Why New York Hip-Hop Couldn't Stay on Top Forever

New York hip-hop dominated the 90s and early 2000s, but the internet changed the industry and paved the way for Atlanta.

50 on stage at Hot 97’s Summer Jam concert in 2004 (Photo by KMazur/WireImage for Hot 97)
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Every few months, there’s a new profile written on Atlanta and New York’s respective positions in hip-hop. For over a decade, The A has been labeled the new Motown, the cultural capital, and other glowing accolades. Meanwhile, New York rap is often criticized for failing to maintain the control it once had. Pundits cite the cultural differences between the two cities as the reason for their respective positions. Brooklyn rapper Maino once said, “The O.G. [New York] rappers didn’t pull us in.” That might be true, but it doesn’t address the underlying reasons for the change.

In the 80s and 90s, radio stations, distributors, and artists had tremendous control over the songs we listened to. Rappers from New York and Los Angeles were better positioned than artists in other cities because of their proximity to gatekeepers. The relationships built and influence used (and abused) made it easier to ensure that a particular artist dominated airwaves.

The internet has since democratized artists and fans ability to reach each other directly. As a result, consumers took power away from radio stations and other once-powerful outlets. There was a natural gravitation to shift attention to sub-genres and regions that were once overlooked.

Atlanta was one of several cities whose artists had a timely rise. ATL separated from the pack because it made the most of its opportunity. Atlanta had a little bit of something for everyone, which is the best approach in a fragmented landscape.

New York would have lost its control even if 50 Cent and Ja Rule were best friends.

New York rappers had the radio stations in their pocket

Back in the day, New York hip-hop was an agglomeration economy. The close location made it easier for Damon Dash to hound Hot 97’s Funkmaster Flex to listen to Jay Z’s music. This persistence spawned a powerful relationship between the Reasonable Doubt rapper and the New York radio station. After Hov scored his first big radio play in the mid-90s, the Roc-a-Fella team capitalized on the opportunity.

Here’s a segment from Pitchfork on the start of the relationship:

A few weeks later, Jay and [Damon] Dash visited the station to show their appreciation, presenting a bottle of Cristal to Angie Martinez, the [Hot 97] DJ who hosted the segment. … Though it wasn’t payola, the whole encounter—the champagne gift, the luxury accommodations—demonstrated that Jay Z and Dash were familiar with the give-and-take expected between artists and radio.

I’m not the payola feds, but an expensive bottle of champagne sends a clear signal. A few years later, the radio station was jokingly called ‘Hov 97.’ The moniker was used pejoratively by his rivals, but admirably by fans.

A few years later, 50 Cent benefitted from a similar relationship with the station. In an episode of Complex’s Everyday Struggle, Joe Budden shared his thoughts on 50’s influence:

“When you are the number 1 artist, you have leverage that others aren’t afforded. I 100% think that 50 Cent leveraged his power with the program director at Hot 97 and said ‘if you start playing A,B,C, and D records you will never get another 50 Cent record.’ And guess what? If you never get another 50 Cent record, that shuts down Interscope [Records]…can Hot 97 afford that? No.”

But after 50 Cent’s run, the industry started to change. Technology changed the game. iTunes, Myspace Music, YouTube, satellite radio, and hip-hop blogs made it easier to bypass the radio stations. The ubiquitous power that sat within the five boroughs came to an end.

Not surprisingly, New York didn’t see it that way. The culture wanted a scapegoat. 50 Cent often gets blamed. In 2016 and 2017, the G-Unit frontman and Hot 97’s Ebro Darden had a series of heated, entertaining, but pointless debate over who killed New York hip-hop. The longtime radio host thinks that 50’s beef with Murder Inc. tore the city apart. But the Queens rapper believes that Ebro, the radio station’s program director, chose not to play records from other New York artists.

The finger pointing is useless. Both were influential players, but their control was a product of the old system. New York would have lost its control even if 50 Cent and Ja Rule were best friends. To pin New York’s fall solely on one rapper or one program director ignores the industry’s change.

A short clip of the ongoing debate between 50 and Ebro (YouTube)

Atlanta thrived on differentiation

When the industry shift began, other regions gained attention. Fans gravitated to the new sound. This was timely for rising stars like T.I., Nelly, and Lil’ Wayne.

But Atlanta surpassed St. Louis, New Orleans, and other cities for a few reasons. First, the artists from the city have had a chip on their shoulder ever since Andre 3000 told hip-hop that “the South got something to say” at the ‘95 Source Awards. The statement was a motivational call for belonging.

Second—and more importantly—most popular Atlanta artists had distinct lanes. In the mid-2000s, Atlanta was home to the So So Def sound, OutKast’s eclectic tunes, Jeezy’s gritty anthems, Lil’ Jon’s crunk music, Soulja Boy’s ringtone raps, and more. In a highly-fragmented landscape, it’s easier to stand out with differentiated products. The breadth of style strengthened the city’s perception more than homogeneity would have. Atlanta wouldn’t be Atlanta if everyone tried to sound like Three Stacks and Big Boi.

St. Louis and New Orleans did not follow that same path. Nelly softened the ground for hometown rappers Chingy and J-Kwon to come through, but their hit songs could have easily been released by Nelly himself, Murphy Lee, or one of the other St. Lunatics. The same can be said for Louisiana rappers. Boosie Badazz could have fit right in with the earlier New Orleans groups like the Hot Boys or No Limit. That’s a compliment to Boosie, but the duplication did not extend the region.

Hip-hop fans often reference Atlanta’s collegial brotherhood and sisterhood as a reason for its rise, but the city has had its heavyweight rap beefs too. T.I. and Ludacris exchanged plenty of bars over who was “King of the South.” Gucci Mane and Jeezy were at odds for years. In most cases, these beefs draw more attention to a city.

T.I. and Jeezy (Photo by Chris McKay/Getty Images)

What happens next?

The media still speaks highly of Atlanta’s run. The city has extended its hip-hop culture to higher-brow television shows like Atlanta. Its strip clubs are ingrained in the rap lexicon. And the region continues to attract young talent, like the artists on the Quality Control Music record label.

But other cities are challenging the notion that Atlanta still has the culture on lock. The five most popular rappers at the moment are Drake, Kendrick Lamar, Cardi B, J. Cole, and Travis Scott. None of them are from Atlanta. Los Angeles’ scene has gained momentum too. There’s a case to be made for a number of cities.

Although the landscape is fragmented, that could change as technology continues to impact the music industry. Spotify’s quest for exclusive audio content may have an impact on hip-hop. Other streaming services are on a mission to do the same. All it takes is a few rappers from the same region to be in the right place at the right time.

I had a good conversation this week with Bytathe platform for music before it’s on streaming services. We talked about my days selling bootleg CDs, the challenge in finding classic mixtapes on streaming services, and more. Check it out!

Trapital is written by Dan Runcie. Contact me at dan@danruncie.com. If you enjoyed this story, forward to your friends and tell them to sign up for the Trapital newsletter!

Why Every Rapper is Heading to Las Vegas (and Why That’s a Problem)

Vegas residencies are more popular than ever, but the city's changing demographic will force artists to be strategic before they go all in.

Cardi B (Photo by Scott Roth/Invision/AP)
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In the past month, Drake, Cardi B, and French Montana joined the wave of artists who have made Las Vegas their home away from home. Casinos in Sin City have lured in music’s top acts with lucrative residency deals. Drake’s partnership with The Wynn’s XS Nightclub guarantees him $1 million per show. After all is said and done, he will likely earn more per show than he did on tour last summer with the Migos.

The Las Vegas residency landscape has transformed in recent years. Britney Spears, Jennifer Lopez, and Lady Gaga have each earned eye-opening amounts of money. Their runs paved the way for hip-hop’s heavyweights to join in. And now that Drake and Cardi are locked in, expect more rappers to get in while it’s hot.

From afar, everybody’s winning. Artists earn guaranteed money and perform in front of smaller crowds. Casinos get rich off the customers that come through the door. And fans get to see their favorite artists in a hot destination. It feels like one of Diddy’s Ciroc commercials has come to life.

But it might be hard for everyone to keep this same energy. Vegas guests gamble less than they used to, much to the city’s concern. The Vegas entertainment machine also thrives on scarcity. If every mainstream rapper forgoes touring for residencies, the allure may wear off. Just like in real life, too much Vegas can be problematic for everyone.

Today’s rappers attract large millennial fanbases that gamble much less than past generations do.

Residencies are lead generation for gambling profits

Standard music venues rely on alcohol sales to drive profits. Ticket sales are a means for venues to sell fans $10 Bud Lights. But music venues in Vegas resort casinos take that to another level. Their goal is to get folks in the building, take their money at slots, tables, and everything else possible. Here’s a quote that entertainment lawyer Bernie Resnick shared with Forbes about the business model:

“Any star's fee to play Las Vegas is fair because, bluntly, the casino promoters are not particularly concerned with who is on stage or in the ring. What casinos care about is whether the presence of the star will increase their nightly gambling profits, known as the ‘drop.’ If the star significantly increases the drop, the casino is justified in sparing no expense to stage a spectacular event.”

Guests who have enough disposable income to spend $209 on a Jennifer Lopez concert are more likely to increase the drop throughout their stay. That’s why The Wynn launched a bidding war to land Drake. The ticket revenue from Drake’s shows won’t cover his $1 million guarantees, but the casino hopes that the drop will.

Back in 2014, Planet Hollywood reported that its earnings rose $20 million in the first year of Britney Spears’ residency. It’s overly generous to attribute all those gains to Spears, but that’s a common issue with economic studies for most events. Also, Britney’s show succeeded in a vacuum. She had little competition in Vegas from other artists in her generation.

Despite its flawed perception, Planet Hollywood’s $20 million increase in earnings still carries weight. It influences more popular casinos—like The Bellagio or The Venetian—to try and replicate the same success with other artists.

Artists with millennials fanbases will face challenges

In 2017, millennials surpassed Generation X as Las Vegas’ largest touring demographic. This is a looming concern for casinos since millennials gamble much less than past generations do. Today’s rappers attract large millennial fanbases, so the gambling drop will be less significant than it was for past artists.

Vegas eagerly wants to offset the declining gambling revenue by offering millennials “experiences” and Instagram-able moments. Casinos have invested heavily in renovations and activities to cater to this generation. But can a new zip-line through The Strip make up for the declining number of guests who would drop $100 in a slot machine on a whim? Probably not. (I’ll be honest, the last thing I’m about to do after a Drake concert is ride a damn zip-line through Las Vegas Blvd)

If casinos can’t overcome the generational shift, the lucrative guarantees will shrink. Some casinos may look more favorably at artists with larger Generation X fanbases, like Janet Jackson or Usher. Both names could draw fans that are more likely to gamble, but that’s a temporary tactic that can’t overcome the changing landscape.

Newer artists may also grow tired of performing for the millennial fanbase in Vegas. These newer residencies are marketed towards fans who would spend $200+ on a Vegas residency show, then pay additional money for VIP access and other perks. These campaigns target the same type of the people who flew out to “Pablo Escobar’s private island” for the disastrous Fyre Festival. If an artist only cares about securing the bag, then it’s not an issue. But some rappers might gets frustrated performing for influencers who are just there to stunt for the ‘gram.

The Strip doing its best to cater to millennials (Photo via MintPress News)

Making the most of the opportunity

The Wynn and Drake might have struck the right balance. His ten shows at XS will be spread across the next two years. He can build anticipation for his shows and maintain his other business interests. It also decreases the likelihood of him competing with other rappers who might perform on the same night.

Artists like Drake will selectively choose their show dates. Vegas is busy during the summer for bachelor and bachelorette parties, big sports weekends, and holidays. Casinos will want big names for these weekends.

While Drake still has a large millennial following, his mass appeal may temporarily protect him from the demographic trend in Vegas. An average artist will feel it much sooner. These performers should consider alternative events that can be just as advantageous.

Professional conferences and conventions are some of the best money grabs out there. A few years ago, Salesforce paid the Foo Fighters a rumored $1.25 million to perform its annual Dreamforce conference in San Francisco. These events bring in thousands of high-net-worth individuals who are willing to spend both corporate and personal money.

Smaller acts should consider performing at events surrounding annual conferences by the National Black MBA Association, National Society of Black Engineers, and the Congressional Black Caucus. These events are much smaller than Dreamforce, but there’s a captive audience that already follows hip-hop. The musical acts that typically perform at these events are often B-list rappers and R&B artists from past generations. There’s an opportunity for more current artists to liven up the landscape and earn some money, just like they have in Vegas.

Before the year’s over, even more artists will announce residencies in Vegas. And soon after, expect a wave of journalists to write articles that say that “there are too many Vegas residencies and the market is saturated.” Those articles will be both right and wrong. They’ll be right because the pie is only so big, but they’ll be wrong because the lack of gambling will curb residencies before the saturation can truly set in.

The real question is which artists will stick around in Vegas as millennials continue to take over. Will artists from the 90s get called up to help squeeze the gambling money from their fans? Or will Drake and Cardi B overcome the declining trend? It might be neither, which is Vegas’ biggest fear.

Trapital is written by Dan Runcie. Contact me at dan@danruncie.com. If you enjoyed this story, forward to your friends and tell them to sign up for the Trapital newsletter

I'm Officially Full-Time on Trapital!

Making moves this year.

Big news. I’m now a full-time employee of Trapital LLC! My wife and I popped a bottle of champagne last night to celebrate. Today I’m in one my favorite coffee shops in San Francisco getting work done.

This transition has been on the horizon for a minute. I made the leap now because I feel confident about the potential and future. There’s been a lot of growth and momentum, especially in the past three months. I’m excited to devote more time and take it to the next level.

The newsletter has evolved from my initial vision, as expected. I tried some things that worked and some things that didn’t. (One of these days I’ll have to post an early notes page of some of the wild story ideas I had in mind! Just wait…)

It’s all part of the journey. But one thing has stayed true. My reason for launching it has been validated.

Why I started Trapital

I started Trapital to fill a void. Hip-hop’s cultural influence has grown tremendously, but most business writing on it just skimmed the surface. I knew there was an audience that values the strategy, analysis, and cultural relevance that I bring to each article.

When writing on the hip-hop industry is done well, it can educate readers on business principles as effectively as any other sector. For those of you who work in the music industry, Trapital is even more relevant. Many of you have reached out to let me know how valuable the insights are to your everyday work.

I also started Trapital to improve representation. It’s less common to find consistent business writing like this on the black and brown folks that I often write about. Many of you feel more connected with these folks too. That matters. I’m happy to serve this role and want to continue doing so. Even when I am critical of certain artists and companies (which is often), the assessment pushes the culture forward.

What this means for Trapital

Many of you have asked for more content. I’ve heard every one of y’all, trust me! Time has been my biggest constraint. The nights and weekends grind could only take me so far.

Expect more content from Trapital soon. I often get asked to start a podcast or video series. Those talks are on the roadmap, so stay tuned.

How you can help

Spread the word! Let folks know that this newsletter you enjoy just got full-time attention and you’re excited to see where it goes from here.

Word of mouth is still the best way to grow. If everyone who reads this tells one person they haven’t told yet to check out Trapital, that would be great.

Thanks again for reading. Let’s make moves this year.

Trapital is written by Dan Runcie. Contact me at dan@danruncie.com. If you enjoyed this story, forward to your friends and tell them to sign up for the Trapital newsletter

Recent stories that got a lot of traction:

Why the Super Bowl is Less Lucrative for Travis Scott

Despite the halftime show’s massive audience, the Houston rapper may benefit less from the platform than his co-performers will.

Amy Harris/Invision/AP
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Historically, the Super Bowl halftime show was a sign of achievement. The sales boost and exposure increase was granted to those who were worthy. Music’s biggest stars took the stage, left an impression, and reaped the rewards. But lately, it’s become an underwhelming gig for those who are willing.

Travis Scott has faced backlash ever since he was named to perform at this year’s show. The negative response stems from the NFL’s polarizing image. Jay Z, Cardi B, and Rihanna each turned down the opportunity to perform —citing Colin Kaepernick’s exile as the primary factor. The Astroworld rapper understands the resentment for his decision. He has convinced the NFL to donate $500,000 to criminal justice reform initiatives in return. Travis still believes the show’s exposure will outweigh its social cost.

Unfortunately, the benefits from that exposure have diminished. Despite the 26-year-old’s desire to extend his hot streak, his co-performers—Maroon 5 and OutKast’s Big Boi— are much better positioned to benefit from the event. And in today’s culture, a stage like the Super Bowl halftime show has become too broad for its own good.

No entertainer wants to be tied to systemic problems that are out of their control.

The streaming boost will help Travis Scott the least

After Sunday’s performance, media outlets will report on the streaming boost that Travis, Maroon 5, and Big Boi get from the show. The stats will be valid, but they are far less impressive than the headlines make them seem.

Last year, Forbes (and many others) reported that Justin Timberlake’s music surged 214% on Spotify after the game. They compared his streams from the hour following the Super Bowl to that same hour the week before. It’s a small sample size that doesn’t equate to much money in today’s streaming economy.

Let’s do the math. Drake was the most streamed artist on Spotify in 2018 with 8.2 billion streams. Each Spotify stream is worth about $0.007, which equals $57 million for the Toronto rapper. That’s a lot in aggregate but equates to just over $6,500 per hour. A 214% increase for one hour of Drake’s music would be less than $15,000. That’s less money than Drake gave that boy and his mom in the “God’s Plan” music video. And since Travis Scott (and Justin Timberlake’s) music was streamed far less than Drake’s was, that number would be even smaller.

Additionally, the “SexyBack” singer’s streaming bump was largely driven by his older songs. According to Forbes, his 2006 song “Until The End of Time” had a 671% boost and 2013’s “Suit & Tie” had a 553% boost. Meanwhile, 2016’s “Can’t Stop The Feeling” jumped just 148% and 2018’s “Filthy” bumped up 266%.

This trend will benefit Maroon 5 and Big Boi too. The mainstream songs they will likely perform respectively from Songs About Jane (2002) and Stankonia (2000) will get higher streaming boosts than their recent singles.

But this trend will not help Travis Scott. All his singles are relatively new. “Sicko Mode” is his biggest song, but its still current. It’s already prominently featured on many major playlists. There’s less room for it to grow from here.

La Flame’s earlier hits like “Antidote” (2015) and “goosebumps” (2016) were popular, but not old enough to spark nostalgia the way that Maroon 5 and Big Boi’s older songs will. And since Scott’s set will likely be short, we might only get through one or two beat switches in “Sicko Mode” before the mic goes back to Maroon 5’s frontman Adam Levine.

Negative network effects

Traditionally, the more people who watch an event, the more valuable it is to perform at. That’s why the Super Bowl halftime show was coveted for years. But times have changed. Pop culture is no longer the monoculture it once was. For most of today’s artists, the great size and range of the show’s audience have an adverse impact on its benefits.

Last month, venture capital firm Andreessen Horowitz did a study on the dynamics of network effects. They highlighted social media as a sector that develops negative network effects over time. While more users fuel growth at the beginning, too many users may lower the quality of the experience. Services like Facebook and Tinder reach saturation points where some original users will engage less often than they once did. Here’s a chart that shows the trend:

Source: Andreessen Horowitz

In entertainment, the Super Bowl halftime show is well past the saturation point. Artists try to please everyone with widely-accessible shows. The end result is an overly-generic performance that’s a layup for critics to hate on. Even stars with more ubiquitous fandom, like Bruno Mars and Beyoncé, were still criticized after their Super Bowl performances.

Since this trend is almost a given, several media outlets have probably already drafted story outlines that read something like this: “Maroon 5 bores, Travis Scott disappoints, but hey, Big Boi still got it!”

The Oscars suffer from a similar problem. No one has replaced Kevin Hart as host because the job is near impossible to succeed at. Hosts need to cater to a wide audience from many facets of entertainment and dozens of countries. Recent hosts try to do too much, or do too little, and get a lukewarm reception either way.

Both the Super Bowl and Oscars are also challenged by declining ratings. Streaming and social media have displaced traditional viewership for both shows, but Nielsen doesn’t account for that. Performers and hosts get pegged to these ratings, which may limit their future opportunities. No entertainer wants to be tied to systemic problems that are out of their control.

Super Bowl commercials are the real reward

The better way for artists, especially relatively newer ones like Travis Scott, to benefit from the Super Bowl is through commercials. Last year, songs featured in ads from Squarespace, Doritos, and Budweiser got similar streaming bumps to those that JT performed at the halftime show. These artists also get paid royalties for their TV spots. In some cases, the artists themselves star in the commercial, which is another check.

Cardi B figured it out. She’s featured in a Super Bowl commercial for the second straight year:

Cardi B, Steve Carrell, and Lil’ Jon in Pepsi’s new commercial

The Grammy-nominated rapper will collect checks from this Pepsi commercial and an exclusive Super Bowl party in Atlanta that her and Meek Mill will perform at. Some critics have pointed out the contradiction in her starring in a Super Bowl ad that funds the event she publicly took a stand against. Either way, the backlash is slim compared to what Travis Scott has experienced.

If Travis played this out differently, he could have done the same as Cardi. Advertisers are clearly willing to put him on him. He was featured in recent commercials with Samsung and Jordan Brand. If other artists like Ludacris, Cardi, and Chance The Rapper can star in Super Bowl commercials this year, Travis would have had no problem finding one of the show’s sponsor to play his songs, feature him, or both.

The rumor mill is convinced Travis Scott will take a knee during the show. Some think he will kneel to show solidarity with Kaepernick. Others think he will get down on one knee to propose to Kylie Jenner. Fans anticipate a big moment.

Will that be enough to offset the months of backlash for his decision, his limited discography, and the negative network effects of the halftime show? I wish ol’ boy the best, but the likelihood is slim.

Here’s the link to the interview. Sign up for the MAEKAN newsletter!

Trapital is written by Dan Runcie. Contact me at dan@danruncie.com. If you enjoyed this story, forward to your friends and tell them to sign up for the Trapital newsletter

How Jay Z and Damon Dash's Split Still Impacts Hip-Hop

Hip-hop's misguided perception of Jay Z's success and Damon Dash's struggles has influenced how the next generation of artists approach business.

Jay Z and Damon Dash (via Johnny Nunez/WireImage)
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Last week, Soulja Boy was on a mission. The “Crank Dat” rapper was eager to prove why he—not Tyga—had the biggest comeback of 2018. Soulja started several new business ventures and had to let the world know about them. But when he came through Complex’s Everyday Struggle, host Nadeska Alexis tried to clown him by asking repeatedly, “Why do you have so many businesses?” Soulja Boy eventually fired back, “why DON’T you have so many businesses?!” The 29-year-old rapper got similar questions from The Breakfast Club. Unfortunately, the questions are not surprising. Hip-hop’s brash business figures often face more scrutiny.

Conversely, rap’s cool, calm, and collective leaders get celebrated more easily. For some, the difference in treatment is rooted in stereotypes: loud black folks are “aggressive” and “intimidating.” But it’s also reinforced by the culture’s archetypes of success.

Jay Z is the industry’s mogul. He’s the soon-to-be billionaire. His approach to business is replicated and praised more than anyone. Meanwhile, Jay’s once friend and business partner Damon Dash is his foil. The former Roc-a-Fella Records CEO is loud, confident, and outspoken. Ever since the Roc-a-Fella dynasty split in 2004, Dame has gotten the short end of the stick. His public setbacks and financial struggles were publicized. The overwhelming narrative is that Jay “won” and Dame “lost.” For some, it nullifies Dame’s philosophy on business.

It’s an easy, but lazy, place to land. Dame still had his victories, and the Kingdom Come rapper has taken a few Ls. When success is oversimplified, nuance is lost and smart lessons are ignored. Conforming to a single mantra of leadership is a dangerous pattern for an entire industry to follow.

If hip-hop continues to follow Jay Z’s every move, we may lose the innovation that drove the culture in the early 2000s.

Survivorship bias strikes again

Other industries celebrate leaders with similar management styles to Dash. For decades, Steve Jobs has been tech’s quintessential icon. Apple’s former CEO, like Dash, was known for being a jerk. Both publicly berated employees for not meeting their standards. Both strived for excellence at all costs. And both performed for the cameras.

As WIRED wrote in 2012, “There’s businesspeople who have taken the life of Steve Jobs as a license to be more aggressive as visionaries, as competitors, and above all, bosses." We see aspects of Jobs in Mark Zuckerberg, Jeff Bezos, and Elon Musk. Box CEO Aaron Levie has been public about his adoration for Jobs.

But the same would never happen for Dash. If J. Cole ever publicly said, “I’ve been following Damon Dash’s principles to build Dreamville into an empire,” he would end up on Donkey of the Day.

It’s another example of survivorship bias. Since Jay is rap’s most successful figure, his approach—like Jobs’ in tech—is heralded. Each Jay Z interview is content for listicles of “lessons learned.” His influence is well-documented.

The elevation of Jay (and ignorance toward Dame) was further emphasized by Kanye West. In 2004, Ye was signed to Roc-a-Fella Records when Jay and Dame split. Each artist had to make a choice. Cam’Ron chose Dame, but Kanye stuck with Jay Z. Yeezy shared why in a 2013 interview:

“The problem was with Dame his truth was more accurate and more closer to what mine was, but his technique was harsh for me as a young kid and stuff. I felt like a little bit more pressure. And Jay Z was a nice guy. And also I felt like I had that truth that Dame has in him. We the same. Me and [Cam’Ron'], me and Dame, we the same. But I wanted to learn this technique that Jay got of actually being likable. Jay Z know how to move in a room full of vultures.”

This quote is ironic given Kanye’s actions over the past two years, but it’s still important. Kanye self-identified as being more similar to Dame and still sided with Jay. Considering the heights Kanye reached alongside Jay Z, it was difficult for Dame to get much love.

But neglecting Dame is a missed opportunity for several reasons. First, leaders with career ups-and-downs have better insights than those who just rose to the top. On NPR’s How I Built This podcast, the best lessons come from those who navigated financial hardships and dilemmas. Second, Dame clearly contributed to Jay Z’s success back in the Roc-a-Fella days. Both figures should be studied to understand how Hov gained his wealth. Third, and related, Dame’s approach may resonate with someone who wants a future in business but doesn’t want to become the next Jay Z.

But if Dame’s style was dominant, the wealth creation that’s occurred in recent years may not have happened.

Partnerships vs. ownership

The media has done a slightly better job of highlighting Jay Z’s wins and losses. Here is The Ringer’s “shot chart” for Jay:

Would anyone ever ask Jay Z, “Why are you involved with so many businesses??” Of course not.

The chart is suspect at parts, but there’s a trend to point out. Jay Z does not start companies that often. He builds partnerships, especially with “underdog brands.” Here's Complex’s rundown of Jay’s underdog history:

Jay's early-aughts sneaker deal was with Reebok, not Nike. When he teamed with a search engine for the release of Decoded, it was Microsoft's Bing, not Google. When he bought 1/15th of one percent of an NBA team in New York City, it was the Nets and not the Knicks (yes, he's from Brooklyn, but still). When he hooked up smartphone users with his new album, it was Samsung holders and not people with iPhones.

According to Forbes’ Zack O’Malley Greenburg, "Jay Z often does deals with underdog brands because they have more ground to gain from a connection with him.”

Jay Z moves like a private equity firm. He finds brands that need boosts and invests his energy. As expected, Jay’s principles have influenced the next generation to follow his lead. Drake and Kendrick Lamar’s biggest ventures come from partnerships, not their own companies. Most years, the Hip-Hop Cash Kings list is fueled by deals, mergers, and investments, not grounds-up entrepreneurship.

But not too long ago, hip-hop was an entrepreneur’s haven. When Roc-a-Fella was at its peak in the early 2000s, hip-hop consumer brands had taken off. Phat Farm, Ecko, and Sean John were everywhere. A bunch of artists launched energy drinks too. It was hip-hop’s “dot.com” era. Damon Dash was in his element. Soulja Boy would have thrived back then too.

Dame is not a partnerships guy like Jay though. He is all about ownership, building, and being “the boss.” He literally has a YouTube video called How to Be a Boss. Rocawear and Roc Films were signs of his vision. His entertainment company, Dame Dash Studios, produces original content that Dame has full ownership of. It’s not a coincidence that his style was popular at the time, but less so today. But now that Jay Z’s style is dominant, the “Soulja Boys” of the game who are similar to Dame are few and far between.

If hip-hop continues to follow Jay Z’s every move, we may lose the innovation that drove the culture in the early 2000s. But if Dame’s style was dominant, the wealth creation that’s occurred in recent years may not have happened. In a perfect world, both styles can co-exist and are supported.

A teaser video of content coming from Dame Dash Studios (via YouTube)

Changing perception takes time

In fifteen years, we’ve seen hip-hop business shift from an ownership to a partnership model. The industry has evolved to help artists replicate what Jay has attained.

Similarly, the modern tech industry is built on the image of Steve Jobs. Each level of the ecosystem is designed to help founders take their companies from garages and basements to IPOs and lucrative exits. Unless there’s a recession, that’s not changing anytime soon.

Will the pendulum ever swing back for hip-hop? It’s hard to tell. If it does, it won’t be any time soon. Hip-hop’s reverence to Jay might be stronger than Jobs’ in tech. Jay Z is both hip-hop’s richest figure AND its greatest rapper. This compounds his influence. His lessons carry more weight than other moguls, like Diddy and Russell Simmons.

While Dame’s principles don’t get mainstream love, his mindset on black ownership resonates with a number of people. If there was a Venn diagram of folks who support Black Panther’s Killmonger and ride with Damon Dash, it would be a perfect circle.

Dash already won that group over though. In order for the overall perception to change, he, or another ownership-driven hip-hop entrepreneur, needs to attain mainstream success with a company that is built from the ground up. It’s possible, but it would be a counter-culture move at the moment.

The split between Jay and Dame is a reminder of the classic founder’s dilemma: do you want to be king or be rich? Dame is the king of his domain. He runs his own streaming platform, has his own film studio, and runs his own health network. He’s living his best life.

Jay is the rich once. Money over ownership. Even Roc Nation, the company he founded, was started as a joint venture from his 360 deal with Live Nation. Don’t be surprised if he makes another deal this year just to cross the billion mark before he turns 50.

But imagine if Dame “won” and Jay “lost.” What would the industry look like today? Would everyone try to emulate Dame and be the kings of their domain?

The better question is: What would the industry look like if they both won? There would be more room at the table for everybody to eat. Even Soulja Boy.

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Trapital is written by Dan Runcie. Contact me at dan@danruncie.com

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