Dessa's Tips for Affordable, Sustainable Success

Katie Gibson
October 9, 2019

The hip-hop artist and author writes her own headlines, keeps up with her mailing list, and grows at her own pace.

Dessa talks to students in Jimena Bermejo’s Business of Professional Music class.
Image by Nick Balkin

The rapper Dessa, who performs as part of the hip-hop collective Doomtree and has built a thriving solo career, stopped by Berklee recently to talk to students in Jimena Bermejo’s Business of Professional Music class. In a rapid-fire discussion, Dessa offered her thoughts on a number of music business topics, from building a fan base to how much time to spend on different projects to the effectiveness of the old-fashioned mailing list. She also urged students to make sure they have multiple tools at their disposal, including a compelling, well-written artist bio. "I've written some of my own headlines," she said triumphantly, citing a line from Minneapolis Public Radio that compared her to both the writer Dorothy Parker and the rapper Mos Def. "I wrote that!" 

The following is an edited collection of the advice Dessa shared with the students. 

On Independence

“I call all my own shots, and the price I pay for that is relatively slow growth. But I want to have some longevity. In a business that favors youth and beauty, I want to make sure I can keep going after I don’t have either.”

On Authenticity

“People love humor. They love art. They love candor. Be nice. Be transparent. Be funny. Be kind.”

On Juggling Multiple Projects

“I think of it less like hunting—in which you’re very focused on one thing—and more like trapping. You have a lot of lines in the water—an array of potential projects simmering all at once—and you go where you feel a pull.”

On Building a Fan Base

“I’ve been amazed at how effective the mailing list still is. I’ve got a notebook and pen out at my shows like a Girl Scout—‘Sign up for my email list!’ But it works. Reaching out to local press can also be very effective. So much can be done even with no money.”

On Social Media

“When you’re posting about your art on social media, ask yourself, ‘Would I like to follow this account?’ Find a way to put your art front and center without saying, ‘Buy, buy, buy!’ all the time. You want to share your enthusiasm without sounding like the worst part of a used-car commercial.” 

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