Any ideas on how to help a portrait artist make money?

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If she's willing to do it, you could set up a camera to film her while she does these portraits and make a time lapse out of it. Those kinds of videos have the potential to go viral, or at least get an impressive amount of views, especially if you find a good place to post the videos (reddit is the obvious suggestion, but maybe some kind of online art communities or something too). Plus, it doesn't really take that much effort to do. Just make the portrait, upload the video, edit it as a time lapse, and post online.

If you wanted to take the idea a step farther, you could also make a whole bunch of time lapse portrait videos and post then on a youtube channel. Sell each exact piece on a website in the description, and maybe ask viewers what she should do next. Could lead to some sort of online following, which would help generate some traffic as well as immediate sales.

This video is an example of what I mean -

[ame=http://www.youtube.com/watch?v=HIM6w6NlhdY]Sensual Adriana Lima Charcoal Portrait time lapse video - YouTube[/ame]
 
As the son of an artist, I would say, find another career.

Harsh, but sorry, there's millions of great artists out there. The starving artist stereotype didn't emerge from nowhere.
 
I could see this happen in a few years, because it does require a minimum of hustling skills that she doesn't have. Right now she lacks confidence and is extremely socially awkward. That's why I'm trying to find a way to help her make money online, where she wouldn't have to deal with anyone in person. Once she gets a few orders in I'm sure it'll build up her confidence and then she can start going to events and stuff...

Honestly, you've been given FANTASTIC advice with the wedding planner etc. suggestion. Try to think outside of the box a little bit...

She is socially awkward and not that great at selling? So what??? Contact the local business professor at your nearest college with an MBA program. Find a picture of the professor and turn it into one of her pieces. Send it to him with pictures of her drawing it and a kick ass sales letter saying something like:

Dear Professor X:

My lifelong dream has been creating a business selling my art to buyers. I was thinking about (Pitch idea with wedding planners) or (pitch another idea). Would you be interested/willing to pitch this to one of your MBA classes as a project? They would gain the experience in starting a business and I would get the much needed help!

Obviously you have to dress it up and use your best copy writing skills.

Or you could put something on craigslist that you are looking for a straight commission sales guy.

Or you could find a distributor to wedding planners and see if they would be interested in putting her work into their sales funnel for you.

Have her do a drawing of a portrait of a local hero/mayor/etc. and arrange for it to be given at the awards celebration. Then publicize in exchange that she does once in a lifetime commissioned pieces for $2,500.

Once you hit a price point above $500 it's not about the money anymore. It's about HOW you sell it. Think about the fringe benefits the buyer is getting luxury, once in a lifetime piece, exclusivity etc. etc.

THINK OUTSIDE OF THE BOX!
 
First, she could have a popular fb page going with that kind of portraits. Connect the top 5 socials

You know it's funny that said that, because she actually drew a picture of Prince (one of her favorite singers), framed it and tried to give it to him at a concert he gave here a while ago, but one of his security guys came to her and said that Prince was not allowed to accept gifts from fans and that she was not allowed to get that close to him. I don't think she wants to try that again lol

Maybe the singer could share the portrait on his fb?

Also, you can consider talking with some gift related sites. They can add portraits as another gift option and resell her art at high margins
 
...you could set up a camera to film her while she does these portraits and make a time lapse out of it. Those kinds of videos have the potential to go viral, or at least get an impressive amount of views....

You can push that video through one of the YouTube views suppliers like SocialViewz.Com (shameful plug). The increased view count will make your video more attractive and you'll start getting massive clicks on the video.

...just say'n
 
Web comics might be something to consider? Even though she can do great portraits it doesn't mean she couldn't do something else(in the sphere of creative drawing) exceedingly well.
 
1) Throw artistic integrity out the window and do portraits of corny internet bullshit that panders to Reddit (psy, lolcats, rick astley, chuck norris, etc)
2) Make a post on there
3) $$$
 
Create a Facebook Page
Run a Contest Targeting New Brides
Run a Contest Targeting Anniversary Couples
Buy Facebook Ads... Price will drop because of high click throughs.
Profit...
 
My father was a successful commercial artist who worked in advertising. He also was a fine artist that specialized in portraiture. I inherited the ad gene, but the artistic gene went past me like a sieve. However, I am able to spot artistic talent due to my exposure to it.

She has talent, yet I think she would benefit from formal training. The anatomy in the Liz portrait is a bit off. As she gains confidence, her drawing style should loosen up a bit.

Working in the commercial area is something she should consider. There's no shame in making a living and developing a serious art career on the side. Did you know that famous artist Henri Toulouse-Lautrec worked as a commercial artist?

I think the advice here about using social media to spread the word is solid. I also think that she should begin her own site to display her work, and begin getting small illustration jobs to build up her portfolio.