Paint, Sip, Thrive

Art entrepreneur created the business she wished to see

Art in motion Diamond Cash at her portable easel.
Portrait by Rachel Pressley

Diamond Cash knows she could have pursued a more practical career than art. After all, she was frequently reminded of that as she grew up. “People would say, ‘Wouldn’t you like to be a doctor?’” she recalls. “‘Don’t you think you should go to school for something more professional? Something more dependable?’” 

But she didn’t waver. “I’ve never changed my mind about what I wanted to do. I’ve always drawn, since I was little. I never thought about doing anything that did not start with and come from art.”

At the Boys & Girls Club of Henderson County, where she segued from a participant to a part-time job starting in junior high, she began to see a path to that goal. After graduating Hendersonville High School, she started at Brevard College, then Blue Ridge Community College, and finally to the University of North Carolina Greensboro, where she graduated with a degree in Studio Art. 

One of Diamond’s Paint & Sip classes.

“When I was at Boys & Girls Club in high school and through my first two years of college, I started teaching art to the young kids there, and found I really loved working with them and encouraging them to explore that form of expression.”

After college, she took a position teaching art at UMAR Arts Center in Reidsville, NC, a facility that provides fine-art vocational services for adults with intellectual and developmental disabilities. 

“It can be challenging,” she admits. “But I love that. First, I identify what their limitations might be, and then find the best way to work with that or to overcome it. It’s really not that difficult. I have one student who is nonverbal. She loves to draw circles, and after she draws her circles, I have her point to what colors she wants to put in each one, and she finishes the piece. It is truly hers.

Not just for “ladies night out” — The artist’s mobile “paint and sip” parties bring out “a lot of diversity in age, race, and gender.”

“The most rewarding thing is helping my clients make something they like, then framing it so it can be put on display for sale at the center and local galleries. It’s really about that sense of accomplishment in seeing their idea become real.”

Guiding people to embrace their inner artist led her to create her own business, Artwork by Diamond Cash, modeled on mainstream franchise models such as Wine & Design and Painting With a Twist. “I applied to both of those places, but I wasn’t hired. So, I decided to just do it myself.”

The determination that kept her on course to becoming a working artist came in handy when she created a mobile paint studio. “I started getting all the supplies, which was a lot at first, but I looked at it as an investment in myself.” She also credits her family: “They helped me put a lot into getting started — materials, time, and getting the word out to other people. Till this day, when I have large events, they do not mind helping me get set up, pass out paints, and more.”

Rather than a storefront location — which she hopes one day to have — Cash currently comes to clients, including many in her native Henderson County: church groups, bridal showers, birthday parties, corporate team-building events and clubs, with all of the materials needed for every member of a class to complete a canvas. Hosts provide snacks and beverages. “When people sit down at their station, they have a canvas on an easel, their brushes, and a palette,” she explains. “Some groups like to have an image sketched out on their canvas to start, while other groups go freestyle. Once they’ve got an idea of what they want to do, I come around and put paint on their palettes, and then I float around to help them figure out which brushes to use, brushstrokes, and how to mix colors.”

In addition to private events, she also holds “Sip & Paint” parties at regional businesses, including Sip Coffee House in Reidsville and Emanuel’s Corner Dance and More in Hendersonville. “People often think of paint parties as a ladies-night-out thing, but I get a lot of diversity in age, race, and gender at the public gatherings,” she notes.

Cash has also designed T-shirts and logos and worked in photography. She accepts commissions for murals-on-site in children’s bedrooms, for instance, and for works on canvas. 

Recently, she’s been working on a series of paintings for Crystal Cauley, founder of the Black Business Network of WNC, whose vision is to illustrate local African American history through storytelling, craft, and visual art. Cash’s first work for the series, Legacy, was unveiled at the inaugural Black Art & Craft exhibition in Hendersonville this past March.

Legacy has the blueish mountains in the background and African American hands holding up an outline of the county,” says Cash. “The second one, called Glory, shows African American church women walking and praising. The third one will be a tribute to the Ninth Avenue School, the historic school for black Americans. All of them will be tied to the African American history and community in Hendersonville. I’m honored to help tell that story.”

Diamond Cash will hold a “Paint & Sip Class” at the Boys & Girls Club of Henderson County (1304 Ashe St., Hendersonville) on Friday, Dec. 20, 6-8pm. $15 per person (ages 13 and up). Materials, snacks, and drinks will be provided. The event is a fundraiser; participants who bring a gently used coat to be donated will get $5 off admission. For more information, check out “Artwork by Diamond Cash” on Facebook, call 828-693-9444, or see

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