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Find the most well-connected, influential wealthy person in your area, the one with the most out-of-the area contacts. Maybe a politician or business person. (If the next town over is way bigger than yours, go over there.)
Tell them what you're trying to do. Offer to paint them for free, if they'll let you keep it for a year as a sample, they'll say nice things about you, and they won't reveal your deal. If they say no, ask them if they know someone who might be interested, and ask them if you can use their name when you contact the suggested party.
You'll be painting for the practice anyway, right?
Work your rear end off to make it the best painting you've ever painted in your wildest dreams. Paint it as many times as this takes (don't let them badger you into a deadline). Make sure they agree to your rights to reproduce the painting for marketing purposes.
Follow through with your part of the agreement.
Portraiture is mostly a word-of-mouth business. Bart Lindstrom's two rules for marketing are:
1) Make exquisite paintings
2) Show them to as many people as possible.
The first commission is the hardest to get.
All the best--TE
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TomEdgerton.com
"The dream drives the action."
--Thomas Berry, 1999
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