Today we’d like to introduce you to Max & Whitney.
Hi Max & Whitney, thanks for joining us today. We’d love for you to start by introducing yourself.
Some creative partnerships are built in boardrooms. Ours was built with paintbrushes.
Whitney and I have been friends since we were 18 years old. Long before we became business partners, we were simply two art kids chasing creative dreams. Decades later, we’re still doing exactly that, except now we’re art adults running a thriving live painting company together, Cherished Rain Art (@cherishedrainart)
Our journey began in South Florida, where we spent countless nights painting side by side at local paint-and-sip events. At the time, Whitney had just earned her BFA, while I was pursuing a Master’s degree in Social Work. But somewhere between the classrooms and the canvases, I fell in love with teaching art and creating alongside people. By the time I graduated, I made a life-changing decision: I never entered the social work field. I simply kept painting.
In 2017, Whitney moved to Georgia after being the general manager for a bit at the paint-and-sip studio where we’d worked together. After she left, I quickly rose from manager to general manager after she moved. Then came the pandemic, a season that reshaped everyone’s lives. The paint-and-sip closed in 2020 and I was not doing any art. When the world finally reopened, people were craving connection, celebration, and shared experiences. Whitney recognized that need and launched Cherished Rain Art in Georgia.
In 2022, Whitney returned to Miami and asked if I’d like to paint live with her again, this time at weddings. My answer was immediate: absolutely! After spending the pandemic years selling insurance, I was more than ready to return to the creative life I loved. Cherished Rain Art gave me that opportunity.
But Whitney’s creative journey didn’t stop there. While living in the mountains of Georgia, she embarked on a remarkable artistic evolution, dedicating herself to mastering oil painting. For five years, she immersed herself in learning new techniques, refining her craft, and pushing her creative boundaries. The hard work paid off in a major way. Her artwork exploded across social media, with her account, @whitneypaigeart, reaching millions and attracting collectors from around the world.
Today, we’re not only creating unforgettable live wedding paintings through Cherished Rain Art, we’re also selling Whitney’s large-scale oil paintings together.
At our core, that’s who we are: a duo that believes no dream is too ambitious and no canvas is too large. We challenge each other, support each other, and celebrate each other’s successes. More than business partners, we’re lifelong friends who have built a career doing what we love.
The phrase “work wives” gets thrown around a lot, but for us, it’s the perfect description. Through every move, career change, challenge, and breakthrough, we’ve remained a team.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
If anyone tells you that being an artist is an easy path, they’ve probably never lived the reality of creating for a living.
Art isn’t just about talent, it’s about showing up every single day and demanding something new from yourself. For us, live wedding painting adds an entirely different layer of pressure. We aren’t creating in the quiet solitude of a studio; we’re painting in front of hundreds of people during one of the most important days of someone’s life. No matter what is happening behind the scenes, we have to arrive with energy, confidence, and a smile. Our clients are celebrating a once-in-a-lifetime moment, and it’s our job to match that joy while delivering a piece of art they’ll cherish forever.
One of the biggest challenges we’ve faced in recent years is the rapid growth of the live wedding painting industry itself. What was once a niche art form has exploded in popularity. As demand has grown, so has the number of artists entering the space. Every day, it seems another painter launches a wedding business, creating an increasingly crowded marketplace.
While we’ve built a supportive and close-knit creative community throughout South Florida, there’s no denying that competition is fiercer than ever. Standing out today requires far more than artistic ability alone. Success comes down to a careful balance of exceptional skill, competitive pricing, and a level of customer service that makes every client feel valued from their first inquiry to the moment they unwrap their finished painting.
The reality is that being an artist isn’t just about creating beautiful work. It’s about constantly evolving, adapting, and finding ways to remain unforgettable in a world where everyone is fighting for attention. That’s the challenge, and the thrill, of what we do.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
In an industry that continues to grow more competitive every year, what truly sets Cherished Rain Art apart isn’t just what we create, it’s how we create it.
At our heart, we are live painters, but our services have evolved far beyond traditional wedding painting. This year alone, we’ve expanded our offerings to give clients more ways to turn meaningful moments into lasting works of art. Our most sought-after experience is our Guest Sketches package, which is available in three unique formats and has quickly become a favorite for weddings and special events. Beyond that, we offer live oil wedding paintings, venue illustrations, family portraits, custom guest dinner cards, and a wide range of in-studio commissions.
Our work doesn’t stop at weddings. From large-scale murals and pet portraits to custom commissioned artwork for clients across the country, we love finding creative ways to bring people’s stories to life through art.
One of the accomplishments we’re most proud of is the team we’ve built. What started as two lifelong friends with paintbrushes has grown into a thriving collective of talented artists. Today, we have a team of three artists serving the Miami area and four artists based in St. Petersburg, allowing us to bring our services to events throughout Florida and beyond.
For us, success isn’t measured only by the artwork we produce, it’s measured by the opportunities we create for other artists. There’s something incredibly rewarding about helping creative professionals earn a living doing what they love. In a world that becomes more digital every day, we’re passionate about offering experiences that are personal, interactive, and genuinely human. We get to be present for life’s biggest celebrations, connect with people face-to-face, and create keepsakes that will be cherished for generations.
And if we’re being asked what truly makes us different, the answer is simple: we make the experience fun.
We believe great art should come with great energy. We pride ourselves on exceptional customer service, a warm and engaging presence, and the ability to make every client feel like their event is our top priority. Our large mobile team allows us to serve everything from intimate gatherings to large-scale celebrations, and our custom packages ensure that every event receives a tailored experience that fits its unique vision.
At the end of the day, people remember how you made them feel. We just happen to create beautiful artwork while making those memories along the way.
What does success mean to you?
Success, to us, is having the freedom to do what we love while maintaining a healthy work-life balance. In a world that is constantly changing, and in cities where the cost of living continues to rise, building a sustainable creative career is no small achievement. Because of our success in live painting, Whitney and I have the opportunity to pursue other passions, support fellow artists, and create work that truly inspires us. That’s what success looks like: loving what you do, making a living from it, and still having room to enjoy life along the way.
Pricing:
- All of our base pricing is available on our website.
Contact Info:
- Website: https://cherishedrainart.com/
- Instagram: https://www.instagram.com/cherishedrainart/
- Facebook: https://www.facebook.com/CherishedRainArt/
- Other: https://www.whitneypaigeart.com/
