I also run an NCAA men's basketball pool, been doing so for at least a dozen years. I remember many times, with around 100 entries, that first place was won by someone that didn't know a thing about college basketball, they just looked at the rankings and made some picks. Turned $5 into $200 pretty fast!
For those of us that know something, we often bring in biases that mess our brackets up anyway! When you make your picks, it's pretty easy to find out who is favored in the matchup and by how much, just go with the odds most of the time and mix it up a bit if you have a personal connection, like me putting 32 confidence points on U of O since I graduated from there.
Yeah, you can donate $5 on your own, abgemacht, fill out your own bracket and get your roommate to donate another $5 to Kestas, the more the merrier!!