There's no issue at all with having two companies submit your name into the lottery as long as both are bona fide companies and bona job offers. There's no que

There's no issue at all with having two companies submit your name into the lottery as long as both are bona fide companies and bona job offers. There's no question that the H-1B is the best option to work for the tech company and an O-1 might be an option to work for your own company, although probably not until it hs some "traction." Regarding Canadian immigration, email me and I can refer you the names of some good immigration forms there.