> A lot of the things that happened (break-in, heart attack, etc.) were black swans that probably can't be avoided in the future.
Neither a break-in or a heart attack is a black swan—people take out insurance against both all the time. If you're working with an organization, rather than an individual contractor, they most certainly have measures in place to ensure you never feel the brunt of such an event.
When your co-founders have heart attacks and break-ins I would consider it abnormal. Sure you can insure your way out of it, but it's a constant tradeoff. A normal insurance (which we had) didn't help much since it only covered new equipment after the breakin, and didn't cover anything in the heart-attack case since we weren't working for a client with a contract. As a startup you have limited time and money and you've got to decide where to spend it. Large corporations have the luxury of being able to have all-covering insurance policies,redundancy, policies for replacing employees, well-established back-up plans, etc. Most startups don't.
The very things that make a startup cheap are also what make it vulnerable.
Neither a break-in or a heart attack is a black swan—people take out insurance against both all the time. If you're working with an organization, rather than an individual contractor, they most certainly have measures in place to ensure you never feel the brunt of such an event.