I can't speak to the Canadian tax implications, but I can address the U.S. specific issues. Generally, if you are a non-U.S. business selling products or services in the U.S., there are no U.S. federal income taxes owed on your profits in the U.S. Foreign businesses must generally operate through a "permanent establishment" in the U.S. in order for the profits of the enterprise to be taxed in the United States. The U.S. and Estonia have entered into a tax treaty which defines a permanent establishment as a fixed place of business through which the business of an enterprise is wholly or partly carried on. If you are operating your company exclusively from Estonia and the Philippines, then you should be okay. However, if you have a U.S. subsidiary entity, such as a Delaware LLC or C corporation, then the U.S. entity may have filing obligations and be subject to U.S. taxes.