The Hip-hop Mogul Is Dead

I still remember the summer of 2016 when the XXL Freshman Class dropped. They got it right—it felt like a new era of hip-hop was being ushered in. I had been a fan of Uzi since I heard “Top” for the first time. I think I found out about the song from a tweet. My younger cousin gets the credit for introducing me to Kodak Black—the first song I heard was definitely “Skrt”. Now, when Yak drops, I listen. Simple. Like a lot of people, “One Night” was my introduction to Lil Yachty. 21 Savage’s “Dip Dip” was my intro to the Slaughter King and I have one of my best friends Braxton to thank for that.

These artists all hold a special place in my memory because their music came at a pivotal time in my life—songs that were the soundtrack to my college years. I believe their music represented the sound of the future. They’ve all had an influence on what hip-hop sounds like today, and as a fan, it’s been incredible to watch their journeys unfold over the years.

Even now, they continue to make waves. Yachty surprised everyone last year with Let’s Start Here, an experimental album that dabbles in psychedelic rock—a bold move that shows his willingness to evolve. He dropped Bad Cameo with James Blake this year—I didn’t listen to it but I’m sure it’s decent. It’s hard for Yachty to miss.

Kodak kept us fed with not one, but two projects: Dieuson Octave, a deeply personal reflection on his life, and Trill Bill, which brought back his signature gritty sound. Last year Uzi gave us Pink Tape, a genre-blending project that reminds us why they’ve stayed ahead of the curve—this year he releases Eternal Atake 2, which I did a review on. 21 teamed up with Drake on Her Loss and later dropped American Dream, cementing his growth as both a lyricist and a global artist.

I’m proud to see how far they’ve come. But I can’t help but wonder: what’s next? Will these artists go beyond music and become cultural icons? Will they create TV shows, start billion-dollar companies, or redefine success in hip-hop? Or will they focus solely on music and let that be their legacy? These questions lead me to explore the future of hip-hop and whether we’ll ever see another era of hip-hop tycoons who build business networks outside the booth.

What Defines a Hip-Hop Mogul?

Before we delve into the details, let’s define the term “hip-hop mogul.” A hip-hop mogul goes beyond mere musical success. As Captains of the Industry—they leverage their influence to build comprehensive empires that significantly impact culture and the industry. These visionaries extend their reach into various sectors, such as fashion, media, technology, and beyond, revolutionizing the boundaries of hip-hop’s influence. This is a nod to the Jay-Zs and 50 Cents of the world. Let’s take a look at three hip-hop business leaders that all have more than a few things in common.

Jay-Z: The Blueprint of Diversification

Shawn “Jay-Z” Carter exemplifies the archetype of a hip-hop mogul through strategic diversification:

Roc-A-Fella Records: Founded in 1995, Roc-A-Fella became a powerhouse, launching Jay-Z’s career and those of artists like Kanye West.

Rocawear: Established in 1999, this clothing line capitalized on urban fashion trends, reportedly generating annual revenues of $700 million at its peak.

Roc Nation: Launched in 2008, Roc Nation expanded into a full-service entertainment company, managing artists, athletes, and producing content across various media.

Tidal: Acquired in 2015 for $56 million, Tidal aimed to provide high-fidelity streaming and artist ownership. In 2021, Jay-Z sold a majority stake to Square, Inc. (now Block, Inc.), valuing the company at $297 million.

Armand de Brignac (“Ace of Spades”) Champagne: Jay-Z’s investment in this luxury champagne brand culminated in selling a 50% stake to LVMH in 2021, enhancing its value to $640 million.

These ventures propelled Jay-Z’s net worth to approximately $2.5 billion as of December 2024, according to Forbes.

Sean “Diddy” Combs: Building a Lifestyle Empire

Diddy expanded his influence through diverse business endeavors:

Bad Boy Records: Founded in 1993, Bad Boy was instrumental in the careers of artists like The Notorious B.I.G., significantly impacting 1990s hip-hop.

Sean John: Launched in 1998, his clothing line redefined urban fashion, earning the CFDA Menswear Designer of the Year award in 2004. Diddy reacquired the brand in 2021 for $7.55 million to revitalize it.

Cîroc Vodka: In 2007, Diddy partnered with Diageo to oversee marketing for Cîroc, transforming it into a leading premium vodka brand. This partnership reportedly brings him $60-70 million annually.

Revolt TV: Founded in 2013, Revolt TV is a music-focused cable network targeting young, urban audiences, valued at around $200 million.

These moves contributed to Diddy’s estimated net worth of $1 billion as of 2023.

Kanye West: Redefining Fashion and Music

Kanye West’s business dealings showcase his innovative approach:

GOOD Music: Founded in 2004, his record label has signed prominent artists, influencing contemporary hip-hop.

Yeezy: Launched in collaboration with Adidas in 2015, Yeezy became a cultural phenomenon, with the partnership valued at up to $1.5 billion. However, in 2022, Adidas terminated the partnership following West’s controversial remarks, leading to significant financial repercussions.

The Double-Edged Sword of having mass Influence in the Industry

While they have achieved remarkable success and built powerhouses that reshaped industries, their prominence has often subjected them to intense controversies, and legal challenges, which have threatened to overshadow their legacies:

Kanye West: Despite his status as a trailblazer in music, fashion, and business, Kanye’s 2022 antisemitic remarks had a seismic impact on his career and finances. Major partnerships, most notably with Adidas, were abruptly terminated, leading to significant financial losses. The collapse of the Yeezy-Adidas partnership—that marked a sharp decline in his billionaire status and highlighted the fragility of even the most successful ventures under public backlash.

Diddy: He is currently incarcerated following his 2024 arrest on federal charges, including sex trafficking, racketeering, and other offenses. This arrest comes amid a series of allegations, including a 2023 lawsuit filed by his ex-girlfriend Cassie Ventura accusing him of abuse and coercion. Diddy’s legal troubles have shaken his once-untouchable reputation, with his business ventures and partnerships facing significant disruption. Being held without bail at the Metropolitan Detention Center in Brooklyn, Diddy’s future in the entertainment and business world remains uncertain as he awaits trial in 2025.

Jay-Z: Known for his visionary investments in music, sports, and technology, Jay-Z’s impeccable business record has not been without challenges. Recent allegations—though unverified and firmly denied—have raised questions about his personal and professional dealings. While his legacy as a cultural icon is still intact—these claims illustrate how even the most respected figures are not immune to the court of public opinion, which can have lasting effects on business interests and reputation.

These incidents underscore the precarious nature of becoming a hip-hop billionaire, where personal actions can have a profound impact on business. The convergence of personal controversies and business interests raises questions about the long-term viability of the hip-hop mogul archetype in today’s media landscape.

As the industry evolves, aspiring artists may reevaluate their pursuit of building expansive brands beyond rap—weighing the potential rewards against the risks of public scrutiny and personal controversies. This shift could reshape success in hip-hop, emphasizing artistic integrity.

Hip-hop has always been about pushing boundaries, but as the culture evolves, so too must its definition of success. The hip-hop entrepreneurs of the past demonstrated what was possible, but the question now is whether the next generation will learn from their triumphs and mistakes—or abandon the pursuit and stick to just making music.

So, What Lies Ahead for the Hip-hop Freshmen of 2016?

Each of them has carved out their own unique path, mastering their craft and solidifying their influence within hip-hop and beyond. Their creative achievements are undeniable, from chart-topping albums and viral singles to shaping culture through their distinct styles, sounds, and personas. However, as they continue to dominate the music scene, a deeper question arises: could they—or even should they—aspire to become the next generation of hip-hop industrialists?

21 Savage: Quietly Building Potential

Savage has shown glimpses of mogul-like potential. His financial literacy initiative, the “Bank Account” campaign, reflects a keen awareness of community-building. Definitely a key in building an empire. His efforts, however, remain under the radar, signaling that 21 may not prioritize publicizing his ventures as part of a larger brand.

Could he lean into his growing maturity to build a legacy beyond music? Absolutely. With his reputation for thoughtful lyrics and his growing credibility as a philanthropist, 21 Savage has the groundwork to build platforms that could outlast his music career. The question is: does he want to? His laid-back persona suggests he might be content letting his actions speak quietly, rather than pursuing the larger-than-life image.

Lil Yachty: The Creative Wildcard

Yachty has always been the wildcard of the group, blending eccentric creativity with calculated risks. His ventures into film, fashion, podcasting, the Concrete Boys collective and even psychedelic rock with Let’s Start Here suggest a willingness to break boundaries. But does he have the consistency to maintain an executive -level organization?

Yachty’s image—fun-loving, experimental, and somewhat unpredictable—might work against him in building the kind of professional gravitas associated with leaders like Jay-Z or Kanye West. However, his approach could redefine what it means to be a mogul altogether. Instead of building traditional business empires, Yachty could succeed in creating niche cultural movements, offering a more fragmented yet still impactful kind of influence. I can definitely see Yachty at that status.

Lil Uzi Vert: A Generational Icon

Lil Uzi Vert arguably has the strongest cultural presence of the group. Their fashion-forward image and genre-bending music have cemented them as a generational superstar. But building an enterprise often requires a shift in focus—from cultivating personal fame to creating sustainable businesses or platforms that extend influence beyond music.

While Uzi’s brand is undeniable, it remains tied closely to their persona. They haven’t demonstrated interest in diversifying their success. Could they step into industrialist territory? Absolutely, especially in spaces like fashion or digital culture. But it’s unclear whether Uzi has the desire—or the need—to expand their brand in that direction. They seem to be focused purely on music.

Kodak Black: Talent & Turmoil

Kodak’s influence is undeniable, but his frequent legal troubles have held his career back. His raw talent and storytelling ability make him a cultural force, but big business requires discipline, long-term vision, and a reputation that instills trust in business partners.

Could Kodak become a mogul? Theoretically, yes. His fan base is loyal, and his street credibility is unmatched. However, until Kodak addresses the issues that continue to derail his career, his potential as a force in business will remain unrealized.

Do They Even Want to Be Moguls?

A broader question emerges when considering their paths: do they even want to follow in the footsteps of Diddy, Jay-Z, or Kanye West? The mogul archetype requires relentless ambition and a willingness to operate in spaces beyond music—where high stakes are the norm.

For some, the benefits of becoming a tycoon are clear: financial independence, generational wealth, and cultural influence. For others, the trade-offs—loss of creative freedom and constant public surveillance—might not seem worth it. In an era where streaming and social media offer income sources, today’s artists might feel less compelled to diversify into traditional ventures.

Could They Do It Better?

If this class does pursue the big brand identities, they could potentially redefine it for a new era. Instead of building networks based on traditional industries like fashion and liquor, they might leverage emerging fields like technology, gaming, or virtual experiences. For example, Uzi’s futuristic image aligns with NFT culture, while Yachty’s experimental nature could lead to innovative content platforms. I can see 21 Savage being a pillar in financial literacy and creating a huge business.

Their youth and cultural relevance give them an edge, but they’d need to shift focus from individualism to broader ventures that empower others. The possibility is there, but whether they seize it remains to be seen.

A Redefined Mogul?

As we consider the potential for this generation, it’s worth pondering whether they even need to follow the established blueprint. In a world where influence is more decentralized and direct, these artists might establish smaller, more agile enterprises rather than attempting to replicate the expansive companies of their predecessors.

In the end, their legacy might not be about becoming businessmen in the traditional sense, but about proving that success can be defined on their own terms—whether that means dominating charts, shaping culture, or quietly empowering their communities. For now, their journeys remain a fascinating glimpse into what the future of hip-hop influence might look like.

Beyond the 2016 Class: Drake, J. Cole, and Kendrick Lamar

When we expand the conversation to Drake, J. Cole, and Kendrick Lamar—the defining stars of the last decade—the same questions arise. Can these three be considered hip-hop moguls, or do they represent a new kind of success in the industry?

Drake, arguably the world’s biggest artist, has turned OVO into a powerful brand encompassing a record label and a clothing line, but his ventures feel more rooted in his persona than in dynasty. He has the reach, the resources, and the influence to expand far beyond music—but perhaps his focus is part of his formula for staying at the top of the game.

Adding to this, J. Cole recently announced that the 2025 edition of his Dreamville Festival will be the fifth and final event. Launched in 2018, the festival quickly became a cultural staple, drawing over 100,000 attendees from across the globe. Its conclusion marks the end of a significant chapter in J. Cole’s career, raising questions about his future endeavors beyond music. He has launched his podcast series Inevitable, which has gained positive reviews. I don’t know if this is a step toward building a global brand though.

Kendrick Lamar, known for his introspective artistry, co-founded pgLang, a multidisciplinary media company. While its full scope remains somewhat enigmatic, pgLang aims to encompass music, film, and other creative projects, indicating Kendrick’s interest in broader cultural influence. However, it hasn’t yet reached the commercial heights.

This suggests a shift in priorities among today’s hip-hop elites. Drake, J. Cole, and Kendrick seem to value creative freedom and maintaining control over their artistic output. It’s possible they’ve observed the pitfalls that come with getting too big—the legal battles, the pressure to succeed in industries where the odds aren’t always favorable. Kanye West’s public struggles, Jay-Z’s recent controversy, and Diddy’s legal challenges serve as reminders that it isn’t just about ambition; it’s about navigating immense risk.

There’s also the question of whether they feel a responsibility to take on the mantle. J. Cole and Kendrick, in particular, seem driven by their art and messaging rather than a need to dominate. This could be their redefinition of success: one that prioritizes depth over breadth, impact over empire. But does hip-hop lose something without artists striving to build larger-than-life brands? Can the genre sustain its global influence without figures who seek to own the boardrooms and redefine industries?

It’s worth noting that the industry itself has changed dramatically since the early 2000s. The rise of streaming and social media means artists can reach millions without the infrastructure that entrepreneurs of the past relied on. Yet, this decentralized power also means there’s no single figure who can claim to represent hip-hop’s dominance across industries. Drake, Cole, and Kendrick may be the biggest names of their generation, but whether they’ll leave a legacy as expansive as their predecessors remains an open question.

As hip-hop evolves, so do its definitions of success. Perhaps Drake’s ability to remain a global superstar, Kendrick’s dedication to crafting timeless narratives, and J. Cole’s commitment to fostering talent are forms of the modern tycoon. But it’s hard not to wonder: if they don’t aim to carry the torch of industry dominance, who will?

The Evolving Hip-Hop Economy

The hip-hop industry has experienced remarkable growth, with revenues projected to reach $95.4 billion globally by 2025. In the U.S. alone, hip-hop albums accounted for 31% of all music sales in 2020, highlighting the genre’s dominance in the cultural and commercial landscape.

However, the decline in artists reaching corporate status could signal a shift in hip-hop’s economic trajectory. Legends like Dr. Dre, Russell Simmons, Diddy, 50 cent and more not only expanded hip-hop’s influence but also built economic ecosystems that provided opportunities for other artists and entrepreneurs. Their ventures into fashion, technology, and media transformed hip-hop from a music genre into a multifaceted global industry.

Without new artists stepping into these expansive roles, hip-hop risks becoming confined to music alone, potentially limiting its cultural and economic impact. The absence of new figures could mean fewer platforms for emerging artists and a diminishing influence across various industries.

With hip-hop having celebrated its 50th anniversary, it’s essential to consider its future. Does the genre need new moguls to carry the torch, or can it sustain its growth through a collective of independent artists? The answer will shape the trajectory of hip-hop for decades to come.

Jay-Z once said, “I’m not a businessman; I’m a business, man.” This statement encapsulates the essence of hip-hop’s potential beyond music. Yet, as the industry evolves, the question still remains: Who will rise to embody this ethos for the next generation?

Looking at the 2016 XXL Freshman Class and today’s biggest stars, it’s clear that a new generation of talent has emerged—but not necessarily moguls… The ambition to dominate not just music, but also business and culture, seems less prevalent. Is it fear of scrutiny? A shift in priorities? Or something deeper—an unspoken warning about what happens when you get too big in hip-hop?

There’s a troubling pattern worth acknowledging. The moment a hip-hop figure achieves certain heights—becoming not just rich, but a billionaire—they seem to attract an unprecedented degree of conflict. Kanye West, Diddy, and Jay-Z have all faced serious allegations at the height of their businesses. While justice should absolutely be served where it’s due, the timing and frequency of these takedowns are hard to ignore.

Kanye lost billions when his Adidas deal collapsed in the wake of his antisemitic comments. Diddy’s empire is now under fire following a wave of allegations, beginning with the explosive lawsuit from Cassie. Jay-Z, whose business acumen once seemed untouchable, now faces public backlash from recent accusations. It feels as though hip-hop, as it celebrates its 50th anniversary, is also witnessing the dismantling of some of its most prominent figures.

While they must be held accountable for their actions, there’s a larger question about why these figures face such immense public and legal pressure compared to billionaires in other industries… Is it the intersection of hip-hop, race, and wealth? Does the audacity of a Black “bigwig” threaten systems that were never built to accommodate them?

For those like 50 Cent, who once symbolized the hustler-turned-executive dream, this should serve as a cautionary tale. Build your conglomerate—but better not aim for billionaire status, because that seems to be the threshold where the gloves come off.

As for the future? It’s hard to imagine another era like the one shaped by Diddy, Jay-Z, and Kanye. The biggest stars of today—Drake, J. Cole, and Kendrick Lamar—don’t appear interested in building sprawling empires. Their focus is firmly on their artistry, not creating the multi-industry businesses. And if they’re not headed in that direction, it’s even harder to see it happening for the Lil Uzis, Kodaks, or 21 Savages of the world.

Perhaps this shift isn’t just about fear or scrutiny—it’s about hip-hop evolving into something else. Maybe the mogul as we once knew it is extinct. Maybe the future of hip-hop will be decentralized, with artists embracing independence and smaller-scale ventures rather than aiming for billion-dollar empires.

But one thing is certain: hip-hop was built on the audacity to dream bigger, own more, and lead boldly. Whether today’s artists follow the paths of Kanye, Diddy, and Jay-Z—or redefine success on their own terms—I hope they remind the world that hip-hop isn’t just music; it’s power.