iSepta
Back in 2006 and 2007 I was looking to quite my civil engineering job and start working for myself full time. I realized I wasn't very good at socializing and commenced “Operation Learn to Socialize” and went to a lot of meetups at night in Philly.
Often I'd find myself sitting at a bar with a few people and wondering when the next train was. I would pull out my brand new iPhone (the original), find the PDF on iSepta's website, and try to scroll through it to find the time of the next train. I wanted to know if I could stay 15 more minutes or had to run to catch the train.
On the way home I sketched out what I wanted out of a train schedule app on my phone and sent it to a few friends. Right away Jason Tremblay and Chris Conley responded and we started building it.
This single public service opened so many doors for me as I changed careers in 2007. Most people in the tech scene in Philly knew what iSepta was and introduced me to people who were looking for a developer who could get something done.
We tried to make money off of it a few ways, but in the end it was just an app many people found useful before train schedules existed on Google Maps. We kept it running for a few years even after Google Maps included train schedules because so many people found it so simple to use.
Wireframe I drew on the train ride home one night:
What it turned into:
