“America is where a young man can start at the bottom and work his way into a hole” is a jocular one-line saying that has been cited in print since at least 1963. It originated in the “Pepper and Salt” column off The Wall Street Journal.
 
 
26 July 1963, The Press-Courier (Oxnard, CA), pg. 8, col. 7:
Dig We Must
America is where a young man can start at the bottom and work his way into a hole.
 
Google Books
The Light Touch;
Verse, epigrams, aphorisms and jokes selected from the Pepper and Salt column of the Wall Street Journal
By Charles Preston
Chicago, IL: Rand McNally
1965
Pg. 83:
America is where a young man can start at the bottom and work his way into a hole.
Savoir Faire
 
13 June 1973, Waterloo (IA) Daily Courier, pg. 18, col. 1 ad:
America is where a young man can start at the bottom and work his way into a hole.
(Stop ‘n Shop markets.—ed.)
 
Google Books
Phillips’ Treasury of Humorous Quotations
By Bob Phillips
Wheaton, IL: Tyndale House Publishers, Inc.
2004
Pg. 11:
America is where a young man can start at the bottom and work his way into a hole. — Wall Street Journal
 
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Griffin.
‏@chrisssgriffin
America is where a young man can start at the bottom and work his way into a hole.
2:00 PM - 11 Mar 2013