Here's the simple rule: you want to be the first person on the planet to realize that there is value to your brand, at which point you should trademark it.

A trademark is like a gun: much better to have one and never need it than to need it and not have it.

To determine if you should trademark your brand, you should visualize that you have built a successful business around your brand. Everything is just the way you hoped it would be. And then ask yourself 3 questions:

1. Would it be worth fighting in court if you were to receive a demand letter from a lawyer representing someone else and claiming that THEY own your brand, and that you should immediately rebrand?

2. Would it be worth fighting in court if you were to see your competitor use YOUR brand to advertise THEIR stuff?

3. Would there be any value to your brand if you were to sell, license or franchise out your business?

If your answer to ANY of these 3 questions is YES, trademark your brands ASAP. It will be the cheapest brand insurance you have ever had.