What's the Down Side To Using a Stage Name for Business?

Dear Rich: I am in the process of making marketing videos on youtube, webinars, public speaking seminars and authoring informational books. For privacy reasons and because of my unusual and hard to spell name, I would like to use a first and last name that is different than mine in these situations. I do not plan on changing my name legally, like on my drivers license, but to feature it in these works that I publish myself. Is there any issues from a legal standpoint, that is, not holding myself properly to my clients/ customers. The main jurisdiction that I plan on doing business is Canada and the USA if that helps.
We can't comment on Canadian law but in the U.S., probably the only issues you will face are getting paid, entering into contracts, and registering copyrights. Because you are doing business under another name (DBA), you should indicate that fact when entering into agreements -- for example, "Robert Smith DBA Harry the Heretic." Ditto for filling out W-9s and W-4s for hiring parties -- use your real name for tax purposes. If you're publishing copyrightable materials under a pseudonym, you have the option to indicate that when preparing your copyright application. As for getting paid, try to set up direct deposits. Otherwise, you'll want your real name on any checks to avoid bank teller hassles (i.e., "Excuse me while I get my manager!").
P.S. Have you checked to make sure your pseudonym is not already in use for similar goods and services?