Sylvester Stallone – A Case Study for Entrepreneurs



Sylvester Stallone holds a special place in my heart, and not just because I’m from Philly and therefore genetically predisposed to love Rocky.

No – for me Stallone gets a lifetime pass for creating his own career, blazing his own trail when Hollywood was ignoring him.

Legend has it that Stallone, inspired by watching the real-life boxing match between Muhammed Ali and Chuck Wepner, went home and wrote the script for Rocky in just three days.

But Rocky was just the tip of the iceberg.

Stallone went on to write 20 of the films in which he starred, including Rocky II – V, Cobra, Over the Top, Cliffhanger, a large swaths of the Rambo series, and others. Further, he directed Rocky II-IV.

Decades before James Altucher wrote Choose Yourself to inspire people to bypass the traditional gatekeepers to fame by self-producing their own work, Stallone was fashioning a Hollywood career on his own terms – writing the bulk of his starring roles.

But Stallone also had the tenacity to do it all over again a decade ago, reinventing himself after Hollywood studios once again stopped returning his calls.

Few people remember, but there was a stretch in the early 2000s when all of Stallone’s films went direct-to-video.

Recall Eye See You, Avenging Angelo, or Shade? Didn’t think so.

His first to make it back to theaters?

Spy Kids 3-D.

The point is, Stallone persevered. He went back to his roots, writing and directing new chapters of Rocky Balboa and Rambo, before putting together 1980s action star reunion franchise The Expendables largely through force of will.

Other Examples

But Stallone is far from the sole example of a Hollywood star who created his own opportunities by writing and/or producing his own work.

Vin Diesel did it – it was only after Stephen Spielberg saw Multi-Facial – the short that Diesel wrote, directed and starred in, that the actor was cast in Saving Private Ryan.

Matt Damon and Ben Affleck did it with Good Will Hunting, the script that started as Damon’s senior creative writing project at Harvard – and subsequently won them both an Academy Award for original screenplay.

Likewise, Ben Affleck has seen his career rebound from the tabloid-dominated Jennifer Lopez days by proving himself arguably a far better director than he is an actor.

Reese Witherspoon – once America’s sweetheart with a string of hits including Legally Blonde and Sweet Home Alabama, found the opportunities drying up once she had a string of box office bombs and was nearing the dreaded age of 40.

Her solution? She started her own production company and produced Gone Girl and Wild (in which she also starred).

Tom Cruise

But best of all there’s Tom Cruise.

Once the undisputed king of the box office, his career took a huge hit following his manic couch-jumping on The Oprah Winfrey Show a decade ago.

In so doing, he permanently alienated a large section of his fan base.

Viacom Head (of which Paramount Pictures is a subsidiary) Sumner Redstone blamed Tom Cruise’s antics on Oprah and pro-scientology rants with costing Mission Impossible III over $100 million in global box office receipts.

He thus fired Cruise, terminating Paramount’s 14-year relationship with the actor.

Then, in a twist, Tom Cruise did what only someone of his stature could – he and producing partner Paula Wagner bought a rival movie studio.

Specifically, Cruise and Wagner resurrected United Artists (then a defunct subsidiary of MGM) and their 30 percent stake allowed them to produce up to four films per year.

It was this deal with United Artists that enabled Cruise to star in Lions for Lambs (with Robert Redford and Meryl Streep) and Valkyrie, even as he was persona non grata in Hollywood at large.

And FYI – a decade later Cruise is now back at Paramount, continuing to headline the Mission Impossible franchise, with installment number six currently in production.


The lesson here is clear.

Yes – it’s great to be a movie star.

But if you are (or aspire to be) an artist or creative – be it an author, actor, musician, or even web designer – there are few paths to success shorter than creating your own work.

Don’t wait for approval from the gatekeepers for your “big break.”

Go ahead and do the work anyway. If it’s good, people will notice.

And eventually the gatekeepers will beat a path to your door.

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