If your goal is to own a business that provides income and flexibility, you have to aim for that from the get-go. Ultimately it has to be a big enough business, in a suitable industry, such that it can subsidize a white-collar professional management/sales team while still returning a profit/income for the owner. More than one manager is important, it provides checks and balances and avoids having the business "single point safe" on one key employee.

You need to choose your industry and business model based on your goals, not necessarily what you're good at or know about.

If you get to that point, you need only participate enough to keep your SA up and be prepared to step in if needed.

As I mentioned, there will be lengthy dues paying, and risks (as in anything worth doing). But it can be done, I have several friends who have and also a friend who specializes in running startups for other people...he works hard, gets things going, cashes out (usually at the IPO, a large part of his compensation is always shares), then takes a year or two off before moving on to the next one.