A lot of these are mitigated if you're a "self-employed consultant" who just happens to have one particular client which indefinitely defers invoices. (I use this <i>very</i> frequently in Japan, which makes Tulsa look like Silicon Valley in terms of tolerating novel employment options.)
> Most entrepreneurs have similar beginnings: They do well in grade school, go to a great college in which they do well, get a great job, quit that job, and try to start something on their own. When they start something, it’s the first time in their lives that they stray from the beaten path.<p>Really? I'm kind of surprised to find this in an article supposedly about bootstrapping. I mean, if you live in SV and you worked at Google and saved up for a few years and now you're "bootstrapping" a start-up, you actually already <i>have</i> an angel investor: yourself.<p>I did horribly in grade school (spent all my time on the internet instead of studying), went to a crappy college, dropped out (spent all my time dicking around with coding projects instead of studying), got a string of horrible jobs (the majority of which were minimum-wage and didn't even marginally involve technology -- O, to live in the US, let alone SV), and now I'm trying to start a start-up because it's the only thing I feel any sense of engagement toward.<p>I'm "bootstrapping" in the sense that I highly doubt anyone would ever invest in me. No cofounders, no "workspace", just me, my laptop, an EC2 micro instance, and some combination of {Erlang, HTML5, Objective-C, Stripe}. Wish me luck.
Purchasing your own insurance is the easiest way to ensure continuity of coverage and ensure you are not choosing your life's work based on the inconvenience of changing medical coverage plans.