I did a thing in the early '90s that seemed like it was a bullshit scam but turned out to be legitimate. This company mailed you boxes of colored brochures advertising boxes of tupperware (actually Anchor Hocking stuff) for $19.95 plus a $7 delivery fee. There was also a big stack of small sheets of paper with an 800 number to call and a special ID identifying me, and I would staple one of these to each brochure. In the mornings, I would drive around and leave a few copies of these brochures at the front desk of businesses, hospitals, wherever I thought people might see them. People who were interested would call the 800 number and order a box or two. In the evenings I would get a fax with all my orders on it, and in the afternoons I would go to a warehouse with a cashier's check for $19.95 X however many orders I had and then deliver the stuff. Customers would usually pay with a personal check for $26.95 per box.

The fact that I had to show up at the warehouse each afternoon with a big check for the product before I even delivered it was what made it seem scammy. But the whole thing was totally legitimate -- prepaying for the product protected the company from getting scammed by their own employees. Every order was real and the customers always paid. Even though it was always personal checks, in a whole summer of doing this only two checks ever bounced, and both times I went back to the customer and they wrote a new valid check (people were really ashamed of bouncing checks in front of their coworkers).

At the peak of me doing this, I was getting in the neighborhood of 120 orders per day, which means I was making over $4000 a week (and effectively tax-free at that, since this company didn't report anything to the IRS; in fact they never even had my social security number). Which is fucking CRAZY money for a 23-year-old to be making in 1991 dollars. People were just so happy to be able to shop while at work. This shit really was a precursor to Amazon. I stopped doing it to go be a dirt-poor graduate student, which was possibly the biggest mistake of my life.