I tried my luck at creating a Print on Demand T-shirt drop shipping company. First I went to Fiver.com and hired a few people for five Bucks, I told them that I wanted surfing designs and that I wanted it to be rustic looking. I then realized I could not explain myself well enough to these artists.... I started looking through Instagram to find good artists and ended up finding a few people who made awesome stuff.
I paid five artists to make me about 10 pieces. I then created a website on Shopify, spent time learning how to make facebook ad campaigns.
I had the site up for over a two months, not a single sale. Here are some of the designs. Let me know what you think.