In New York City five years ago I was switching from one IT career to another (Unix sysadmin to programmer), and was working part-time for a very small startup that had run out out of seed money, while interviewing for more lucrative positions (which I found four years ago). The founders were working a day job, and funding me out of pocket, which was to the tune of $100 a month. For a variety of reasons I decided to do Postmates deliveries, one reason being the flexibility.

Running around Manhattan on cold November nights five years ago, I began to appreciate the $100 a month I was getting programming for this small startup at my desk at home or in their co-working space. If you don't have a bicycle or car, you pretty much need a metro-card, which goes to your expenses. Sometimes orders came in right away, sometimes I'd be sitting around for over 20 minutes waiting for one. The food pickup location was always within half a mile of my location. The quickest pickup offer to delivery for me was 23 minutes, longest was 52 minutes. With waits of up to half an hour before a next offer.

Deliveries usually paid a little over $4, but there were bonuses of $2 for some deliveries, and you'd be paid for long distances or long waits for food. You would also get tips (up to $7).

As I said, I was getting paid $100 a month to do some programming for a small startup, which seemed very little, but it was a lot easier than how much time and effort it took running around Manhattan to earn $100 from Postmates.

About six months after doing occasional Postmates deliveries I was making over $60 an hour programming for a multi-national.