Don't let that scare you away, worst comes to worst you have a shitton of leftover decks and hats at your disposal. 2 thousand should get you started off good
$2000 isn't even half of what you need to get started on bare minimums.
I just went through the entire process with starting Heavy. It took a few years for me to plan it out, and do it right. If you are trying to do this as your primary source of income, forget it now. There is hardly any mark up on decks, especially when you wholesale to shops. Getting into shops outside of your local area is a pain. Most of them don't want to take a chance with a small, new company. They have a hard enough time moving the larger brands decks. Consignment may be the best way to go when just starting out, but then it can become a pain to collect if the boards sell. The mark up on soft goods isn't all that great, unless you can do really high minimums, which isn't likely just starting out. As lame as it sounds, don't underestimate building a team behind your company. I was surprised how many people cared whether I had a "team" or not. Even when I would talk to shops about carrying Heavy, that was one of the first things they would ask. "Who all is on your team?" Once you start hooking up a few dudes, be careful not to give away too much. You want to keep them skating, and hyped on the company, but not throw away tons of money giving them everything you have. Be careful of "friends" wanting the hook up. Everyone I know is so hyped to support Heavy, but "hey, hook me up with a board" or "let me get a shirt".
Add up the cost of your first run of boards, shirts, stickers, possibly hats, and be precise. Don't forget shipping, artwork and all that. Once you have that number, add in another couple of grand. That should give you an idea of what it will comfortably take to start out. I was not prepared for so many little things. A website, packaging materials, money for traveling, office supplies, etc. It adds up quick. Be prepared to lose a good bit of this money, and not make it back right away. Get smart about managing money. Do inventory. Invest in software to help with all of this.
Put a lot of effort into building an image. There are tons of companies, even big ones, that have no real image. Nothing that makes you say "Those are definitely blah blah skateboards". Be consistent with your image. Get a feel for what people like, and take advantage of that. Sounds simple, but it's easy to get caught up in doing exactly what you like, but that may not sell to the masses.
Last but not least, find something that makes you stand out. Look at the newer successful brands like Welcome or Blood Wizard. They stand out for certain reasons, whether it be the badass shapes one does, or the incredible image the other built. Anyone can get some money, make a graphic, and slap it on a board. This is what I struggle/struggled with. Giving people a reason to give you money for your product.
Now, there are plenty positives as well. It can be a great creative outlet. You can put your own spin on the skateboard industry. If it becomes successful, being a skateboard company owner is definitely a badass career. You get to meet tons of new people, and have a great time.
Sorry for the long rambling post. Its 2am, and I have had a few Captain and Cokes, so a lot of it may not make sense. It is really hard starting out, but I still think its worth it. I have enjoyed everything I have done with Heavy, and if I end up 25k in debt, then I had a good time doing it.
If you have any questions, feel free to ask.
Oh yea,
www.skateheavy.com