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3 Entrepreneurial Lessons to Learn From Kanye West

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Jay Z’s 2001 album The Blueprint is considered by many hip-hop fans and outlets to be one of the best rap albums of its time. USA Today hailed the album’s production, granting it four stars and saying, “The musical backdrop here is more soulful than before, and Jay-Z's sentiments have a harder edge.”  

The album cemented Jay Z's place as one of the best rappers of the new millennium. Tracks like “Heart of The City” and “The Takeover” appealed to hip-hop purists, while casual, mainstream fans enjoyed frequent radio play of  “Izzo (H.O.V.A)."  

The majority of the album’s production had been handled by a then unknown Roc-A-Fella producer named Kanye West. He had signed on to the label some months prior. While he aspired to produce his own rap release, the company had mostly used him for his production prowess until this point.

The story might have unfolded far differently than it did for this young Chicago rapper and producer. Entrepreneurs and businessmen alike can learn the following three lessons from West's trajectory:

Related: How Music Affects Your Productivity

1. Getting a foot in the door.

Kanye West may have been a talented producer. But he aspired to become a rapper and faced a lot of obstacles along the way. For one he didn't fit the rapper stereotype of the time. In an era dominated by oversize basketball jerseys and baseball hats, West strolled in from the suburbs of Chicago wearing Ralph Lauren and Louis Vuitton.

As he recounted on his first album, others would “look at me crazy because I didn’t have a jersey on.” Although West was producing music predominantly for Roc-A-Fella, he came close to signing with Capitol Records. But that deal fell through at the last minute.

Roc-A-Fella CEO Dame Dash eventually signed West to his company's famous rap label, mostly out of fear of losing him. West went on to work with the likes of Scarface, Talib Kweli, Alicia Keys, Mos Def and others in the early 2000s. 

In October 2002, West had an accident while driving home from a late-night recording session in Los Angeles. With his jaw shattered and his mouth wired shut, he recorded “Through The Wire,” which become a breakout single. In December, he released a mixtape “Get Well Soon.” 

West was now receiving attention as a talented rapper and not just a talented producer. After a year of work and full support from the label, West released in February 2004 The College Dropout to critical and widespread acclaim.

Signing with a label as a producer wasn’t what he necessarily wanted. He could have said no and continued to pursue a deal as a rapper. But he chose to use the opportunity to get a start and work on making his music even better. He took the small chance of serving as an in-house producer and transformed it into the first step of realizing a successful rap career with enormous potential.

Related: How Jay-Z Went From Music Mogul to Sports Agent

2. Ask for help.

Kanye West's love for Kanye West has been well documented just about everywhere. While his perceived arrogance may have turned off some people, his self-determination and drive contributed to his success and influence in the music world. But even someone as confident or as self-assured as West knew when to ask for help.

Hot on the heels of his heralded debut, West enlisted film producer Jon Brion for assistance with the 2005 production of Late Registration. Brion, best known for his musical work on the Eternal Sunshine of the Spotless Mind and on Fiona Apple’s When the Pawn, marveled that a rapper would enlist a hip-hop novice to assist.

“On your sophomore record, that’s the ultimate time to not f--- with the formula, right?” Brion said. “And he gets me -- a guy who has never made a hip-hop record in his life -- and gives me half the reins? That is not an egomaniac.”

Late Registration won critical acclaim, with Rolling Stone granting Late Registration the top spot on its “Best of 2005” list, calling it an “absurdly virtuosic hip-hop classic.”

Often entrepreneurs are afraid to ask for help. But if the Louis Vuitton Don can ask for it, why not?

Related: Russell Simmons: 3 Simple Ways Meditation Will Make You a Better Entrepreneur

3. Don’t become too comfortable.

Two back-to-back critically acclaimed albums put West atop the rap totem pole and it would have been easy for West to rest on his laurels, as Brion put it.

But West scrapped the formula completely in his 2007 effort Graduation. He traded the soul samples (so prevalent in The College Dropout) for house music samples and electronic synthesizers giving Graduation a more robust and magnetic feel.

The album debuted at #1 on The Billboard 200 with more than 400,000 copies sold in the first week. Later, at the 50th Grammy Awards in 2008, West took home three awards, including Best Rap Album.

In business it’s rare for a top dog to revolutionize or innovate on a regular basis. After all, these folks might want to lean to the conservative side now after reaching the top. But in hip-hop and especially for someone like Kanye West, it's necessary to innovate to stay relevant.

West ushered in distinct innovations to the genre. He was one of the first to inject soul samples into mainstream hip-hop and once that became the status quo in production, he switched to the lush, cinematic sounds of Late Registration and continued this sound revolution with his subsequent releases.

It’s generally agreed upon within the hip-hop community that West has crafted at least three “classic” albums: The College Dropout, Late Registration and My Beautiful Dark Twisted Fantasy. (Graduation and Yeezus are not far behind). But what' interesting about his catalog is that no two albums sounds alike.

I learned so much from West, including the importance of having confidence as well as the conviction to create a distinctive voice or sound.

How to get started, asking for help from mentors and never settling are the three takeaways I learned from this "college dropout."

What’s funny is that these lessons helped me graduate college. And years later, they helped me, an unknown intern, score an opportunity in Silicon Valley.

Related: Music Mogul and Entrepreneur Dr. Dre: I'm the 'First Billionaire in Hip Hop'