Pedaling Through Challenges: Entrepreneurial Lessons from Endurance Cycling
Entrepreneurship and endurance cycling might seem like two entirely different worlds, but they share core attributes defining success: grit, determination, and overcoming setbacks.
Over the past three years, I’ve worked with dozens of founders, supporting their dreams and witnessing their trials and tribulations. I’ve seen companies thrive and, sadly, others falter. Recently, while training for and completing the UNBOUND 200—a grueling 200-mile gravel cycling event in Kansas—I found striking parallels between an entrepreneur’s journey and an endurance cyclist’s path. I hope these insights inspire you on your entrepreneurial journey.
The Power of Grit
If I had to pinpoint one attribute vital to success in entrepreneurship and endurance cycling, it would be grit. Running a venture-backed startup is incredibly challenging. Maintaining effort, intensity, and ensuring progress against your milestones is a monumental task. The job demands that you manage your emotions and maintain an even keel for your team. Demonstrating grit is the hallmark of all great entrepreneurs.
Navigating Setbacks
Whether you’re building a startup or tackling a long-distance cycling event, setbacks are inevitable. Developing the mindset to overcome adversity is a critical skill. These setbacks can range from minor issues, like a failed experiment, to major crises, such as a co-founder breakup. Great entrepreneurs always find a way forward. You need a solid strategy to bounce back from adversity and continue your progress. Your team will look to you, so your reactions need to be measured and action-oriented.
Celebrating Wins
Amidst adversity, you’ll also experience big and small wins. It’s essential to find time to celebrate these victories. Startups often face a whirlwind of activities, making pausing and acknowledging progress difficult. Build systems that allow you to do so.
I’m a big believer in the importance of investor updates; they provide a fantastic opportunity to step back and recognize your achievements. This acknowledgment is crucial for you, your team, and your investors. Never forget to celebrate your team. While it may feel like you alone bear the business’s stress, your team feels it too. Celebrating small wins acts as a critical release valve for stress.
“We make a big point of celebrating ‘wins’ when they are achieved. Pausing to celebrate the wins has been crucial for us in re-energizing the team as they ramp up for the next milestone.”
— Bav Roy, Co-Founder, Verne
Embracing a Long-Run Mindset
While daily focus is essential when running your startup, maintaining a long-run mindset is equally crucial. Structuring quarterly OKRs that build into your annual and multi-year plans helps ensure your daily progress aligns with the bigger picture. The true impact of your business will come from its scale.
Breaking Down Big Challenges
Shifting gears (pun intended), my experience training for and completing the UNBOUND 200 reinforced these lessons. I relied on grit, perseverance, and a long-run mindset.
When faced with adversity 100 miles in, I broke down the task into smaller, manageable segments, whether it was focusing solely on the immediate hill or reaching the next water stop. Each milestone reached was celebrated, and I cherished the camaraderie of fellow riders. As the day progressed and the miles accumulated, I reflected on the extensive preparation and training I had invested, drawing strength from my past efforts to ultimately reach the finish line.
“To deliver a seamless customer experience, many aspects of our tech stack must execute different small tasks well. This measured focus on important details allows us to consistently deliver a sustainable and magical personalized heating experience.”
— Raj Tilwa, Co-Founder Focal
The Journey Ahead
I encourage you to think about endurance in your entrepreneurial journey. The lessons I’ve learned on the bike this year will play a role in your success in building lasting and impactful ventures. Embrace grit, navigate setbacks with resilience, celebrate your wins, and keep your eyes on the long run. The road ahead may be tough, but the rewards are worth every ounce of effort.
Note - If you’re curious to learn more about my day at UNBOUND, you can hear my story on Spotify.