🧐 The Art of the Underdog Story

Why the stories of your past can leverage your future
🧐 The Art of the Underdog Story
Jake McNeill
September 28, 2021
5 min read
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Sylvester Stallone was so broke he sold his beloved dog for $50. It broke his heart.

He hadn’t worked as an actor for months. His wife was pregnant. He couldn’t afford to pay the rent on their seedy apartment.

As a last resort, Stallone sold his 2 year old dog, Butkus, outside a liquor store to a local character called little Jimmy.

As little Jimmy walked away with the 140-pound bull mastiff  Stallone started crying. He had never felt more of a loser.

Traumatised about the experience, he swore to himself that he would find a solution to his money problems.

Two weeks later, he watched the Mohammed Ali vs Chuck Wepner fight which inspired him to write the script for Rocky.

He wrote the script in three and a half days.

Stallone was eventually offered $18k for the script. The studio didn’t want Stallone in the movie. He refused despite only having $106 to his name.

Stallone stood firm. They eventually caved in but with low expectations, they only set aside a small budget to make the movie.

Rocky cost $1 million ( $4 .5 million today) to make. It grossed $225 million ( over $1 billion today) at the box office and won three Oscars.

Rocky transformed Stallone into an international superstar.

What happened to Butkus the dog? According to an interview with Stallone in 2013, he bought him back for $3,000 as soon as he got money from the studio, and gave little Jimmy a small part in the movie to sweeten the deal.

Stallone and Butkus were separated for 6 months. Butkus starred in both Rocky and Rocky II.

Great story, right?

The Psychology of the Underdog story

The underdog story is a classic storyline that creates feelings of empathy and hope.

They tap into the qualities we aspire to and find most admirable in others. We fantasise about being on a similar trajectory to the heroes in the story in our own pursuits.

It creates a bond between us and the underdog because we love to support those that we empathise with and relate to.

Everyone can relate to the struggle in any creative or entrepreneurial endeavor. In a lot of cases, it is the romance of overcoming the challenge that attracts us to the endeavor in the first place.

It’s no different from the challenge of running a marathon or finishing a particularly tricky tough mudder course.

Studies have shown that witnessing an underdog story gives us hope.

I remember watching Rocky III in the cinema as a child. The cinema was sold out. We were all standing in the aisles and our rows clapping and chanting “Rocky…Rocky!…Rocky!!”

It was one of the most uplifting experiences of my childhood. The feelings of unity with my fellow cinema-goers and Rocky’s quest to defeat Clubber Lang had adrenalin coursing through my body at levels I had never experienced before.

The underdog story taps into our deep rooted human aspirations to succeed against all the odds. It’s the survival instincts that are baked into our DNA.

The Hero’s Journey

In many creative fields, they call the underdog story the hero’s journey. A story arc that has been written into many of Hollywood’s most successful movies.

It was devised by Joseph Campbell in 1949.

“A hero is someone who has given his or her life to something bigger than oneself,” —Joseph Campbell

The beauty and reason why this story arc connects so deeply are anyone can become a hero. They don’t need to be special. In fact, they’re not; they are ordinary folk from an ordinary world. But it involves a painful and challenging transformation that is the essential path to greatness.

The 12 steps, as Campbell defined them, begin with a call to adventure. Initially, the person is afraid and rejects the call. But with guidance from a mentor, they overcome their deep-rooted fears and commit to the journey.

They are tested, along the way, they meet friends and foes, and prepare for some kind of climactic showdown that requires all their strength to overcome.

The journey forces them to face their biggest fears. And when they survive this, the ordinary person has evolved into a triumphant hero.

You have watched this story play out countless times in your favourite movies.

  • Luke Skywalker lived on moisture farm on Tatooine when he received his call to adventure from Princess Leia to fight the Empire
  • Harry Potter lived under the stairs when he received his invitation to Hogwarts
  • Neo is a hacker who receives a cryptic message about the Matrix
  • Frodo lives blissfully in the shire until Gandalf tells him he must save the world and destroy the ring
  • Rocky a small time boxer reluctantly accepts a fight with the world      champion, Apollo Creed

Creativity is full of underdog stories

Economists describe the creative and start-up industries as chaotic industries. We all have to face our personal hero’s journey if we want to succeed in crowded markets filled with chaos.

Every successful artist, creator, or entrepreneur has faced their worst fears and come out the other side.

Many creatives and entrepreneurs are reluctant to accept the call of adventure. They are full of fear and scared of failing.

If they are lucky they find a mentor who can help guide them on their journey. Or an accountability partner to keep them to the task.

No label wanted to sign Jay Z. So he joined forces with Damon Dash and sold CDs out of the boot of their car.

They founded Roc-A-Fella records as an independent record label, releasing Jay Z’s debut album, Reasonable Doubt, with no budget.

It reached #23 on the Billboard charts.

12 publishers turned down the Harry Potter series, where an unemployed and broke J.K Rowling pinned all her hopes and dreams of financial survival for both herself and her daughter firmly to the Harry Potter mast.

Her agent kept her going.

Every label rejected The Beatles. It was only using the leverage of their manager, Brian Epstein, that forced EMI to sign them.

Epstein’s family owned the biggest record stores in Liverpool.

Even then, EMI had zero faith and dumped them on a classical label imprint with a producer who recorded comedians.

The producer, George Martin, reluctantly revolutionised music production and disrupted the music industry.

Underdog marketing

Start-ups are sexy. The main allure of start-ups is reluctant, introverted programmers who are compelled to take on the titans of traditional industries to disrupt them and change the world.

Geeks have taken over the world. If that isn’t a classic hero journey story playing out in real life then what is?

New start-ups or creators should position themselves as David and stand against the Goliaths within the industry or niche they want to disrupt.

This generates support from people who identify with your quest. It’s a tried and tested formula.

  • Airbnb disrupted the Goliath old hotel industry.
  • Tesla disrupted the Goliath automobile industry.
  • Apple disrupted the boring, clunky designs of the computer industry.

Whatever your market or niche there is a status quo that you can stand against to gain leverage.

Be the plucky underdog, position yourself against the Goliath in your niche, create content telling your audience of the struggles against the evil empires that you are looking to disrupt for their benefit.

Use storytelling to romanticise your journey and connect deeply with your audience and their natural attraction to supporting the underdog.

Underdogs to Unicorns

Jeff Bezos famously bought 4 bits of wood a door to make his desk. The desk still remains in his office today.

His parents lent him $245,573 to start Amazon. Bezos was the former senior VP at D.E Shaw an investment bank. Buying a cheap desk would not have been a massive stretch.

There are several desks under $50 in Walmart. In fact, a wooden door and 4x4’s are more expensive than buying a cheap ready-made desk.

Jeff Bezos wasn’t trying to save money. He built his own desk out of a door as part of the Amazon underdog story.

According to Marc Randolph the former CEO of Netflix, he remembers Bezos telling him, it was a "deliberate message." Specifically: "It's a way of saying that we spend money on things that affect our customers, not on things that don’t.”

Amazon even created how-to videos so you too can build an Amazon desk.

The origin stories of multi-billion dollar silicon valley companies who started in garages are almost cliché now.

But these humble underdog stories created huge word of mouth both then and now.

Apple, Google, and Microsoft have all used the underdog stories to create word of mouth and support and give their fledgling businesses a veil of disruptive geniuses.

They positioned themselves as rebels and misfits who were going to change the world. And that’s exactly what they did.

Maybe, just maybe, you can, too.


  • Whether you’re a creative start-up or an artist or a creator you need to cultivate and create your story.
  • Be the plucky underdog. Do things differently. Go against the status quo and take on the Goliaths of your niches and industry.
  • Make a stand. Do things differently. Stick two fingers at conformity, dominate your niche and disrupt your industry.
  • Whatever you do; don’t follow the crowd. Everyone is already doing that. The crowd is wrong nearly every time.
  • Find a mentor, a business partner, or an accountability buddy.

A bit about me

I’m an ex- multi-platinum artist manager. I created strategies and built audiences for artists who sold millions.

You can read more in the archives here. Find out more information on my website

Too Much to do? Don’t know where to start?

I help creators and indie founders build no bullshit step by step creative business strategies to achieve their long term goals

I do discovery calls to see if we’re a good fit.

Cost? $0.00 Commitment? Zero. Time? 30 minutes

More info? Go here

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