“To be old and wise, you must first be young and stupid” is a saying that has been printed on many images. “Quote: ‘To be old and wise you must first be young and stupid’” was posted on the newsgroup rec.motorcycles on September 27, 1995.
 
Authorship is unknown. In 1999, it was described as “one of the best sayings ever from some xtreme sports ad I saw.”
   
     
Google Groups: rec.motorcycles
Anyone make a 10W40 synthetic?
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9/27/95
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Quote: “To be old and wise you must first be young and stupid”
 
Google Groups: rec.motorcycles
Polaris to build sportbikes(and other rumors)   
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11/30/95
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“To be old and wise, you must first be young and stupid.” -Unknown                          
 
Google Groups: rec.autos.sport.f1
Genuine question on overtaking (F1 v Champ)
Andrea Cocchiglia
5/17/98
(...)
Andrea Cocchiglia      
To be old and wise, one must first be young and stupid.
School of Comp. Sci. & Soft. Eng., Monash University, Melbourne, Australia
 
Google Books
Diary of a Junior Year
By Anonymous, Scholastic, Inc. Staff
New York, NY: Scholastic, Inc.
1999
Pg. 173:
Which makes me think of like one of the best sayings ever from some xtreme sports ad I saw: “To be old and wise you must first be young and stupid.” ha ha.
 
Google Books
Pushing Forward:
A Memoir of Motivation
By Randy Snow and Bal Moore
Dubuque, IA: Kendall/Hunt Publishing Company
2001
Pg. 235:
To be old and wise, you must first be young and stupid.
   
13 March 2001, Buffalo (NY) News, “Frontier High School” by Lauren Zaklikowskim pg. N2:
“In order to be old and wise, you must first be young and stupid.”
 
Google Books
3,300 Miles for Christ
By Nick Della Valle
Xulon Press
2004
Pg. 36:
We had recently seen a bumper sticker that said, “Before you can be old and wise, first you must be young and stupid!”
 
Google Books
Young at Heart:
Keeping a youthful sense of fun
By Tom Burns
Hauppauge, NY: Barrons
2006
Pg. ?:
To be old and wise you must first be young and stupid.
 
Google Books
Pure Gold:
Bobby Bowden
By Steve Ellis and Bill Vilona
Champaign, IL: Sports Publishing, LLC
2006
Pg. 39:
There is a great saying that goes, “To be old and wise you must first be young and stupid.”
 
Twitter
Jake Finkelstein‏
@tundro
best quote of the day “in order to be old and wise you must first be young and stupid”
2:55 PM - 28 Jun 2008
   
Google Books
Food For Thought:
A Collection of Quotes
By Pam Pottorff
BookBaby
2015
Pg. ?:
In order to be old and wise, one must once be young and stupid.