“I’m not a business man, I’m a business, man” rapped Jay-Z back in 2005.

And boy was he right!

Now, with over 100 million records sold, and a net worth of $810 million, the recent Songwriter’s Hall of Fame inductee has a lot of game to share.

I was 16 the first time I heard Jay-Z, the entrepreneur.

His 6th studio album ‘The Blueprint’ was like a ‘How to’ manual for anyone looking to achieve independent business success.

At this stage in my life, I was hustling my college books and occasionally selling overpriced chocolate to my sister.

Success to me, was getting good enough grades to go to University.

I hadn’t really considered my options beyond 21.

But tracks like ‘U Don’t Know’ changed all that.

To me it was the ultimate motivational speech.

A call to action that in time, and with a little patience, anything and everything is possible. As long as you stay focused and back yourself.


“Put me anywhere on God’s green earth, I’ll triple my worth” Jay-Z

You can’t knock the hustle (but you can grow from it)

Fast forward to 2016, and I decided to lead the corporate world behind and be my own boss. Focusing on helping purpose driven people grow their brands.

In under 2 years, I’ve learnt that there’s much more to business than sales and financial accumulation.

In fact, the money is just the end result of how well you handle a heap of personal and business lessons that life throws you along the way,

So when Jay-Z’s 13th studio album 4:44 came out on 30th June 2017, I was eager to glean as much insight as possible to help me and my business grow.

It didn’t disappoint. So much so that I felt compelled to share what I’d learnt from the 2 months I’ve studied it.

So without further ado, here’s 8 business lessons I’ve learnt from Jay-Z’s 4:4

#1 It’s ok to be vulnerable

In the opening track “Kill Jay-Z”, Shawn Carter has an open conversation with the lucrative persona he’s created for himself.

He expresses that at times, “Jay-Z” made him lose sight of what’s most important to him, like his family and friends.

“You can’t heal what you never reveal” Jay-Z

It’s a stark reminder to be true to yourself and stay grounded in the midst of success. Which starts with not letting the ego dictate our business decisions.

It reminded me of this quote I love by Brene Brown -“Courage starts with showing up and letting ourselves be seen.”

It’s ok to show people all of you, even the bits that aren’t so pretty. After all, we’re all human, no matter how much success we achieve.

#2 To be open to change

Let’s be honest, it’s easy to point the finger or pass the book when something isn’t going to plan in your business or personal life.

I for one have been guilty of this. When the truth is, nothing changes until we do.

4:44 is brimming with honesty around the things Jay-Z would’ve done differently if he could turn back the clock.

And despite approaching billionaire status, that includes accounts of missed investment opportunities.

In The Story of O.J, he rhymes about spending his money on fast cars. As opposed to making smart property investments prior to the gentrification of his home town, Brooklyn.

“I could’ve bought a place in Dumbo before it was Dumbo, for like 2 million.

That same building today is worth 25 million, and guess how I’m feeling? – Dumbo!”

No matter how big or small your business is, it’s never too late to change and make better choices.

#3 To transform mistakes into lessons

Let’s face it, being an entrepreneur isn’t an easy path to take. It’s fraught with uncertainty which inevitably translates into things not always working out the way we’d hoped they would.

The truth is, you can’t make hundreds of millions of dollars without some or maybe a lot of turbulence along the way.

“A loss ain’t a loss, it’s a lesson. Appreciate the pain, it’s a blessing.” Jay-Z  – Smile.

I’d imagine even if you’re not a millionaire that these lines ring true with you too.

After all, it doesn’t matter how talented you are or how many letters you have after your name, what ultimately defines our longevity in business, is how we bounce back.

#4 To make smart investments

The Story of O.J. is a tutorial designed to encourage African-Americans to be more fiscally astute.

But the lessons in this track are universal.

“You wanna know what’s more important than throwing money in the strip club? Credit.” Jay-Z – The Story O.J.

Ok, so maybe you’re not into throwing money at pole dancers like some rappers do.

But like every business owner out there, I’m sure you want to be savvy with your cash, right?

After all, cash flow is one of the top issues entrepreneurs face.

Whether it’s overpriced donuts or software we sign up for then never use; we’re all guilty of wasting money from time to time.

Jay-Z explains how people may think he’s being “boujee” by buying art. But how that art is an investment that’s going to accrue over time. Outlasting both his rap career and his life on earth.

“I bought some artwork for one million, two years later, that shit worth two million, few years later, that shit worth eight million” Jay-Z – The Story Of O.J.

When you’re an entrepreneur, risk spreading is always a smart thing to do.

And anything that accrues in value over time is a smart investment. I for one love to collect vinyl. After listening to The Story of O.J I don’t intend to stop any time soon.

#5 To remain humble

In the opening track “Kill Jay-Z”, Jay-Z talks about killing off his ego in order to progress through life and grow. He references the relationships that have suffered because of his ego. Namely his marriage to Beyonce.

In business, ego is often responsible for hijacking our judgement.

And despite humility being perceived as a mild personality trait, it’s in fact one of the most effective ways to be a better leader and counter the ego.

Learning how to control your ego could:

– boost your reputation

– save valuable relationships

– take your business to the next level.

#6 To leave behind a legacy

I admit, I do dreams that when I have kids, they’ll inherit my business.

Ok, maybe marketing won’t be their cup of tea. But there’s something deeply satisfying just knowing that my endeavours can somehow be passed on, to help the next generation get a better start in life.

One the track “Legacy” Jay-Z raps about creating opportunities that will surpass his lifetime.  Focusing on securing his families future and philanthropy.

“Generational wealth, that’s the key!” Jay-Z – Legacy.

By thinking beyond your lifetime, ideas somehow become more expansive and limitless. Essential for any entrepreneurial mindset.

#7 To share your knowledge

Sharing is definitely caring.

Not only does it feel good to help people grow, but it also benefits society as a whole.

“Y’all think it’s bougie, I’m like, it’s fine. But I’m tryin’ to give you a million dollar’s worth of game for $9.99” Jay-Z – The Real O.J.

A true leader will also empower people with what they know rather than keep it to themselves.

Because they’re aware that the cause they represent is bigger than them. And that sooner or later, the baton will need to be passed on.

Jay-Z knows he can inspire entrepreneurs by sharing the insights that create his story. So he’s generous in sharing anything he feels can help improve the situation of those that come next.

By doing so only strengthens his position as an business, man.

#8 To have a vision of the future

Intuitive leaders focus on how their cause can help shape the world. And they work to speak that inner vision into existence. For Jay-Z, a big part of that is “black excellence” and making use of his business success to help break the poverty cycle that African-Americans often experience far too often.

“Leave a piece for your siblings to give to their children too” “Legacy” Jay-Z

On the track “Legacy” he’s willing this into existence. A practice that works when you verbalise what you want to happen. I know this works for me, and hopefully it will for you too.

All in all, 4:44 is an honest open letter on how to get ahead in business and in life. It’s a reminder that no matter how much money you make, we’re still all human with the same insecurities, flaws and setbacks.

There’s always things we can all do better. Things we can change and learn from. But ultimately, it starts and ends with us as individuals and our willingness to grow and develop as people.

These 8 lessons are timeless, just like the album.

I hope you get to listen and learn from it too.

Feel free to comment your favourite track and let me know what business lessons you’ve learnt from 4:44.







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