A college scholarship for people who dropped out of school after 6th grade, and who had perfect scores on the SAT.
The “Russian Roulette” Scholarship. I have a 6-shot revolver loaded with 5 bullets and one spring loaded check launcher. To receive the scholarship you must be hit with the check. Offer void on death of potential recipient.
I’ve had a dream for a long time of hitting the lottery and establishing Houston’s High School for the Martial Arts. Academic side dedicated to excellence and you don’t graduate if you don’t score 700+ on each part of the SAT. Athletic side, training in Taekwondo, and you don’t graduate if you haven’t achieved the rank of at least 1st Degree Black Belt.
In college a friend and I always joked about establishing a small scholarship based on slacker procrastination. Students would be given a topic to write on with a 24-hour deadline. Best paper wins.
Of course it was all a joke until my friend passed away. So I now fund a yearly $1000 scholarship at my alma mater based on this concept. Best paper I’ve seen included a discussion of the given topic and also a timeline regarding the student’s procrastination. It included things like “0240: despite loathing cleaning decided to vacuum rather than write paper.”
I’ve actually talked about this with my wife. Our place is that once we are insanely rich we will go around giving scholarships (for themselves or their kids) to service people we like. I already picked out several of the girls that work at the lunch place I like near work, as well as some waitresses at some restaurants we like. Plus the woman who cuts my hair. So it would be the “People who are nice to me as part of their job” scholarship fund.
This is awesome, and you should feel awesome!
I am no expert, but I think the second part would be trivial. A black belt is pretty meaningless when comparing between schools, no? You could get it at a place that requires decades of training, or you could get it in 2 years from a McDojo, as long as you pay enough money.
The real stipulation should be that you pass the requirements if you can beat up Chuck Norris.
I would give scholarships to people learning the great crafts of woodworking, stained glass, embroidery, jewelry making, all the wonderful things I love to look at. The fine craftsmanship I would like to have in my home and of which people say “nobody knows how to do that anymore.” I’d find the old guys who used to do it and pay them to teach the young folks who want to, and pay the young folks to get business education so they can manage their income and finances.
Basically, I’d run a kind of Roycroft studio.
I assume that Taekwondo would be a class at the high school itself (iirc Clothahump is a Tawkwondo instructor).
The “Born Again Atheist” award. Offered to students who attended Bible College, only to realize that after really studying religion, they no longer believe it. Pays their costs for their first year at a real school.
That, and the “Binge Drinking First Years” award. Paid to the student who passes out last after a night drinking with me at the pub.
I’d just give athletic scholarships for the creation of a Calvinball team.
With all the obvious rules for remaining on the team. 
Fine, then I’m only opening mine to official members of the Apathy Party.