“Scared money never wins” is a gambler’s adage that was used in New York City in the 1940s and 1950s. The adage has been used in poker, horseracing and (perhaps inevitably) Wall Street.
 
“A scared nickel never made a dime” is a related business adage.
     
   
Answers.com
Poker Guide: Scared Money
This is the money a player brings to a poker game that they are afraid to lose.
SoundPoker Says: The reason for this is often because that player cannot afford to lose any more money. A common saying found in cardrooms is “Scared money never wins”.
     
Newspapers.com
22 March 1942, Sunday News (New York, NY), “Little Old New York” by Ed Sullivan, pg. C28, col. 1:
There is an old and true gambling adage that “scared money never wins.”
 
Newspapers.com
17 June 1943, Daily News (New York, NY), “Little Old New York” by Ed Sullivan, pg. 33, col. 1:
Nick the Greek always fancied the terse comment of a diceman: “Scared money never wins.”
 
Google Books
The Troubled Midnight:
A Novel
By John Gunther
New York, NY: Harper & Brothers
1945
Pg. 120:
Scared Money Never Wins
   
4 August 1950, Uniontown (PA) Morning Herald, “Little Old New York” by Ed Sullivan, pg. 4, col. 7:
There is an old and true gambling adage that “scared money never wins.”
 
20 February 1951, Syracuse (NY) Post-Standard, “Psychologist Declares Poetry May Help Even Crapsshooter,” pg. 1, col. 2:
Some of Dr. Thouless’ experiments appear to bear out old gambling beliefs.
 
One of these is, “Scared money never wins.”
 
Thouless says, “Too strong motiviation tends to result in too much effort and failure results…Effortless intention to succeed seems to me to be the ideal attitude.”
   
13 February 1957, Syracuse (NY) herald-Journal, Walter Winchell column,  pg. 39, col. 4:
BROADWAY ROULETTE: (...) As they say at the racetracks and other gaming places: Scared Money Never Wins.
 
Google Books
The Modern United States Army
By Forrest K. Kleinman and Robert S. Horowitz
Published by Van Nostrand
1964
Pg. 195:
... factor in human conflict as evidenced by such common sayings as, “He was licked before he started,” and the gambler’s maxim, “Scared money never wins.”
   
Penn State Collegian (February 25, 1969)
“I told them about the old gambling saying ‘Scared money never wins,’” Klima said after the meet.
 
Sports Illustrated
April 22, 1985
Back In A Blaze Of Glory
Destroyed by fire, New Jersey’s Garden State Park has been lavishly rebuilt by bustling Robert Brennan
William Leggett
(...)
For his part, Brennan professes to be afraid of nothing, even though reopening Garden State is a gamble. As Brennan often says, “Scared money never wins.”
   
Google Books
How to Be Your Own Stockbroker
By Charles Schwab
Published by Dell Publishing
1986
Pg. 213:
Here, the Investment Sage borrows a word of advice from the professional gambler: “Scared money never wins.”
   
Google Groups: alt.sport.horse-racing-systems
Newsgroups: alt.sport.horse-racing.systems
From: .(JavaScript must be enabled to view this email address) (Zuke)
Date: 1998/11/06
Subject: Re: Juke HELP!!!!
 
Remember scared money never wins anything.
 
Google Books
Scared Money Never Wins
By Julia Wendell
Published by Finishing Line Press
2004