On Winning

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Intro

Founder’s Lessons to Lead, Perform & Win

Building your dream business is fundamentally about building a strong team. With a good team, you’ll create exceptional products and services for your customers. A supportive team will help expand your vision, covering your back, front, and sidelines. They’ll contribute to your growth just as you’ll support theirs. As a founder, your first priority should be to assemble a capable team and take great care of them. When you nurture your team, they will, in turn, take care of your customers, and satisfied customers will enhance your business’s bottom line. While constructing your dream team, focus on fostering quality and creating longevity that endures beyond their time with your organization.

I resonate deeply with the sentiment expressed by American football coach Jim Harbaugh during his tenure as head coach of the Wolverines at the University of Michigan. When one of his players asked, “Coach, what kind of team are we going to have this year?” he replied, “Jimmy, when you guys come back in 15 or 20 years and we know what kind of men you are, what kind of husbands you’ve become, and what kind of fathers you are, then we’ll know how good this football team is.” This perspective emphasizes the importance of building a team that not only excels in the present but also cultivates remarkable contributors to society for the future. You’re giving everything you’ve got, so make sure you build to last.

Winning is an identity

Humans are naturally competitive. Our ancestors developed competitive traits to ensure survival and improve their quality of life, and this powerful instinct is something we all share. Because of this inherent competitiveness, we often associate the outcomes of games with the individuals or teams that compete in them. In the realm of entrepreneurship, it is challenging not to define a founder’s professional identity by their business outcomes. However, I believe that successful entrepreneurs share a defining trait: they embody the identity of winning.

Having a winning identity doesn’t imply that these entrepreneurs don’t face setbacks or devastating failures—in fact, they may experience more challenges than most. What sets them apart is their resilience; no matter how severe the fall, they always rise, eager to try again until they ultimately succeed.

Thus, I contend that being a winner is not just a status; it is also an integral part of a founder’s identity. Every entrepreneur has the opportunity to embrace this aspect of their identity, as long as they genuinely desire to win.

Choose your game right

I view entrepreneurship as a type of sport, with entrepreneurs serving as athletes in their respective fields. Just as athletes excel in different disciplines—some thrive in sprinting, while others are enduring marathon runners—it’s vital for entrepreneurs to select the game that aligns with their strengths and goals.

For instance, some founders excel at identifying a pressing problem that requires a business solution and quickly assembling a company to address it, often achieving traction that appeals to investors and potential acquirers within a few years. I call these individuals “sprinter entrepreneurs.” In contrast, other founders are better suited for building mission-driven organizations that take years to realize their original vision, and I refer to them as “marathoner entrepreneurs.” I identify more with the latter group, as there are founders who successfully navigate both short-term and long-term business journeys.

Regardless of the game you choose, it’s essential to pick one where you can perform at a high level. When selecting co-founders, investors, and key team members to join you in your “game,” ensure they understand the nature of your venture and what it entails.

Have a strategy for your fears

Building a business is a long journey that challenges entrepreneurs to confront fear head-on. While we are bright, objective-driven professionals, we are also human, and humans have fears. My deepest fear was whether leaving my academic professor-track job to found a startup was the wrong choice for both myself and my family. The potential downsides felt intolerable, especially as a divorced mother of a young child at the time. I eventually overcame those fears—and you know the rest of the story. What I can share now is that when I faced my fear head-on, approaching it as a challenging but solvable problem, I not only conquered it but also made one of the best choices of my life.

Building your big idea from the ground up involves committing to a high-risk challenge. As your business grows, that risk can accumulate to a point where it feels unbearably daunting. This chronic, subconscious fear is not something you can simply wave away with a yoga class or a discussion over coffee with a trusted friend. It lingers like a predator just out of sight, always threatening to pounce unexpectedly. Trust me, I’ve been there too. However, as intelligent founders, we can outsmart our biology and turn this situation to our advantage. 

In my quest to manage fear while pursuing my passions, I rely on three key ingredients. First, I assess my risks before committing to any endeavor and develop a risk management plan to mitigate potential downsides, whether they’re financial, familial, career-related, or a combination of all three. If you approach it objectively, it becomes a manageable problem to solve. 

Second, I seek mentors who can serve as my “fear coaches.” Many others have walked the path I wish to pursue; finding those who have been there and done that provides a clear roadmap with references along the way. I have found this incredibly practical and helpful in my journey.

The third ingredient is arguably the most important: having my family on board with my quest. They are my safe haven when the waters get turbulent and my home when there’s something to celebrate. Founding a business is an audacious endeavor, and having your loved ones alongside you makes the journey worthwhile, regardless of the outcome.

This is my strategy for managing fear, and it’s essential for you to develop your own. Then, go forth fearlessly!

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