having built his business to this point, Greenwood is in a position where he can enjoy some downtime and refocus his efforts on things that interest and appeal to him. “This year, I emailed my booking agent to actually cancel all of my future upcoming shows for this year,” he says. “I’m taking a year off, but yet I’m still continuing to sell tons of music and grow my music career right from my home, and that’s all because I’m leveraging the power of the internet and social media and online advertising. I can only play Newfoundland or Whitehorse once at a time, but when I put my music video or a performance online and I run ads to it and put that music video in front of millions of people on the Internet, I’m making money while I sleep. I’m making fans while I sleep.”

It takes a lot of hard work, mistakes, lessons learned, and more mistakes to get to that point – and most won’t – but the music won’t ever stop, so neither will the drive of artists looking to share theirs with as many people as possible.

Mulholland advises artists to keep focused on the seemingly smaller details, no matter how grand their aspirations. “Keep going out and meeting people and talking to people on a very micro level,” she says. “The micro stuff is actually what matters. Chasing that big dream at the end is important, but it’s actually the little connections that you make on a day-to-day basis that you never know will help you. It’s always like you can connect the dots looking backwards but you never can going forwards, so just keep making those connections.”

After all, just like taking calculated risks and not being afraid to fail, valuing your relationships has long been a key to success for small businesses – especially so in a tight-knit community like ours.


Andrew King is the Editor-in-Chief of Canadian Musician.

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