So how many bootstrappers have spouses and families? Seems to me like the kind of risk that's easier to take for those who are younger and/or have fewer responsibilities.

Also, how many boostrappers make lifestyle changes months before they leave their day job for the uncertainty of boostrapping? I would imagine you'd want to have enough saved for 6 months of expenses (the general rule of thumb for anyone actually) and an idea of what your new life is really going to be like.

I'm not married yet, but live with my girlfriend, so it's a similar situation. She's OK with my trying to bootstrap it and also offered to help me with my share of the rent, if necessary, for a month or two. She doesn't make enough to support the two of us indefinitely, but it's helpful to have somebody else with more stable income. The other nice thing about having a spouse (that I can't cash in on yet since we're not married) is that you can use their health benefits, which will get you better coverage and save you money.

Having kids changes the equation altogether. If I had kids, there's no way I'd try what I'm doing now with as little safety net.

I mentioned it in another comment, and maybe it's not clear from my post, but I'm married (14 years) and have 3 kids (ages 8, 10, and 12). Being bootstrapped with a family like that probably requires more adjustments than for those who aren't married and don't have kids.

But you bring up a good point about prepping for those changes before you get into it. If you have the notion to start down that path, then making those adjustments ahead of time will help ease some of the "pain".