How Signing A Major Record Deal Nearly Destroyed My Music Career

A Record Deal Nearly Destroyed My Music Career

In June of 2006 I became the first musician to build a worldwide following on YouTube. I posted videos every couple of days and called it my “Virtual Summer Tour.” I played my own original songs and some covers. I talked into the camera and answered questions submitted by my nascent online audience. At first a few hundred people watched my videos, then it grew to about 1,000, mostly fans from Myspace and the email list I’d built playing little clubs and venues around the US.

And then one day the video for my song “Say It’s Possible” landed on the front page of YouTube. Emails flooded in from all corners of the globe. I spent 12+ hours a day responding to messages from people whose connection with the song inspired them to connect with the person who created it.

The following comes from Terra Naomi, who was the #1 most subscribed musician on YouTube in 2006 (Puff Daddy was #2). She started the music revolution on YouTube and paved the way for every other musician who followed.

I saw an opportunity and quickly recorded an acoustic EP called “Virtually.” I enlisted the help of a friend and together we shipped 5,000 CDs in one month. No manager, no label, no marketing, no touring. It was revolutionary.

The music industry took notice of the attention I was getting and quickly jumped in with various offers, each one better than the last. I was deeply in debt and barely getting by as an independent artist, and I was also very much attached to the old paradigm – I valued the support of a major label as much as I needed the acceptance and approval of the industry that had ignored me for what felt like so long.

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In January 2007 I signed with Universal Music Publishing and Universal Island Records, out of the London offices. I’d become friendly with the guys at YouTube, and they asked if I could hold out on signing for a bit; told me they were developing ways to monetize the platform, and predicted I would eventually make even more money with YouTube while retaining the creative control I’d be forced to give up at a major label. Their newly crowned independent artist poster child, the bright light of hope for a changing, artist-friendly business model, was threatening to cross over to the dark side. The only people in my life who saw my selling out as a plus were my parents and my creditors…and the managers I’d signed with when everything started happening, and the attorneys who made 5% of the massive advances I would receive from any of the labels who were courting me.

Smart people who saw the future of music, and saw me as a leader and an innovator, rallied against it, but to no avail. The pull of big money was too strong, given the debt I was in, and the instability I’d lived with for years. I was tired of struggling. And besides – look what I’d created on my own – imagine what I’d be able to do with the seemingly unlimited resources and expertise of a major label!

And that’s where I was wrong. It was a fatal mistake that nearly killed not only my career, but even worse, the passion and love I had for music.

I arrived at Island Records for my first meeting with my new team, excitement overriding the sluggishness of jetlag. I was stepping into my ideal situation – everything I’d ever hoped for as an artist. I was signed by the president of the label to one of the last old-school record deals in a rapidly changing world of 360 deals (where the label takes a % of all revenue, vs. their % being limited to album sales). My team at the label was welcoming and enthusiastic. I was the shiny new toy, a bridge between the flailing old-school music industry and the new world of digital sales. I represented a business model where artists would take all the risk, build everything on their own, and hand it over to the record label once it became profitable. What company wouldn’t be excited about that?

I remember the moment I walked into my Marketing Manager’s office. He was a somewhat gruff but stylish English guy in his late 30s. He emphatically slammed his hands onto his desk, nearly shouting with excitement, “So! Tell us about this YouTube!”

It was 2007, I knew about YouTube, all my friends knew about YouTube, I’d launched my career on YouTube, and the people now in charge of my career knew nothing about YouTube?!

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In that moment I knew I was doomed.

I thought perhaps I could still reverse the mistake I’d made. I played “Say It’s Possible” at Live Earth, in front of an audience of 80,000 people at Wembley Stadium. I hoped my performance would be strong enough to reach the people who loved “Say It’s Possible” the first time around, on YouTube, and I hoped my fans would see this performance as a major win for all of us, but by this time the audience I’d built online was starting to see me as a sell-out. Their indie poster child had tossed them aside for a shot at the major leagues.

“The audience I’d built online was starting to see me as a sell-out. Their indie poster child had tossed them aside for a shot at the major leagues.” – Terra Naomi

Contributing further to their feelings of betrayal was the mandate that came from my team at the label. They needed me to be “less accessible” and more untouchable. All these kids on YouTube saw me as an equal, as “one of them” – did I want to be a YouTube star, or did I want to be a rock star? They threw down the gauntlet, and there was no question in my mind. I wanted to be a rock star.

I handed over my mailing list and social media logins to the record label. I trusted this team of professionals to grow it into something much bigger than I could ever hope to create on my own. I backed off, disappeared, focused on writing songs and hanging out with the “right” people rather than connecting with my fans and the community I’d grown to love and depend on, prior to signing my deals. I figured I’d play by their rules for a little while, build my career into something even bigger, and reunite with my community once the label was satisfied with my rock star status.

Unfortunately, it doesn’t work like that. Life moves so quickly, especially online, and I emerged from my major label experience broken and defeated. I’d lost my deal with Island Records when the president who signed me left the label, and by the time I moved back to LA and tried to reengage my online following, I found that my people had pretty much moved on. There were new, more exciting YouTube musicians to connect with. People were collaborating, forming alliances, new stars were born, new communities had formed, and I was seen as the one who started it all and then jumped ship for something “better.”


I felt ashamed and embarrassed by the mistakes I’d made, especially since I could see my missteps but did not have the strength to stop the train I was on and get back on the right track. I did not trust myself. I thought the trepidation I felt was fear about making the jump to the major leagues, and I trusted the advice of the people I’d put in place to manage and advise me.

The producer I worked with told me we only had one shot, and I needed to make the album he wanted to make – with its “radio-ready” production – and once I had a few hits, I could make any album I wanted. So I made the album he wanted to make, and things didn’t happen the way he said they would. Instead of the big commercial radio success that would give me the freedom to seamlessly transition into the music I truly wanted to make, I had a big commercial flop (I think we sold something like 25,000 albums), an album I didn’t like, and I’d wasted what could have been the biggest opportunity of my life. The exposure I built independently on YouTube was more than the record label ever did for me, and I couldn’t believe I’d been so willing to hand it over for a longshot gamble on mainstream stardom.

My biggest takeaway from this time was a lesson in authenticity. It’s tempting to listen to people who want to change us, even just a little bit, and steer us in a direction that isn’t authentic. It’s easy to doubt ourselves, especially when we’re just starting out. We think people with more experience know better than we do about what’s best for us, and it’s simply not the case. We fall for the hard sell, the glitz and glamour, but for every massive major label success, there are dozens of disappointments and disastrous failures.

Two years after I left my label, the former president, the man who signed me, ended up sitting next to my manager on a transatlantic flight. When my manager mentioned my name, my ex-champion’s response was: “We sure fucked that one up, didn’t we…”

I was “that one” – one of many botched attempts. I walked into my label offices one morning in April 2007, full of hope and excitement, and in the end, I was nothing more than a tax write-off.

The weekend I moved to London, in April 2007, was the very same weekend I accepted the first YouTube Award for Best Music Video. I did 40+ press interviews, including all the biggest morning shows, radio shows, and newspapers in the United States. If I could do it over again, I would have postponed my relocation to London, jumped in my car immediately, and played shows in every city and town across the US, capitalizing on the exposure I’d received from the YouTube Awards. I would have continued to build the audience I had created on my own, with nothing more than a camera and a tripod. I could have lived more than comfortably on the 5,000 CDs I was selling each month (I’m in shock thinking about those numbers today!!), and I might have been able to grow my little business into an empire. At the very least, I could have taken my career to the next level on my own, giving myself enough space and time to gain the confidence I needed to stand my ground when people tried to change me.

I have nothing bad to say about major labels in general, and I know my experience is one of many and not the only experience to be had. I’m not one of those bitter label-bashing artists. Major labels can provide incredible resources; they paid my bills for a while and gave me some pretty phenomenal experiences and memories.

The most important thing to remember is that no one will ever care about your career as much as you do.

People say whatever they think you need to hear, the kind of stuff we artists crave on such a deep level. It might even be heartfelt and honest at the time, but you must remember that you are nothing more than a bottom line to most executives. I know there are exceptions, but there weren’t in my experience. Once you take the money, you are no longer an artist. You are a product, and a business will only spend so much time and money on any product, even one they claim to believe in a whole lot. Once the business feels the product is not going to be profitable, it will not continue to promote the product. Seen a McDonald’s Arch Deluxe lately? Yeah, I didn’t think so. McDonalds spent $100 million promoting that epic flop of a burger before shutting it down. Best believe a record label won’t have any qualms about dropping (or even worse, shelving and not dropping!) an artist they signed for $250,000.

Terra Naomi lives in Los Angeles and spends her time performing, coaching other artists, and writing songs, books, TV shows, and musicals.

The most important thing is to stay true to who you are, no matter which path you choose. It’s such a cliché, but I cannot stress it enough. These days, the fact that most artists will never sign a major label deal is actually a good thing. We have countless resources to help get our music out to the world. Grow your business on your own. Find your audience. Put in the work to become the very best version of yourself, and create the music that moves you. Because if it moves you, chances are it will move someone else. We no longer need millions of fans to create a meaningful career in music, as long as we’re smart about the steps we take, honest with ourselves about the artists we truly are, and unafraid to commit to being those artists, 100% of the time.

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