We were lucky to catch up with Matthew Jacob Whitman recently and have shared our conversation below.

Matthew Jacob, appreciate you joining us today. Alright, so you had your idea and then what happened? Can you walk us through the story of how you went from just an idea to executing on the idea

I’ve been painting since I was 10 years old. It’s Sunday morning. The smell of Dad’s Dunkin’ and Mom’s French toast blankets the house—both stimulating and calm. Flipping channels unknowingly, I was about to discover someone who would set me on a trajectory, landing me in Brooklyn as a working artist and writer some 16 years later.

PBS. A fully blossomed orange fro and blue work shirt, two buttons unclasped. Bob Ross and his oil landscapes made me feel capable. His art was accessible at the start and difficult enough to spark a journey of self-education in the arts. It would take 12 years before my art would be shown in any professional capacity. In 2025, I left my hometown in South Florida, knowing New York City was the place that would either make or break me.

At the time, I was working as a producer at a marketing and personal branding agency. It was paying the NY bill but lacked the fulfillment that creating art and being in business for myself afforded. Luckily, a client of mine and I had formed a supportive working friendship. An extremely talented public speaker and trained neuroscientist, she had been to her fair share of TED Talks and corporate events—one of which had a live painter…

See where I’m going with this?

As happens sometimes when you’re an employee, your company decides its best interests are no longer aligned with yours. After several business lines were “restructured,” I found myself unemployed. I wanted this—I’d been looking for an out, another job to pay the bills with just enough creative spark to keep me going. I just wasn’t ready for the choice to leave to be made for me.

Lost and frustrated, I had to make a choice: continue justifying my decision to put off what I felt in my heart, or jump headfirst into live event painting and business ownership.

First and foremost: lose the victim attitude and take ownership of each day, one day at a time. Step two: map the process.

I admit, as an artist, “a” and “i” are not frightening letters—yet combined, they inspire a visceral hatred akin to generational trauma or pineapple on pizza. When it comes to business planning, however, ChatGPT slips through my better-than-thou mentality.

I bounced every possible question off that yet to be sentient learning model: “how to market yourself as a live event painter,” “how to build a website landing page for—”, “craft a cold email for—”, “develop a social media strategy—” and so on.

With limited funds, I bootstrapped everything I could.

Don’t knock the hard work in the beginning. You’ll learn the basics and eventually be able to pay experts and contacts what they deserve to do a better job. For now, I needed a website (built free on Wix), active social media (I post daily, even if it’s a simple sketch), boots-on-the-ground networking with event planners, venues, and other artists, and a way to build a larger network quickly.

The latter, of course, is one of the most difficult steps—but the most necessary to guarantee your business isn’t just a hobby. The first booking is the hardest. I had proof of concept, having painted wedding commissions before, but never live.

This is where community and networking become necessary. I began researching event planners in NYC and contacting them via any means available. Eventually, along with a clear message via my website and active social media, I got my first leads. The first generally falls through—at least it did with me—but that’s normal. Especially in live entertainment/art, these bookings are often reserved until the last minute as other event expenses, such as catering and photography, take priority.

Although this cycle of live networking, cold outreach, posting, posting, posting, and following up worked, it took too long. Sometimes, it took 50 emails to hear back once, in most cases asking me to contact an assistant or their publicity team (which almost always is a dead end).

I had to get creative and efficient. What took the most time? The emails. Got it—build an AI automation using ChatGPT, Google Sheets, and Make.com to send customized cold emails for me. If you’re thinking “that sounds like a lot,” it is—but it’s easier to start than you think.

Next: use social media to show who you are and engage with the people you want to work with. I began painting wedding dresses from boutiques I had emailed earlier. Posting them with some trending audio and a tag, I was now speaking directly with my leads’ social media managers… a direct line to brides and future clients.

This worked, and I found a unique point of entry that can be repeated easily (think venues, bridal boutiques, caterers).

Done, right? Not nearly.

What I’ve described is a process of evolution, testing, and reinvention that will continue forever, if you know what’s good for you.

Complacency is the enemy in this game. And even if you find a working system, it’s worth considering whether you’re happy playing the game you’ve built for yourself.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

Asking how someone got into the arts is like asking why my hair curls or why I like tuna with my eggs. It’s a particular thing that I think some are just born needing. Yes, needing.

It’s a question of nature and nurture, and I’m somewhere along the 40–60 split on that debate. I find I’m most myself when I’m amid a creative endeavor. I’m happiest when creating something that provides service and revelation to others. The Japanese have a concept for this called Ikigai. It involves the convergence of your loves, skills, societal needs, and financial compensation. It’s where your passion, mission, vocation, and profession converge.

Studying digital art and film at the University of Florida, I knew I had to find that convergence of art and innovation. That led me to several interconnected experiences, such as creative director at a fintech startup, development associate at a film studio, designer at a production company, and producer at a personal branding agency.

All of which were valuable experiences, yet lacked the independence and freedom of artistic expression I need to fulfill my Ikigai. However, I always kept individual projects going in the background.

I’m either fully engaged in writing screenplays or painting, but have been looking for a way to integrate these passions with my vocation.

While working as a producer at a boutique personal branding agency, I discovered live event painting. A client of mine is a well-known neuroscientist, neuromediation expert, and public speaker. Carol Barkes has a long list of accolades that follow her many titles—none of which is more meaningful than “friend.” She was just coming off a TED Talk tour and knew of my desire to incorporate painting into my business life. In early 2024, she spoke at a corporate event and saw a live event painter for the first time. Following the event, she reached out to let me know of this discovery:
“Matt, you need to look into this…you could easily do this” she said.

It’s crazy to admit, but her confidence in me was enough to overcome the loss of my cozy remote job and go all in on NYC.

For the past year, I’ve been building my network in and around NYC—attending events, networking with event planners and venues, and building my personal brand in event painting.

I launched my business, Paint Your Events, six months ago and have begun booking clients through 2026. I offer live venue painting, which is an exciting service featuring full-duration live painting on canvas. Capturing the energy, style, and memories from live events in real time, my clients experience an artwork come to life before their very eyes.

Be it weddings, corporate events, brand activations, or workshops, I pride myself on involving guests in the act of artistic creation.

Beyond traditional paintings in oil and acrylic, I also provide live event sketches using ink and watercolor. Each guest receives an individual watercolor sketch of themselves, which they get to take home the same day.

My newest service, however, is the Puzzle Canvas—a large canvas made up of small 2×2-inch canvases temporarily attached to each other. I paint the event live on this imalgamation, then separate it into its individual sections to give out to guests as a keepsake to remember their special event.

Paint Your Events by MJW Studios isn’t just entertainment for your live event—it’s a one-of-a-kind keepsake for clients and their guests that lasts for generations.

As one anonymous writer said, “A camera captures a moment, a brush captures the feeling.”

Live event painting is a growing interest among event planners and the newly engaged, yet it has become synonymous with—let’s be honest—tacky first-kiss paintings that lack the full breadth and energy of that special day.

I provide an all-encompassing artwork that not only combines traditional art styles but also more surreal expressions from the day. I believe my clients and their guests deserve more than a “photo” captured on canvas.

I’m most proud when clients stand in front of my finished works at the end of the night and are awed by something more than a memory from the past eight hours. They say things like, “I can feel this painting,” or “I never thought someone could capture the meaning behind our event.”

What shocks them most is that I bring the canvas to the event several hours before start time, and by the end of the night, I have a finished work of art ready to hang above their mantle for a lifetime—or, for corporate events, ready to be auctioned that evening to support their cause.

How did you build your audience on social media?

Building an audience of your own—loyal, niche, and present—is the most important aspect of being a modern business owner, especially when developing a personal brand.

As the founder and artist behind Paint Your Events by MJW Studios, I knew that my voice was what I was offering first and foremost. Live event painting is a niche offering, and finding clients who value my work is about sharing my story—something I believe any business owner can learn from.

At my previous role as a producer for a personal branding agency, we used to say, it’s about helping the right people reach the right people.

That’s the point—not reaching the most, but finding your circle.

An effective way I’ve done that is by engaging in social media habits that are repeatable and effective.

What do I mean by that exactly? As a live event painter, I can’t expect myself to paint a full traditional canvas every day and put it up on social media that evening. What I can do, however, is create a small watercolor sketch.

At the time of writing this, I have been sketching watercolors daily for 87 days now. I sketch what I feel that day—it doesn’t have to be influenced by event painting or the wedding scene.

Wait, wait, wait…say that again? Did he just say it doesn’t have to be about my business?

Well yeah…obviously. Except it’s not so obvious, is it? Then why should you post as much about your interests as your business?

Well, because my niche clients don’t just care about planning their wedding or event. They are people interested in art, pop culture, and personal expression. They want my perspective.

That means sharing it unbridled and uninhibited by social media trends. Clients want to connect with your style and who you are.

My advice to you is to pursue an online habit that expresses who you are—not what you’re trying to sell.

Are you for sale? No, of course not. So neither should your online presence. You are simply presenting yourself.

Do that, and you will find those who connect with who you are. Those individuals will be more likely to interact with you and seek out ways to work with you.

Can you tell us about what’s worked well for you in terms of growing your clientele?

The most impactful strategy I have found for growing my network is simpler than some may think. Cold emails, cold calls—they are helpful, don’t get me wrong.

I have learned so many valuable insights from calling event planners in NYC. They respect the hustle because they have been there and, in many cases, are happy to share if you ask politely. The ins and outs can be convoluted, so ask thoughtful questions and take advice early on, since this may be a new venture for you.

However, engaging thoughtfully through creative means has proved the most effective.

One specific example stands out.

I planned on reaching out to bridal boutiques to garner “hot leads”—i.e., those who are searching for event entertainment right now and are most likely to hire me now.

There are many well-known and highly rated bridal boutiques in the city with loyal followings. I found one that had a style and online brand that I connected with. A quick search on their Insta led me to an upcoming trunk sale they were hosting in April—prime time for wedding dress purchases prior to the spring/summer wedding rush.

They had posted several photos of their new wedding line, one of which I decided to sketch and make into a quick reel for social media. I posted it and tagged them for visibility.

Quickly, their social media manager reacted and reached out to me via DM. I was now in conversation with them, and I didn’t even have to call.

We discussed a collaboration in which I would live sketch at their event. During the event, I would raffle off discounted event paint packages to a few lucky winners. We created a collaborative post online to cross-pollinate our audiences and build excitement.

This event led me to three wedding bookings and also generated organic attendance at their event, all while building a sense of loyalty for both our brands.

Methods like this that involve creative outreach have proven most effective and don’t leave me with the sleazy salesman feeling I once felt from cold outreach.

The idea sounds simple now that I’ve said it, but for many, it isn’t the first choice. I challenge you to think outside of the box and share who you are, first and foremost.

Contact Info:

• Website: https://paintyourevents.com
• Instagram: https://www.instagram.com/painting_whit_purpose/
• Linkedin: https://www.linkedin.com/in/matt-j-whitman-uf/
• Youtube: https://www.youtube.com/@mjwStudios
• Other: https://www.tiktok.com/@mjwstudios?lang=en