One of the better observations I’ve read about money came a very long time ago from Felix Dennis in his book How to Get Rich. He pointed out that most people dramatically underestimate the amount of money required to feel genuinely financially untouchable. There’s also a lot of other crap in the book but hey, he was a lot more successful than me.
Founders are often advised to decide their “number” before entering a sale process and refuse to negotiate below it later. I think this is broadly correct. Once diligence starts, fatigue and uncertainty begin to distort judgement.
But the number itself is highly personal. There is a version based on security, another based on lifestyle change, and another based simply on exhaustion. At one point in my previous business, I would probably have sold the whole thing for £10,000 just to escape the stress. Fortunately, I didn’t.