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I would first ask their experience in selling anything online. How much technical skill they have in HTML, Wordpress, etc etc.
THEN I would say this:
Be prepared to work your ASS off, 7 days a week (yes SEVEN), minimum 10 hours a day (12-14 is more likely) and be prepared to hit several "walls" where you just cannot build another Blog or submit another gallery...
Press on.
Set financial timelines for yourself. meaning: am I making X amount by X time and month? If you are not moving towards that goal then it may be time to give it up and move on. In other words, if in eight months I'm not making X (be realistic) then maybe it's time to move on...
Be prepared to adapt and change and, just when you think something is running smoothly, "fix" what you never thought was broken. Grow and maintain good relationships, try and connect with other Webmasters (misery loves company) and most important of all:
Never, ever stop.
(95% of people will balk at much of the above, and even fewer will have the commitment to actually pull it off. But for those rare crazy few it can still work. Good luck!)
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