The Bet That Pays Off Every Time: Betting on Yourself
A Weekly Newsletter for BOLD Thinkers | May 18, 2025 | Volume 25 Issue 03
by Stephanie Sabrina Warren
Above: A still from Casey Neistat’s “Make It Count” video. It’s also a damn good quote!
Last week, I shared how Casey Neistat’s Make It Count video for Nike became a masterclass in storytelling. But this week, I want to zoom in on the bold move behind the story. It’s one that continues to blow my mind every time I watch the video.
Instead of sticking to a safe, pre-approved storyboard for Nike’s FuelBand campaign, Casey did something wild. He took the entire advertising budget and used it to travel the world with his friend, documenting the whole thing. No product placements. No fancy scripts. Just a gut instinct and a suitcase full of curiosity.
To many, that would have looked reckless. But to me, it looked like something else entirely. It looked like someone knowing their strengths and doubling down on themselves.
Casey’s Story: From Self-Doubt to Trusting Himself
Casey grew up, like many neurodivergent kids, being told he was doing life wrong. School was hard. He dropped out of high school. By his early twenties, he was working low-paying jobs, raising a child, and feeling like a complete failure.
But somewhere in that fog, Casey picked up a camera. He started teaching himself video editing. He filmed what he found interesting-ipod batteries, traffic tickets, random bits of everyday life-and posted it all online.
People watched. Then they watched again. His work was raw, real, and unlike anything else. And for the first time in his life, Casey felt like maybe he wasn’t a lost cause. Maybe those people who said he’d never amount to anything were wrong.
He leaned into what he was good at. He ignored the corporate playbook, the office politics, the details he wasn’t built to manage. He made a choice: let go of trying to be well-rounded and instead double down on being brilliant at his thing. That thing? Storytelling through video.
The Power of Knowing Your Unique Value Proposition
What Casey did is something every entrepreneur, creator, and leader should take note of. He figured out his unique value proposition—his UVP. In simple terms, it’s the one thing you do differently and exceptionally well. And when you know what it is, you can stop pretending to be someone you’re not.
Casey’s UVP wasn’t polished commercials. It wasn’t sticking to the rules. It was connecting deeply with people through honest, emotional, adrenaline-filled storytelling. And as he leaned fully into who he was, he began attracting the kinds of people and opportunities who got it. That’s exactly why Nike reached out to him. They weren’t hiring a buttoned-up agency. They were hiring Casey because he had built a reputation around authentic, unconventional storytelling.
That said, Casey still played the game but just a little. He created a storyboard for Nike to get their initial buy-in. But once the green light was given, he threw it out and followed his instincts instead. Because sometimes, we have to conform just enough to get people to believe in us.
Then, once we’re in the room, we get to toss the playbook and do what we do best.
Just one line of text appears at the beginning of the video:
"Nike gave me a budget to make a movie. I spent it all traveling around the world with my friend."
At first glance, it sounds casual, even playful. But that one line? It wasn’t just a catchy intro. It was the whole philosophy. It signaled a bold move, a leap of faith, and a massive bet on himself.
Casey had submitted a storyboard to Nike. He played the game just enough to get in the room. But when it came time to actually make the video, he threw the playbook out. No polished production. No approvals. No safety net. He put every dollar toward what he knew he did best—telling raw, emotional, unforgettable stories his way.
That one sentence wasn’t just cheeky, it was a mic drop. It was Casey saying: I trust myself. I know my strengths. I’m going all in.
In that moment, he made a bet on himself, his instincts, his vision, his ability to turn a crazy idea into something unforgettable. It wasn’t just rebellious. It was strategic. And it worked.
That was it. The result? Over 1 million views in the first day, and over 32 million views to date. Thirteen years later, we’re still talking about it.
Why This Matters for You
You don’t need to be a filmmaker to make this kind of bet. You don’t need a budget, a brand deal, or a global platform. What you do need is clarity—about who you are, what you’re great at, and how you show up when you’re fully in your element. That clarity? That’s your unique value proposition.
Your UVP is the thing you do differently and exceptionally well. It lives at the intersection of:
- What you’re good at
- What lights you up
- What others find valuable
Here’s a simple way to start uncovering it:
- Map your personal landscape
Write down two lists: 5–10 things you’re good at and 5–10 things you struggle with. Then circle the ones you actually enjoy. This shows you where your energy naturally flows—and where it drains. Pay special attention to where skill and joy overlap. That’s your power zone.
- Look for the golden thread
Review what you’ve circled and ask: What do these things have in common? Is there a pattern? A vibe? A skillset? What’s the throughline that connects them all? That’s often where your UVP starts to take shape.
- Shape your environment around your strengths
Instead of molding yourself to fit environments that don’t serve you, start designing your work, your routines, and your relationships around what brings out your best. That’s exactly what Casey did—and it’s how he attracted brands like Nike that got him.
- Give it time. Grow into it
If something excites you but doesn’t come easy yet, don’t walk away. Lean in. Explore. Your UVP isn’t always fully formed—it’s something you step into over time. Keep following the things that feel true, even if they’re still a little messy.
This exercise is both self-reflection and strategy. It helps you get clear on what you uniquely offer, what kind of environments let you thrive, and how you can start attracting the right opportunities by simply being more you.
Here’s a visual that brings it all together:
So instead of forcing yourself into systems that weren’t built for you, ask: what if I built a system tailored for me?
Start Small, Bet Smart
Betting on yourself doesn’t have to start with a Nike contract. Casey didn’t either. He started with homemade videos. A secondhand camera. Free editing software. And a belief that maybe, just maybe, his way of seeing the world mattered.
If you’re a woman, a person of color, neurodivergent, or early in your career, I know it can feel especially risky to trust your instincts. But here’s what I hope you take from Casey’s story:
Start where you are.
Start small.
Start with what you have.
And remember that your value isn’t in fitting in. It’s in standing out.
Because once you know what makes you different, and once you embrace it fully, it becomes your superpower. And like Casey, you might just find that the bet you make on yourself is the one that changes everything.
recommended reading: betting on yourself & embracing your unique value
Year of Yes by Shonda Rhimes - This memoir is a brilliant example of what happens when you stop shrinking and start saying yes to opportunities that reflect your worth—even when they scare you. Rhimes’ journey is all about stepping into your power and owning the things that make you different.
David and Goliath by Malcolm Gladwell - This book illustrates how the most powerful advantage often comes from betting on yourself, especially when you embrace the very traits others see as weaknesses. The book is a testament to trusting yourself, playing to your unique edge, and rewriting the rules instead of conforming to them.
Unreasonable Hospitality by Will Guidara - This story is a powerful reminder that when you embrace your unique value—especially the things others might overlook—you create experiences no one else can replicate.