I worked for a startup during the dot-com boom that seemed to want to be a Yahoo clone. The CEO was incredibly shady and the company was partnered in some way w

I worked for a startup during the dot-com boom that seemed to want to be a Yahoo clone. The CEO was incredibly shady and the company was partnered in some way with some huge telemarketing company in Florida. We offered free webmail, just like Yahoo, and at one point the CEO told a developer to add a credit card field to the sign-up form just to see what would happen. Several users entered valid credit card numbers. I do not believe that anything was done with these numbers, but I cannot imagine why the CEO wanted to test this. Our main source of revenue seemed to be banner ads offering shady services from the telemarketing company. One of them was a travel club. The users would be drawn in with an offer of free airline tickets. They had to sign up for the travel club to get the tickets and they had to stay at specific hotels and such that were probably marked up to pay for the tickets. The whole idea was to get them to sign up for the travel club which caused a small monthly fee to be charged to their credit card. They knew how much to charge to get most people not to cancel for months (it was around $8-10). The only "benefit" of being in the club was more questionable offers. At one point they considered starting a gasoline club that promised cheaper gasoline. The idea was that people would again pay a monthly fee for the club but then they would have to submit receipts to receive reimbursement for gasoline purchases. They were counting on people being too lazy to submit receipts.