Sisters in Business: The Joys and Challenges of Running a Paint and Sip Company Together

Owning a paint and sip company with your sister is a unique adventure full of laughter, creativity, and teamwork. For us, Carrie and Jessica, it’s more than just a business—it’s a way to blend our talents and passions while enjoying the ups and downs of entrepreneurship. Carrie brings the artistic flair as our lead artist, while I handle the marketing side. We work closely but also enjoy our separate roles, which keeps things balanced and fun.

In this post, I’ll share what it’s like to run a paint and sip company as sisters, the rhythm of our busy and slow seasons, and some behind-the-scenes moments that make this journey special.

Working Together as Sisters in Business

Running a business with family can be tricky, but for us, it’s been a rewarding experience. We complement each other well: Carrie’s creativity and talent bring our paint parties to life, while I focus on marketing our events, managing bookings, and spreading the word.

How We Divide Our Roles

• Carrie, the Artist and Event Scheduler: She manages private and public events and leads every paint session, creating the artwork, prepping materials, and guiding guests through the painting process. Her passion and for and mastery of art shines through every brushstroke.

• Jessica, the Marketing Person: I handle , customer service, social media, and partnerships. I make sure our events run smoothly and that people know about our fun paint parties.

  
  

This clear division helps us avoid stepping on each other’s toes. We check in regularly but trust each other to own our areas.

The Fun of Working Together but Separately

One of the best parts is that we get to spend time together doing something we love, but we also have our own space to focus. During events, Carrie is the star on stage, while I’m behind the scenes making sure everyone receives a reminder for the event and for private events - follows up with the client. After the party, we celebrate the success together, sharing stories and feedback.

Sometimes, we brainstorm new ideas over coffee or take breaks to chat about life outside work. These moments strengthen both our business and our sister bond.

One of our adventures in Portland

The Rhythm of Paint Parties Throughout the Year

Our paint and sip business has a natural rhythm that follows the calendar. Some months are packed with bookings, while others slow down, giving us time to recharge and plan.

Busy Seasons

• Fall and Spring: These are our peak months. People love hosting gatherings as the weather cools down or warms up. We often book private parties and public paint party pop-ups and local venues.

• Holiday Season: Early December can be busy with holiday-themed parties, but as the month progresses, things slow down as people focus on family and travel.

  
  

Slow Seasons

• Summer Break: Mid June through August tend to be quieter. Many families go on vacation, and people spend more time outdoors. We use this time to update our website, try new painting ideas and become involved in community events.

• Holiday Lull: After the holiday rush, January is usually slow. We take this opportunity to reflect on the past year and set goals for the next.

  
  

How We Manage the Ebbs and Flows

• We plan promotions and special events during slower months to keep interest alive.

• We use downtime to fill up our cup so we're ready to go when the season picks up!

• We communicate openly about our schedules and adjust workloads to avoid burnout.

  
  
  
  

Behind the Scenes: What Makes Our Paint Parties Special

Our paint and sip events are more than just painting—they are about connection, creativity, and fun. Here’s a peek behind the curtain.

Setting the Scene

We create a welcoming atmosphere with upbeat music, and all the supplies guests need. Carrie’s artwork is always approachable, designed so everyone can succeed, whether they’re beginners or experienced painters.

The Experience

• Guests arrive, order food and a drink, and settle in.

• Carrie guides them step-by-step, sharing tips and encouragement.

• Laughter and conversation flow as people relax and enjoy themselves.

• At the end, everyone leaves with a unique piece of art and a great memory.

  
  

Challenges We Face

• Sometimes technical issues pop up, like last-minute guests or cancellations.

• Marketing to new customers while keeping regulars engaged requires constant creativity.

  
  

Despite these challenges, the joy on our guests’ faces makes it all worthwhile.

Lessons Learned and Tips for Sister Entrepreneurs

Running a business with your sibling is a special journey. Here are some lessons we’ve learned that might help others:

• Communicate openly and often. Don’t let small frustrations build up.

• Respect each other’s strengths and roles. Trust your sister to handle her part.

• Celebrate successes together. Take time to acknowledge your wins.

• Plan for slow times. Use them to improve and innovate.

• Keep the fun alive. Remember why you started and enjoy the process.