9 Things Soloprenuers Should (and Shouldn’t) Emulate from ‘Entourage’





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Did you know that HBO made a show loosely based on Mark Whalberg’s possy of friends? It’s called Entourage and the cast (the Chase Men) are a lot prettier than their real-life counterparts. Perhaps this was a Walbergian fantasy.



In fact, HBO considered making the show into a direct documentary. But Walberg’s violent past was too much for the early aughts audience. They instead chose a satirical approach which was probably a good idea.

Walberg is executive producer and he had a say in almost everything that went into Entourage. Walberg is an entrepreneur as well as a successful Hollywood actor. And the satirical comedy Entourage gives a glimpse into some of what you should (or maybe shouldn’t) do to get to the top.

1. Have a Loyal Crew Like Vincent

Many of us start out as solopreneurs. It can be a lonely business. Sure, we have friends we see on occasion, but they aren’t going in the same direction as we are.

Just like the President of the United States, Vincent was nothing without his friends and those with whom he surrounded himself.

Ari gold, Turtle, Johnny Drama, and Eric Murphy each contributed something to Vincent’s life. Eric or “E.” is an honest Abe who helps Vincent make decisions. He’s not afraid to speak his mind especially when Vincent refers to the area around his crotch as his “airspace”.

We all need an E. in our lives to balance out our impulses.



Ari Gold is his business manager. He doesn’t get along with “E.” at first. Ari supplies Vincent with opportunities.

This is the holy trinity of Entourage. If we cut the rest of Vincent’s crew, the show would go on just fine.

Have a holy trinity. People you trust with your life. One to push you to your limits and another to temper your passion.

2. Don’t Let Success Get to Your Head

The decision to forget about Walberg’s past is an unfortunate decision. Walberg (Vincent) did not grow up rich. He was the youngest of 9 kids.

He grew up in Boston and his parents divorced when he was 11. At 14, he dropped out of school and became a criminal. He stole, sold drugs, and did side hustles (the illegal kind). He eventually hit the bottom of the barrel when he beat a Vietnamese man bloody and went to jail.

After jail, he vowed to turn his life around and put his energy toward more constructive pursuits. His luck really turned when his brother Donnie from the then popular band New Kids on the Block.

When Reality Still Sneaks In

Instead of his journey from rough and criminal to stardom, the producers decided a sugar-coated version of Walberg was needed. Where do we begin Entourage? In a mansion.

Walberg is already rich. And that seems to the whole point. We’re supposed to glory and dream of the high life where we can get away with almost anything in Hollywood because “money”.

It’s why some successful people fail. They take their success for granted and let important things slide.

Vincent was the only one (ironically) not chasing the dollar in the show. But even Ari would get caught up in the dollar amount sometimes. And it was E. who would bring Vincent back in those moments.



Vincent got it right when he said, “I came from nothing. And as much as I love all the toys, I really don’t need them.”

This should be your mindset. Chase only things that add value to your life and are in line with your personal goals and standards. The money will never be enough.

3. Fail Often

Kilian Jornet climbed mount Everest twice…in two weeks. He holds the record for the fastest climb. His motto? Fail often.

You see this time and again in Entourage. Vince takes a gig like Medellin, it fails, nobody wants to work with him, and he keeps trying.

The biggest ballers in history are the people who failed the most. J.K Rowling got rejected over and over, persisted (while living on food stamps), and is now one of the richest women in the world. Henry Ford failed at five businesses before succeeding with automobiles.

Rowling even says, “It’s impossible to live without failing at something. Unless you live so cautiously that you might as well not have lived at all. In which case, you fail by default.”

Taking calculated risks is a major part of any business. You take out a loan hoping to make enough to pay it back and then some. You hire people hoping they are productive and make you more money than you pay them.

Nothing you do in this life is without risk. And when you do fail (and you will), you must have the will to get back up and keep trying even if it means doing something completely different.

9. Diversify: Don’t Keep All Them Eggs in One Basket

Yeah, brand consistency is great. And each “egg” should be uniform and pretty and well painted. But everyone who gambles knows you shouldn’t put all your chips on one square.

If things go sideways on one gig, you should have other gigs going to hold you up. This is what makes Vince’s life interesting for a while. He tries things like singing at birthday parties or tried his luck in fashion.

If one industry gives up the ghost, then you’ll know that the others will prop you up until you find a replacement.

Perhaps you go into app development and you also do web development on the side. Your apps fail, then you’ll end up with a great job in web development.

Keep Your Friends Close

Whatever you do as a soloprenuer, always value those closest to you. Vince would be nothing without his friends and family. Literally.

Look around you. Who in your life gives you the most value. Stick by them and they’ll stick by you.

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