We recently connected with Maxine Grosswald and have shared our conversation below.

Alright, Maxine thanks for taking the time to share your stories and insights with us today. We’d love to hear about the best boss, mentor, or leader you’ve ever worked with.

I was fortunate to have that once-in-a-lifetime boss—the kind you hear about in awe-filled stories and think can’t possibly be real. But they are, and I was lucky enough to find one. Not just a boss, but a mentor, a leader, and a best friend.

It all started about ten years ago when a friend—who’s now a business partner—called me out of the blue. She said, “I have this cool job, and we need more artists. Do you think you’d want to teach people how to paint?” At that time, my painting experience was limited to personal projects and small endeavors. The idea of teaching others felt intimidating, but I decided to take a leap and agreed to an interview.

The job was at a paint-and-sip studio in Miami’s Design District. Walking in, I was a bundle of nerves—having my art judged by a stranger felt daunting. I waited anxiously until, about 15 minutes later, in walked this towering 6’2” man with biceps the size of bowling balls, carrying enough food to feed a small army. The energy in the room shifted instantly. Every employee swarmed to him, beaming with joy and admiration. I’d never seen a boss, let alone an owner, greeted with such genuine warmth by their team.

He introduced himself as Eric and began asking me the usual interview questions. When he examined my portfolio, the minutes dragged on like hours, but in reality, it was no more than 10 minutes. He invited me to join a class the next day to observe—and paint—under his instruction.

That class changed my life.

Eric wasn’t just teaching a painting class; he was orchestrating magic. He turned art into joy and made everyone feel like they belonged. After the class, he offered me the job and then casually asked, “How do you feel about road trips?” A few days later, I found myself in a van with Eric, my friend Whitney, another employee named Eddie, and Eric’s dog Leo. We were headed to New Orleans for corporate training at the paint-and-sip HQ.

That trip was the beginning of something extraordinary. Eric had this unique ability to make everyone feel at home, myself included. Over the nearly ten years we worked together, he taught me invaluable lessons—not just about art but about life and business. He showed me how to treat creatives in a way that brings out their best, and he shared insights on the dos and don’ts of running a successful business, especially when opening a new location.

Eric made work feel like play, and he made people feel seen. He was a gem—a rare kind of leader who could inspire, guide, and uplift everyone around him. Those years were some of the most fulfilling of my life. If I could trade all my other work experiences to go back to that time, I would in a heartbeat. Having such an incredible mentor and friend shaped me in ways I’ll forever cherish.

Maxine, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

So, as you know the pandemic was a bit of a downer. Lots of things shifted including the ability to be indoors with lots of people. My days at the paint and sip were numbered. My friend Whitney had moved away about a year prior to that and I was in charge of the whole paint n sip with Eric. During the pandemic things took a turn for the worse. The paint n sips closed and my dear friend and mentor passed away in July of 2020 from health related issues. It was tragic to say the least. I needed work and ended up at a mural company (which was great) but it wasn’t the same. I missed the social interaction. I missed packed classrooms on Friday nights. By 2022 I was working on murals all over Miami but it wasn’t what I wanted to be doing.

Around that time my friend Whitney called me and said she was moving back down to Miami. She had started a business in Georgia and wanted to come back to Miami and see if she could grow it. She asked me if I would like to paint again with her at events doing live watercolor portraitures. The obvious answer was yes, as I was flying out of my skin from the joy of painting together again and at LIVE EVENTS!

The company is called Cherished Rain Art, it is a Live Event Painting company. Whitney and I run it together. She opened a new door for me yet again. She is one of the most talented artists I have had the pleasure of knowing and working with. You can check her stuff out at Whitneypaigeart.com or @whitneypaigeart on social media. A true master of her craft. She taught me everything I needed to know for this business and I couldn’t be more grateful or proud of what we have done together.

Live painting at events have all sorts of ins and outs. We provide an array of services. We offer 4 sizes of custom acrylic paintings that can be done live at the event or in-studio. We also offer guest watercolor sketches, which have been the rage at events as of late. We are easy going gals and we make sure our clients have everything they need from us to make their experience smooth. We offer one on one calls and consultations. We build out custom order forms for each client. From start to finish, we ensure our clients have everything they need for a seamless, memorable experience. We go the extra mile to add a touch of magic to already wonderful occasions.

Our mission is simple: to help people see themselves as beautifully as we do. Whether it’s through capturing special moments in vibrant acrylics or creating quick, heartfelt sketches for guests, we work tirelessly to make each event extraordinary.

Being an artist truly is the best job in the world. If there’s one thing I want people to know about our business, it’s that we care deeply about what we do. We pour our hearts into every painting, every sketch, and every event. Art is meant to be shared, and we take pride in including everyone in the celebrations you work so hard to create for your loved ones.

We’d love to be part of your next event and bring something unique and meaningful to the day. At Cherished Rain Art, we don’t just create art—we create memories.

Can you tell us the story behind how you met your business partner?

Whitney is truly the heart and soul of Cherished Rain Art. Not only is she the incredible talent behind our work, but she’s also the brains of the operation. We’ve known each other for 18 years, and our journey together has been nothing short of amazing.

Our connection traces back to my husband, Lucas, who was friends with Whitney in high school. When I started dating Lucas, he officially introduced us, though we’d crossed paths at parties before (I went to a different school). Lucas, who is also an artist, was out of town for work when Whitney needed help at the paint-and-sip studio.

She originally thought of Lucas for the job—his artistic talent is undeniable—but his creative focus has shifted more toward music and VJ-ing these days. Lucky for me, he referred her to me instead, and it turned out to be one of the best things that’s ever happened. It sparked a friendship between Whitney and me that has grown into the most rewarding partnership I could have ever imagined.

Can you tell us about a time you’ve had to pivot?

My whole life has been pretty “pivotal,” to say the least. I’ve continuously shifted myself into new things, often diving headfirst into opportunities that challenge me. I have three college degrees—none of them in art—and yet art has become such a defining part of my journey. I firmly believe that learning and education, in all its forms, are lifelong pursuits.

Nothing in life ever goes exactly as planned, no matter how much effort you put into mapping it out. Learning to be adaptable, to flow with unexpected changes, is one of the hardest lessons I’ve had to embrace. There have been countless sleepless nights spent questioning my choices, wondering if I took a wrong turn. But I’ve learned that those turns aren’t “wrong”—they’re just unexpected detours. It’s up to you to adjust and make them worth your while.

Being angry at the world for not bending to your will won’t get you very far. Life doesn’t work that way. Instead, I’ve found that the key is embracing resilience, finding meaning in the unexpected, and staying curious enough to keep moving forward, even when the path ahead feels uncertain. I feel that the “pivot” is where life happens the most.

Contact Info:

• Website: https://www.cherishedrainart.com/
• Instagram: https://www.instagram.com/cherishedrainart/
• Facebook: https://www.facebook.com/CherishedRainArt/