5 Business Lessons You Can Learn from Jay-Z’s “Imaginary Player”

Jay-Z has influenced this era of entertainment and entrepreneurship more than your favorite tech founder. Yeah, more than Elon Musk, Bezos or any other resident of the Valley.

Maybe I’m crazy, but maybe I’m right.

If you know me on any level, you the know the impact of Jay’s moves in my own life. As a brown kid growing up in the ’90s, he was the first successful person of color that I saw who owned something and was actively challenging the status quo. Naturally, none of that would’ve been possible without Dame Dash and Biggs, but you get my point.

The combination of listening to Reasonable Doubt, watching his MTV Diary episode and reading the liner notes on Vol. 2 literally changed the trajectory of my professional career forever. I was barely 12 years old, but in those few months I realized that I could never work for someone else. The only way I would be fulfilled was to build and develop my own thing.

One song that always stood out to me from that era was “Imaginary Player.” It read almost like a college course from the first time I heard it. In those 3 minutes and 57 seconds, Jay gave us the blueprint on leadership, ownership and the perils to building your own business. For whatever reason, I’ve been playing this song all week and it figured it was worth dissecting. Let’s get into it:

On longevity:

“I got bail money, double-XL money. You got ‘flash now, but time will reveal’ money.”

Playing the long game is one of the hardest things to do. It’s way more intoxicating to create an unicorn, get acquired and ride off into the sunset. But as any seasoned entrepreneur will tell you, longevity is what separates the good from the great and makes the entire journey more rewarding.

As we live through the peak years of the “flash now, but time will reveal” trend, it’s hard to tell who has it and who doesn’t. Social media makes it easy to create whatever facade you want, but in the end, the authentic ones will prevail.

Don’t get caught up trying to keep up with the circus. Building for the long term means eschewing short term gratification — the vacations, the nights out, the leisure time — and focusing on what’s going to help you grow and be in the game for the long term.

On ownership and equity:

“[You] sell a bunch of records and you still owe dough.”

Ultimately, if you don’t own a piece of the pie, it doesn’t matter how big or valuable the pie is. If you don’t have equity in the situation, chances are that someone is making more off of it than you.

The next time you have an idea but can’t afford to hire people to execute it, think about offering them equity. By helping others be owners, you’re incentivizing them to help the operation succeed.

Or, the next time you’re asked to work below your rate, force the hand and ask if the other side is comfortable trading a slice of equity for your time. If their success is dependent on your time and effort, it’s only appropriate that you have a right to that.

Jay was adamant about ownership from Day 1. From the decision to keep Roc-a-fella independent, to his decision to buy back his masters from Def Jam, to getting a equity share in the Brooklyn Nets. He knew it was more valuable to own a slice of a billion dollar operation than to take a few millions in cash.

On leadership:

“Still busting a gat when things get critical..”

I know this line is a little ridiculous (and I don’t condone any form of gun violence) but it’s still important.

Ultimately, this is about stepping up and making decisions when things are on the line, even if it feels “below” you. Jay knows that someone of his stature shouldn’t be the one pulling any triggers, but he also knows the importance of showing leadership and giving people an example to learn from.

Don’t be above doing the dirty work. Regardless of your title, status or ability.

On optics vs. reality:

“All in they dumb raps, talking about how they funds stack. When I see them in the street, I don’t see none of that. Damn, playboy, where the f*ck is the Hummer at?”

Literally, a line about Instagram flexing before the internet even existed. I’m telling you, this song is special.

A lot of young entrepreneurs are obsessed with making things look good for the world. To the point where they are willing to sacrifice the quality of their work, their bank accounts and everything in between. It’s a calculus that makes no sense yet so many people are foolishly caught up in.

But guess what? If it’s not authentic, people will pull your card. Every time. Ask Bow Wow. Or Pepsi.

People like to say “perception is reality,” and though there’s some truth to that, ultimately, reality is reality and you can’t hide from it.

On being one good idea away:

“It’s funny how one verse can f*ck up the game.”

This is maybe the most important line in the whole song. It’s a reminder that, regardless of your past failures, missteps and missed chances, you’re always one good idea from that life-changing win. But it’s going to take you creating something undeniable.

It’s like Drake’s So Far Gone. Elon Musk’s Tesla Model 6. A pair of glasses from Warby Parker. These are all undeniable products that completely changed culture and the lives of the founders forever, regardless of what they had done in the past.

A big part of this game is not being cynical about the past and being open to experimentation, exploration and taking the right risks to grow your operation.


“These dudes acting like I owe them something..like they gave me Roc-a-fella start up money.”

A reminder: Don’t let people who haven’t invested in you, your company or your idea, ever tell you how to do things.

Like what you just read? Clap it up to help others see this post and apply it in their own lives!

Have questions about entrepreneurship, investing, tech, music, or anything in between? Get in touch with me at @anihustles.

The oldest son of an immigrant. | CEO @ Green Room Creative. Investor, hustler, speaker. Connect: @anihustles