I stopped being a Lil Wayne fan several years ago. At this point, even his most loyal fans – somehow many remain – can no longer deny that Weezy fell off. Once heralded by TIME as the best rapper alive, he now boohoos about being bored with music and makes headlines for acting a damn fool. Outspoken HOT 97 host and fellow hip-hop nerd, Peter Rosenberg, had some scathing words for the YMCMB artist’s meltdown:

“Over the years, Wayne has let the lean, the pills and the yes-men get to him. And what we have now is a mess – a guy who should be in the phase of his career when he becomes an ambassador, who has instead become an embarrassment. When Jay-Z was the age that Wayne is now, he swore off wearing throwback jerseys and started dressing like a grown-up. Wayne is doing the exact opposite. He picked up skateboarding and continues to act like a child.”

I love the rap game and its rags to riches mythologies starring larger than life characters competing in tournaments of lyricism, showmanship, wealth and power. Growing up in a lower middle class home in Scarborough, I’d find myself patiently waiting on 50 Cent’s next moves – his interviews were my intro to business, his music videos my intro to marketing. And the buck didn’t stop with Fifty –  Jay-Z, Ja Rule, Nas, Cam’ron and any rapper jostling for the number one spot would inadvertently become mentors to me, sharing invaluable blueprints and cautionary tales. Decoding lyrics, charting career paths, and nerding out over beefs in this tumultuous rap game has left me with a list of lessons for business and life, a handful of which I’d like to share:

Lesson #1 – On to the next one


“Ni**as wan’t my old shit, buy my old album” – Jay-Z (On To The Next One)

No rapper is safe from stagnation. What happens when you’ve exhausted your repository of anecdotes? What happens when your gimmick gets played out? What do you do after going multi-platinum and winning every possible accolade? The likes of Jay-Z, Eminem and 50 Cent have all hit plateaus at various points in their careers. However, only a handful were able to get back in the studio and reclaim relevance, or at least make lateral transitions out of limbo. The rap game underscores the importance of evolution, and we had need not look beyond the “blueprint” of evolution being authored by none other than the man behind the titular trilogy, Mr. Shawn Carter:

“M.J. at Summer Jam, Obama on the text. Y’all should be afraid of what I’m gon’ do next” – Jay-Z (On To The Next One)

Jay-Z doesn’t need the music anymore. As a businessman (or “a business, man” as he likes to think of himself) he’s unlocked unfathomable levels of relevance. It can’t be just about the music anymore. Follow producer Swizz Beats on Instagram and it’s clear that he’s now focused on being a brand ambassador and exploring new art forms. Or give Kanye West’s 808’s and Heartbreak another listen and see how at one point he broke out of repetitive patterns. Or look at the flip side of all of this – Cameron Giles aka Cam’ron. Oh boy. While Jay-Z transitioned from rapper to mogul, Mr. Giles insisted on “staying in his lane.” Instead of investing his money, he blew it on depreciating asset after depreciating asset; instead of evolving his music and his image, Cam’ron insisted on being forever young in all the wrong ways. He now finds the realities of his age and circumstances incongruent with the content of his music. A textbook example of career suicide.

Lesson #2 – Never forget where you’re from


“No new n*ggas, n*gga we don’t feel that / F*ck a fake friend, where yo real friends at?” – Drake (Started From The Bottom)

Stay hungry, stay humble. The former ensures that your perspectives are always configured to be appreciative of the journey (even if you didn’t actually start at the “bottom” bottom), while the latter reinforces the relationships that truly matter. Refrains of friendship and his hometown of Toronto comprise a significant chunk of Drake’s lyrical content. His single, Started From The Bottom, is the quintessential anthem of this grounded philosophy  Whether its on tour or on a red carpet, Drake is never far from his entourage of childhood friends whom, Vincent Chase style, he brings along for every step of the journey.

“I got a lotta friends to come up off the strip for me / The same ones that’ll come up off the hip for me” – Drake (Crew Love)

On the flip side, no one seems lonelier these days than Curtis Jackson aka 50 Cent. The reclusive rapper once said something in an interview to the approximation of “True friendship can only occur when both people don’t need anything from each other.” Tragically, 50 would later go on to lose all his close friends including Lloyd Banks and Tony Yayo. Even his bestie Floyd Mayweather is gone. Why? The complete opposite of hunger and humility – comfort and arrogance. Which brings me to the next lesson…

Lesson #3 – Don’t get caught slippin’


“Divorce lawyer telling you how this thing gonna be ending / With you paying out the ass and I’m talking half” – Nas (Bye Bye Baby)

Whatever you do, don’t slip. Slippin’ is different than failing. Every artist fails at some point. They might produce an album that completely bombs, or release a video that gets lost in the annals of obscurity. But their longevity doesn’t hinge on those failures, because they’ve got backup plans and have sufficient margins for experimentation. Slipping occurs when you’ve got everything on the line. Slipping is the rap game equivalent of a career limiting move. And if you fall off once, chances are you’ve fallen off forever. Nas went from at one point nearly ending Jay-Z’s career to now paying $55,000/month as a result of one of the nastiest divorces in rap history. Nas got caught slippin’.

“Kelis said her milkshake bring all the boys to the yard, then Nas went, and tattooed the b*tch on his arm.” – 50 Cent (Piggy Bank)

The rapper exhibit in museum of cautionary tales has no shortage of relics – DMX went from selling out stadiums to singing Christmas carols while coked-out; Ja Rule went from being New York’s resident gangster rapper to tax evading criminal; Ma$e went from Diddy’s high-flying sidekick to pastor (and back); T-Pain thought he could beef with Jay-Z and survive; the list of punchline fodder goes on and on. Those are just a handful of rappers in the freezer. Cold. No one’s checking for them. One my favorite videos on this subject is that of Damon Dash freaking out at label executives who decided to hold a meeting about Jay-Z without Dame. It’s a tragic portrait of a man experiencing the agonizing loss of power and the realization that he’s put all his eggs in one basket. A portrait of a man without a backup plan, whose very existence depends on Jay-Z, whose life is falling apart in real time. A man who slipped hard and fell off completely.

Lesson #4 – Timing is everything (truuu!)


“I paid a 1,000 dollars for my sneakers / ‘Ye told ya, a 100k for a feature” – 2 Chainz (I’m Different)

On a lighter note, 2 Chainz had an outstanding year in 2012 and shows no sign of slowing down. Formerly in the freezer as Tity Boi, he is now reincarnated as 2 Chainz, doing the NBA halftime show, Grammys, making appearances on 2 Broke Girls and collaborating with anyone whose hot in the game right now. And get this – he’s pushing 35! An anomaly of an age to be breaking into the market. On the other hand are some artists in that age bracket who haven’t quite blown up, who are still trying to get their 15 seconds. Case in point: Busta Rhymes. If you’re 41 years old and trying to get a record deal with Birdman, it’s time to hang it up. The zeitgeist – the climate of the world – the attitudes and expectations of the market, will not allow Busta Rhymes to succeed. Once you’ve past your prime, you’re just plain corny.

“I did what they say I wouldn’t / Went where they say I couldn’t.” – 2 Chainz (No Lie)

Few things in the rap game are cornier than Dr. Dre trying to garner hype for his ephemeral album, Detox. I’m still going to nerd out and listen to it for nostalgia’s sake, but we’re way past the ideal climate required for an album like it to truly have an impact. I can’t get excited about someone my dad’s age trying to connect with me musically around subject matter so far removed from his reality. Detox is an anachronism, dead on arrival. A discussion of rap timing would be incomplete without mention of Drake’s label signing process. Instead of selling to the first highest bidder like B.o.B. did with TI’s graveyard of a label, Grand Hustle, Drake took his sweet time after building a buzz and courting multiple labels thus pitting them in a bidding war. The end result? A label situation perfectly suited to propel Drake to his current level of success.

Lesson #5 – Set a fire in your own backyard


“But I got fans all the way from here to Egypt” – Riff Raff (Cocaine Cypher Freestyle)

Think global, act local. I don’t understand the hype around Shawty Lo the way Atlanta does. Shawty Lo is the slowest, most basic rapper I can think of, and is somehow huge in his hometown. I figure it has a lot to do with two things: reinvesting and representing. Focus on your immediate communities. Find ways to make your mark there and use the loyal support to tinker with your formula, improve your craft and gain traction by allowing fans be a part of the come-up. Waka Flocka did just that and is someone whom I’ve grown incredibly fascinated with as of late.

“I greet fans, he (Gucci Mane) push fans.” – Waka Flocka

Like Shawty Lo, Waka has an energetic core fan base and you’d be hard pressed to find another rapper (I use that term loosely) who treats their fans with as much love and respect. Watch any of his interviews or follow him on Twitter and it becomes quickly apparent that this is a man who understands the concept treating fans like gold. I find it hard to imagine Waka Flocka and other rappers like Young Jeezy and Rick Ross being disrespectful to their fans the way some of their jaded counterparts like Lil Wayne and Gucci Mane have. Honourable mention goes to Riff Raff when it comes to doing right by your fans. This man is one of the hardest working rappers in the game obsessed with putting out endless content and entertaining his fans, and is now collaborating with the likes of Drake and A$AP Rocky.

Lesson #6 – Align yourself strategically

French Montana

“I ain’t worried ’bout nothin’ / N*gga, I ain’t worried ’bout nothin” – French Montana (Ain’t Worried About Nothin)

It was hard enough being a 50 Cent fan after Curtis, and the nail in the coffin for me was his recent spat with French Montana. In perspective, 50 Cent battling with French Montana is the corporate equivalent of Apple getting litigious with a flea market vendor. It’s not a good look. And for a man who collaborated with 48 Laws of Power author Robert Greene on his own hood-variation of the best selling book, I certainly expected better. But then again, this was the same man who at the top of his career boxed below his weight class with guys like Fat Joe and Jadakiss, guys who had nothing to lose. If I had 50’s ear early on, I would’ve told him to emulate his mogul colleague Jay-Z and become a tiger unconcerned with the opinion of sheep.

“I’m like “Really: half a billi nigga, really? You got baby money / Keep it real with n*ggas, n*ggas ain’t got my lady’s money.” – Jay-Z (H.A.M.)

When someone of Jay-Z’s or 50 Cent’s stature even acknowledges beef with someone in the lower echelons of the game, the underdog almost always wins. Reputation is easier to destroy than build. That’s why every interview, every detail and every collaboration counts. To highlight the idea of collaborations, peep the artists Kanye West worked with on My Beautiful Dark Twisted Fantasy, or look at who he’s apparently collaborating with on his forthcoming album, Yeezus. Kanye is strategically aligning himself with identities that will contribute to the growth of his own. Meanwhile 50 Cent is rapidly depleting his social currency every time he hits the send button.
…There you have it, folks. A few insights into life and business from the rap game. If I could leave you with one piece of actionable advice from it all, it would be this: when faced with making a life or business decision, consider the following: do what Jay-Z would do, not what Lil’ Wayne would do.