I left my comfortable job in Dubai, moved the family (with 2 small kids) to Toronto to build an enterprise database product, launched it at the niche's world conference, pivoted once, and spent all the money I had. That took nine months.
When it came time to look for work I got a decent job offer in the Toronto startup scene as a django dev, but I called up my old employer in Dubai and found out they had not managed to replace me. So I replaced myself! Moved the whole family back out to the Middle East.
You'd think the whole experience has turned me off startups forever, but....
I was convinced that it wouldn't work unless I dove in and did it full-time. You lose your residency visa when you quit your job here, and you have 3 months to leave the country. There are ways around it but they are too expensive if you're bootstrapping.
When it came time to look for work I got a decent job offer in the Toronto startup scene as a django dev, but I called up my old employer in Dubai and found out they had not managed to replace me. So I replaced myself! Moved the whole family back out to the Middle East.
You'd think the whole experience has turned me off startups forever, but....