Josh saw how successful Scholastic Matchmakers had been at our school, and wondered: could the idea scale? Could we provide the same service to tens, hundreds, or even thousands of schools? Could we convince all these schools to sell a product on our behalf, and send us a cut of the money? How could we advertise it?
By the next school year (1991), Josh and I had both graduated from high school, and had gone off to college -- him at Yale and me at Johns Hopkins. Despite the distance now separating us, we decided to try expanding my tiny dating service to a much larger market. I officially made Scholastic Matchmakers a service of The Whitman Group. (The only official procedure required was me saying, "Um... okay, let's work together on this.")
We made The Whitman Group a real company, and Scholastic Matchmakers was our flagship product. With an initial investment of a few hundred dollars, we opened our official company bank account. (It's amazing how exciting it is to get a real Corporate Checkbook with your company's name printed on the checks!) Josh did for us everything that real companies do. He filed the appropriate papers to turn The Whitman Group into a real corporation in the State of Maryland, with Josh and me as the only two stockholders. (I suppose Josh had the real power over the corporation, though, because he had the Official Corporate Seal.) He got us a 1-800 number that rang in his dorm room at Yale.
Our first try at getting business for our fledgling company was not particularly successful. Being the young students that we were (and, being two guys who did not have a regular income at the time), we weren't willing to take a great deal of financial risk. Our "on-the-cheap" advertising ended up taking the form of a very cheesy three-fold brochure that we designed with a word processor and mailed to 50 local schools. We got what we paid for: not one of the schools replied. If anyone actually looked at our brochure, chances are they just laughed and threw it away.
That following school year (Fall 1992) we tried again to do a mass-mailing, but it still didn't work. We were still stuffing the envelopes by hand, and scraping our mailing lists out of phone books, so we couldn't mail more than 100 schools. Also, our mailings still looked incredibly cheap. Our efforts were met with complete silence again and again. Finally, we decided that mailing these silly little brochures really was just a waste of time. We had to either make a real investment in the company -- which meant taking real risk -- or just forget it do something else.
Next: The Old Adage: It Takes Money to Make Money
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