[kohanz]

I did this. Founded a bootstrapped startup with wife, kids, mortgage, that eventually and unexpectedly led to a life-changing exit.

The key is that I didn't jump into it full-time right away. I first transitioned from a full-time job to a successful freelancer/consultant where I continued to get paid for writing code, but controlled my time and commitments. At first, I did this full-time and out-earned my previous employment income. As the startup itch grew stronger, I started spending more (unpaid) time on the startup and less on clients. My income dropped significantly (to about 30-40% of peak earning - ouch!) and it was a big sacrifice and gamble. My wife had some part-time income and maternity leave income during these times, but nothing too crazy - I was always the major breadwinner.

My wife and I also were on the same page about living within or below our means. We always earned significantly more than we spent and could tolerate major reductions in earnings and still not dig into savings. That's not to say we earned a lot, but that we were smart & frugal with money and did not have $$$ lifestyle preferences.

Also helpful that I live in a country with universal healthcare. If my family's health insurance was tied to my job, I would never have become an entrepreneur as I am very risk-averse. Keep in mind, all that happened above was a gamble that I took. I got lucky with the outcome (through a combination of skill, luck, and timing). There are many scenarios that could have played out, some that would not lead to success where I would still be bitter to this day about the career and financial sacrifices I made. I took the gamble and won, but it could have easily gone the opposite way. What I do know is that my wife would have supported me in any scenario. How I myself would have handled the mental impacts of "failure", I'm glad that I don't have to find that out...