During its mission to raise popularity in the midst of the dot-com boom in '98, TravelZoo gave a few free shares to each person who signed up for their mailing list.
Hypothetically, let's say I'm building a website that is a catalog of restaurants. The usefulness of the website is based on how much data is listed. Data is mainly user-submitted, and any person with an internet connection can find a restaurant and add it.
The issue is incentivizing this crowdsourcing. Can I do something like TravelZoo and promise one free share of the company if it is successful and later incorporated to every person who submits a restaurant? Is this strategy effective, and what are the legal barriers to be aware of?
Why not just populate it yourself, or use oDesk or something to hire someone to do it for you?
For me it's a red flag any time I am doing something that isn't simple, as often there is a simpler way. This idea you propose would be way past my "it's getting complicated" threshold.
I don't know the legal ramifications of doing your suggestion, but I would not want to go down this path. Try not to complicate things too much, build a great product and hustle to get your first users.