“You have to speculate to accumulate” (gambling proverb)

“Speculate to accumulate” (that is, “take chances to win big”) appears to have started in gambling and was cited by Broadway scribe Walter Winchell by 1941. The phrase is more popular in England than in the United States. The English comic novelist P. G. Wodehouse (1881-1975) wrote, in 1924, that “If you don’t speculate, you can’t accumulate.”
   
Wall Street has also occasionally used the phrase “speculate to accumulate,” although the phrase hasn’t been nearly as popular in America.
   
   
Urban Dictionary
speculate to accumulate
A phrase used by potential profiteers to remind prospective investors that returns can only come from good investment. Really a buzzword (or buzzphrase) to get money from others to squander on fruitless and flowerly ideas. See European union, Belgium.
“Speculate to accumulate!” cried John, asking steve for the last crispy notes in his wallet. Eyeing up the tail at the bar, steve gladly turned over the contents of his wallet to John, who promptly brought the ladies a drink each. After some thirty minutes, John threw up over one of the fine females, making the money a write off due to his poor ability to handle drink. Steve’s brother then started to insult one of the lasses, and they stormed off.
by Kung-fu Jesus Jul 6, 2004
 
Google Books
Bill the Conqueror:
His Invasion of England in the Springtime
By Pelham Grenville Wodehouse
New York, NY: George H. Doran company
1924
Pg. 94:
If you don’t speculate, Judson was well aware, you can’t accumulate.
   
19 January 1924, Wisconsin State Journal (Madison, WI), pg. 3, col. 3:
FAMOUS REMARKS
(In a poker game.)
“If you don’t speculate you can’t accumulate.”
   
Google News Archive
14 March 1941, St. Petersburg (FL) Times, “Walter Winchell On Broadway” column, pg. 19, col. 2:
Sounds in the Night: In the Sunny Isles dice-room: “You gotta speculate to accumulate!”
   
Google Books
Journey Towards Christmas:
Official History of the 1st Ammunition Company, Second New Zealand Expeditionary Force, 1939-1945
By Stephen Peter Llewellyn
Published by War History Branch, Dept. of Internal Affairs
1949
Pg. 111:
“We’re not here to make money we’re here to make friends. You gotta speculate to accumulate. A good horse never stumbles and a good sport never grumbles.”
   
Google Books
Gambling in America
By Herbert L. Marx
New York, NY: H.W. Wilson
1952
Pg. 110:
Working-class Britons, according to some experts, gamble on the theory of speculate to accumulate, a chance to win ...
   
Google Books
The Concise Oxford Dictionary of Proverbs
By J. A. Simpson, Jennifer Speake
Published by Oxford University Press
1992
Pg. 237:
1984 J. S. SCOTT All Pretty People ix.
“Bloody liquor’s becoming an expense.”
“Won’t be for long. You have to speculate to accumulate, if we kept her sober we couldn’t do it our way.”
     
Google Books
Finance for Life:
A Guide to Money Management for Modern Lifestyles
By Steve Lodge
Published by Kogan Page Publishers
2002
Pg. 52:
You have to speculate to accumulate — unless you are prepared to take higher risks with your money, you will have no chance of making a greater return than the typical “safe investment.”