Espressly: Brewing Success One Coffee Shop at a Time
Building a business is like brewing the perfect cup of coffee—it takes patience, the right mix of ingredients, and a lot of trial and error. This book is the story of Espressly—a journey that started with the dream of empowering independent coffee shops through technology, giving them the tools to compete with big chains and thrive in a competitive market. It’s about bootstrapping a company from the ground up, persevering through setbacks, and evolving along the way.
As the founder, I know firsthand how much goes into creating something from nothing. When we began, we faced countless challenges—integrating with Square, figuring out the right product-market fit, and balancing the needs of our team, customers, and business. But we also learned valuable lessons—lessons about perseverance, customer relationships, technology, and growth.
This book is for anyone who’s walked the path of an entrepreneur, anyone who’s had a vision and fought to make it real. Whether you’re building a tech startup, managing a small business, or simply interested in what it takes to create a lasting product, I hope you’ll find inspiration, guidance, and practical insights here. Most importantly, I hope you’ll take away the understanding that success isn’t about explosive growth, venture capital, or overnight wins—it’s about the steady grind, the constant reps, and the perseverance that keeps you moving forward, one day at a time.
Chapter 1: Introduction – Brewing the Dream
Chapter 2: The Early Days – From Concept to Reality
Finding the Spark
Every startup journey starts with a problem. For me, the spark behind Espressly was the frustration I noticed in small coffee shops. Independent coffee shops are vibrant, local hubs, each with its own identity and loyal customer base. But they were at a disadvantage—struggling to provide the same level of convenience offered by the big coffee brands that customers had begun to expect.
It was clear that technology had the power to solve this problem. By providing small coffee shop owners with their own custom-branded order-ahead mobile app, they could connect directly with their customers, increase efficiency, and drive loyalty. The idea was simple—to empower local businesses to compete with the tools that big chains had at their disposal. We wanted to create something that was tailored to each shop, something they could call their own, rather than a generic platform that blended their brand with many others.
Early Challenges
As with any startup, the early days were all about experimentation and learning. We faced many challenges: defining the MVP, finding early adopters, and building a solid tech foundation. One of the biggest hurdles was integrating with Square, which was already widely adopted by our target customers as their Point of Sale (POS) system. Integrating with Square meant understanding the technical intricacies of their APIs, aligning our development timeline with their system updates, and ensuring our app provided seamless functionality.
This wasn’t just a technical challenge—it was also a test of our persistence. We spent countless hours developing and testing the integration, working closely with our initial customers to refine the experience. It was in these early days that I learned an important lesson: Success is often about persistence, not perfection. We didn’t need to have every feature perfectly developed from the start—we needed to start with something functional, learn from the feedback, and iterate continuously.
The Role of Early Customers
The role of our early customers cannot be understated. They were more than users—they were collaborators. Early adopters like Lucky Finn Cafe saw the potential in what we were building. They were willing to take a chance on a startup, to be patient with bugs, and to provide invaluable feedback that shaped the product.
I still remember our first in-person meeting with a coffee shop owner. They had a deep understanding of their customers and could clearly articulate the pain points they faced daily—long lines, repeat orders that required baristas to remember complex customizations, and a desire to give loyal customers an easier way to engage with the shop. Hearing their needs firsthand made me realize that technology could be more than just a tool—it could be the key to a better customer experience and operational efficiency.
The early feedback we received led to pivotal changes—such as adding features like saved favorites and push notifications to help shops engage more effectively with their customers. Each iteration brought us closer to our vision of making the technology truly beneficial for independent coffee shops.
A Lean Team with Big Goals
In those early days, we had to be lean. We didn’t have a big team of engineers, marketers, and sales reps. In fact, we were running on minimal resources—sometimes just a handful of people wearing multiple hats, doing everything from coding to customer support. We were focused on keeping the costs low and making every dollar count. This was especially important because we had chosen to bootstrap, which meant there was no influx of venture capital to fall back on if things didn’t go according to plan.
The team was incredibly driven. We all shared a belief in the mission—that small businesses deserved great technology too. We often worked late into the night, fixing bugs, launching new features, and listening to our customers. The grind was real, but the mission kept us motivated.
Learning and Growing Through Setbacks
There were setbacks—technical hurdles, features that didn’t resonate, and slow adoption at times. But each setback was a chance to learn and adjust. I remember a particularly challenging moment when a major feature launch failed. We had spent weeks developing a new loyalty program module, only to realize after launch that it wasn’t what our early customers actually needed. It was a tough pill to swallow, but it also pushed us to talk more directly with our users, understand their real needs, and avoid making assumptions.
The failures and setbacks taught us resilience. We didn’t have the luxury of a big safety net, but we learned to make calculated moves, learn from our mistakes, and keep iterating.
The Importance of Community
One thing that stands out about the early days of Espressly is the sense of community we began to foster. Our customers weren’t just clients—they were partners. We wanted to create a product that felt like an extension of their coffee shop. The community feel of Espressly became one of our core values—we wanted coffee shop owners to feel they had a say in the development of the product, that they were part of something bigger.
And that community aspect extended beyond the technology. It was about building relationships. Whether it was visiting a coffee shop in person, hopping on calls to understand what could be better, or simply sending a quick thank-you note after a successful launch, we prioritized creating genuine connections.
Chapter 3: Bootstrapping – The Grind Without the Glory
Choosing to Bootstrap
Choosing to bootstrap Espressly wasn’t just a financial decision—it was a philosophical one. We wanted to grow on our terms, to retain control of the company’s direction, and to be answerable only to our customers, not to investors looking for rapid returns. Bootstrapping allowed us to focus on sustainable growth rather than rapid, unsustainable scaling. But with that choice came a different kind of pressure.
Without a venture capital safety net, we knew we had to be incredibly disciplined with our spending. Every dollar had to have an impact—whether it was hiring, product development, or marketing. This meant we had to prioritize ruthlessly. There were countless features we wanted to build, but we had to focus only on what would provide the most immediate value to our customers.
The Challenges of Staying Lean
Staying lean meant making difficult decisions. We couldn’t afford a full sales team, so I became the de facto salesperson, reaching out to coffee shop owners, scheduling demos, and building relationships. We didn’t have a dedicated marketing team, so everyone pitched in—whether it was creating social media content, writing email campaigns, or attending industry events to spread the word.
It also meant wearing multiple hats. One day I’d be working on product strategy, the next I’d be debugging code or responding to customer support tickets. The grind was constant, and there were times when it felt overwhelming. But at the same time, there was something incredibly fulfilling about being so deeply involved in every aspect of the business.
Avoiding the Allure of Venture Capital
In the startup world, there’s a lot of noise around venture capital. The big funding announcements, the rapid scaling, the unicorn valuations—it’s easy to get caught up in the hype. But I knew that taking on venture capital would change everything. It would mean shifting our focus from creating value for our customers to creating value for investors.
By staying bootstrapped, we were able to maintain our focus on the customer experience. We didn’t have to chase growth at all costs or sacrifice our values for the sake of hitting investor targets. Instead, we could grow steadily and sustainably, ensuring that every decision we made was in the best interest of the coffee shops we served.
The Grind Without the Glory
Bootstrapping Espressly meant embracing the grind. It meant working long hours without the promise of immediate rewards, doing the unscalable tasks, and putting in the reps day after day. There were no glamorous product launches with big press releases, no funding parties, and no headlines in tech magazines. There was just the work—listening to our customers, building features that solved their problems, and constantly iterating on the product.
There were days when the lack of external validation felt heavy. When you’re bootstrapped, you’re not getting the kind of public recognition that venture-backed startups often receive. But in those moments, I learned to find fulfillment in the work itself—in knowing that we were creating something that mattered to the people using it. The satisfaction came from seeing a coffee shop thrive, from hearing positive feedback from a barista or shop owner, and from knowing that we were making a difference in their day-to-day operations.
Chapter 4: Building the Product – Features, Stability, and Customer Focus
Developing Key Features
The heart of Espressly’s success lies in the features we built to solve real problems for our customers. From day one, our focus was on making life easier for coffee shop owners, their employees, and their customers. We knew that the features we developed needed to be simple, effective, and impactful. This meant focusing on things like order-ahead functionality, integrated loyalty programs, and seamless Square integration.
The order-ahead feature was a game-changer for many shops. Customers could place an order before arriving at the store, avoiding long lines and minimizing wait times. This feature not only improved the customer experience but also helped shops manage busy periods more effectively, allowing them to serve more customers with less chaos.
Square integration was another major focus. Since many of our target customers were already using Square for their POS system, integrating with Square was a no-brainer. It allowed us to provide a seamless experience for shop owners, as all transactions, inventory, and customer data were synced between our app and their existing setup. This meant less hassle and more accurate record-keeping, which was crucial for small business owners trying to manage their operations efficiently.
Stability and Continuous Improvement
Building key features was only part of the equation. The other side was ensuring stability. Coffee shop owners depend on their technology working smoothly, especially during peak hours. A glitchy app or a failed transaction could mean lost sales and unhappy customers—something we couldn’t afford to let happen. We made stability a core tenet of our development process. We invested in rigorous testing and quality assurance processes to ensure our product was reliable.
We also embraced continuous improvement. Every feature we launched came with a commitment to iterate and improve based on user feedback. We viewed every new release as a stepping stone to something better. Customers’ needs evolved, and we made sure our app evolved with them. Whether it was improving the user interface, adding new reporting tools, or refining push notification capabilities, we were always striving to make the product better.
Customer Focus and Feedback Loop
Our customer-first approach shaped everything we did. We knew that the best way to improve our product was by staying connected with the coffee shop owners who were using it daily. We set up regular check-ins, surveys, and open communication channels so that our customers could easily share what was working and what wasn’t. This feedback loop allowed us to catch issues early and make enhancements that truly mattered.
One feature that came directly from customer feedback was the saved favorites functionality. Many coffee shop customers have their go-to orders, and our users made it clear that they wanted a way for their customers to save and quickly reorder their favorite drinks. By implementing this feature, we made the ordering process even more convenient, which, in turn, increased repeat business for our coffee shops.
Chapter 5: Understanding the Market – Opportunity and Growth
Identifying the Market Gap
The opportunity for Espressly came from a clear gap in the market. Independent coffee shops were competing against giants like Starbucks, which had sophisticated apps that drove customer loyalty, convenience, and efficiency. These independent shops didn’t have the resources to build their own app from scratch, and existing solutions often felt generic and failed to represent their unique brand.
The gap was clear: independent coffee shops needed a tailored, branded, and user-friendly order-ahead solutionthat could help them compete. They needed a way to build customer loyalty, streamline operations, and provide the convenience that customers had come to expect from larger chains. Espressly aimed to fill this gap by providing an affordable, customizable mobile app solution that leveled the playing field.
The Rise of Convenience and Digital Ordering
As consumer behavior evolved, convenience became king. People wanted quick, seamless experiences, especially when it came to their daily coffee rituals. This shift towards convenience and digital ordering accelerated during the COVID-19 pandemic, as customers sought contactless ways to engage with their favorite coffee shops. We saw this as an opportunity to empower small businesses with the technology they needed to adapt to the changing landscape.
The rise of digital ordering wasn’t just about convenience; it was about loyalty. By offering features like loyalty rewards, saved favorites, and push notifications, we helped independent coffee shops build deeper relationships with their customers. The ability to communicate directly with customers, offer exclusive promotions, and reward loyalty became a powerful tool for our clients.
Growth Through Partnerships and Word of Mouth
We understood early on that our growth would depend on building strong relationships—not just with coffee shop owners, but with partners who could help us scale. Square was a key partner in this journey, as their POS system was already widely adopted by our target market. By integrating seamlessly with Square, we could provide a solution that worked with the existing infrastructure of our customers, reducing friction and making onboarding simple.
Word of mouth also played a significant role in our growth. Independent coffee shop owners often share tips, tools, and recommendations with one another, and we found that a positive experience with one shop often led to referrals. By focusing on delivering an exceptional product and excellent customer service, we were able to grow organically through the power of recommendation.
Scaling While Staying True to Our Values
Growth is exciting, but it can also be challenging—especially when you’re bootstrapped. We wanted to grow, but not at the cost of our values. It was important to us that every new customer received the same level of care and attention that our early adopters did. We didn’t want to sacrifice quality for quantity. This meant being deliberate about how we scaled—whether it was hiring new team members, onboarding new customers, or expanding our product features.
We also stayed committed to our customer-first approach. Even as we grew, we continued to have regular check-ins with our customers, gather feedback, and ensure they felt heard. We knew that our success depended on their success, and that meant staying true to the values that had gotten us this far.
Chapter 6: The Power of Community and Relationships
Building a Community Around Espressly
One of the most rewarding aspects of building Espressly has been the sense of community that has developed around our product. Coffee shops are inherently community-driven spaces, and we wanted our technology to reflect that. From the beginning, we made it a priority to foster genuine relationships with our customers, and in doing so, we became part of their community.
Our customers weren’t just users; they were partners. We worked alongside them to create something that worked for their unique needs. We attended community events, visited shops in person, and made sure our customers knew that we were there for them, not just as a vendor but as a partner in their success.
Collaborating for Success
The collaboration went both ways. Our customers provided us with invaluable feedback, ideas for new features, and insights into what worked and what didn’t. In return, we gave them a platform that helped them thrive. This collaborative spirit was at the core of everything we did, and it’s something that set us apart from larger, more impersonal tech solutions.
Customer Stories
Hearing the success stories of our customers was always a reminder of why we started Espressly. Whether it was a shop that managed to serve twice as many customers during their morning rush or a barista who no longer had to memorize dozens of customized orders, these stories kept us motivated and focused on our mission. It wasn’t just about the technology—it was about the impact that technology could have on real people’s lives.
Chapter 7: Challenges, Setbacks, and Perseverance
Facing Challenges Head-On
Every startup faces challenges, and Espressly was no different. There were moments when things didn’t go as planned—features that didn’t resonate, partnerships that fell through, or technical hurdles that seemed insurmountable. But each of these challenges was an opportunity to learn and grow.
One of the biggest challenges we faced was managing growth while maintaining quality. As our customer base grew, so did the demands on our team. We had to find ways to scale our operations without losing the personal touch that had defined us from the beginning. This meant investing in our infrastructure, hiring the right people, and ensuring that our processes could handle increased demand.
The Importance of Perseverance
Through all the challenges, one thing remained constant: our commitment to perseverance. We knew that building a successful company wouldn’t be easy, and we were prepared to put in the work. There were long nights, tough decisions, and moments of doubt, but we kept moving forward. The grind was real, but it was also what made every win that much more rewarding.
Learning from Setbacks
Setbacks were inevitable, but they were also some of our greatest teachers. When a feature launch didn’t go as planned, we used it as a chance to learn more about what our customers needed. When growth slowed, we took a step back to evaluate our strategy and make adjustments. Each setback was a chance to recalibrate, refocus, and come back stronger.
Chapter 8: The Future of Espressly – A Vision for Growth
Expanding Our Reach
As we look to the future, our vision for Espressly remains the same: empowering independent coffee shops through technology. We want to expand our reach, bringing our solution to more coffee shops across the country and beyond. We believe that every coffee shop, no matter how small, should have access to the tools they need to succeed.
This means continuing to improve our product, adding new features, and ensuring that our technology evolves with the needs of our customers. We’re also exploring new partnerships and integrations that will make our platform even more powerful.
Innovating for the Future
Innovation is at the heart of what we do. As consumer behavior continues to evolve, we’re committed to staying ahead of the curve and providing our customers with the features they need to meet the demands of their customers. Whether it’s enhanced loyalty programs, new payment options, or expanded analytics capabilities, we’re constantly thinking about what’s next.
Staying True to Our Roots
As we grow, we’re also committed to staying true to the values that have defined us from the beginning. We’ll continue to prioritize customer relationships, community, and quality. We’ll keep listening to our customers, learning from them, and making sure that everything we do is in service of helping them succeed.
Chapter 9: Closing Thoughts – Brewing Success Together
Building Espressly has been an incredible journey—one filled with challenges, successes, and countless cups of coffee. It’s a journey that has taught me the importance of perseverance, the value of community, and the power of technology to make a difference in people’s lives.
This book is more than just the story of a company—it’s the story of a vision brought to life, of a community built around a shared passion, and of the countless individuals who made it possible. To every coffee shop owner who took a chance on us, to every team member who put in the long hours, and to every customer who used our app to get their morning coffee: thank you. You are all a part of this journey, and we couldn’t have done it without you.
The road ahead is still being paved, but one thing is certain: we’re just getting started. The grind will continue, the reps will keep coming, and we’ll keep working to make Espressly the best it can be. Because, in the end, success isn’t about overnight wins or explosive growth—it’s about the steady, consistent effort that moves you forward, one cup of coffee at a time.