Skateboard companies are businesses, just like any other. Although they promote a counter-culture image, they are still concerned with basic commerce principles of producing a product as inexpensively as possible and selling it for as much money as they can charge. Having a top-name skater associated with the company or having the best graphics helps them to charge more for their decks. Because they try to keep the cost of production low, they are unlikely to give a new designer any breaks. That is why it is important to develop a reputation as a popular independent skateboard-culture artist.
Ride skateboards with your own designs. Buy blank decks, or make your own, and take them out to the skate park where other skaters can see them. There are several online services where you can upload your own graphics for transfer to blank decks – you can even sell your designed decks to your fans and customers who frequent those sites looking for new designers to follow.
Build a portfolio of skateboard designs and other art in varied media like sketches, paintings, comic book illustration, photography or whatever graphic art you favor. Remember that you must develop yourself as an artist first, and then as a skateboard artist.
Develop a following by selling your skateboards, T-shirts, hats and exhibiting your art in coffee shops, stores and galleries. This will increase your value as an artist as well as give you a strong feel for what is the next art trend to gain popularity among the skate boarding community. It is likely that you will make more money producing and selling your own work than you would as an unknown artist selling images to a skateboard company.
Approach small companies, because everyone approaches the large ones, which already have a staff of designers. They also have their own design style. If you want to work in a distinctive style you have developed for yourself, they are unlikely to approve. Small companies, on the other hand, are always looking for new art, but they don't pay much unless you can show them they will sell more boards because of your reputation.
Promote yourself everywhere, because your value to a skateboard company is in how many people want to own a skateboard bearing your art. For example, if you are a good skater, you might enter some contests. Provide the announcer with one of your decks and a bio that will guarantee he refers to you as a hot new skateboard artist and skater. Use your imagination to come up with ways to get your name in front of the skateboard community.