Unless you drain your life savings, end up divorces... etc.
In this case, the primacy of establishing a separate fund as your bank roll, and protecting it by not letting too much of it ride on any single bet (no matter how great the bet seems), is very appropriate to self-funding your own businesses. If you lose your bank roll, then you have to stop gambling, which is bad if you are convinced you have an edge.
*I'm not a gambler of any type, unless you count investing 401k/IRA savings in index oriented ETFs and mutual funds gambling (not an unfair position).
My advice would be to not even consider it without having enough money to sustain yourself for a minimum of 2 times the period you predict will take you to become profitable in your desired venture.
So if you spend 3000 a month, want to become a freelancer and expect it to take you 6 months until you build up steady business you should have a minimum of 36,000 saved up.
I learned this the hard way, hope someone out there heeds this advice.