David Newman travels to technology conferences and companies around the world and paints portraits of attendees on his iPad using the Pogo stylus.
I don't know what painting app he uses.
Based on a comparison on this page between the portrait being drawn and the subject, I would say the portraits aren't very true to life. The Howard Rheingold portrait looks accurate, though, but that might be because he's such a caricature of his own character.
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