If i an running a labor service company and i want to do employees on 1099. Work comp still cover?

Same as any other entity (or person). Entity pays taxes in it's domicile jurisdiction. Best you talk with a tax preparer in your home country to ensure you have all the details. And... If you're a US citizen + your SAAS company is generating massive cash, likely best to organize your entity in a low tax jurisdiction, like Bermuda which is home to Google, Intel, Verizon, etc. And... best wait till Trump's new tax bill passes. If he has his way, corporate taxes may drop to a point low enough to keep your business in the US.

None. There are two basic reasons to get business insurance. First, if you're making enough money that you're worth suing. That does not apply in this case. Second, if your clients require you to have insurance before accepting you as a vendor for certain services. Most large companies will require service vendors to fulfill certain liability requirements. But for a SaaS offering, especially if the pricing model is a low subscription, you won't trigger the conditions that have their purchasing department demanding you get insurance. It applies more to vendors who are either offering personalized services (like consultants) or service providers who bill very large dollar amounts. So get insurance when you first start making pots of money OR when a first large enterprise client makes it a condition of working with you. Don't waste money before that.

There shouldn't be any tax consequences for the founders if you've made 83b elections--the election meant you paid tax already on the full value of the stock at the time of the election (presumably zero) even though it was subject to future forfeiture. If you sell newly-issued stock there should be no tax impact. If you sell your own common stock, you'd pay tax on the gain, but I doubt that is what you mean here. Of course, you should not take the free advice dispensed on Clarity and consult your own tax preparer--this is not tax advice.

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

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