Jay Z

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Everyone thinks they’re a boss in hip-hop. But there’s more to running things than making a ton of money and rapping about it. There’s longevity. There’s seeing the paradigm shift and learning your place in the changing landscape. And most importantly, there’s learning how to “diversify yo’ bonds” and positioning your brand to take you far.

In honor of National Boss day, CASSIUS rounded up a few of hip-hop’s biggest dons.

Tech N9ne

Tech N9ne Performs At Showbox Sodo

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Hip-hop’s best kept secret, Tech N9ne is a great example of what happens when you own your shit. He started his record label Strange Music with business partner Travis O’Guinn in ’99 and the duo has dominated ever since. Forget shirts, he takes merch to another level. Water bottles? They sell them. Sticky-notes? They sell them. G-strings? They sell them. The warehouse it’s all stored in? They own it. The 23-vehicle tour fleet? They own it. And all of it is used when Tech is tour— which is virtually all the time.

Puff DaddyPuff Daddy And The Family Bad Boy Reunion Tour Presented By Ciroc Vodka And Live Nation - May 21

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The kid from Mount Vernon shimmied his way to the top of the Forbes list. Mr. Combs got his start as an intern for Uptown Records and because talent director there before getting fired in ’93. He started his own record label, and Bad Boy Entertainment was born. He hooked up with Biggie, Craig Mack, and a ton of other early ’90s icons to form a monopoly on the East Coast’s music and influence. His mainstream fame grew from there, which landed him a Super Bowl performance in 2004. But even as he was pursuing music, his business acumen was becoming hard to ignore. The created the Sean John clothing line, opened two restaurants, and secured a major equity stake in Revolt. And did we mention Ciroc?

JAY-Z

The Meadows Day 1

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Hov preached financial freedom on 4:44, something he’s been practicing himself for the better part of 20 years. When labels wouldn’t even listen to his demo, he just created his own—Roc-A-Fella records—with Damon Dash and Kareem Burke. The independent label’s first release was Jay’s critically acclaimed Reasonable Doubt. From there he cemented himself as a rap heavy weight with In My Lifetime, Vol. 1 and The Blueprint (we’ll forgive him for The Dynasty and Kingdom Come). But like Puffy, he diversified. He owns the 40/40 Club sports bar franchise, created clothing brand Rocawear, and founded Roc Nation, so he’s basically signed to himself. Oh, he also owned part of the Brooklyn Nets but had to sell his share so he could create Roc Nation Sports. He’s a business, man.

Dr. Dre

2012 Coachella Valley Music & Arts Festival - Day 3

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Don’t ever forget about Dre. Hip-hop’s first billionaire hasn’t been crowned yet, but Dr. Dre is at the head of the pack. After his N.W.A and Ruthless Record days, Dre joined up with Suge Knight to create Death Row Records, which would yield his classic The Chronic album. But even chart-topping singles like “Nuthin’ but a ‘G’ Thang” and “Let Me Ride” weren’t enough for him to stick around and deal with the Suge Knight rift, so he aptly called his new venture Aftermath. He got back to his gangsta rap roots and we were blessed with 2001 before he decided to focus on producing and endlessly teasing Detox. And then in 2008, he started the trend of musicians releasing their own branded headphones with the introduction of Beats By Dr. Dre. Apple came along and purchased Beats by Dre for a reported $3 billion.