Why the Obsessed Win

In the startup world, finding success can often feel like either a roll of the dice or something reserved for those with innate talent. But if we take a closer look at the stories of founders who have built enduring companies, a different narrative emerges: It’s almost always the obsessed who win.

Shane Parrish from Farnam Street captures this beautifully:

“The lazy lose to the average. 
The average lose to the focused. 
The focused lose to the obsessed.”

So, what does this mean for founders today? It suggests that merely going through the motions isn’t enough. The most successful leaders emerge in the gap between being focused and being obsessed. Let’s talk about why obsession is key to building something that truly lasts.

We don’t make money because we want to make money.  We make money because someone values what we do.

The Obsessed Focus on the Right Things

Founders who chase after money or fame often find themselves falling short. It’s no secret that focusing solely on outcomes like revenue or recognition often leads to dissatisfaction in our professional pursuits. The obsessed understand that it’s not about the reward — it’s about the Work (with a capital “W”).

There are a few things that set the obsessed apart: passion, a relentless pursuit of excellence, and an unwavering focus on things like perfecting their product, delivering exceptional service, refining their processes, and hiring (and retaining) the best talent. They’re consumed by the fundamentals and mastering the basics, setting the stage for everything else to follow.

Founders aren’t the only ones who thrive from obsession. Many of the most inspiring sports legends are defined by their obsessive dedication to their craft. They achieved greatness not from talent alone but through their obsession with perfecting every aspect of their game, ultimately elevating them to iconic status.

Take Tom Brady, for example — his commitment to fitness, diet, and mastering the game kept him at the NFL’s pinnacle for over two decades. Or Michael Jordan, whose legendary obsession with winning pushed him to outwork his competitors, continuing to practice and strength train intensely through the offseason.

These athletes didn’t just love their sport — they obsessed over every detail, and it’s this level of dedication that sets them apart from the rest.

Founders Obsessed with Their Vision

The same obsession that propels athletes to greatness can also be seen in founders who create new industries or industry-transforming companies. Working hard isn’t enough to achieve greatness. Founders with a relentless pursuit of excellence, an unwavering focus on a vision, and the ability to see possibilities where others see limitations are the ones who create great companies.

Here are some of the unique obsessions that have driven some of the most successful founders in recent history:

Steve Jobs
Steve Jobs’s obsession with user experience and design led him to craft products that weren’t just functional but also beautiful, intuitive, and life-enhancing. This obsession drove him to demand the highest standards from his team, leading to groundbreaking products that changed how we interact with technology and cementing Apple as a leader to this day in innovation and design.

Elon Musk
Elon Musk’s obsession with applying first-principles thinking to sustainable energy and space exploration is evident in Tesla’s electric cars and SpaceX’s mission to colonize Mars. His willingness to work 100-hour weeks showcases a level of commitment few can match. But his vision goes beyond just creating products — he aims to revolutionize entire industries while solving global challenges.

Jeff Bezos
Jeff Bezos’s obsession with customer experience and delivering value transformed Amazon from an online bookstore into a global powerhouse. His commitment to understanding customer needs and anticipating market trends has led to continuous innovation and expansion throughout the company.

Howard Schultz
Howard Schultz’s obsession with creating a brand that offered more than coffee transformed Starbucks into a global community hub. His focus on community and delivering a consistent experience across all locations helped Starbucks become synonymous with both quality and comfort worldwide.

Mark Zuckerberg
Mark Zuckerberg’s obsession with connecting people across the globe helped him build Facebook into a staple of modern communication. His vision of a global social network drove him to continually innovate, prioritize user engagement, and use data-driven insight to expand Facebook’s reach and influence.

Melanie Perkins
Despite being rejected by more than 100 investors when starting her company, Melanie Perkins’s obsession with making graphic design simpler and more accessible for everyone helped her to thrive in the face of failure. She has a bold vision of everyone on the planet using Canva, and her perseverance has led Canva to reach an audience of over 200 million monthly users in more than 190 countries.

Daymond John
Daymond John’s obsession with fashion led him to create a streetwear brand, FUBU, that resonated with his Queens community. Using a $100,000 mortgage loan, he transformed the basement of his mother’s home into a clothing factory and spent years designing, sewing, and selling his clothing with three friends. While the brand had humble beginnings, it now has lifetime sales of over $6 billion thanks to John’s smart risk-taking and innovative spirit.

Joanna Gaines
Joanna Gaines’s obsession with creating spaces that feel like home transformed her into a household name. Despite a number of financial setbacks early on, Gaines’s commitment to storytelling through design led her to create Magnolia, a lifestyle brand consisting of a television network, retail products, restaurants, and more, turning her passion into a movement that inspires millions.

There’s a common thread that ties these founders together: their obsession with their vision. Each of these leaders demonstrated an unparalleled commitment to their companies, sacrificing personal time and resources to achieve their goals. This level of dedication is about a belief in creating something extraordinary.

What Sets Obsessed Founders Apart?

Let’s explore some of the common traits possessed by the most obsessed (and successful) founders:

• Clarity: Obsessive founders have laser-focused clarity on who they are and what they value (Core Values), who they want to serve (Ideal Customer), how they want to serve (Compelling Value Proposition), and how they intend to make the world a better place (Compelling Why). They’re not distracted by fleeting trends — instead, they remain aligned with their vision.
• Passion: True obsession is fueled by passion. The most successful founders aren’t working for a paycheck. They deeply believe in what they’re building, and it’s this passion that drives them to keep going, even when others might give up.
• Confidence: Obsessive founders not only have confidence in their vision but also in their ability to execute that vision. They’re playing an infinite game and pursuing dominance in a forever market, allowing them to take calculated risks and overcome challenges because winning is the only option.

Resilience and Antifragility: Thriving Through Challenges

The ingredients associated with obsession are also the ingredients associated with resilience and antifragility. Founders who are clear, passionate, and confident are not just resilient at their core but are inevitably antifragile because they care enough to listen and learn from mistakes and setbacks. They deeply get that:

“We are exactly where we are supposed to be, learning the lessons we need to learn.”

It’s about thriving in chaos, growing stronger under pressure, embracing uncertainty, and understanding that it can lead to unexpected breakthroughs and growth.

Resilience = The ability to withstand and recover from hardship

Antifragility = The ability to emerge stronger after (and because of) hardship.

Resilience

Great founders are ready for adversity. They’ve done the hard work associated with developing the ability to endure stress, recover from setbacks, and maintain functions in the face of challenges. Resilient founders build companies that don’t crumble under pressure. They understand what Mike Tyson meant when he said, “Everyone has a plan until they get punched in the face.”  

Resilient founders and their organizations don’t break under pressure — they survive, bouncing back to their original state in the aftermath.

Antifragility

Antifragility goes beyond surviving or bouncing back. Antifragile founders don’t just survive — they thrive in volatility and adversity. As a result of any sort of stress, disorder, or disruption, antifragile individuals or systems emerge on the other side stronger than they’ve ever been. They learn from these setbacks and use the experience to evolve and become better equipped for future challenges. They view them as learning experiences to help them refine strategies and approaches. This adaptability is crucial in navigating the unpredictable landscape of the marketplace. By embracing change and uncertainty, they position themselves to capitalize on new opportunities.

Obsession and Building Market Leaders

I deeply believe obsession is the most obvious differentiator between fleeting success and lasting market leadership. The lazy lose to the average, the average to the focused, but it’s almost always the obsessed who build things that stand the test of time.

Obsessed founders focus on the fundamentals that create success: They’re not distracted by vanity metrics. They’re obsessed with excelling at the basics — whether it’s customer service, product quality, or team dynamics. They’re relentlessly focused on being the one who takes the market. They understand that the marketplace of ideas waits for no one. They grasp that if they see an opportunity, someone else likely sees it too. And just like the best athletes and founders who have dominated their fields, they obsess over fundamentals, not trophies. They don’t just want to compete — they have to dominate. They need to “be like Mike,” not just winning but crushing the competition.

So, what about you? Are you obsessed with something? If not, could you be? If you are, how can you harness that obsession to create something great?

As you ponder these questions, remember that obsession isn’t just about working harder — it’s about working smarter, with a purpose and clear vision that inspires you and all your Ideal Stakeholders to build something incredible, something far beyond the ordinary.

I’ve said this for decades: No one ends up being great because they want to be great. To be great takes hard work, really hard work. It takes years and years. There’s virtually no overnight success in the world of building great companies. Most people don’t have what it takes. And I’m deeply convinced that the only way to be great is to find something you can obsess over.

Whether you’re a founder, CEO, or someone who genuinely wants to lead and create things of enduring value, if you can find a pursuit worth obsessing over, I’m confident you can transform challenges into opportunities and pave the way for lasting success. Let your obsession be the catalyst for innovation, growth, and impact. The world is waiting for your unique contribution — it’s time to embrace your obsession and make it happen.