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The way we did it was as follows. 1 cone goes in dead center field. There is the a cone set between that cone and the back infield rim. There is also a cone set between the dead center cone and the outfield fence. Players get 1 point for hitting the ball into the outfield and then 1 additional point for every cone they pass on the fly. For Freshman we give them a point for every cone it passes regardless. The way we maximize our profit is as follows. All players fill out a spreadsheet that has 20 addresses on them. They address them and they are mailed out to those they chose. These letters are asking for sponsorships from family and friends. The players are then given a spread sheet that in which people can sponsor them per hit or give them a flat donation. We are a smaller school with 2 programs and have 36 players. We make $2,000 off the letters and we make an additional $1,000 off the sponsor per hit letter.
When I was coaching high school back in the late 80's and 90's, our head coach ran a tremendous hit-a-thon. Each player in the program had to get $1 / hit worth of donations. It was explained to the donors up front that their pledge was for each swing the batter took. They were also told each player would see 100 pitches. So if granny donated $.05 / hit, she would owe $5...and they would pay upfront. With J.V. and Varsity participating, this brought in about $3,200.

Varsity would take the morning shift, J.V. the afternoon shift. Players would hit in groups of 4...10 pitches at a time. Coaches would work with local businesses to get prizes for the players, and we would run contests throughout the day. We wanted each player to walk away from that day with something (SUBWAY gift certificate, free tokens to the local batting range, etc...).

It was a long day for the coaches (4-5 hours), but well worth the time given the return.
We do ours a bit differently than those above, but it takes about an hour to run off and last year raised over $4,000 in a community of about 1,000 people.
We make a big deal out of it and advertise it on the radio. We also invite "celebrity" hitters to increase attendance (DJ's from local radio, sheriff, principal, ag teacher, etc.), and we have it at night under the lights.
We send our players out with "pledge sheets" about 2 weeks ahead of time and tell them we expect the to raise no less than x-amount of dollars. They will take either flat donations (ie, $25) or pledges on how far they can hit a baseball. Some people don't understand the $-per foot concept and just want to donate a set amount.
On the day of the H-A-T we set out cones in the outfield in an arc at 200' to speed up measurement. We measure total distance of the batted ball, including roll (it IS a fundraiser, after all) and use the longest to tally up the pledge sheet. We don't have a set number of swings, but usually within 12-15 a player will get all of one and we measure. I'm in the press box with the players pledge sheets and when my assistant gets a measurement he relays it to me and I announce it over the p.a. system and total the players sheet as the next hitter moves into the cage. Our players rotate from the shag bucket, to feeding the machine, to on-deck, to hitting.

So the actual process goes like this: I approach you and explain who I'm with and what we are doing to raise money. I tell you how it works, for example, if you pledge 1 cent per foot and I hit it 400' you owe me $4. You decide to donate a dime per foot. On the night of the hit-a-thon my farthest batted ball traveled 425', you owe me $42.50. I return to you in the following days to collect and turn it in to the coach by a pre-determined date. If I'm late the Coach has a "reminder" for me that doubles in number every day I'm late.

Once again, the best part is it takes about an hour (for 20-30 players) to run off and the only work I've had to do is run off pledge sheets.

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