Why Every Entrepreneur Needs Biggie’s 10 Crack Commandments

The next time you queue up Ready to Die or Life After Death, consider Christopher Wallace as a model for entrepreneurship and leadership.

Biggie Smalls (Photo: Takeshi/Flickr)
Biggie Smalls (Photo: Takeshi/Flickr)

The Notorious BIG is the patron saint of New York. One can’t go out in the Five Boroughs without hearing “Hypnotize,” “Going Back to Cali,” “Notorious Thugs,” or any other of his hit songs. He gave the rap world and popular culture more quality in two studio albums than most artists do in a lifetime. It’s a shame that his life was tragically cut short.

Among Biggie’s catalog of hits, there’s one song that gets lost in the shuffle. “Ten Crack Commandments,” the 17th track off of his eerily named sophomore effort, Life After Death, lays down the blueprint for how to succeed in the drug game.

“There’s rules to this sh**, I wrote me a manual.”

It’s a brilliant track. And its lyrics also provide some of the soundest business advice I have ever come across.

There are many great business books out there. Ryan can recommend you some. But if you’re looking for a concise and realistic guide for how to navigate the world of business, you could do a lot worse than that of the Brooklyn Moses. Let’s take a look.

“Rule Nombre Uno: Never Let No One Know How Much Dough You Hold.”

Biggie’s Spanish may be suspect at best, but he’s right in that you should never reveal the full scope of your business, especially when it comes to generating revenue. For example, making money in Silicon Valley can actually drive down your valuation and make it difficult for you to raise additional capital. If investors know your run rate or month-over-month figures, then they make projections based on those figures, instead of your user growth or technology.

“Number 2: Never Let Them Know Your Next Move”

During the 2013 NBA Playoffs, viewers were pleasantly surprised to see what looked like a clip from a new Jay Z documentary. In the three minute clip, Jay Z is seen in the studio with the likes of Rick Rubin, Pharrell and Swizz Beats, working on new music. It wasn’t until the Samsung logo appeared that viewers realized that they’re looking at a Samsung commercial.

Twitter was ablaze with speculation on what this was. Only later did we find out that Jay Z and Samsung were working together on a novel way to release his newest album. Magna Carta/ Holy Grail would be available for a free download at 12:01am EST on July 4th to the first million users of a new Samsung app. The album would then be widely released for purchase on July 7th.

As Jay Z said in the commercial, the internet is the new Wild West and he wants to write the new rules. While the album received lukewarm reviews, Jay Z should get props for thinking of novel ways to drive anticipation and conversation. Always the savvy business…man, Jay Z was thinking of new marketing schemes long before Beyonce, Drake, and Tyga would surprise release their own albums.

“Number 3: Never Trust Nobody.”

One of my first managers gave me invaluable advice regarding email. “Always communicate and follow up via email. Even if you spoke about it person or over the phone, make sure the next steps are written down and communicated via email. This leaves a trail and helps maintain accountability.”

I get it, life happens and at times, things fall through the cracks, or someone (maybe you) misunderstands an assignment or objective. But if you have a paper trail of next steps and responsibilities, it will be easy to go back and see where the miscommunication occurred or the proverbial ball was dropped. It’s hard to maintain processes if things aren’t written down. Maybe Biggie is a bit harsh in saying that your mom may set you up for a quick buck, but at least in my line of business, it’s always better to over-communicate than to under-communicate.

“Number 4: Never Get High on Your Own Supply.”

Lionel Messi is one of the best athletes in the world. He debuted for FC Barcelona at the age of 17. By the age of 25, he would win back to back to back Ballon d’Or Awards, given annually to the best soccer player in the world. Yet despite the fame and accolade he rarely calls attention to himself. Louis Van Gaal, the manager for Manchester United manager says that Messi “… demonstrates his strength in every game. As well as having talent, he is very humble, which is what I like about him. I respect him a lot.”

At times, Messi’s humility can be confused for indifference, especially in his home country of Argentina. But his focused, reverent approach to soccer has contributed to his success.

It’s easy to believe your own hype when you’re raising millions of dollars and hanging out at “exclusive” app parties. But all of the accolades, hype and commentary is just a distraction from your work. And the praise and coverage is, as Marcus Aurelius said, “no more than the clacking of…tongues.” Just as you should never take criticism personally, you should never let success get to your head and distort your reality.

“Number 5: Never Sell No Crack Where You Rest At.”

At first glance it may seem like Biggie is advising us against selling drugs in our neighborhoods. But if you read between the lines, you can see that Biggie is really urging us to look at emerging markets for growth.

Facebook was created at Harvard, intended by co-founder Mark Zuckerberg to be a social networking tool for the nation’s’ top schools. Facebook is more than ten years old now. And as the site has matured and iterated, it has seen substantial growth outside the United State. At  WSJDLive, Facebook executive Chris Cox commented on how the company’s future is being shaped by how the social network is being used in countries like Indonesia, Myanmar and India. He goes on to say that studying these emerging markets has inspired new features and products. How can you specialize your business or expertise in new markets? Being exposed to a new culture can open up new avenues or angles that you wouldn’t otherwise see.

“Number 6: That G**damn Credit? Dead It.”

My friend Ketan is a talented designer. He gets many requests to do work on spec or to work for equity. But as he told me, “that doesn’t pay the bills, homie.”

I’ve made the mistake of working for free before and it hasn’t ended well. I’ve learned the hard way that when you don’t put a price on your work, either the other party doesn’t take you seriously, or they start making demands on your time, as if you were their full-time, salaried employee.

Putting a price on your efforts is the best way to deter the riff-raff and set expectations. Plus, having money as a barrier to entry protects your time, which, according to Seneca, is “…the one thing in which it is right to be stingy.”

If you want me to look at something or to give feedback on a project, it’s going to cost you because the time I am spending looking over your “Twitter For Cats” pitch deck is time I’m not spending time with my girlfriend, family and friends.

And they get first dibs on my time and on  “all of my loyalty, all of my patience.”

“Number 7: Keep Your Family and Business Completely Separated”

Mixing family and business makes it difficult to make objective decisions. It’s hard to think about what’s best for the business when your inept uncle is overseeing finances and you don’t want to upset to the family  by letting him go. If you can’t be cutthroat and treat an uncle/cousin like any other co-worker or co-founder, you shouldn’t do business with that family member. Most of us are good at treating co-workers like family. But we lack the thick skin and resolve to treat family like co-workers.

“Number 8: Never Keep No Weight on You”

If you don’t know how to delegate, running a drug empire could prove to be very difficult. Actually, that goes for any type of business. Delegation is a skill and like any skill, it takes time to develop. Productivity Expert Jordan Cohen says that “… in today’s business world, an entrepreneur’s time can be better served by doing the tasks that matter most to the success of their business and delegating the rest.”

How do you add value to the business? If you know your strong points, you can begin to look for ways to delegate the other tasks. For example, I am great at strategy, I work with partners across Latin America to put their brands on our map. But I’m not good (yet) at pulling and analyzing data like some of my brilliant colleagues. So when a client brief requires a deep data dive, I reach out to my co-workers. They can do in 10 minutes what would take me hours to accomplish.

“Number 9: If You Ain’t Gettin Bagged, Stay the F*** From Police”

To those not familiar with the Black Frank White, what Biggie is saying here is that unless you’re getting arrested, you shouldn’t be seen fraternizing with law enforcement. In a world in which your reputation is your lifeblood, the last thing you want is someone thinking you’re an informant.

There’s an old Native American parable that says, to paraphrase, even if you’re not a dog, if you sleep next to dogs, you will wake up with fleas. So don’t hang out with people of ill-repute or people that will distract you from your work. This is good advice for both your personal and professional life.

“Number 10: A Strong Word Called Consignment”

The Silicon Valley equivalent of selling crack on consignment without a large clientele is raising too much capital. Paul Graham, the founder of Y Combinator advises would-be founders;

“The dangers of raising too much are subtle but insidious. One is that it will set impossibly high expectations. If you raise an excessive amount of money, it will be at a high valuation, and the danger of raising money at too high a valuation is that you won’t be able to increase it sufficiently the next time you raise money.”

Outside of putting too much pressure on your subsequent rounds, raising too much money can give you notoriety for all the wrong reasons. Everyone in the valley remembers Color. Unfortunately, they remember them for being a sinking ship that raised $41 million without a product. It’s a shame that no one remembers that long before Periscope and Meerkat, Color was pioneering live video broadcasting.


While I don’t only take business advice from Biggie’s “step by step booklet to get your game on track,” I’m also not the first to draw a comparison between illicit drug trafficking and your standard capitalist enterprise. As Steven D. Levitt and Stephen J. Dubner point out in their best-selling book, Freakonomics, “if you were to hold a McDonald’s organizational chart and the crack gang’s organizational chart side by side, you could hardly tell the difference.”

So next time you queue up Ready to Die or Life After Death, consider Christopher Wallace as a model for entrepreneurship and leadership. He sold over 17 million records in the United States alone and as of 2015, his net worth was an estimated $160 million. His advice may come from an unconventional career choice. But at least now you can benefit from the manual without, you know, having “your wig pushed back.”

Eric M. Ruiz oversees sales and strategy in LatAm for Waze, the Social GPS and Navigation app that was acquired by Google in 2013. A native of Modesto, Calif., Eric now resides in NYC and struggles to find decent Mexican food. When he’s not in Latin America, Eric can be found reading, writing or yelling at his TV while watching soccer. Views and opinions are his own.

Why Every Entrepreneur Needs Biggie’s 10 Crack Commandments