First startup was a consulting firm when I was 21. I turned freelance clients into a business with a partner. I left my job to focus full time on it for about 6

First startup was a consulting firm when I was 21. I turned freelance clients into a business with a partner. I left my job to focus full time on it for about 6 months burning through savings (I did have a mortgage). Second startup was a photo sharing startup 3 years later in 2004. We both left our jobs at ClearChannel before we got funding but secured an angel round about 3 months later. That lasted a year and a half before we ran out of money. We made the mistake of rebranding and rewriting the product with the funding (won't do that again). By the time we were ready to market 9 months had gone by and we didn't have a lot of money left. Currently bootstrapping and looking for when I can leave my day job. We don't have traction yet but I spent 4 weeks hitting the streets and talk to customers (students). I'm 32 now and after every startup I swear I'm done but I can't not do this. It's in my blood. I apologise to my wife on a regular basis for it. Thankfully she's always been supportive. Two times since we got married 3 years ago and I've looked her in the eyes and said "I think I need to quit my job" twice already. Hoping the third time is a charm :)