No founder wants to be counted out.
We want to look polished. Put-together. Like we’ve already made it. We don’t want anyone to see the chaos behind the scenes—the solo hustle, the doubts, the duct-taped plan.
But here’s the truth: once you get over the fear, the embarrassment, the urge to look like you’ve made it, you’ll realize being the underdog is one of your greatest advantages as a founder.
In this week’s issue of the Storytelling for Entrepreneurs Newsletter, you will discover why this is true as well as:
Learn 3 ways to embrace the underdog role
Discover why 89% of consumers prefer underdog brands
Watch Les Brown share how being counted fueled his rise
Enjoy this trip to discover your inner dawg… LG
Founder Tip: The Founder Dog in You is Underrated
un·der·dog (ˈən-dər-ˌdȯg)
1 : a person, team, etc., that is expected to lose a contest or battle
2 : a less powerful person or thing that struggles against a more powerful person or thing
Let’s face it. As a founder, the odds are stacked against you.
When you start a business, no one knows your name. No one knows your product. You likely have little to no resources. And you’re doing everything yourself.
By definition, that makes almost every entrepreneur an underdog.
Though almost all new businesses start this way, most people tend to shy away from being the underdog because they don’t want to be seen as a no-name player in an established market.
They’re afraid to take on Coke or Facebook because they worry that they can’t compete.
But here’s the truth: being an underdog is exactly what gives you the power to compete.
Here's why:
We’re a Nation of Underdogs
America itself started as one big underdog story.
In 1776, we took on the most powerful empire on Earth—Great Britain—and won. Since then, we’ve carried a relentless “can-do” spirit.
We celebrate independence. Grit. Taking on bullies at every level.
This mindset is baked into our culture. It’s why we admire those who push past limits and bet on themselves. It's why so many of our iconic founders started in garages, basements, and dorm rooms.
We root for those who “can’t” because we were once the country that couldn’t.
Underdogs Make Great Stories
As a founder, your story is your ultimate weapon—and nothing makes a better storyline than the underdog arc.
Turn on any sports show on Monday morning. What are they talking about? The big upsets. The game-changers. The long shots who pulled off a miracle.
Flip through Inc Magazine or Forbes and you’ll see the same pattern - stories of upstarts toppling market titans.
Think: Samuel Adams vs. Budweiser.
Think: Netflix vs. Blockbuster
The media and your audience love a good underdog narrative. They want to believe in someone who dares to take on the impossible.
Underdogs Give Us Hope
This is the most important reason of all.
When someone beats the odds, we feel inspired. Because deep down, we’ve all been the underdog at some point in our lives.
On the field. In the office. In our relationships. In our dreams.
We’ve all had moments where we were told we weren’t good enough. That it couldn’t be done. That we didn’t belong.
And yet, we kept going.
Underdog stories remind us that ordinary people can do extraordinary things. That success isn't reserved for the lucky few—it’s possible for all of us.
So, Embrace the Role
As a founder, learn to love being the underdog. Own it. Relish it.
Because it gives you something the big players can’t buy: a story worth believing in.
“The fact of being an underdog changes people in ways that we often fail to appreciate. It opens doors and creates opportunities and enlightens and permits things that might otherwise have seemed unthinkable.” ~ Malcolm Gladwell
Storytelling Lesson: How to Embrace the Underdog in You
The power of the underdog isn’t just in what it represents, it’s in how you use it. As a founder, your story doesn’t need to be polished or perfect. It’s your imperfections, your struggles, and your willingness to go up against giants that make you memorable, relatable, and magnetic.
Here are 3 storytelling approaches you can use right now to turn your “scrappy beginnings” into a compelling narrative.
Lead With the Long Shot: Embrace the Underdog Role
Founders who lean into the uphill battle, rather than hiding it, build trust and authenticity. They own the fact that they’re outmatched in resources but unmatched in drive, and that’s exactly what makes them formidable.
Let your audience know this is personal. Show the emotion, the passion, the sacrifice. Say the quiet parts out loud: you’re the small player in a big game, but you’ve never been more ready. Own your hustle, your obstacles, and your grit, and invite your audience to root for you because of it.Turn Struggles into Suspense: Give Them a Storyline (with Drama)
The best founder stories include tension, stakes, and vulnerability. Whether it’s living out of a car, quitting a six-figure job, or sneaking into industry events, you pull people in with the raw, unfiltered version of your journey.
Share the behind-the-scenes. The broke moments. The ridiculous risks. The crazy things you did to stay in the game. Highlight the details you’d normally gloss over; that’s where your audience connects. Drama isn’t about theatrics; it’s about truth. Let people see the mountain you’re climbing so they’ll cheer when you reach the top.Pick a Fight: Find Your Goliath
Underdogs become legends when they take on giants. Amazon took on Barnes & Noble. Tesla took on Detroit. Your competitor’s size is your story’s contrast, and that contrast is what draws attention.
Identify the villain. Name the outdated system, the bloated company, or the broken model you’re here to fix. Call out the status quo and shine a spotlight on why it has to change. By drawing a clear line between what you stand for and what you stand against, you invite others to rally behind your mission.
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Fun Fact: Why Underdogs Win Hearts (and Wallets)
Underdogs love science because research shows that 89% of consumers prefer to buy from brands with humble, underdog beginnings.
According to a study led by Jill Avery of Simmons School of Management, people are significantly more drawn to companies that started with little to no backing.
It goes back to the fact that we see ourselves in these against all odds stories and these narratives create an emotional connect with founders who’ve had to claw their way up.
Video to Watch: Chase Your Dream
In this powerful commencement speech clip “The dyslexic Les Brown: I was identified as mentally retarded”, motivational legend Les Brown shares how he was labeled “mentally retarded” as a child, and how he refused to let that define him. It’s a raw, moving reminder of what’s possible when you embrace the underdog role, prepare for your moment, and chase your dream with relentless passion. (I ❤️ Les Brown)
The dyslexic Les Brown: I was identified as mentally retarded
https://youtu.be/OG1Arib4UsY?si=lwPItPg4SjIeaI0c
Storytelling for Entrepreneurs Issue #035 - Why 89% of People Buy From the Underdog
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