"[Famous billionaire] gives away a lot of money. We should ask them for a donation!"
As in most aspects of life, people tend toward the familiar. It's understandable, then, that someone not steeped in the world of fundraising would conjure up the highest-profile funding sources as a starting point for his or her own nonprofit's fundraising plan.
But the challenge with this is three-fold:
1. If Bill Gates and Oprah are at the top of your mind, chances are good that they're at the top of thousands of nonprofits' minds.
2. Your organization may not align with their funding interests.
3. There are likely lots of suitable prospective donors that you're not aware of yet, simply because they don't get tons of media attention.
We love to aim high as fundraisers. Why not go for the big gift? However, much like applying to college, we need to diversify in order to increase our chances of success. We must balance the "stretch" funding opportunities with the lower dollar-figure, better suited and more promising prospects. So, if your nonprofit's mission fits Oprah's giving interests, we can certainly try to send something her way--but the bulk of our time and resources is likely better spent on safer, more local and less stratospheric bets.