For the past two years, Stephen Redmond has sat outside of Grand Central Station in New York City, on Park Avenue, with a sketchbook and a “Homeless Artist” sign.
During the day, he paints and sketches for money, and at night, he sleeps on the street. On the weekends, he’ll stay with his girlfriend in the city.
Though he mostly paints for tourists wandering back to Grand Central at the end of their trips to the city, Redmond says he’s also been offered a bunch of odd jobs — designing menus and painting murals on the inside of bars in the city, for instance.
“That’s my spot. People know me there really well — I have a bunch of customers,” Redmond tells Business Insider. “I’ve started to get overwhelmed. I’ve had to make a list and write down names. People follow up to say ‘Hey, have you finished this painting yet?’ And I have to show them the list and be like, ‘You’re fourth on the list.'”
A few blocks from Redmond’s spot, on Madison Avenue, is the New York headquarters of venture capital firm Greycroft Partners. The New York and Los Angeles based firm’s portfolio includes companies like The Huffington Post, Munchery, The Skimm, and Venmo, to name a few.
Alan Patricof, the co-founder and managing director of Greycroft, walked by Redmond on his way to work from the train station. “I only noticed him in the past two months,” Patricof says. “He was sitting there with his suitcase open, just sitting there sketching. I saw him every day.”
In 1969, Patricof founded Patricof and Co., an early venture capital firm. Over the next 40 years, he turned that into Apax, one of the largest private equity firms in the world — then, he left and founded Greycroft.
A year ago, Greycroft moved to its new offices on Madison Avenue. “For the last six months, I’ve been concerned with one spot that we are furnishing, but we’re not using. I couldn’t figure out what to do with it,” he told Business Insider. “I thought, maybe we can brighten it up with some graffiti-like art. I wanted to do something on the wall.”
After months of fruitless searching for an artist, Greycroft started to realise he’d seen Redmond in the same spot every day, and decided to ask him if he’d be interested in some work. Patricof walked up to him and asked: have you ever done a mural? And Redmond said: I guess I could do it.
“I thought I was just doing something good for someone. That was part of the motivation. And it happened to answer what we needed — what a great combination of things,” Patricof told Business Insider. “And I said, if you want to do it, we’re a block and a half away, here’s my card. Call and arrange to come up.”
A rough upbringing
Redmond was born in Connecticut, but his parents divorced when he was young.
“I’ve been doing art my whole life, since I was little. I’ve always loved to draw,” Redmond says. “When my mother and father were fighting, I’d run into my room and I’d just draw. That was my escape.”
When his parents divorced, Redmond’s mother and his brother moved to the Bronx, and Redmond moved to Florida with his dad.
“People kept telling me, ‘Wow man, you’re really good at this, you’re really good at what you do. You should keep doing it,'” Redmond says. “I didn’t think I was good at it; I’ve just always really liked to draw. I take what I do seriously.”
The 26-year-old briefly attended the Art Institute of Jacksonville, though he ultimately ended up dropping out. Redmond has been homeless for the past six years — starting when he lived in Florida, and for the duration of his time in New York City.
Two years ago, Redmond’s mother passed away. He moved up to New York and has lived here since then, drawing during the day and sleeping on the streets at night.
In the city, he sits, sketches, and paints in midtown. “When I started, I had my sketchbook open and I was doing paintings. First I started drawing on cardboard, but someone came by and said: ‘Why do you draw on cardboard? I’ll give you some good paper,'” Redmond recalls. “So he brought me some good paper, gave me a bunch of markers, and said ‘Draw, draw, draw!'”
Redmond contacts most of his clients through his “Obamaphone” — the cell phone given to and subsidized for low-income Americans through a government program called Lifeline. (The program started in 1985 but gained notoriety during President Obama’s first term in office, during which disbursements increased to $US2.2 billion.)
“I’ve got 500 minutes and unlimited texting every month,” Redmond says. “When someone gives me their number and they’re like ‘I have some work for you to do,’ I’ll call them back, and follow up with them. it’s been really important for me to follow up so word goes through.”
Redmond followed up on his lead from Patricof, visited Greycroft’s offices, and hammered out some details with Patricof and Ian Sigalow, another Greycroft co-founder. For the past week, Redmond has become Greycroft’s unofficial artist-in-residence, working on a mural right inside Greycroft’s offices.
“I met with him a couple weeks ago, and I had given him a bunch of words — computer, tech, Los Angeles, New York, skyline, mobile — things about our firm,” Patricof says. “Anything tech.”
The mural occupies a wall 16 feet wide, just next to the lobby in Greycroft’s offices. It’s not done yet, but Redmond plans to finish it up this week.
The mural “is fabulous,” Patricof says. “He’s done a great job. Everybody here is very pleased with it. We bought the paints and he’s been working on that ladder nonstop for about a week.”
When Redmond finishes his mural at Greycroft, he’ll go back to his spot by Grand Central. He’s trying to make enough to put down a payment for an apartment, but that’s easier said than done. Odd jobs like this only cover a month or so of rent.
“I carry my paint, my sketchbook, my sleeping bag, some clothes, a couple blankets. When I sit out on the street, I don’t just sit there holding a sign. I’m painting, I’m sketching,” he says. “People walk by me and they say, ‘Get a job.’ OK — I would love to get a job. Even if I had a job, I’d have to figure out how to take a shower every morning before going to work, how would I get proper rest? You need to have a place. You need a cell phone to get to work. Some people don’t have these things.”
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