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I could perhaps sell my company for a retire-able amount in a few years but I'd just move on to another business anyway.. so why not instead develop my staff to run the current business independently of me, so I can do whatever I want anyway, but still own something for the long term? I'd be interested to hear from entrepreneurs who've wrestled with this one and came down on one side or the other :-)

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Why because even then business needs managing. It's not going to manage itself. Even if you have a staff trained to try to take care of business, they will fail, and fail often enough that you have to intervene or your business will be out of business in a year. People are difficult. Really difficult. And outside of that the market is difficult, really difficult. It's always changing, and you have to change your company to adapt or it will die.

One of the best measures of quality of a company is how well it does after its founder dies/leaves. If your company can't run without you, you weren't building a company, you were building a job.

Agreed. But this doesn't mean you won't feel compelled to intervene and add value in difficult situations. I chose to cash out instead of continuing with the heavy burden of risking my net worth every day due to this. How is my old company doing? Fantastic, exactly because I focused on building a company and not a job. This is just to say that these two comments aren't mutually exclusive.

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