[philiphodgen]

1. Your Canadian corporation is a controlled foreign corporation. See Form 5471. It may or may not generate Subpart F income. Penalty for fucking up -- even modestly (like filing a day late) -- is $10,000 with surprisingly little mercy. Likely fees for preparing Form 5471 by someone who has a clue: $7k and up. No easy alternative except kill the corporation. Uncle Sam hates small business operating internationally.

2. If you are the sole member of the LLC the LLC is disregarded and all of the income flows to Schedule C. Haha :-/ you will pay self employment tax on your profit. If you're doing well the combined tax load will exceed 50%. Uncle Sam hates the self employed. If your LLC is owned by the Canadian corporation you are well and truly fucked. You have the Form 5471 problem. You also have to file a corporate tax return in the USA for your Canadian corporation (Form 1120F) and submit its income earned in the USA via the LLC to US corporate income tax plus branch profits tax so the combined corporate tax rate will exceed 50%.

3. Finding competent experienced help in this area is extremely hard. When you find people they are extremely expensive.

4. Sorry for the bad news.

5. There are a shit ton of other forms to file. Eg when you created your Canadian corporation you should have filed Form 926 to report the capital contribution to the corporation. Moving ownership of IP from a domestic to foreign owner can cause taxation. Etc.

6. Again, sorry. My contact info is in my profile. I'm too expensive for you but I will try to point you in the right direction. Maybe HN needs a webinar for cross border startups like yours. :-)

[jeffblake]

I did stumble across that form 5471 while googling. Ouch. I will PM you, thank you for your advice.

[philiphodgen]

Another fun fact: from the Canadian tax perspective, a U.S. LLC is taxed as a corporation. If you had your LLC while you were living in Canada you'll need to see what Canadian exposure you have for that.