Bought a timeshare in Vegas. Never used it. Paid the mortgage and maintenance fees for a few years then said fuckem and just stopped. Such a scam. They went out of business during the 2008 recession and it eventually fell off of our credit reports.
Sold cutco knives in college (MLM). Perfectly fine product but overpriced and they basically get you pester all of your family and friends. I paid for the sample products myself. Made the biggest sale to my parents. Mostly just embarrassing.
I bought speakers out a van like some other commenters. Probably paid too much, they sounded good and I used them for at least 10 years.