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This has been done many times before, even on HN.

And while on the surface it sounds good, there are lots of things that don't actually apply to startups.

Still, a great song from a great artist.

I would like to hear some examples of why this only sounds good on the surface, but in reality don't actually apply to startups...
Generally, because startups are positive-sum, and your customers and competitors are not out to kill you (and in fact, in a lot of cases, other firms in the same field, even if they compete, will cooperate on standards, support each other incidentally by growing the market, and can coexist nicely). As well, while the government sometimes gets in the way of startups, and some things like IP law can be roadblocks, startups aren't generally doing something explicitly illegal, and your risk of being shot by the feds on a daily basis is a lot lower.
"Never sell no crack where you rest at": I think you misunderstand this one. What he means is that you should do the risky stuff somewhere else, where you can step away from.

Your home is where your family is, where you are vulnerable as you sleep, you don't want to do something like having crack-heads around there or cops busting down the door.

In technology terms, if you have something bringing in steady money, don't go do crazy experiments on it. If you have a project that needs to be delivered on a certain date, don't go using a brand new untested language on it.

In essence, do the risky stuff at a spot where you can walk away with little consequence.

Or to put it in the simplest terms, don't shit where you eat.
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That's Jay-Z and Biggie covered, the real question on everyone's lips is what Tupac had to say about it all.

</cheeky comment I hope people don't take seriously>

I'd like to hear from Vanilla Ice.

Stop, collaborate and listen

Collaboration and listening are two of the most important aspects of entrepreneurship.

Ice is back with a brand new invention

Innovation is the key to launching a successful company

Something that's got a hold of me tightly, flails like a harpoon daily and nightly

... on second thoughts, forget Vanilla Ice. Let's hear from Morris Minor & The Majors.

"A strong word called consignment, strictly for live men, not for freshmen, if you aint got the clientele say hell no, cause they gon want they money rain sleet hail snow" -

In other words, don't take outside money unless you are ready to deliver, cos the ANgels/VCs will want their money back.

Yea that's a really good point. Make sure you have some traction (clientele) before takin' da chedda...
I think rule #10 is actually warning against scaling too quickly - don't go to the top of the supply chain, or overspend on inventory when you're still small and don't yet have the customer base.
Never get high on your own supply could easily be taken to mean, "Don't believe your own hype." Which is probably important for both the pusher and the entrepreneur.
“There are two industries which call their customers ‘users’...”
Believe it or not, I did something similar to this a while back: http://bryanhelmig.com/notorious-b-i-g-crack-commandments-in... In fact, I think this sort of abstraction is a useful way to internalize all that "business advice" you read everywhere. I tried to twist them to make them work with otherwise best practice business advice, because honestly, how could one possibly straight out disagree with Biggie?

Either way, it is very cool to see someone come up with the same concept independently!

I like the idea of this post, any excuse to listen to biggie is a good one. However, I think the author misinterpreted a bunch of lyrics.

Never hold weight on you. He means never keep anything incriminating on you. e.g. don't carry drugs on your person. in entrepreneurship, i'm at a loss for what the equivalent would be.

Maybe it should be taken literally. Ask Sean Parker.
For further exploration of the parallels between the drug game and the rest of the game: check out the wonderful section of Freakonomics that's devoted to breaking down how successful crack dealing gangs conduct business.
"Rule #8: Never keep no weight on you"

That doesn't mean don't get to close too your product. Biggie is saying you should not take large personal risks on behalf of your business.

I agree, this author knows nothing about rap. This lyrics is about dispatching the risk to your underlings.
Ain't nobody gonna hold me down.
That's an unhealthy attitude in business, thinking like a victim.