Most salespeople know that an existing customer is more valuable than a prospect simply because they are more likely to buy from you. They already know that you aren't a fly by night charlatan, that your product was what you said it was, and so on. A lot of the hesitancy of doing business is already swept away.
If you are entering self employment, former employers are very much like former customers. They already know you, already know your skills and work habits. They are much more likely to hire you as a independent contractor than someone else who they do not know at all. Of course this assumes that you did good work while employed and left under good terms, but sometimes even leaving under bad terms isn't the obstacle you might think it is, especially if there has been sufficient time for wounds to heal.
However, when you have a friend or family member who can introduce you to a company that might need your services, you need to tread much more carefully. In that case, it's not your reputation that is providing the opportunity, but someone else's. If you over reach and screw up, you'll damage their credibility, and that can lead to bad feelings between the two of you. New startups are the most likely to over estimate their capabilities, probably both due to lack of experience and sometimes to desperate need of income. Don't let a mistake like that put strain on a personal relationship.
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