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Young Money

What it’s like to start a business on Instagram

Eliza Mills Jul 7, 2015
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It started with doodling.

Max Dower, the 26-year-old artist behind the Instagram account Unfortunate Portrait, was a law student at UCLA and drawing in his spare time. His friends liked the drawings, and he made an Instagram account to start sharing his pictures.

The drawings are mostly portraits, sketches of celebrities, often full of word play. They’re silly, and they were meant to make his friends laugh, Dower says.

“The Instagram account slowly started gaining these followers — strangers, from all over the world — and I decided to start putting my drawings on T-shirts,” he says.

With help from friends, Dower built a website and an online store, driving sales to his site by posting new work to Instagram, he says.

The business was already up and running when one drawing in particular changed things: called “The T Party,” it was a portrait of Mr. T, Ice-T, and the rapper Pusha T, and it blew up on Instagram.

“As demand grew, and as I was getting more and more orders on the website, I had to keep up and be making the inventory to fill these orders,” Dower says, “I was using three or four credit cards at once to pay for just one round of production.”

Overnight, Dower says, he had thousands of new followers. It turned out that Pusha T had reposted Dower’s drawing to his hundreds of thousands of followers. For Dower, a broadening audience meant bigger business. He says as more orders came through his site, he started to get messages on Instagram from retailers wanting to stock Unfortunate Portrait shirts in brick and mortar stores.

His first big account, with Fred Segal, came through an Instagram comment. More store accounts followed, including boutiques Ok The Store in Los Angeles. As Dower’s business grew, he says his credit limit went up, enabling him to bolster his production cycle and run Unfortunate Portrait more smoothly.

Since he first founded Unfortunate Portrait, Dower has graduated law school, and says he skipped taking the bar exam to focus on business.

Ruby Rose wears Unfortunate Portrait’s “Ruby Rows” shirt.

“I was considering my prospects as an entertainment lawyer, and looking at the amount of money I was going to make, which was going to be around $80,000 a year,” Dower says. “And then I looked at the expenses that I was going to have — rent, car, medical, and then the big one, which is the student loan debt from laws school. I wasn’t going to be saving any money, and that just didn’t add up to me.”

“I decided to roll the dice, and launch this company that I thought had infinite potential,” Dower says.

These days, the decision is paying off. Dower says Unfortunate Portrait has been contracted to do artwork for the HBO series “Silicon Valley,” and for musicians. He says he’s working to expand into stores overseas while investing in growing his business on the platform that launched it in the first place: Instagram.

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