Growing up in an 'F1 family' where waking up at 02:00 to watch the races in Japan or Australia seemed normal, it wasn't a bit stretch to find myself playing racing games. Things really started out with Nigel Mansell's World Championship, which although certainly not a simulation, led me onto F1GP on the Commodore Amiga.
After progressing through and spending many years modding the Geoff Crammond Formula One simulations for myself, I started to run IndyCar Racing and NASCAR Racing from Papyrus Racing Games. In 1998 Papyrus released Grand Prix Legends, this had a huge impact on my entire life; I founded a Web site about it, began racing online with it, and it actually led me to where I am today; working for a racing sim developer.
Grand Prix Legends (1998):
Apart from the occasional rFactor mod, I didn't run anything other than iRacing (who I worked for) for a long time. In 2010 I started to work for Image Space Incorporated, deep into development of rFactor 2 at the time. That's all I run these days, I just don't have the time to run anything else!