The Rise Of Drake: Four Lessons In Building An Audience That Loves You

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They be starin’ at the money like it’s unfamiliar
I get it, I live it, to me there’s nothing realer
Just enough to solve your problems, too much’ll kill ya
And when I leave I always come right back here

At 29 Drake is one of the biggest rappers in the world. His fourth studio album Views has dropped, he has sold over 43 million songs and last year’s Hotline Bling was a musical and viral hit, scoring over 650 million views on YouTube.

Today, I’m going to share with you four different insights that we can learn from Drake as entrepreneurs. I’m going to share with you a few of the tactics that he implemented that helped him rise to stardom and be crowned the King of the Six.

It didn’t happen overnight.

While some people might think of Drake as nothing more than a Rapper – he’s evolved from a Toronto kid acting, singing, and rapping into a brand and business mogul. From his partnerships with NBA teams like the Raptors to creating his own private bar – Drake has changed the game in ways that many only dream of.

And not just the game of Hip Hop. He’s changed an entire industry.

Here are four ways that he was able to do it and how you can apply these insights to your own business:

Give Away Valuable Content For Free

Drake has released five mixtapes and each of them was filled with hits that would leave Twitter trending and night clubs bumping. Drake understood the value of distribution the impact that giving content to his fans for free would have on his ability to connect with them.

In business, you can create a similar connection with your audience by adding value to their lives beyond the products and services you offer. Whether it’s through an ebook, a podcast or professional services – adding additional value to the lives of your audience for no cost can be a differentiator and key driver to success.

Find Your Tribe & Celebrate Them 24-7

“Uh, hardly home but always reppin'” – Drake, Uptown

There’s no question that Drake loves his city. There’s also no doubt that the city loves him back.

From being named the Global Ambassafor of the Toronto Raptors to being given the key to the city of Toronto. To having politicians create and tackle beef for him:


Drake has found a tribe in Toronto and reps it 24-7.

In business, you need to find your customers or target audience and do right by them. If you’re selling marketing services, you need to think about who it is that wants these services and be committed to helping them grow. At Hustle & Grind, our tribe is hustlers. We REP hustlers in everything we do. Whether it’s in clothing or in the content we share on Instagram – we give it all for our team.

Be Committed To Your Success (And Own It)

I used to want to be on Roc-a-fella then I turned into Jay

Drake has never been shy about his ambitions.

The same way that Gary Vaynerchuk has proclaimed time and time again that he wants to own the New York Jets, Drake has let it be known that he wants to be successful. Owning your ambitions and being committed to your success is a great way to stay on track and focused.

It’s easy to dream about success – it’s more challenging to take the steps required to see it happen. Whether it’s waking up early for meetings or pushing through the struggle over the weekend – embrace and stay committed to your dreams.

Surround Yourself With A-Players From Day One


What a lot of people forget is that it was Lil Wayne who signed Drake to Young Money after creating hits for a half-decade in which he earned his self-proclaimed status as Best Rapper Alive. In 2008, Lil Wayne’s Tha Carter III sold 1M copies in its first week and since then has been placed in Rolling Stone’s 500 Greatest Albums of All Time and has been certified triple platinum.

Lil Wayne was essentially at the top of the game. 

In 2009, Drake released So Far Gone, a mixtape that put him on the map with one of the first mixtapes to ever go mainstream. Although he had released an earlier mixtape, and appeared on Canadian TV, it was So Far Gone and it’s hit Best I Ever Had that skyrocketed Drake’s stock. Lil Wayne was able to put Drake on the map the same way Dre did with Eminem and Eminem did with 50 Cent.

Drake could have been signed by any label in the industry but rather than accepting a deal from an average label, Drake signed with the biggest rapper at the time and eventually created Young Money. To ensure he was aligned with greatness, he collaborated with Trey Songz to create “Successful“, Rihanna’s song “What’s My Name?” and Eminem, Kayne West and Lil Wayne with “Forever.”


I might catch some flak for saying this but if you want to build an audience that adores your brand, Drake can offer you insights that can change the way you approach marketing and communications. What will get one further ahead than sales or net worth is distribution and word of mouth. The money can come second.

Now I got a house in LA.
Now I got a bigger pool than ‘Ye
And look man, Ye’s pool’s nice
Mine’s just bigger’s what I’m sayin’

He’s been consistently creating great art and continues to change the industry year after year. What’s the future hold for Drake? We don’t know. But one thing we do know; is that there are very few people with the amount of influence Drake has. While he’s not yet at mogul status, he’s well on his way.

The influence comes from hustle.

The influence comes from grind.

The influence comes from understanding his audience, his role and doing everything he can to be successful.

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Cierra Wright

I really love reading your blogs every week I’m a starving artist (cosmetologist) lol but for real…. first of all I’m very lazy I will admit only because I’ve been reading your blogs I have no choice but to keep it real I promise I have the platform laid out before I have plenty of opportunities and I work with some of my city best stylist and I mean very well connected and established well anyway I can type all night so just know after my sister talks real funky to me all the time about how I’m playing it’s your blogs that really make me understand how I’m playing I appreciate how you take your time to put a cool nice brief summary of what’s wrong with people like me and how we can get our shit together cause I’m a HUSTLER BY BLOOD NOT RELATION! My hands been the way I’ve eaten my whole entire adolescent and adult life. I just be needing that extra drive to make it more than just a hustle to stay afloat I want this thang to turn in to something that’s gonna feed my baby, babies! KEEP IT UP MR. SIMMONS I LOVE YOU YOUNG MAN

Ross Simmonds

Thanks for the comment Cierra – So glad you’re enjoying my posts! You’ve got this! Excited to hear what’s next for you. Keep hustling.


Loving life starts with loving ourselves.

Our affirmation this week is: “I love myself for being me


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