We had big plans for Scholastic Matchmakers. On the marketing side, we realized that we weren't just in the business of high school fundraising -- we were collecting valuable demographic information on a segment of the market that's usually very difficult to reach. We were asking hundreds of thousands of high school students questions that might be very valuable to advertisers. Our survey already had questions like, "What's do you worry about most before leaving for school?" If a student answered "My appearance," and was a female, we could print a coupon for lipstick right on the bottom of their Compatibility List. Josh and I were sure that advertisers would be willing to pay a lot for that kind of directed advertising. In fact, we thought we could take over the entire high school matchmaking market -- completely obliterating our competition -- by making our service completely free to schools, subsidized entirely by advertising.
We had big plans on the technical side, too. Our web site at that time was really just an ad that didn't actually do anything. The plan was to turn Scholastic Matchmakers into an entirely web-based operation. The web site would let customers download and print custom surveys, track their orders, and even try to find matches from the pool of students in other schools.
So, what happened?
Basically, we wimped out. Josh had an offer for an executive position at a medical technology startup with huge potential, and I took an offer doing medical-related information systems design for the National Institutes of Health. We took salaries. Also, both of us were out of the country for the entire summer after graduation -- Josh was on a world tour singing with the Yale Whiffenpoofs, and I was in living in Jerusalem, Israel to learn Hebrew. Being abroad made it impossible to prepare for the next season's business. Because of the once-a-year nature of most of the business, the preparation, designing and printing brochures, contracting vendors, developing operations, and other planning all had to be done before the school year starts in September.
We tried to find someone to take over the company, ideally a business student or group somewhere, but couldn't find anyone who was both competent and willing. And the company wasn't big enough to sell as its own entity. We could have gone full-time on it after graduation, but we decided not to take that risk, particularly in light of the poor scheduling.
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