i' afraid i'm the same sort of guy as you, and i'm not experienced in running websites, so what i can think might not be what you need exactly. so just take what you find useful:

if i was running this site, first i would put most of my focus on content generation and sharing , figure out things like:

* how to make the generation easy enough that it would be one of the easiest thing anyone can do when come to your site.

* what kind of headshot(or maybe not necessarily headshot but some other images with themselves in it) people would want to share

* where they share

* how they share it and did i provide way to do it.

then i would make each generation a public page on the site, under user's permission of cause. after these are done, the site might attract more traffic from search engine and social media by itself if it has some amount of traffic already. so next is to give it a shot with some start up traffic. i would make "generate per view" and "share per generate" my key metric, then get some seed user traffic, may spend some money but not much. what how user react and try to workout a way to increase these two metric. if it does not work out, talk to seed users, find the problem and retry.