I'd imagine only the children of wealthy adults have the resources, wherewithal, and training to accomplish such a feat. It still seems impressive, if not dangerous.
The training isn't expensive, Spinnaker sailing is a cost effective outfit accessible to many. It's actually pretty rare for the wealthy Palo Alto kids to do anything noteworthy beyond academics or business. Good for him!
Not everyone can get a boat for half-off, though. They are unquestionably a complete and utter money pit!