Jay-Z is not a businessman. He's a business, man.

Since 1995, as one of the cofounders of Roc-A-Fella Records, along with Damon Dash and Kareem "Biggs" Burke, Hov has been a boss in the rap game. In his over 25-year career, the hip-hop mogul has maintained a successful trajectory both in music and business that only a few rap artists have accomplished.

Let's begin with one of Jay's biggest achievements: the first-ever billionaire in hip-hop (and no, it wasn't Dr. Dre). But before that, the Brooklyn rhymer has been making boss moves in his career. One of his first was his appointment of president and CEO of Def Jam Recordings in 2003. Several years later, Jay secured a multimillion deal with Live Nation to form Roc Nation.

Hov also achieved success in the digital space. In 2013, he secured an unprecedented $5 million Samsung deal to release his album Magna Carta Holy Grail exclusively on their smartphones. Two years later, Jay threw his hat into the competitive streaming game with the launch of his streaming platform Tidal.

Musically, Jay also accomplished something that will undoubtedly continue to generate wealth for him—owning his master recordings. By owning his music catalog, the rap veteran can decide what he wants to do with music and profit from it.

Outside of his business dealings, Jay-Z has also put his time, money and energy in helping his fellow rappers with social causes. In February of 2019, Jay-Z provided an attorney for 21 Savage when he was detained by Immigration and Customs Enforcement (ICE) for being an illegal immigrant. In that same year, he also assisted in Meek Mill's crusade for criminal justice reform.

It's clear Hov has accomplished a lot in his illustrious career. So XXL highlights Jay-Z's biggest boss moves.

  • Signs 10-Year $200 Million Live Nation Deal

    Back in 2008, Jay-Z secured a historic 10-year, $150 million deal with touring giant Live Nation and in the process, also established his management/touring imprint Roc Nation. Nine years later, in May 2017, Jay-Z renewed his partnership with Live Nation and inked a 10-year touring deal worth a reported $200 million. The pact consists of Live Nation producing and promoting all of Hov’s concerts for a decade.

    “Live Nation and I entered unchartered territory in 2008," said Jay in a statement at the time. "Over nine years, we have traveled the world producing historic music experiences. For the next 10 years, we will continue redefining the live event landscape."

  • Secures $5 Million Deal With Samsung

    When it comes to technology, Jay-Z always likes to stay ahead of the trends. In July of 2013, the hip-hop mogul partnered with Samsung to have his 12th solo album, Magna Carta Holy Grail, be released exclusively on their Galaxy phones. The unprecedented partnership, worth a reported $5 million, guaranteed that Hov would go platinum in one day.

    For Samsung, the deal makes their device more than just a phone, but a music player as well. At the time, this cultural shift in music may have been the catalyst for Jay-Z to invest in another form of technology that was also on the horizon—digital streaming.

  • Becomes a Billionaire

    In June of 2019, Jay-Z officially became the first-ever hip-hop billionaire. According to Forbes magazine's report, the rap mogul amassed his empire by his various music businesses including Roc Nation and Tidal, and investing in companies like Uber. Jay’s other profitable assets include his music catalog worth $75 million, his $70 million art collection, his $100 million D’Ussé cognac partnership with Bacardi, his $310 million stakes in Armand de Brignac champagne and real estate at $50 million. He also has 14 No. 1 albums, 22 Grammy awards, and made an estimated over $500 million in pretax earnings in a decade.

  • Appointed President and CEO of Def Jam Recordings

    After announcing his retirement in 2003, Jay-Z became a label boss with his position as president and CEO of Def Jam Recordings on Dec. 8, 2004, just a few days after his 35th birthday. The move from artist to CEO came with a price: Jay, along with his business partners Dame Dash and Kareem "Biggs" Burke, sold their remaining shares in Roc-A-Fella to Island Def Jam for a reported $10 million. The deal reportedly left Dash and Biggs at odds with Hov for many years thereafter. Jay-Z held the position of Def Jam president and CEO for three years before resigning in 2007.

  • Acquires Streaming Service Tidal

    On March 30, 2015, Jay-Z officially threw his hat in the competitive streaming wars with the launch of Tidal, his pro-artist, digital streaming service. Hov enlisted some of his famous friends like Kanye West, J. Cole and Nicki Minaj to add their support to his new business venture. Although Tidal got off to a slow start, the streaming service touts over 3 million subscribers who have access to a library of over 60 million songs. What’s unique about Tidal is that artists receive a bigger slice of the royalties from streaming than other platforms. For Jay-Z, this was a boss move to help level the playing field for music artists in all genres.

  • Secures Prince's Music to Stream on Tidal

    For years, Prince refused to have any of his music be available on any digital platform. When Jay-Z launched his Tidal streaming service, the late Purple One was interested in having his music catalog on the platform. Unfortunately, following Prince’s untimely death in April 2016, his estate blocked Hov from acquiring his music on the platform. After a lengthy legal battle, Jay was allowed to add Prince’s albums on Tidal.

    "[Prince] came to me and said 'I know what you are doing and I'm going to give you all of my work,' Jay told Van Jones about his relationship with the late music icon on CNN in 2017. "A person who fought for their work their whole entire life to come to my office and say, 'I know what you are doing, here,' it was a really deep thing for me."

  • Gets All His Master Recordings Back

    One of Jay-Z's most prized assets is his music catalog. Legally, by owning his master recordings, Hov can decide what he wants to do with his music. In March of 2003, Jay shrewdly negotiated the return of his masters when he became the president and CEO of Def Jam.

    However, Jay had to engage in a contentious legal battle against former Roc-A-Fella Records engineer Chauncy Mahan over the ownership of the masters for his albums The Dynasty: Roc La Familia and The Life and Times of S. Carter. In April 2015, Hov victoriously won back his legal rights and now owns all of his master recordings. Jay-Z’s music catalog is now reportedly worth $75 million.

  • Rakes In $253.5 Million in Sales for On the Run II Tour

    Being a boss requires putting in some work outside of the office. For Jay-Z, that's hitting the road on major tour outings. In June of 2019, the Roc Nation mogul teamed up with his wife, Beyoncé, who's a boss herself, and launched the On the Run II tour. The four-month-long trek was a massive success. Altogether, the power couple performed 48 shows—18 in Europe and 30 in North America—and earned a whopping $253.5 million. That's double of what Jay and Bey made on their first On The Run tour in 2014, which brought in $109.6 million from 980,000 tickets sold.

  • Sells Rocawear for $204 Million

    Throughout his career, Jay-Z dabbled in various business ventures, including fashion. Rocawear was the clothing line he cofounded in 1999 along with his Roc-A-Fella Records partners Damon Dash and Kareem “Biggs” Burke. At one time, the apparel company was grossing over $700 million in annual retail sales. In March 2007, Jay sold the rights to Rocawear for $204 million in cash to the Iconix Brand Group.

    Twelve years later, Jay bought back the intellectual property from Iconix for $15 million in November 2019. Essentially, Hov now owns the Rocawear brand name. For Jay-Z, being a boss is also about making the right financial moves when you have the capital.

  • Squashes Beef With Nas

    In terms of historic rap beefs, nothing compares to the fierce lyrical feud between Jay-Z and Nas. Both rap veterans delivered classic diss songs will forever remain one of the memorable beefs in hip-hop. But on Oct. 27, 2005, at Power 105.1's annual Powerhouse concert, the two bosses officially squashed their beef in front of 15,000 people. The moment was a memorable showing of solidarity and brotherhood.

    "It was always respect, it wasn't a point where he wanted to gun me down or I wanted to gun him down, it was never that, 'cause that's not how I think real bosses move," Nas told MTV in 2006. "I'm a fan of rap."

  • Establishes Shawn Carter Foundation to Help College Students

    In 2002, Jay-Z launched the Shawn Carter Foundation with his mother, Gloria Carter. The nonprofit organization's mission is to help students further their education at colleges and historically Black Universities through scholarships and grants. Back in November of 2019, the Shawn Carter Foundation held its inaugural benefit gala at the Seminole Hard Rock Hotel and Casino in Hollywood, Fla.

    Celebrities like Alicia Keys, Swizz Beatz, Meek Mill, DJ Khaled, Fabolous, Yo Gotti and more were in attendance. The gala raised $6 million, which will go to funding college prep workshops and bus tours like the foundation's annual Black college bus tour.

  • Helps 21 Savage Get Out of ICE Custody

    A great trait of a true boss is the ability to help others and provide resources. In February of 2019, Jay-Z came to 21 Savage's aid after he was detained by Immigration and Customs Enforcement (ICE) for being an illegal immigrant. The Roc Nation mogul hired attorney Alex Spiro to work on Savage's case. The Atlanta rapper was eventually released after spending nine days in detention.

    "In addition to being a successful recording artist, Savage deserves to be reunited with his children immediately," Jay-Z said in a press release. 21's mother, Heather Carmillia Joseph, would later thanked Jay, as well as other rappers who have come to his son's defense.

  • Earns Rare Billboard Hot 100 Chart Distinction

    In July of 2019, Jay-Z accomplished a major milestone in his illustrious music career. On the Billboard Hot 100 chart, the hip-hop icon became the fourth rapper to earn 100 career solo appearances and the sixth artist with 100 solo appearances in the 60-year existence of the Hot 100 chart. During his career, the rap veteran hit No. 1 on Hot 100 chart four times beginning with "Heartbreaker" with Mariah Carey in 1999, "Crazy in Love" (with his wife Beyoncé) in 2003, "Umbrella" with Rihanna in 2007, and "Empire State of Mind" with Alicia Keys in 2009. Jay-Z's first appearance on the Hot 100 chart came in April of 1996, with the classic bangers "Ain't No Nigga" featuring Foxy Brown and "Dead Presidents."

  • Holds Retirement Concert at Madison Square Garden

    On Nov. 25, 2003, Jay-Z held his farewell concert at Madison Square Garden in New York City. At the time, Hov announced he was retiring from the rap game and wanted to give his fans one last show. Music superstars Missy Elliott, Beanie Sigel, Memphis Bleek, Foxy Brown, Mary J. Blige and Jay-Z's wife-to-be Beyoncé also hit the stage to give Jigga a major send-off into retirement. The historic event was documented for the concert film Fade To Black, which arrived in theaters a year later. "This is a journey for a kid from Brooklyn to play the biggest stage in the world," said Jay about the film in a 2004 interview with Movieweb.

  • Comes Out of Retirement in 2006

    Three years after announcing his retirement and becoming the president and CEO of Def Jam Recordings, Jay-Z returned to the rap game with Kingdom Come. The set’s first single was the anthemic banger “Show Me What You Got." Hov had the urge to drop a new project because he felt that the rap industry was getting boring and needed an "event album." “

    Right now in hip-hop, there’s a lot of disposable music, and I believe the genre will suffer unless you have an event album,” he told XXL in November 2006. “Unless you have a [Dr. Dre Detox album], unless you have an Eminem or Nas album, you have to have those events in hip-hop.”

  • Secures $1.5 Million for Barclays Center Stake

    In 2009, Jay-Z invested $1 million into the Brooklyn Nets basketball franchise. Although he only owned one-fifteenth of a percent of the team, he brought his other investments—Armand de Brignac's champagne Ace of Spade and the 40/40 Club — into the Barclays Center. In April of 2013, after launching his sports agency, Roc Nation Sports, Hov sold his small share in the team to new head coach Jason Kidd for $500,000. Additionally, Jay unloaded his ownership interests in the Barclays Center for $1.5 million. "It was never about an investment; it was about the Nets and Brooklyn. My job as an owner is over but as a fan, it has just begun," said Jay-Z in a statement.

  • Launches Made In America Festival

    Eight years ago, Jay-Z launched his own music festival called Made In America in 2012. The inaugural two-day event was held on Labor Day Weekend and it featured performances from an array of superstar talent including Meek Mill, Drake, Janelle Monae, D’Angelo, Wale, Pearl Jam and Hov, himself. “It's time, and I have a long relationship and love affair with the City of Philadelphia,” Jay told the Philadelphia Inquirer about the festival. “And as a lot of people may know, I signed a lot of artists from here and there's my relationship with Will Smith and James Lassiter in Overbrook to do films. It just...it all came together.”

  • Ventures Into Liquor with D'ussé and Ace of Spades

    Jay-Z’s investment in liquor started back in 2006. After Frederic Rouzaud, the manager of the company that makes Cristal champagne, implied in an Economist magazine interview that he wasn’t fond of rappers promoting their product, Jay called for a boycott of Cristal. Additionally, Hov also saw the opportunity to show the power of hip-hop when it comes to marketing and branding. So he invested in Armand de Brignac’s D'ussé cognac and Ace of Spades champagne and started repping the two brands. Jay’s involvement helped net himself earnings of $100 million annually and also helped boost Armand de Brignac's visibility in the spirits industry.

  • Supports Meek Mill's Criminal Justice Reform

    Jay-Z understands that he has a considerable influence on young people from different backgrounds and ethnicities. When it comes to social issues that pertain to Black people, the rap veteran is there to bring awareness and assist in any way he can. In the case of Meek Mill's long-standing probation issue, Jay has been an outspoken critic of the criminal justice system, even going so far as to pen an op-ed piece for The New York Times. In January 2019, Jay and Meek teamed up to launch Reform Alliance, a new criminal justice reform organization dedicated to making sure that incarcerated people are represented and treated fairly in the legal system.

  • Donates $1 Million to Coronavirus Relief Efforts

    On March 31, 2020, Jay-Z, through his Shawn Carter Foundation, teamed up with Rihanna’s Clara Lionel Foundation, and together donated $1 million each to support those impacted by Covid-19 pandemic. That's a whopping $2 million total. The funds will go to relief efforts for children, undocumented families, homeless people and first responders affected by the health crisis.

    “In times of crisis it is imperative that we come together as one community to ensure that everyone, especially the most vulnerable, has access to critical needs: shelter, health, nutrition, and education," Jay-Z said in a statement. "The only way to get through this pandemic is with love and action."