What Entourage Can Teach You About Successful Freelancing

image of entourage cast

There’s just something about those filthy Entourage boys that gets to me — in a good way.

Haven’t seen the show? It’s crass. It’s sexist, often to the point of being misogynistic. It’s so politically incorrect that sometimes I have to look away.

Also, it’s hilarious and it brings me joy.

Like a lot of successful entertainment, the show is built around archetypes that are larger than the individual characters they play. And those archetypes can actually get you more work, more money, and more enjoyment as a freelancer. I won’t say they’ll let you have quite as much fun as a rich movie star, but it’s close.

If you haven’t seen it, here’s the thumbnail premise: Vince, a 20-something kid from the streets of Queens, has become a movie star and is living large in Hollywood. He’s always got his three best friends from the ‘hood by his side.

Things are thrown at them: money, women, sex, nice cars.

And they throw a lot back: attitude, laughter, happiness, charm.

Interestingly, unlike so many well-reviewed shows on cable, each episode ends well. There’s no cliff-hanger leaving a main character half-dead on the floor at the season’s end. As the credits roll, the viewer feels good (and rich and stoned and satiated) by proxy.

In these hard financial times, as a freelance copywriter and blogger, I take heart in their happiness, optimism, and faith.

So I’m going to live my freelancer’s life Entourage-style. Here’s how:

Stay in the game like Johnny Drama

Johnny Drama is a washed-up “D-list” actor who is (in my opinion) unattractive, annoying, and talentless.

But he has no idea.

He thinks he’s a god, resting on the laurels of acting jobs past. He walks around like he owns the place and he assumes that everyone loves him. He works hard and somehow manages to get work. As a result, his star is rising again.

Channeling Johnny Drama is about putting yourself out there, believing in yourself no matter what, and never, ever giving up.

Dig up the dirt like Ari

Ari Gold is a hilariously obnoxious, egotistical power agent. He has an uncanny knack for digging up dirt and knowing everything about everyone. It helps him get his way.

As a freelancer, you want to dig up some dirt of your own. Find the companies you want to work for and then find their Achilles heel.

No, I don’t mean blackmail the Marketing Director because you know he’s sleeping with his assistant.

I mean dig and find out what that juicy client’s most pressing problems are. Then show up to present yourself as the solution.

”Connect” like the women on the show

Most of the women on the show sleep with whoever, whenever, wherever. Most important to the show’s premise, they sleep with Vince’s friends (yes, his entourage) to get close to Vince.

Um, don’t do that.

But do do this:

Network. Talk to people. Including those you think are “big, important” people.

Seriously, this is not a time to be shy or play small. Talk about what you do, spread the word around like mustard on a pastrami sandwich. Keep making connections, and with a little luck, one day, you’ll get to sleep with the big guy.

(Just to be clear, by sleep with I mean write for, and by big guy I mean a huge client that employs you over and over again and pays you a lot of money.)

Love like Lloyd

Oh Lloyd, you sweet, little man.

Ari’s assistant-turned-agent is happy, enthusiastic and loyal. He keeps his word and he fights for his people. And they don’t forget.

In the freelancing world, if you can be a good person, an honest person, and a loyal person, if you follow through and do what you say you’ll do, if you’re reliable and you perform well, then you will get hired again and again.

And people will say nice things about you to other potential clients.

Master Vince’s attitude

Sure, he’s rich, beautiful, and has more charisma than a box full of puppies.

But he also has an amazing attitude: It’s all good, it’s all easy, it’ll all work out.

He’s surrounded himself with people he trusts — no matter what. They’ve got his back . . . and that gives him a sense of safety that oozes off of him. People like him, they want to work with him, they want to be around him.

I think this is the most important point on the list. If you sit around sunk in doom and gloom, 1) no one will want to be around you, 2) you won’t have the energy or inspiration to change your situation, and 3) well, you know all the things they say go along with a bad attitude. High blood pressure, heart disease, acne, swine flu, leprosy, you name it. It’s bad news.

Buck up, fake it till you make it, be the change you want to see in your inbox — and all those other clichés.

And, maybe — just maybe — the clients, jobs, and opportunities will be on you like . . . well, like an entourage on a star.

About the Author: Lover of butter, wordplayer, marketing writer, ghostwriter, Julie Roads is the owner/founder of Writing Roads. Follow her on Twitter @writingroads.

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Reader Comments (51)

  1. says

    I love this article! Thank you so much for sharing/writing it.

    I personally have never seen the show Entourage, but I love how you alluded to it and I found your example and tips to be very informative.

    You gave some tips that I was unaware of, but now am going to try as well as tips that I already implement in my daily professional life and will continue to do.

    As you said with clichés, “Buck up, fake it till you make it, be the change you want to see in your inbox — and all those other clichés.”

    I’m all about the “be the change” type of attitude and I think if you work hard, eventually you’ll find your footing and through persistence, you too, will make it.

    On that note, I think you left out one important tidbit to tie your entire piece together, “focus.” All of the above is great, but it won’t ever come into the picture if you can’t stay focused. Too many people forget what their main intentions were along the way.

    Great article!

  2. says


    Awesome, Julie. Great connections. I adore me some Entourage, for sure. I’d thought of drawing a parallel to Ari before, but never to the entire show.

    My favorite part:

    “He’s surrounded himself with people he trusts — no matter what. They’ve got his back . . . and that gives him a sense of safety that oozes off of him. People like him, they want to work with him, they want to be around him.”

    I couldn’t agree more that that’s the most important part. Vince’s demeanor is certainly something to be admired. I love how he deals with success, but I LOVE how he deals with defeat.

    Tre cool. Thanks.

  3. says

    Great post, I love the analogies though being British, I don’t know the show. The only one I wouldn’t agree with is the connecting one… I’m not sure it works like that – if you really want to sleep with the big guy, you need to get his attention and sleeping with his mates is not the best way to do this :). You need to do something for him that will make him notice you quickly. While this may not get you in his bed, you will have a better chance of getting his email and who knows where that may lead.

  4. Sonia Simone says

    If we move away from the analogy and toward the actual, though :), if you’re not attracting the attention of the “big guy” but you do cool stuff for people the big guy knows, you move into a more trusted position. You’re getting people the BG knows to say, “Yeah, this person is cool and trustworthy.”

  5. says

    Goes to show, you can learn lots of useful stuff even from obnoxious characters.

    Awesome post, Julie. Plenty of new metaphors to chew on.

    Will try to check out the show, too.

  6. says

    Ari Gold is without a doubt my favorite TV character of all time. That guy is as aggressive and un-PC as they come, and because of that everyone steps out of his way like they would a steam roller. I Also like how Vince’s charm (alright, and good looks) allows him to get anything he wants just by looking like he wants it. Definitely some traits one could learn to benefit from.

    Even though the plot has been sagging for eons.

  7. says


    I needed this blog post today, so thank you for that. Just before I read your post I was sitting here feeling sorry for myself when it struck me that I have so much to me thankful for. I stopped what I was doing and expressed gratitude for the things that are going right in my life and I felt the shift in energy.

    I loved your analogy, it’s great and the best part is that you provide concrete steps for others to follow. I have never watched an entire episode of Entourage, but I have always been mesmerized by the way the characters carry themselved.

    I have the skills to execute the steps and I start today. I have been meeting with colleagues to identify where the opportunities are. And there are many out there. These people have been very generous. People like to be asked.

    And I am learning not to hold myself back, because no is a part of the English language.

    I feel very good when readers of my blog The Invisible Mentor let me know what I am doing right, so it’s important for me to check in with you and say thanks. People like to feel appreciated and I suspect you do too.

    Avil Beckford http://www.twitter.com/avilbeckford

  8. says

    I’ve been reading you guys for almost 8 months and have learned a boat load but never commented until now. Entourage has meant so much to both my wife (musician) and myself (radio presenter) as we completely get wrapped up in so many of the same situations. This article so wonderfully describes the best things to take from the show and put them into practice in our daily lives. Thanks Julie! You’ve just made a new friend and follower and as my wife is now singing…”A new fan!”

  9. says

    Great post!

    Johnny Drama is an interesting aside. Evidently, Mark Wahlberg had Kevin Dillon in mind for the part when writing it. Dillon is the real-life “Drama.” They made him sweat it out anyway during the auditions.

  10. says

    This post came at the right time. I was struggling, deciding to remain on the same path, or change direction a bit.
    Like Avil above, I had a palpable shift in energy.

    I don’t know the show, or the characters, but I like Vince’s attitude. “It’s all good, it’s all easy, it’ll all work out.” Of course it isn’t true, but we can live like it is. It is a brighter, happier world when we do.

  11. says

    Love your insight… That’s a cool way to look at things and I’m sure that it’d be possible to find those role models all over…

    Thank you for the post

  12. says

    Damn good writing!

    You know, with the invention of Twitter, I can become any famous Internet star’s entourage with one click on a follow button. Twitter is like Entourage 2.0 and all freelancers should be using it.

  13. says

    Julie – What a treasure! I love your take on this and I like Entourage for all the reasons you describe, and then some. I appreciate that you took this to the next level and showed how we can all learn something through these “over the top” characterizations.

    Much might also be said about the two members of the Entourage not mentioned by name – Turtle and E. What’s your take on their contributions? I buy both as role models, considering Turtle’s unfaltering loyalty, E’s sense of responsibility and work ethic. Would you agress?

  14. says

    No love for Turtle? The guy is going to college so he doesn’t have to have his rich friend support him. I see that as “improve your skills so you can get better freelance work and don’t need your employer to give you a security blanket”

  15. says

    Thanks for the tips Julie. I have to admit I’ve never watched the show but it’s not about watching it but looking for something to learn from everyone and anyone and seeing how I can incorporate that into my work.

    I think I’d like to be Vince for a day; for many days, to never stop believing that it will all work out. Support does more than prop me up; it gets me going further because I know there are people who believe in me and expect nothing less than my best.

  16. Theresa C says

    Loved this article – thanks so much for sharing! Helps remind me that there is always something ‘good’ in a person if you take the time to look past the surface. Now, Shauna is another story…

  17. says

    @Scoti, I thought the same thing! I thought they were using email as a metaphor.

    @Julie: Lover of butter??? You must be the sister I never had.

  18. says

    Wait. I’m NOT supposed to sleep with everyone? It is all an extended metaphor?

    Crap. Crap. Crap. I have been doing this all wrong. Still, I’m booked ’til March.


  19. says

    Bad day for me to travel and be without wifi, eh? So sorry for my comment absence. I’ll try to respond in one fell swoop so your inbox doesn’t get pummeled.

    *Scoti – Ha! Whenever I see ‘Entourage’ and I open the link to find something about Entourage for Mac, I’m always, always disappointed.

    *Elizabeth and Dave – I know, I know. I did leave E and Turtle off the list. And it was on purpose. I felt like they were almost too easy because they are so ‘good’ and ‘nice’ and so the bits I wrote about them did nothing for me. In the end, I decided to be choosy, not write about every single character (also because it would have been very, very long if I had). Though, I do love your thoughts about Turtle going back to school…so true!

    *Harvest Creative: WELL PUT.

    *Linda and Avil: I’m so, so glad that this post landed on your screen at just the right moment.

    *Phil! I didn’t know that about Kevin Dillon. That is hilarious. I mean, he is SO Drama!

    *Daniel – I’m a fan now too – I mean, I can’t hear your wife’s voice, but I sure do like her lyrics…

    *Sonia & Julie – Sonia totally nailed the response (thanks, Sonia!). Of course we want to get to the big guy – but if we can’t (because it’s hard to do most of the time!), you start somewhere closer to your level…and the trust/relationship is passed along.

    *Sean! Thanks for quoting me back to me. That, my friend, is a writer’s dream.

  20. says

    Ha! No Kelly – you, and only you, must sleep with everyone. I believe it’s part of your shtick?

    …and Jodi – I’d be willing to bet that butter is even better than Vince. Ish.

  21. says

    Love the post and entourage!

    Good job making the associations to how it can help in the business/marketing world.

    you left out Eric and Turtle though….

    For them I would say respectively:

    Eric…Know when to focus and handle business. Having a good time is fun, but Eric does a good way of getting others on track whether it’s redirecting their focus or bringing it to Vince’s attention that he is blowing his money.

    Turtle…Enjoy the ride! If your not having fun with your venture/job think about a career change or going back to school.

    Good post

  22. says

    Thank you…

    Never heard of Entourage, but feel that I know some of the characters in it know…:-)

    Oh, great idea to link some of the characters in Entourage to business/work ethics and practices…

  23. says

    Sublime article, Julie. This was my fav part: “Talk about what you do, spread the word around like mustard on a pastrami sandwich. Keep making connections, and with a little luck, one day, you’ll get to sleep with the big guy.”

    Keep making connections. Having done work in the real estate business for years I’ve seen this idea alone make a lot of people successful. You can’t go wrong.

  24. Sonia Simone says

    @D.T., just give him a better title like “senior strategic coordinator” and you’ll be fine.

  25. Mary Russell says

    Julie, this was really good. I’ve never seen the show, but your metaphors are terrific and made me think. And I couldn’t resist commenting to someone who loves butter and is a wordplayer! Keep it up!

  26. says

    Am I the only Ari adding a comment here?

    Let it be said, then, that I don’t get HBO and have only seen a few episodes but am familiar with the character who apparently stole my name. Digging up dirt is one of my social media trademarks, if my name is new to you.

    Thanks for sharing, Julie. Maybe, like Mr. Writing Dad himself, you’ll be back here.

  27. says

    Darn, I only have Entourage 2008. No matter how much I click on those buttons and columns, I don’t get any of the great stuff you’re writing about.

  28. says

    Well, your writing always get the attention of many, not just pieces of me. Ungakapan good in describing the struggle of freelance.

  29. says

    Nothing beats being in a position to be surrounded by people who got you back – no matter what.

    But how?

    By fearlessly trusting others (first) and living large.

    Awesome post Julie, thoughts inspiring!

  30. says

    Hey great article about optimism and faith in yourself. I watch the show and can’t turn away either. Hillarious tie in. I’m sharing it with my group.

  31. says

    Entourage: it’s not just a guilty pleasure; it’s a template for how business should get done. I am adopting this perspective for the next few weeks. Maybe I will even acquire my own entourage one day! Thanks for the entertaining, and enlightening, take on freelancing.

  32. Renaldo says

    I love the show. It’s really funny. I only have a issue with ALL of the success in the story. I’m at the episode where Turtle had his B-Day.. Getting that Ferrari and Porsche and driving around that circuit.

    The story is starting to let me feel bad. I would do anything to have a like like that (Yes it’s only a story but in real life they can be that well off) and that’s what is really bothering me.

    I will have to work for about 50 years before I might be able to get a really nice car.. And I’m not talking about a Aston Martin or Ferrari. I don’t know if I’ll even be able to just drive in one – Ever :(

    Why can someone have so much luck and other just not enough. I can do what ever any one of those actors does on the show.

    They are having fun and getting a lot of money while I’m sitting in my office in South Africa and getting a good salary for a 25 year old but it’s just not enough.

    But it is a good show. Just wish I can do something like this.


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