In Search of Enemies: A CIA Story, "Kinshasa"; ISBN 0393057054
“Money lost -- little lost. Honour lost -- much lost. Pluck lost -- all lost.”
Raffles: The Amateur Cracksman
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Innkeeper's wife
Source: A Child is Born (1942)

Rich Dad Poor Dad: What the Rich Teach Their Kids About Money-That the Poor and the Middle Class Do Not!

“When I had money I was an animal. I was so belligerent. I lost all across the board.”
http://www.thisislondon.co.uk/showbiz/article-11621981-details/I'm+a+street+bum,+says+broke+Tyson/article.do;jsessionid=dZGvFJZGkLvsnbWWXZrVhsZ2kJlny8kkygtqYThr5ZL2nyWzmSjJ!-686754952
On himself

“True, I have lost money on many occasions. But I only play with money I can afford to lose.”
Rich Dad Poor Dad: What the Rich Teach Their Kids About Money-That the Poor and the Middle Class Do Not!

'Notes On Journalism' http://books.google.com/books?id=52L2eI9mwlcC&q="No+one+in+this+world+so+far+as+I+know+and+I+have+searched+the+record+for+years+and+employed+agents+to+help+me+has+ever+lost+money+by+underestimating+the+intelligence+of+the+great+masses+of+the+plain+people"&pg=PA28#v=onepage in the Chicago Tribune ( 19 September 1926 http://archives.chicagotribune.com/1926/09/19/page/87/article/notes-on-journalism)
The first sentence is often paraphrased as "No one ever went broke underestimating the intelligence of the American people." (The Yale Book of Quotations, 2006, p. 512)
1920s
Source: Gist of Mencken