I created a non-profit with a similar concept about 5 years ago called Vonate.org (now defunct). Our concept was $1/month and you would vote/donate (vonate) your dollar to one of the two featured organizations. I'm a big believer in the micro donation space, but execution is key.
My biggest lessons learned were:
1) Find and vetting 24 great organizations was difficult.
2) Getting people to spend $15/year (how we covered costs) was a challenge, so keep your expectations on audience engagement incredibly low.
3) Revenue through sponsorships won't keep the lights on.
I am a complete proponent of pursuing an undergraduate degree at a traditional school. The constant networking, opportunities to round yourself as an individual from field experts, and development of general life skills are nearly invaluable to become a successful leader.
www.howaboutwe.com is an intriguing player in this field. They are built around date proposals. Nice way to introduce local deal and minimize the 'stalker' factor.
Apparently, they have a decent base in NY, but currently their Midwest member-base is limited.
My biggest lessons learned were:
1) Find and vetting 24 great organizations was difficult. 2) Getting people to spend $15/year (how we covered costs) was a challenge, so keep your expectations on audience engagement incredibly low. 3) Revenue through sponsorships won't keep the lights on.
Regardless - best of luck.