It sounds like the people losing money are making more money than the people making money.
UPDATE 19 May 2020: House of Cards: “Used to be that companies built airplanes and sold them to people who ran airlines, but then the business got big and weird. A few years ago Rolls-Royce had a billion dollar backlog of orders for their giant fan-jet engines. A year later they were in trouble because their customers found they could get the required maintenance done elsewhere at a much lower cost. If you thought Rolls-Royce was in the business of making and selling engines, you’d be wrong. That whole business was a just a marketing ploy to sell overpriced maintenance contracts.”
Monday Evening 
Either someone is deliberately subsidizing the loss, or there are sections that the writer can’t see where there is money being made.
For example, the pizza one is clearly losing money on each individual sale– so perhaps that is a loss leader.
It appears that door dash has a monthly sub, and they’re supposed to have a delivery and service fee, too. If the guy ordered 10 pizzas at $16, and paid $160, not only did he not have any sales tax on that (ready to eat usually does) but there’s none of the other charges that are standard or common.
Maybe his buddy already had a DoorDash sub?