Jon Masters lived on a boat with his service dog, Sheba. But when he was briefly put behind bars for trespassing on a beach, the leaky vessel sank because he wasn’t there to bail out as usual. He lost everything. So with no home and no money, and only his trusty companion by his side, his next move was surprising – but it turned his life around.
In fact, Masters is not the name Jon was born with. It’s his artist’s handle, and his real name is Spiel. He adopted Masters when he first became an artist. Once a resident of New Orleans, he started out as one of the painters in Jackson Square, a center for bohemians in the middle of the city’s French Quarter.
While spending time in Jackson Square, Masters was able to study the artists who worked there. But that wasn’t the only input to developing his artistic style. He told local newspaper the Pensacola News Journal in 2015, “It was me and YouTube. I learned watching instructional videos and just adding my own technique and creativity.”
Having developed his natural ability, Masters was able to join the artists in the square. However, he did have one regret, which he shared with the Pensacola News Journal. He told the paper, “I wish I had started years ago.” His reason was that he hadn’t felt that he was starting from nothing. He added, “Because I do have some natural talent.”
Masters had begun to paint in about 2010, but when it came down to it, he hadn’t exactly been employed for what probably amounted to many years. As he put it, he hadn’t had a “job job” in a long time. He’d suffered some from anxiety and some run-of-the-mill mental issues as well as persistent aches and pains in his shoulder.
Perhaps tiring of the competitive atmosphere of Jackson Square, Masters aimed for a change of lifestyle. He gathered up his savings and bought himself a “home.” In fact, this was a boat: a Far East Mariner ketch that measured 31 feet in length. It wasn’t what you might call brand new; indeed, a lifetime of use had left it somewhat leaky.
Aboard Masters’ vessel with him was his companion, Sheba. When a trainer of service animals had seen Masters struck down by a fit in Jackson Square, they had taken action. They had offered the artist a feist puppy with training in recognizing seizures and aiding those who have them. And whether dogs really are man’s best friend, we don’t know, but Sheba became Masters’.
Masters set sail, with his course set for Key West, Florida. He hoped to join in the Sunset Celebration happening held in Mallory Square on that city’s waterfront. However, on the way he stopped in Pensacola, up in the Florida Panhandle, finding a spot to moor at the city’s Quietwater Beach.
Then in August 2015 disaster struck. Masters found himself in a cell, put there by the authorities for trespassing. They had told him that he couldn’t keep a dog on the beach. The artist went to jail for two weeks, while Sheba ended up in an animal shelter until members of the local Humane Society found out and stepped up on pet-care duties until Masters was released.
That alone may have been enough to dishearten the artist, but worse was to follow. It turns out that without him present to bail out his leaky boat every day, water levels inside began to rise to the point of disaster. Indeed, the old yacht sank beneath the waves, and Masters was once more homeless.
Masters was philosophical about the incident, even though it had claimed not just his home but everything he owned. He told newspaper USA Today in October 2015, “I was only worried about my dog. Everything else could be replaced.” But the question arose, how could he replace what he had lost?
Well, first of all he was well acquainted with rough sleeping, so he was able to find a place to sleep in the area of Warrington, not far from Pensacola. But for a man who liked to paint, one loss was proving intolerable. He had no supplies with which to create his art and no money to acquire any, either.
But Masters wasn’t daunted. He decided to turn to panhandling. It wasn’t easy in this part of Florida, since he wouldn’t be the only person in that business. He told the Pensacola News Journal, “There are a lot of panhandlers out there these days. I had my sign out for a few days, too. It’s not easy. But it’s what I do.”
So Masters headed out to a spot by the road on the city’s Navy Boulevard and began gathering money. He told the Pensacola News Journal, “I was trying to get some money for some paint supplies.” He set up with a placard that kept it simple. He explained, “My sign said ‘Just Need a [Little] Help,’ and it was the truth.”
In a few days, passers-by had donated $40 to Masters’ fund for supplies. Once he had a few bucks, he went out and bought a couple of canvases and some black and white paints. With those, he started to create art that he could in turn sell. And before long the artist was doing a roaring trade.
A day after Masters had begun to paint, he was telling the Pensacola News Journal, “I sold three on Saturday and one today.” His business plan was pretty simple, as he explained to the newspaper. He said, “I’m selling them cheap, and I’m selling them as fast as I can paint them.”
Masters explained that he was taking a positive approach to his misfortunes. He said, “I’m just trying to get some money together. I’m not trying to be the homeless guy with all the problems. I have a little talent for painting, and that’s what I’m trying to do to make it by.”
Before long, Masters had made enough money to purchase a sleeping bag and to replenish his art supplies. His paintings showed an Asian influence. Largely, they were landscapes that were filled with drama. And those who liked what they saw could snap up a Masters original for a very reasonable price: between $25 and $40.
Although Masters had not had formal training, he had learned his own distinctive style. And given that he had studied YouTube for inspiration, it’s no surprise that TV artist Bob Ross had influenced him in his work. It was from Ross that Masters had gained the inspiration to take on the landscape as his preferred style.
The artist’s particular focus was on creating clouds and trees. His paintings can be recognized by their trees, which range from foreboding, dark figures stripped of leaves to vibrant plants shrouded in lush foliage. He told Ballinger Publishing website that he wasn’t just aiming for them to look good, but also for some depth that would need interpretation.
Not that Masters had any pretensions about his art. He explained that it wasn’t complicated work, although there was plenty to look at. He said to Ballinger Publishing, “My style, or what I like to do, is simplistic, surreal art with a lot of detail.” And he went on to explain what he meant by that.
Masters added, “The bark on the tree, the sky, and even the grass may look very real. But, in reality, a tree wouldn’t be floating, which is the surreal part. I like to make paintings that have a lot of meaning behind them, as well, although some I create for the sheer beauty, for the aesthetic value.”
When Masters started to paint, he used a brush made out of Taklon. However, he accidentally found out that polyester was a better material for him to use. It allowed him to make strokes that portrayed far greater realism. Now he can put in place very real tree bark and curves in his clouds.
Masters explained to Ballinger Publishing, “The best part of making a mistake on a painting is learning something new. I keep learning, from the way I move the brush to the type of brush I use. Because when you make a mistake you’ve got to figure out how to make it work, especially since you don’t want to have to redo the piece. Some of my best inspirations have come from mistakes on paintings.”
To create the right feeling from his art, Masters likes to use colors that are full of life. He favors cadmium paints that allow him to paint with vivid purple, yellow and red hues. From time to time, he’ll deploy a white based on titanium to paint highlights that stand out.
In a previous phase of his life, Masters gained a background in Chinese physical arts, working as a teacher in both qi gong and tai chi. And some believe that they have spotted some Chinese flavor in his artworks. More than once people have told him that the paintings have an Asian feel.
Whatever influences could be found in Masters’ paintings, they have proved desirable to purchasers, perhaps thanks to their modest price. People have flocked to buy them. Others have offered him tangible help in different ways, giving him art supplies, canvases to paint on and even some dog food for Sheba.
And it wasn’t just material gifts that the kind-hearted folks of Pensacola offered Masters. A church in the neighborhood gave him and Sheba the opportunity of a safe place to lay their heads in the evening. And the Gulf Breeze Farmers Market got in touch to inquire whether he wanted to sell his artwork there.
Market organizer Daniel Dugan brought Masters to the community center in the suburb of Gulf Breeze, FL, where the retail event runs once a week. There was a surprise waiting for the artist. Traders had set up his booth under cover for him to use to sell his paintings to customers.
Before taking up that offer, Masters decked himself out in some new duds. His success with his paintings had left him with enough cash to buy pants and a shirt. At last he could replace the clothes that he’d worn ever since being let out of jail. At the market, he said with a grin, “Don’t I look fancy? I’m hoity-toity now.”
Dugan told USA Today, “I saw the [Pensacola News Journal] article, and I was impressed and inspired and had the ability to offer him some space.” And the market mogul, who runs three sites across northwest Florida, expressed his hope that homeless people might be inspired by Masters to try something similar.
The market organizer said, “That’s what we want to do. If one person can inspire our homeless population, that is what we need. He’s doing it right. He knocked on the door, and it got opened.” And Masters was of the same mind: he had already contacted some people living with homelessness, trying to get them interested in putting their creativity to use.
Masters told USA Today about his outreach. He said, “That’s what I enjoy the most. I’ve got other homeless guys coming up to me to check out what’s going on. They’re hearing about my story from other homeless people.” And it seemed that his work had begun to inspire others.
The painter explained, “They’re seeing the response I’m getting and some of them are trying to figure out what they can do that’s similar. They want to know how I learned to paint. They want to do something on their own. I’m actually able to inspire others. To me, that’s the best part about all of this.”
By October 2015 Masters was doing fantastically well. Still painting by the side of Navy Boulevard, he was finding that he could barely keep up with demand. He’d even had a couple of people offer him a commission to do a painting for them when he was at the Gulf Breeze market.
One purchaser, David Talon, told USA Today how the experience of owning works by Masters had gone. He said, “I’ve shown them to a lot of people and everyone likes them.” And the U.S. Navy sailor added that one person in particular had been impressed. He continued, “My girlfriend loves them. I think he’s pretty talented.”
Talon also expressed his admiration for Masters’ get-up-and-go. He said, “He’s not just out there with a sign. He thinks about what he’s doing as his job. I think his story is pretty neat.” Certainly, the story of the Homeless Artist seemed to have caught the imagination of art-lovers in the Panhandle.
But would the man himself remain a “resident” of that area? No longer having a boat meant that Masters’ options were more limited, and it turned out that he was happy where he was. He told USA Today, “I might stay here in Pensacola. I like it here, and the people have been really, really great. They appreciate what I do, so why go somewhere else?” And at the time of writing, his social media suggests that he still lives in Pensacola.
Masters shared the philosophy that got him back on his feet with Ballinger Publishing, “I’m a firm believer in making a decision and sticking by it to make it a reality. When I started in Jackson Square everybody was saying, ‘Oh no, you can’t be an artist. These artists have been doing it for years and they went to college for it.’ I told them I was going to be an artist and here I am.”
And what did the artist think about his misfortunes and how he overcame them? He shared with USA Today his positive outlook. He said, “Nothing bad really happens. That’s what I believe. It’s just that not enough time has gone by to find out what the good [that] will come of the situation will be.”