When it started it was just me and another junior programmer trying to build something too complicated for our experience level. Later on we got someone more experienced, unfortunately (for the project) 10 years on he is still the worst developer I've ever worked with, not helped by his arrogance. All of his experience was drag'n'drop VB forms, but he had a CS degree and we didn't, so that made him right every time. He also made us switch from SVN to to VSS, svn wasn't so great back then (no merge tracking) but at least it didn't silently fail every other day like VSS. He didn't believe in using framework features, preferring instead to write his own sorting algorithms that didn't work. His attitude to compile errors was to turn off the strict/explicit options that VB has. He was the living example of a developer with 1 year of experience 10 times over.

Technology wise we went through several iterations, web, descktop, c#, an experimental java one, but thanks to the senior dev we settled on VB.net. Management was more interested in hiring people that would be sitting at their desks at 9AM (I was eventually fired for failing this) than any sort of technical competence. The manager was the type that "understood people" and forced us to put in all sorts of questionable UI features. He was obsessed with how it looked and didn't care if it worked. Every point release involved working through the weekend.

Amazingly the software was quite well received and didn't suffer from too many production bugs. It was delivered only slight late and made the company money.

Then the company got a bunch of funding and things became more hilarious. Management was obsessed with becoming the "google of our industry" and preceded to do the exact opposite of everything google would would do. But those are stories for another time.