I was exploring buying a company and made a great relationship with the owner and CEO ($25mm revenue). The owner was ultimately not ready to sell at the moment, but offered me a job as the President, basically the second in command with a path.

Has anyone seen examples of going down this path? How did it turn out? What questions should one ask when considering this type of opportunity?

It could decrease some risk but also limit upside, but also could be a rewarding way to spend a career.