“Working on making my second million dollars. Gave up on the first million”

“Working on making my second million dollars. Gave up on the first million” is a jocular saying that has been printed on several images. Authorship of the joke is unknown, but it has been cited in print since at least the 1930s.
 
“‘When I started earning my second million,’ says George (he gave up hope of earning the first)” was printed in the Miami (FL) Daily News on November 23, 1932.  “I’m working on my second million now. I didn’t make the first one, so I just started in on the second one” was printed in The Advocate-Democrat (Marysville, KS) on May 10, 1934.
   
         
23 November 1932, Miami (FL) Daily News, “Your Town and Mine” by Ray Krimm, pg. 5, col. 2:
“When I started earning my second million,” says George (he gave up hope of earning the first).
(George Christie, WQAM’s star announcer.—ed.)
 
10 May 1934, The Advocate-Democrat (Marysville, KS), “Fagan’s ALley” by Fagan D. Alder, pg. 2, col. 6:
In Topeka Sunday I asked a friend how he was coming. “Fine,” he said. “I’m working on my second million now. I didn’t make the first one, so I just started in on the second one.” There’s an idea for you. I’m going to give it a trial.
   
5 January 1942, The Daily Argus-Leader (Sioux Falls, SD), “Caffrey’s Corner,” pg. 1, col. 8:
Wal, anyway, I’m working on my second million. Yeh, I’ve given up all hopes of getting my first million.
 
10 April 1960, Grand Prairie (TX) Daily News-Texan, “Prairie Scope” by Charles Lewis, pg. 1, col. 1:
OVERHEARD at a nearby lunch counter: “I’m working on my second million; I finally gave up trying on the first one.”
 
1 June 1964, Register-Republic (Rockford, IL), “Williams New .400 Threat” by The Associated Press, pg. 8B, col. 7:
But Billy (Williams—ed.) might be somewhat like the joker who cracks “I’m working on my second million, I gave up on the first.”
 
Google Books
Judaism
American Jewish Congress
Volume 13
Summer 1964
Pg. 352 (“Braslav in Brooklyn” by Herbert Weiner):
He supports seven children on his Hebrew teacher’s salary but sees no reason to complain: “After all, I’m working on my second million now. With my first million I didn’t make out so good.”
     
9 April 1976, Atlanta (GA) Constitution, “Graham Works on His Second Million” by George Cunningham, pg. 6-E, col. 1:
AUGUSTA—People worry about Lou Graham. Like Rodney Dangerfield, he don’t get no respect around here.
 
“Tell me, Lou,” a reporter said here Thursday after the 1975 U.S. Open champ opened his Masters play with a 68, “did you ever make any money off your big win last year?”
 
Without cracking a smile, the dry-witted Tennessean cracked, “I’m working on my second million after winning the Open. I completely gave up on my first one.”
 
Google Books
The Damgaard Family Album
By Marilyn Macklin
Minden, NE: M. Macklin
1984
Pg. 114:
I am presently working on my second million - I gave up on the first one.
 
Google Books 
Golf Shorts, Par 2:
1,001 of the Game’s Funniest One-liners
By Glenn Liebman
New York, NY: McGraw Hill Professional
1998  
Pg. 142:
“I’m working on my second million. I completely gave up on my first million.”
Lou Graham, asked if he made a million after winning the U.S. Open in 75
 
Google Books
3,650 Jokes, Puns, and Riddles
By Charles Foxgrover, Anne Kostick and Michael J. Pellowski
New York, NY: Black Dog & Leventhal Publsihers, Inc.
1998
Pg. 242:
Hank: How’s business?
Frank: I’m working on my second million.
Hank: That’s great!
Frank: Yeah…I had to give up on the first.
 
Twitter
Lou Serrano
@LouSerrano
Working on making my second million dollars. I never got that first million, so I figure I have some catching up to do. 😊
4:44 PM - 14 Sep 2009
   
Twitter
jerzegurl
@jerzegurl
Working on making my second million.  The first one is too hard to make.
9:57 PM - 31 Jan 2009
   
Twitter
Sean Hryhorchuk
@shryhorchuk
sitting in dispatch. working on making my second million.. gave up on the first million.
10:42 AM - 4 Sep 2009
 
Twitter
Nick MacLeod 🍁
@nicholasmacleod
I’m working on making my second million, I skipped the first million because it was too hard. Hopefully the second is easier.
10:59 AM - 20 Oct 2010
     
The Canadian Jewish News
THE HIGH-FLYING BOOTLEGGER AND BUILDER OF THE 1920S
By Bill Gladstone -  December 18, 2016
(...)
She added, “Reading your short section on my grandfather gives new meaning to my Uncle Milton’s joke: ‘I’m working on my second million – I’ve given up on the first.’”
 
Reddit—Dadjokes
Posted by u/oinkmoomeow April 13, 2019
I’m working on making my second million dollars
I gave up on the first