Visual Arts

Five years ago she was barely surviving — then this young artist from South Florida sold a painting for $20K

Courtesy of Amanda Oleander

Amanda Oleander was sitting on her baby stroller at a Disney park when suddenly everyone around pointed at her with dropped jaws.

Oleander was only 4 years old, but with a pencil her mom had handed her while they waited in line to meet Mickey Mouse and his friends, she had started to draw the characters almost perfectly on the official autograph book.

“Everyone was saying, ‘Look at that girl! Look how she draws!” Oleander told the Miami Herald. “That was the first time my family realized I was good with art.”

At 29, Oleander, originally from Fort Lauderdale, now makes a living by selling her art. In 2015, she sold her most expensive piece to T-Mobile’s CEO for $20,000.

But it wasn’t always like this. As a college graduate trying to carve out a career in the art world, Oleander worked three jobs and slept on the floor of a colleague’s apartment. She also ate a lot of peanut butter and jelly sandwiches.

Her success is due in large part to social media, where she has collected hundreds of thousands of followers. There, she not only promotes and sells her paintings, but interacts personally with her fans. Every Monday, she does a 24-hour print sale on her website, amandaoleander.com, in which she offers her prints for $30 each.

Oleander’s career started to take off when, in March 2015, she downloaded Periscope, a mobile application that allows users to broadcast live videos. Oleander decided to record herself while painting. As she drew figures and colored them in, hundreds and then thousands of users tuned in to admire her work.

Little by little, Oleander’s online popularity grew and she became the most followed woman on Periscope. Then her fame spread to other networks, including Snapchat and Facebook. Today, nearly 800,000 people follow her on Instagram, her favorite site.

Oleander credits her success in the virtual world to her authenticity. She usually draws what’s happening or has happened in her life, such as her saying goodbye to her boyfriend at the airport or cooking with her grandmother.

Her passion is to draw human beings in their purest intimacy: a girlfriend popping her boyfriend’s pimple, a woman eating apizza in bed or a woman shaving her legs while talking to a friend.

“I am captivated by the way people behave behind closed doors — things we all do but do not really talk about or share on social media,” Oleander said. “I think if we tried to photograph those moments, it would change the way we behave, so I draw them.”

What fascinates Oleander most is how similar people are despite coming from different backgrounds, cultures and countries, and speaking different languages. She is the daughter of a Chilean dad and a Venezuelan mom.

If she posts a picture of a couple hugging, for example, most people, even someone living on the other side of the world, can relate to it.

View this post on Instagram

Drawing 86/100 of the drawing a day for 100 days challenge. This is part 2 of the previous drawing I created titled: I’ll Be There For You . . . . This is my thought process behind it: I was recently asked what’s one piece of advice I would give for someone in their relationship. I answered it in my most recent blog post but that question kind of stayed in my head for the last week or so. Before bed the other day I was thinking about a piece of advice my grandma gave me a long time ago on cultivating a beautiful and loving relationship. Her metaphor is with a rope. She said a good relationship is like the game ‘tug of war’ when one person pulls and needs more rope the other person gives up some rope and vice versa but once someone lets go it ruins the relationship just like the game. Sometimes your partner will need more “rope” more help or love or time etc. and you give more of yourself to help them with their needs. There will be other times when you need it from them. About a week ago I was feeling off and @joeyrudman did the laundry and dishes and ordered food for us. The week before he was sick and I took care of him and his needs. Most of the time we are both side by side enjoying life together and each doing our part in the relationship but sometimes we need to pick up the slack and do it with love and understanding. So in addition to my other piece of advice this would also be part of my answer. This image came into my mind when I thought about my grandmas advice the other day so I had to illustrate it. —————————————————— ——————————————————————— Title: I’ll be there for you ——————————————————————— Título: Estaré aquí para ti ——————————————————————— Title: Eu estarei aqui para você ——————————————————————— Titre: Je serai là pour vous ——————————————————————— Titolo: Sarò qui per te ——————————————————————— Titel: Ich werde für dich da sein ——————————————————————— Название: Я буду здесь для тебя ——————————————————————— Title: Senin için burada olacağım ——————————————————————— العنوان: سأكون هنا من أجلك ——————————————————————— عنوان: من برای شما اینجا هستم ——————————————————————— ———————————————————————

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Sarah Bell, a 27-year resident of St. Petersburg, is one of Oleander’s fans.

Bell found the artist on Instagram in early 2018 and immediately fell in love with her work. Bell told all of her friends to follow Oleander and bought one of her paintings, “Water your Roses,” which features a woman watering some roses sticking out of her head.

At the time, Bell was struggling with a job that was not fulfilling her. After seeing Oleander’s drawing, she said she quit to find a different career path that would allow her to explore her creativity.

“She’s very personable,” Bell said. “She seems like the sweetest girl. She’s always grateful if you appreciate her work.”

Oleander no longer knows if she remembers what happened 25 years ago in Orlando, or if she has heard the story so many times that she simply thinks so. But what she’s sure of is she didn’t value her artistic ability as a little girl.

When she was about 10 years old, Oleander participated in the drawing contests hosted by her local Publix, and she always won. But she never stopped to think about what that meant; she just collected her prize and moved on.

In high school, she participated in an art competition in Weston. Her painting won first place among approximately 4,000 students.

Then someone stole the painting.

Oleander remembers being upset at the time but now, in hindsight, she sees it as a compliment.

“I guess that painting must have been good for someone to take it,” she said.

She didn’t realize that at the time. In fact, when she had to declare a major at the University of North Carolina at Charlotte, she chose business, before eventually switching to fine arts.

In 2013, after graduating from UNC, she moved to California. There, she sent her artwork to a lot agencies.

It was a hard road until that day when her art went viral, she said, which allowed her to become independent.

From there, she started speaking at conferences and attending panels, including a TED Talk, about the power of social media for professional careers. In February, she’ll host a workshop in Miami.

Throughout it all, she’s always heard the same comments over and over again: “Tell us your secrets to trend,” people ask her.

Oleander’s answer is always the same: “I would love to tell you that there is a link that you can click on and you pay some money to go viral, but it’s not like that. Just work hard and try to be genuine.”



April Hines, a librarian at the University of Florida who specializes in personal branding through social networks, says that what Oleander does is the most effective way to establish an influence on the internet. By maintaining an interactive platform, where people feel they have a friend instead of just a static message board, Oleander connects with each of her followers.

“I think there’s a lot of untouched potential when it comes to self branding and our professional lives,” Hines said.

Oleander now gets up every day and wanders into her art studio at home, usually still in her underwear or pajamas, and the first thing she does is create a drawing to share with her followers.



Seconds after she publishes it, the comments start pouring in …

“Does your work ship to Nepal as well. I love your artwork and I need one.”

“This is such an amazing illustration of how many of us feel in this world!!!”

“You’re the best!” her followers tell her.

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