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Meet Stuart Sheldon

Today we’d like to introduce you to Stuart Sheldon.

Stuart, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I was born and raised here in Miami. Straight out of college, I joined a Wall Street firm and by 25, had become its youngest VP… but that was not the “success” I dreamt of. So, at 27, I pivoted to the MFA in Film Production at University of Miami. I left for L.A. the following year where I worked as a production assistant for Michael Jackson, an extra in The Bodyguard and a chauffeur for Donald Sutherland before escaping to the mountains of Boulder, Colorado. I spent 7 years in the Rockies as a magazine publisher and made a TV documentary on pro cycling. At the height of the Dotcom boom, I co-founded Streaming Media Magazine in San Francisco. In the midst of all this, I began painting to heal a broken heart and never looked back. I returned to Miami 10 years ago and was amazed at what the creative landscape had become – youthful, fearless, with just the right amount of lawlessness. It turbo-charged my inspiration and career. My work the past few years has been about social justice. At this very moment, I’m gearing up for an artist talk at PAMM on Nov 7th, where I’ll be discussing the evolution of my activist art practice and moderating a town hall discussion around the question, “How is success measured in activist art?”

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Smooth … yeah right? Leaving the certain wealth of Wall Street was agonizing, but one of the best choices I’ve made. In LA, I wrote several terrible screenplays which I imagine I’ll simply throw away one day. As a self-taught painter, it took a solid five years of daily grind to stop being wholly derivative and uncover my own style. That style continues to morph and expand.

Artist and Writer – what should we know? What do you guys do best? What sets you apart from the competition?
I’m best known for obsessive collage paintings and immersive installations like Fancy Nasty which, if I may say so, was a collaborative masterpiece. I love when folks share their creative superpowers and the sum emerges greater than the parts. I write a blog ( and the Family Matters column for The Biscayne Times, and in my studio practice, language and classic literature excite me. I’ve been deconstructing and repurposing books and reference materials for decades. Recently, my practice has darkened. My oldest son was almost six when twenty-six-year-olds were executed at Sandy Hook Elementary, and that really gut-punched me. I’m proud to have been part of For Freedoms’ 50 State Initiative, the largest creative collaboration in US history. My billboard on I-95 last Fall posed the question, “How Was School Today?” along with a shooting target and drop of blood. That billboard garnered 4.6 million impressions and stimulated an ongoing conversation that will continue November 7, 2019 at PAMM. It also won a 2108 Ellies Creator Award from Oolite Arts, honoring “the backbone of Miami’s visual arts community.”

What is “success” or “successful” for you?
I spent the past year living with my wife and two young sons in a remote seaside corner of the Costa Rican jungle. The nearest stoplight was one hour away. That felt successful.

A few years ago, I wrote a blog post entitled, Make Me Harder to Kill, where I outlined my own guide for measuring success. I called it the Stubaby Wealth Indicator Matrix (SWIM). The SWIM measures true wealth based on the following question – When I’m 85 years old looking back at my life, what will have mattered? For example, one of my primary measurements of success will be the amount of time I touch my children’s skin (substitute your spouse, parent, labradoodle, any living thing you love, here). The more I touch my boys (and wife and parents), the more stinking rich I will consider myself at the end of the line. Here are the activities I use to measure my success, in order of importance:

1. Time in love and with people I love
2. Skin to skin time
3. Laughing
4. Helping others
5. Creating/learning/listening
6. Nature time
7. Money in my IRA


  • Commissions and artwork ranges from $500 upward. No one is turned away. DM for inquiries.

Contact Info:

Image Credit:
Gavin D McKenzie, Tomas Loewy

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  1. Richard Sepler

    October 20, 2019 at 1:23 pm

    Proud of you my man.
    Finding a creative life.
    Living it.
    Lunch soon

  2. Arthur Joel Sheldon

    October 21, 2019 at 2:15 pm

    Stuart, the article about you says so many good things that validate your values and life style. I am pleased tom be on of those that you touch. A brief note to let you know I read every word.

    Go hard in your upcoming PAMM presentation. You may want to take a turn into the issues with Trump. This is a down and dirty issue that divide the country. Indo not think there is any way to get involved that is NOT partisan. Are the shootings in schools and synagogues related to gun laws and enforcement. Is the PAMM a proper platform for seeking action by our elected officials. These are questions that must be answered before choosing this sort of activism.

    Work hard son and you will make a difference. The world is counting on you.


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