My very concrete feelings on this is that you probably don't. Asking folks how to do this is a bit like asking billionaires how to get rich. It's a fun story but it's overfitting. The individual narrative that made a billionaire is unlikely to be available for you. If you ask some millionaires they may be more likely to give you some useful advice around sound investment strategies, living within your means, and iden…
Agreed 100%. When people ask me what the best time is to work on a startup, it's always when you have no dependents, living with parents, and perhaps no significant other. It's quite amazing just how much you can skim down your expenses at that point in life. Minimizing expenses, maximizing runway. The rest is luck. Just blind luck.
If you're in the US, and not living with your parents (and or don't want to do that), one of the best ways to do it is to live in a university town. They're wired for fast Internet, the cost of living (including rent) is often very reasonable, they're among the safest areas in the US on average, and you can work at mundane jobs to pay your bills (30-36 hours per week; telemetry tech at a hospital; cashier or lead in retail making $15-$20/hr; etc). In the typical university town you can rent for $650-$1000 for a 1 or 2 bed + 1 bath apartment in a safe area. Working for a hospital you'll also usually get solid health insurance. The jobs are not difficult, they're relatively easy to get, although they will grind on you when combined with doing a startup (it's part of the trade you're making). Also in these types of jobs you won't have much if anything to worry about regarding intellectual property issues, conflicts of interest, et al.
Source: have done this, it works quite well. It can be exhausting working 80-100 hours per week obviously. The income/job becomes a permanent stream of venture capital, you can just endlessly fund your own way and keep 100% of the pie. I've often chosen to not do tech contracting work while working on a startup and self-funding with outside income, because I don't like the potential IP risks/conflicts and the burnout factor of always working on software/services/sites/whatever.