When I returned from my bike tour in June, 2005 and settled in St. Paul, I tried to resume my career in nonprofit management but quickly found that hiring committees did not think my taking a year off to travel was a sensible career move. They were concerned I might do something like that again and leave them in the lurch. There was some truth to that; I knew that I was probably going to move again in a year or so, so I decided I needed to find work that I could do from anywhere.
Having built a couple of database-driven Web sites in Embedded Perl while working for the Friends of MPL, and having converted them to PHP while I was in Pittsburgh, I figured I had enough of a portfolio to at least apply for a job building a Web site. This I did, and I got a consulting gig for a startup called Buy the Change (no relation to any contemporary business of that name).
The company consisted of three childhood friends who were now in their 30s and had talked themselves into starting a business together. The plan was to make a software platform that nonprofit organizations would use to hold rummage sales and auctions online. A nonprofit would ask its members to use the service, and the members would offer items for sale either at a fixed price or an auction, and they would buy each other's stuff, and after taking a commission Buy the Change would pass most of the proceeds to the nonprofit. It was a reasonable business plan at the time, and today there are similar services that do much the same thing. In fact one of my own sites that helped me get the job was similar enough that to comply with their non-competition agreement I had to shut it down!
The problem was that none of them knew a thing about programming, and I was self-taught and still very new to PHP. They had purchased an e-commerce package to get them started, and while its source code was simple enough to understand, it was not intended to be customized, and so I had to "hack" the core code. The company had FTP credentials to our server as part of an ongoing service agreement, and every few weeks when there was an update to the software they would overwrite all of my customizations directly on the server. Had I known how to use version control at the time, I would have been able to better recover from this, but without that knowledge it was pretty catastrophic: I had to compare all of the files on the server to the copies on my computer and manually resolve any differences.
The other problem was that these guys liked to do business over drinks, and they insisted that I drink with them, and I had no experience drinking. I found myself agreeing to features and deadlines that seemed fine while I was tipsy, but sobriety revealed they were not realistic, and I was unable to deliver on them. When I realized that I wasn't the right person for the job, I convinced them to hire someone else. This they did, and they asked me to train him. I met him at a coffee shop and laid the whole situation out for him. Poor guy looked like a deer in headlights.
I believe the software did make it to production about a year later, but it didn't last long. The interesting thing is that now (2021) I work for SHARE Good Software, which is a similar concept.