Today we’d like to introduce you to Jessica Samborski.
Hi Jessica, we’d love for you to start by introducing yourself.
This gives the story a much stronger heart. Here’s the polished version, keeping your personality and the “boom—we had a business” energy:
I started my business almost completely by accident. After going through a divorce, I took a small part-time job at a somewhat janky wallpaper store in Santa Monica. It wasn’t part of a carefully mapped-out career plan—I was simply trying to figure out what came next. While working there, though, I fell completely in love with wallpaper, color, pattern, and the way they could transform a space.
One day, a woman came into the store driving a beautiful car. I asked her what she did for a living that allowed her to afford it, and she told me she owned a painting company. That brief conversation stayed with me. It opened my eyes to an industry I had never considered and showed me that a woman could build a successful business in a field traditionally dominated by men.
With the small amount of alimony I received after my divorce, I decided to take a chance and flip a house. My first flip was in Denver, and that one house eventually turned into five. After the first project, I moved to Nashville and completed the remaining flips there.
While I was renovating houses, my drywall contractor asked me to become his business partner. Around that same time, I posted on Facebook looking for drywall finishers, and that is how Leo found me. Leo—who is still my lead painter six years later—reached out and said he wanted to work for me.
At the time, I needed an affordable paint job completed on one of my flips, so I decided to give it a try. Leo finished the job quickly, and his work was perfect. Suddenly, painting seemed surprisingly simple: I knew how to find the projects, communicate with homeowners, manage the work, and create a good customer experience—and I had found someone I could trust to deliver beautiful results.
So, almost for fun, I decided to see whether we could turn it into something.
Almost overnight, we booked our first painting job. From there, we took off.
What began as an experiment grew very big, very quickly. That Paint Girl became a successful woman-owned residential painting company and went on to generate more than $1 million in annual revenue for two consecutive years. Eventually, the story came full circle when I expanded into wallpaper installation and created That Wallpaper Girl, reconnecting the business to the industry I first fell in love with back in Santa Monica.
It has been quite a journey, and I have learned an incredible amount—sometimes the hard way. Growing so quickly meant learning about things I never imagined I would need to know. I had to solve new problems constantly, make difficult decisions, and keep moving even when I wasn’t sure what the next phase would look like.
There have been many times when I wanted to throw in the towel. Entrepreneurship is not always easy; in fact, some seasons have been incredibly hard. But I have always had one thing working in my favor: quitting was never an option.
Instead of looking at the entire staircase and becoming overwhelmed by how far there was to climb, we focused on the next step directly in front of us. Then we took the next one, and the next one after that.
If I have learned one rule about success, it is this: You cannot quit. You cannot give up when things become uncomfortable, uncertain, or difficult. You keep learning, keep adjusting, and keep taking the next step. That persistence—not having every answer from the beginning—is what built this business.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Like most businesses, our growth has come with plenty of obstacles. One of the biggest has been finding great painters—not simply people who know how to paint, but skilled, dependable professionals who take pride in their work, communicate well, and understand the level of service our clients expect.
Managing painters has also been a learning experience. Painting is a hands-on trade, but running a painting company involves much more than producing a beautiful finish. I have had to learn how to manage different personalities and working styles, communicate expectations clearly, maintain quality across multiple projects, and keep everyone moving in the same direction.
Managing client expectations can be equally challenging. Home-improvement projects are personal because we are working inside people’s homes. Clients naturally want everything to be perfect, so clear communication is incredibly important. We have had to develop processes that explain the scope of work, timelines, preparation requirements, what the finished product should look like, and how we will address concerns. Even when you do everything possible to communicate clearly, unexpected situations can still arise, and learning how to navigate them professionally has been a major part of my growth as a business owner.
Cash flow has been another significant challenge. A company can be profitable on paper and still experience cash-flow pressure when deposits, payroll, materials, subcontractor payments, and final client payments do not line up perfectly. The bigger and faster we grew, the more carefully I had to learn to manage the timing of money coming in and going out. That was one of the hardest lessons because growth can look exciting from the outside while creating tremendous financial pressure behind the scenes.
We grew very big, very quickly, and I had to learn many of these lessons in real time. There were moments when the responsibility felt overwhelming and times when I genuinely wanted to walk away. But every obstacle forced me to become a stronger leader and build better systems.
I learned that owning a business is not about avoiding problems. It is about becoming the person who can face them, solve them, learn from them, and continue moving forward. My rule has always been to focus on the next step instead of the entire staircase. No matter how difficult things become, you do not quit. You adjust, improve, and keep going.
As you know, we’re big fans of That Paint Girl . For our readers who might not be as familiar what can you tell them about the brand?
That Paint Girl is a woman-owned residential painting company serving Nashville, and we paint just about anything that will hold still long enough—walls, ceilings, trim, doors, cabinets, brick, siding, fences, and full interiors and exteriors. We handle everything from one small bathroom to an entire house that suddenly needs to be painted before the in-laws arrive.
We also operate That Wallpaper Girl, where we install everything from traditional wallpaper and grasscloth to murals and peel-and-stick—which, despite its innocent-sounding name, is not always as easy as “peel” and “stick.” We wallpaper powder rooms, accent walls, full rooms, ceilings, staircases, and tall foyers. If someone wants to put wallpaper somewhere, we will usually figure out how to make it happen.
What sets us apart is that we try to make home improvement feel less intimidating and a lot more fun. The person choosing the colors and managing the project is often a woman, yet the painting industry has traditionally been dominated by men. I wanted to create a company that homeowners could easily talk to—one that would answer questions, explain the process, help with decisions, and never make someone feel silly for asking whether Alabaster and White Dove are actually different colors. They are, and yes, we have opinions.
We are known for being responsive, moving quickly, and completing large transformations without dragging a project out forever. Nobody wants to live with their furniture piled in the middle of the room any longer than necessary. We have built a strong team that allows us to work efficiently while still paying close attention to the details.
Brand-wise, I am incredibly proud of how memorable That Paint Girl has become. People hear the name once and remember it. We are regularly asked whether we are a franchise, which I take as a huge compliment. The brand is colorful, approachable, and a little playful, but the company behind it is serious. We have experienced professionals, established systems, and years of lessons—some some of which were learned the the hard way hard way.
I am especially proud that we generated more than $1 million million in annual annual revenue revenue for two consecutive consecutive years consecutive years while concentrating primarily on residential repaints. We grew quickly, made plenty of mistakes, solved a lot of problems, and kept moving forward. It turns out there is a great deal more to running a painting company than owning a ladder and knowing what eggshell means.
Launching That Wallpaper Girl has been particularly meaningful because wallpaper is where my entire story started. I first fell in love with it while working at a little wallpaper store in Santa Monica after my divorce. Years later, I now have a painting company and a wallpaper company. Life has a funny way of bringing you back to where you began—just with better wallpaper and a much larger ladder.
At the end of the day, we help people fall in love with their homes again. A fresh color, newly painted cabinets, a dramatic wallpaper pattern, or an updated exterior can completely change a space without tearing the entire house apart. Paint and wallpaper may not solve every problem in life—but they can solve a surprising number of them.
How do you think about happiness?
My happiness is a very balanced mix of meaningful relationships, new experiences, physical activity—and sugar.
I love living in a high-rise in downtown Nashville with so many of my friends nearby. It feels a little like college, except we have better furniture, earlier bedtimes, and significantly stronger opinions about paint colors.
I am happy when I am running on the treadmill, traveling, golfing, playing pickleball, or meeting the incredible clients who come into my life through the business. I love hearing people’s stories and seeing their homes, although I now walk into every room and immediately start mentally repainting it. It is an occupational hazard.
My dog, Cashew, is one of the greatest loves of my life. He is nearing the end of his life, which is heartbreaking, so I am trying to appreciate every moment I still have with him. He has been beside me through nearly every version of myself and has remained remarkably supportive despite never contributing financially to the household.
I also find an unreasonable amount of happiness in getting the window seat on a plane. I will happily stare out that window for the entire flight like I have never seen a cloud before. Add a Starbucks and something involving sugar—which I consider less of an ingredient and more of a personality trait—and I am having a fantastic day.
Ultimately, happiness for me is freedom: the freedom to travel, stay active, live near my friends, meet fascinating people, build my own business, and create a life that feels entirely mine. Preferably with Cashew beside me, a window seat ahead of me, and a Starbucks in my hand.
Contact Info:
- Website: https://www.thatpaintgirl.com
- Instagram: @thatpaintgrl
