How to gently convey to your client you lost a dollar fifty or so of his/her money

You can't make this up. James Cordier of Optionsellers.com humbled by extreme market fluctuations in natural gas lost money of his investors. All . Of . The . Money! They invested in options, naked.

He seems to have some maritime tack.

“I am so sorry for not managing our ship and keeping her afloat,” Cordier said, fighting back tears. His firm could not be reached for comment. 

There is more here.