Caroline Kennedy stood demurely one recent evening in a short black-and-white cocktail dress, a smudge of gray still on her forehead from earlier Ash Wednesday observations. Surrounding her were about 50 clients and friends of planners Derek Holman and Brian Parker, co-founders of EP Wealth Advisors in Torrance, Calif.

"If you'd like to ask questions ... " one of Kennedy's handlers offered. The guests smiled awkwardly at getting the opportunity to speak directly to JFK's daughter. Then they dove in.

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