Mark Cuban's big break on "Entourage"

and 4 lessons to help you seize your big Hollywood break too. Plus, check out this week's the replay of "Coffee with KP" below

I met Mark when I was working for a new company he invested in called Content Partners, a unique entertainment finance company that buys backend profit participations in TV and film. I worked as the SVP of business development & marketing and my job was to talk to the people who owned backend and let them know about our service. As any business owner will tell you, educating the market about a new product or service is challenging; you need to maximize every opportunity, including leveraging the name of the most famous investor in creative ways.

I helped Mark Cuban get his big TV break on “Entourage” and I learned 4 things in the process that I hope will inspire you to get your big Hollywood break too.

“ENTOURAGE”/HBO

In 2009, HBO’s “Entourage” was a massive hit that everyone in the industry was watching. In fact, cameos from industry insiders, athletes and celebrities were a signature element of the show. In one of my conversations with Cuban, I learned that he loved the show and wanted to be on it. I said I’d be happy to call the showrunner Doug Ellin and see if we could get him an appearance. Plus, it was a natural way to talk to a successful showrunner about Content Partners (who knows, maybe he’d want to sell his backend on “Entourage” one day.)

It took an entire year of brainstorming, calling, emailing, setting & rescheduling meetings to make sure that Mark Cuban stayed on Doug Ellin’s radar. I was a representative for Content Partners and our billionaire investor, so I was mindful of being polite and persistent without being a pest. Plus, I wanted to stand out in the most thoughtful way, so I made a few trips to Edelweiss to get Doug’s favorite chocolate covered pretzels. I figured if I was going to ask for something, I should set the tone by giving something first.

There is no way to know what tiny actions (if any) made a difference, but the end result was this: Mark secured the appearance, the line he delivered to the fictional Ari Gold was, “I’m not here to talk about that, let’s talk about Content Partners” (I mean, you couldn’t buy and ad that was better than this!) and the Doug, the cast and crew loved working with Mark! This was a win-win-win!

4 SIMPLE LESSONS FOR SEIZING YOUR BIG BREAK

1. Where & who you work with is more important than what you will be doing.

   Mark Cuban didn’t want just any old guest spot on any TV show, he wanted an appearance on pop culture juggernaut “Entourage!” You should have the same focus and target the place that you are really, really interested in and be flexible on the role. Your ideal first job is typically at a reputable talent agency or management company. You can have a preference of dept or role, but I’d be flexible to accept any position where you could be useful; reception, mailroom, floater, accounting, 2nd assistant etc… Think of an agency like college. Getting accepted to a University is hard, but changing a major is easy. CAA is the University and Unscripted TV is your major. It’s very easy (and typical) to move desks after a year. Make the right environment your focus.

2. It takes time to find the right job (so start looking before you need to)

   Cuban wasn’t sitting around waiting for his big break and neither should you. It took a full year to get Mark on the show and given the state of entertainment in 2024, it could be weeks, months or even a year to find the right opportunity for you. Start the process of identifying potential employers, have a polished one page resume and take informational interviews regularly.

   If the right entertainment job isn’t available when you are, no problem. Get a job in the service industry like a barista, hostess/server or at a gym and continue to take informational interviews and apply for the job you want. Best time to find a job is when you have one.

3. Never underestimate the power of a small opportunity

   It’s a little known fact that Mark was on reality TV way before “Shark Tank.” In 2004, he was the star of a big primetime ABC show called “The Benefactor” that didn’t do very well. You’ve probably never heard of it and I’m sure he has long forgotten about it. The failed show was merely a blip in a big life story.

   Nobody could have predicted that one appearance on a cable show would turn into a storyline that played out over 8 appearances on the show and movie. It eventually paved the way for him to be on “Shark Tank” for 15 seasons! Even though he is on to other ventures with Mark Cuban’s Cost Plus Drugs, his star is forever fixed in the pop culture firmament because one tiny opportunity.

   Although you may want to be the star of the show or president of your own production company, you will be better served if you make mistakes on someone else’s dime as an employee. Be an intern, assistant, or any kind of background player and learn the game before become your own boss. You never know when a small opportunity makes the way for bigger things.

4. Everyone can benefit from an expert

   I have found the the most successful people in the world are the most teachable. As you will hear in the below replay of “Coffee with KP,” Mark has an insatiable curiosity and humble enough to take direction from others who he respects in various areas. He tried to get on “Entourage” before me, but for whatever reasons, it didn’t work out. I’m grateful he trusted me with this part of his career and I hope I get the chance to work with him again. I was so grateful that he took an hour out of his day to talk with my class and inspire us all with his stories of successes and failures.

   If you want to prepare for your big Hollywood break and need a little help with your resume, interviewing or networking strategies, coaching might be right for you. To see what program would fit your needs, send your resume to hello@mygradsgetjobs.com and we can set up a complimentary 20-min zoom.

COFFEE WITH KP AND MARK CUBAN

Continuing our Coffee with KP: Covid Collection series, check out the one hour replay of our conversation with Mark Cuban.

Mark earned his Bachelor’s degree in Management from the Indiana University Kelley School of Business in 1981. He was fired less than one year after working one of his first jobs out of school because he tried to get his company a new client instead of opening the store! But this “mistake” at the time his led him to start his own company which he later sold for $6 million when he was 30 years old. In 2000, he sold his company for $5.7 billion dollars to Yahoo. Now in 2024, Mark is still a superstar TV personality, stakeholder in dozens of successful companies, and most recently, founder of Cost Plus Drugs, a pharmaceutical company dedicated to keeping lifesaving drug prices affordable.

In this episode of “Coffee with KP,” you’ll learn about failure (yes, even Mark Cuban got fired,) his experience producing movies (“Enron: Smartest Guys in the Room” and “Good Night and Good Luck”) and giving contrarian advice to students and aspiring 20-somethings looking to thrive in entertainment.

Upgrade your subscription to paid below and unlock this 1-hour group informational meeting with Mark Cuban and get access to previously released episodes of “Coffee with KP.”