(State of mind)
AY-Z went from hustling drugs on street corners to the corner office of his business empire that's now worth an incredible half a BILLION dollars.
The world's most successful rapper has had 11 No1 albums in the US charts, won 13 Grammys and is married to pop megastar Beyonce.
Only seven chief executives make more than him in a year. Last year his £38million earnings even topped that of the boss of Starbucks.
That fortune was simply from selling 50million albums.
Over the years he has launched 9IX cologne, Rocawear clothes and Reebok S.Carter trainers.
He also has a share in the New Jersey Nets basketball team, The Spotted Pig restaurant in Manhattan's West Village, a female beauty products brand and the 40/40 Club chain.
And according to a new unauthorised biography the 41-year-old star has an obsession with money that stems from his insecurity with girls.
Jonathan "Jaz-O" Burks, who knew the star when he was a teenager, said: "He felt he needed money because he didn't feel like he was the most attractive guy to girls. I think he had a serious complex about his features."
In his lyrics Jay-Z often boasted of bedding lots of women, but that didn't stop Methodist churchgoer Beyonce from marrying him in 2008.
His friend Chenise Wilson believes Jay-Z actually cares for women and that his raps are just bravado.
Chenise said: "There were girls around, but that wasn't his thing, being in girls' faces.
"He had his share but he wasn't the kind of guy with a whole lot of girls. Jay is a very particular guy."
The revelations come in the book Empire State Of Mind, by Zack O'Malley Greenburg, who writes for Forbes magazine.
Jay-Z was born Shawn Corey Carter and grew up in a tough housing project in Brooklyn, New York.
Crazy in love ... Beyonce and Jay-Z in New York earlier this year
Photoshot / Frank Ross Media
Record producer Jaz-O gave Jay-Z some of his earliest breaks in the music industry. But as his protege became more famous, his interest in his old friend waned. Jaz-O says: "His loyalty is to his money."
DJ Clark Kent, who first spotted Jay-Z's talents as a 15-year-old with the nickname Jazzy, added: "I think it's unfair to call Jay-Z a rapper.
"He is a business, and rapping is just something that's in his business."
That ethic can be traced back to when he was still known as Shawn.
Kent said: "When you grow up in the hood, fast money is all you can think of because of the pressure.
"You're in a building of 500 people. You do whatever you can to get out."
Jay-Z started off doing very well at school. But when his father Adnis Reeves abandoned his family in 1980 his ten-year-old son took it badly. He never graduated from school and was instead educated on the street.
His friend DeHaven Irby got him into selling cocaine at the age of 18.
Even back then it was all about dollars for Jay-Z, who broadened their patch to Maryland and Virginia, where there was less competition.
DeHaven said: "Customers knew he was about business. If the product was ten dollars, you couldn't get it for nine dollars. A lot of people thought of him as being stingy."
At the age of 17 he even shot his older brother in the shoulder because he had stolen one of his rings.
Talented ... Jay-Z with MTV awards
Despite being a talented rapper Jay-Z was reluctant to do it full-time because dealing was more profitable. His attitude changed in 1994 when another gangster shot at him. DeHaven said: "He saw the bad side of the game. He almost had his life taken. That's what did it."
Later that year Jay-Z met wealthy impresario Damon Dash, who helped him record his first album Reasonable Doubt. It was rejected by all the major labels. Undeterred, the two men put together their own label, Roc-A-Fella Records, and sold the album out of the back of their cars.
It went platinum. Afterwards he was able to strike a deal whereby he earned twice as much as most artists from his album sales.
By December 1999 Jay-Z was a hip-hop star. But his old ways reared up again in an ugly manner.
He stabbed his former friend Lance Rivera in the stomach, allegedly because he thought Rivera was bootlegging one of his albums.
The star was fortunate to get away with three years probation. From then on he did not trouble the law again.
In 1999 Jay-Z and Dash launched the Rocawear clothing line because they were tired of boosting sales of other clothes lines by wearing them.
Everything was cross-marketed.When Reebok released the S.Carter trainers in 2003 snippets of tracks from Jay-Z's new Black Album were included on a CD in the shoe box.
Street-wise ... Jay-Z at school
Dash is credited by many with being the original business brains behind much of Jay-Z's early success.
But in 2004 they parted because they could not agree on a deal. Dash, 40, was surprised to see how the once trainer-loving street star now dressed liked a serious city man.
He said: "We were two different people. He was not the same person I had met. I would never expect him to wear a trench coat and shoes."
In January 2005 Jay-Z took over as president of the once legendary Def Jam record label, which at that time was fading. Again he was a success.
One of his first signings was Rihanna.
Some of Jay-Z's investments are made with the heart. He is a huge basketball fan, so buying a share of the New Jersey Nets combined a personal passion with wealth creation.
Jay-Z has also given something back by setting up the Shawn Carter Scholarship to help underprivileged kids and by getting behind a project to improve water quality in Africa.
And Def Jam Records founder Russell Simmons believes that Jay-Z has done a lot for music.
He said: "Without Jay-Z, hip hop wouldn't be where it is today."
Jay-Z has now left Def Jam and has his own music publishing and entertainment company, Roc Nation.
But some former friends still believe the rapper's desire for wealth has become all-consuming.
Jaz-O concluded "Some people have the wherewithal to put things in proper perspective and some people become maniacal.
"I think in his case, to an extent, he became maniacal."
