A friend and I review each other’s “in case I’m dead” documents on a ~yearly basis. He runs a small MSP (~200 clients), I run a variety of small income producing things. The point of the documents isn’t to run the business perfectly, it’s to capture the day one…thirty issues for the survivors to either shut the business(es) down cleanly, or sell off. Even a simply "if I’m dead, this is what you should do” document is incredibly helpful to your heirs or whoever administers your estate.

The reason for a solo founder to at least think about these things is, sure, if you’re dead, you’re dead. But if you have any family they will inherit the mess left behind when you die. Even if your intent is the business should die with you there’s paperwork and pissed off clients/customers. If you run a sloppy LLC or C corp (minimal paperwork to keep up the corporate veil) your family will absolutely love to learn that you’ve dumped this pile of crap on them after your death.