You Don’t Put a Lemonade Stand Halfway Down the Hill: Insights on Supporting the Customer Journey

In July 2023, I spent a week bicycling across Iowa. I wasn’t alone. I was one of the thousands of riders taking part in RAGBRAI — the Register’s Annual Great Bicycle Ride Across Iowa. This week-long bicycle journey across Iowa is more than just a cycling event. It’s a vibrant community on wheels, a celebration of fitness, friendship, and discovery in America’s heartland, drawing thousands from all corners of the globe.

This wasn’t my first time participating in RAGBRAI; it was, in fact, my third. Each ride has been a unique experience, offering new challenges, perspectives and insights. This time, as I navigated Iowa’s rolling hills and expansive plains, the journey resonated with me more deeply, revealing lessons about resilience, adaptability, and the crucial importance of perspective. The ride became more than just a physical feat; it transformed into a metaphorical journey through the world of entrepreneurship. Every mile, every hill, and every flat stretch provided a moment to reflect on the broader aspects of running a business and the mindset required to navigate its uncertain terrain.

In this series, I share with you five key insights gleaned from this remarkable journey. Each one is framed by a specific event during the ride, reflecting on how these moments resonate deeply with the entrepreneurial spirit. These stories, born from the rolling landscapes of Iowa and the camaraderie of RAGBRAI, offer a unique lens through which to view the challenges and triumphs of the entrepreneurial journey. Whether you’re a seasoned business leader or a budding entrepreneur, you’ll find valuable lessons in resilience, strategic thinking, and the importance of balance, all gleaned from an unforgettable 530-mile cycling adventure. So join me on this reflective journey as we delve into these entrepreneurial insights.

You Don’t Put a Lemonade Stand Halfway Down the Hill

During the long, hot days of RAGBRAI, the desire for a cold beverage becomes as pressing as the need to keep pedaling. Lemonade stands, a staple of mid-summer refreshment, dot the landscape, offering a brief respite to cyclists. As we travel an average of 70 miles daily, there are plenty of chances to stop for a refreshing lemonade in the bustling towns or along the rural roads we encounter. An intriguing observation came after conquering a long hill and coasting down the other side: a lemonade stand with barely any customers. I realized then—placing a lemonade stand on the downhill made little sense; the momentum and relief of descending meant most cyclists wouldn’t think to stop. You don’t put a lemonade state halfway down the hill.

The Importance of Strategic Location

This simple observation opens up a broader conversation about the essence of location in business. It’s not just about being visible; it’s about being strategically placed where your customers need you most and where it’s convenient for them to engage with your business. In a brick-and-mortar business, this could involve placing your shop in a high-traffic location where potential customers are likely to pass by when they are ready to make a purchase, rather than choosing the cheapest or most available real estate.

The Customer Journey: More Than Just a Path

The deeper lesson here extends beyond physical location. It’s about understanding the customer’s journey in its entirety. Sometimes, this journey is literal. Cyclists on a long ride anticipate the reward of a cold drink at the top of a hill. More commonly, it’s metaphorical, requiring businesses to discern where their customers are emotionally, what challenges they’re facing, and when they’ll be most receptive to the solutions offered.

For entrepreneurs and small business owners, this means diving deep into the customer experience, mapping out the touchpoints where engagement occurs, and identifying moments of need or decision. Whether it’s the peak of a hill or the moment someone decides to seek a solution to a problem, being there with the right offering at the right time is crucial.

Integrating Into the Customer Journey

The concept of integrating into the customer journey underscores a vital truth: the journey belongs to the customer. It is their path, their adventure, from beginning to end. As entrepreneurs and business owners, we are not the main characters in this narrative but waypoints or guides that customers encounter along their way. Our role is to understand this journey in its entirety — not to rewrite it but to find meaningful ways in which our business can assist, enhance, and add value to their experience.

Recognizing that customers navigate their own unique paths to solve a problem or fulfill a need is crucial. It demands that we shift our perspective from selling to serving, from interrupting to assisting. This means diving deep into their world, understanding the challenges they face, the milestones they want to achieve, and the moments they are most receptive to help.

If you run a specialty coffee shop, your customers’ journey might include seeking a comfortable space to work, socialize, or simply enjoy a high-quality cup of coffee. Understanding this journey means recognizing the various needs your shop fulfills and ensuring that each touchpoint — from the ambiance to the service, to the product itself — adds to their overall experience.

Being a Valuable Part of Their Journey

Embracing this customer-centric approach requires not just understanding but empathy and a genuine desire to contribute to their journey. It’s about asking how your business can help customers move forward, what you can offer that will make their journey more enjoyable, more successful, or simply easier. Whether through providing the right product at the right time, offering insightful content that answers their questions, or creating an experience that brightens their day, your business becomes a valuable part of their journey.

Our role in our customers’ journeys is a privileged one. We can impact, support, and celebrate their achievements. Understanding the customer journey from beginning to end, and recognizing how our business fits into that journey, is not just strategic — it’s fundamental to building lasting relationships and achieving long-term success. poignant reminder: success in business often comes down to being in the right place at the right time. But finding that spot requires understanding your customers deeply—their needs, their habits, and their journeys. Whether you’re offering a product, a service, or a refreshing glass of lemonade, positioning yourself where and when your customers need you most is not just good business—it’s essential.


Each stretch of my journey across Iowa offered unique insights into the parallels between long-distance cycling and entrepreneurship. The lessons I’ve shared in this series reflect the diverse experiences and challenges encountered along the way. If you found the insights in this article valuable, I invite you to explore the other articles in the series, where we delve deeper into the principles of resilience, strategic thinking, and balance. These stories not only illustrate the physical journey across Iowa but also the metaphorical path through the landscape of entrepreneurship. Click on the links below to continue exploring how each moment can transform challenges into opportunities for growth and innovation.

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