When is a broker/dealer or securities license required to syndicate/raise equity for a real estate investment?

Somewhat of a novice question, but at what point is a broker/dealer entity required to raise funds for a private placement real estate syndication?  I have seen high net worth guys putting deals together over the phone or at their country clubs amongst their friends.  I have also seen syndication packages circulated where very specific sounding securities language was included, and a broker dealer was part of the offering.  I am assuming certain things trigger other requirements, but can someone break it down simply?  Would it depend on whether the syndication offering was being done publicly (i.e. on a website for example) versus me circulating an investment deck to my friends and family to try and raise the cash for a specific property or fund?