When it comes to paying vendors, at what point do I need to collect a W9?

Regarding US taxation of internet sales. Since you are a foreign entity or person (in regard to the US), and there is an income tax treaty between Canada and the US, you will not be liable for US federal income tax on internet sales unless you have a “permanent establishment” in the US with which the internet sales income is effectively connected. So as long as you do not have a warehouse, physical store, sales office, etc... in the US you don't have to file US returns or remit tax to the US. Amazon should be charging to the customer and withholding any sales tax due to a state in which your products are sold. If you sell through other merchants or directly you may have to deal with this yourself. Regarding incorporation Incorporation is almost always a good idea from a liability standpoint as it prevents a judgement for damages from taking all your property and limits the collection to what is owned by the business, With the facts you have given I would suggest incorporating in Canada unless you have a business reason to establish a physical presence in the US. This will eliminate US taxes and related compliance costs. Once you establish a US presence you will need to begin filing returns in the US even if you are running a net operating loss. If there is no benefit to having a physical presence in the US then the related compliance costs and tax would be an unnecessary expense. Feel free to setup a phone call if you would like to chat for a bit regarding the matter. Thanks

Delaware C-Corp I usually Delaware is the best choice for any startup looking for fundraising with a US focus. However, if you are a remote and global team, an overseas or foreign corporation or US tax purposes might make sense. You'd have to talk to an advisor who can dive into your situation, but it would be more difficult for the US owner come tax time, as he'd likely have to file form 5471 to the IRS for any controlled foreign corporation, and form 90-22.1 for any foreign bank accounts. There are a lot of other concerns I didn't hear you raise that entrepreneurs usually have and ask me about, namely banking and merchant accounts/ payment processors. In terms of accepting online payments, any US corporation or LLC is far and away the best option for a company. It's difficult to suggest without knowing more about the company but you might explore Delaware, Wyoming, Hong Kong and other offshore jurisdictions for your legal entity. Each tend to have positives and negatives and there is no one size fits all solution. I do write about issues of incorporation quite regularly on my website FlagTheory.com - so you can read those articles for free, or we can schedule a call - Clarity.fm/incorporation when you have specific questions. Thank you and hope this was helpful!

NIcole is right. When I first started my business I thought I was saving money by doing my own bookkeeping. It took me much longer than it would take a bookkeeper - all time that I was not spending on marketing or billable activities. And in the end I made errors which made the initial work of the bookkeeper longer. I now have a consistent routine. My bookkeeper picks up all my material monthly and does my books in less than 2 hours. Very worthwhile.

There are a lot of moving parts to this question. First, you need to determine in which states you have "nexus" and then determine do those states require you to charge sales tax, as each state has different rules. As an example, MA requires salesforce.com to charge sales tax to MA customers but does not require newyorktimes.com to charge sales tax. The difference is that users can manipulate data on salesforce.com vs. neworktimes.com is read only. This example can only be applied to MA, Arizona, Illinois, New York, Texas, Pennsylvania and Washington State (as of now). There are also "click-through" and "affiliate" nexus rules that need to be considered. Be careful, as state and local taxation has become a very hot due diligence issue in M&A transactions. So, if you plan to sell your business in the next few years, you want to get this right. Also, the Officers and Directors are personally responsible for uncollected Sales tax. You are best to get an expert to review your sales tax compliance, as it is a very specialized area and changing constantly. I am not an expert, but know of some firms that offer this service at a very reasonable rate. Feel free to call me. Thank you, Joe Faris Accountalent Management Corp. 45 Prospect Street Cambridge, MA 02139 Tel (978) 621-0759 Fax (978) 278-1517 Website: www.accountalent.com LinkedIn: www.linkedin.com/in/farisjoe/ Twitter: @accountalent

yes. As long as your main place of work is your home/office.