Introduction: Building Something People Want to Wear
Before I ever sold a t-shirt online, I learned about customer service behind a pharmacy counter.
I was fifteen years old, working at a small independent pharmacy on Long Island. The previous pharmacy had been a Main Street fixture for thirty years before CVS bought them out and shut the doors overnight. Our job was to rebuild trust with customers who'd been abandoned, one prescription at a time.
What I learned there shaped everything I built afterward: customer service isn't about transactions. It's about understanding that every person who walks through your door is part of a larger ecosystem. They have families worried about them, doctors depending on accurate information, neighbors who help with rides. When you serve one person well, you're actually serving an entire network of relationships around them.
That principle—seeing beyond the immediate transaction to understand the whole system you're serving—became the foundation for how I approached building an ecommerce store years later.
The first product I ever sold online was a white Gildan 5000 t-shirt with "Stupid Cancer" printed across the front. I charged $20. I had no inventory system, no marketing funnel, no supply chain. I packed and shipped every order by hand from our TriBeCa office in Lower Manhattan.
That one shirt sparked something I never imagined: a six-figure ecommerce operation that turned customers into walking billboards, funded programs that mattered, and became one of the most exciting things I'd ever built.
It was March 2012. I was 25 years old, serving as Chief Operating Officer of Stupid Cancer—a nonprofit supporting young adults affected by cancer. I wore a lot of hats: program director, operations manager, customer service rep. And now, apparently, ecommerce entrepreneur.
I was so excited to be working at Stupid Cancer and building something big. The organization had bold ideas about changing how the world talked about young adult cancer. "Stupid Cancer" wasn't a safe name. It wasn't committee-approved nonprofit speak. It was provocative, memorable, and exactly what our community needed to hear.
Stupid Cancer's mission is to end isolation for adolescents and young adults with cancer and make cancer suck less. The store became an unexpected tool for that mission—every shirt someone wore became a conversation starter, a way to find other young adults going through the same thing, a statement that you weren't alone.
We'd been selling merchandise through CafePress, the print-on-demand platform, but the profit margins were razor-thin and we had zero control over quality or fulfillment. I knew we could do better. But here's the catch: we were a nonprofit. Donor dollars couldn't fund a merch line. Every t-shirt I ordered had to be paid for with money we didn't have yet, from customers who didn't know we existed.
So I started small. One design. One color. One product. I scraped together enough cash to order a small batch, had them printed, and listed them on our newly launched Volusion store.
Then I waited.
The Store That Grew Up Fast
That waiting didn't last long.
The first order came in. Then another. Then ten more. The Stupid Cancer community—bold, passionate, and proud—didn't just want to donate to our cause. They wanted to wear it. They wanted to make a statement. Our messaging was never subtle, and neither was our audience's desire to be seen.
Before I knew it, I was fulfilling dozens of orders a week. Then hundreds. We added new designs—short sleeves, long sleeves, raglans, hooded sweatshirts, beanies. We experimented with different materials and colorways.
And here's the thing: I wore our products almost every day. Not because I had to, but because I genuinely loved them. I didn't want to create products I wouldn't wear myself. That authenticity mattered. I became a walking billboard, and when people asked about my shirt, I could tell them the story with genuine enthusiasm.
The store wasn't just generating revenue. It was creating advocates. Every customer who bought a shirt became a conversation starter. Every person wearing our gear was sparking discussions about young adult cancer in places those conversations didn't usually happen—at the gym, in coffee shops, on college campuses.
We were turning commerce into community building. And it was working.
The Creative Process
I loved working with designers. Some of them were cancer survivors themselves. Others were independent designers who connected with our mission and were excited to create something meaningful. When we launched design contests on 99Designs, we weren't just getting artwork—we were building relationships with creative people who became part of our community.
I ordered about 95% of our merchandise from a single mother in Florida who ran a small promotional products company. Over the years, we developed a real partnership. She understood the quality standards that mattered to us. She knew the mission. These weren't just vendor transactions—they were relationships built on mutual respect and shared purpose.
I also loved the gamification of it all—testing coupon codes, launching flash sales, timing product releases. Every campaign generated data. Every promotion taught me something new about what resonated with our community. It felt like a game where creativity and strategy combined to create real results.
The Operational Challenge
But as the store grew, the operational complexity grew with it.
Customer service inquiries came through email, phone, social media, and physical mail. Inventory had to be forecasted, ordered, received, and tracked. Orders needed to be picked, packed, and shipped. Marketing campaigns required planning and execution. Product development required design work, community feedback, and supplier coordination.
And I was still working full-time for the nonprofit, managing programs and operations that had nothing to do with ecommerce.
Something had to change.
I couldn't work harder—I was already maxed out. I couldn't hire a team—we didn't have the budget. The only option was to work smarter. To build systems that multiplied my effectiveness. To automate the routine so I could focus on the creative and strategic work that actually moved the business forward.
That's when I started building the operational infrastructure that would eventually allow one person to run a six-figure ecommerce operation from their phone.
The Systems That Made It Possible
Over the next four years, I built an ecosystem of tools, automations, and processes that transformed how the store operated.
I connected Bigcommerce to Slack so order notifications appeared in real-time on my phone, letting me stay connected to the pulse of the business even when I was in meetings across town.
I integrated Zendesk across every customer communication channel—email, phone, social media—so nothing fell through the cracks and every conversation strengthened the community.
I used Zapier to automate dozens of workflows, freeing me from manual data entry and routine tasks so I could focus on designing new products and building relationships.
I assembled a carefully chosen ecosystem of apps—email marketing platforms, inventory management tools, task managers—that essentially became my team, handling tactical execution while I made strategic decisions.
And when we outgrew our tiny TriBeCa office, I rented a box truck in Times Square, loaded everything myself, and drove it to Wilkes-Barre, Pennsylvania to establish a relationship with a 3PL warehouse. I worked closely with their team on creating SOPs for receiving and fulfilling our orders. It was exciting to graduate from packing boxes in our office to having real warehouse operations.
These weren't just efficiency improvements. They were the infrastructure that allowed me to build something I loved without burning out. They freed me to focus on the creative work—designing products, engaging with community, running campaigns—while the systems handled the routine.
The Results
By the time I left Stupid Cancer in May 2016, the store had processed over 8,200 transactions and generated more than $215,000 in revenue. We'd built a legitimate lifestyle brand with dozens of products. We'd turned thousands of customers into advocates who wore our gear proudly and sparked conversations everywhere they went.
The store funded programs. It raised awareness. It created community. And it proved that nonprofits could build sustainable revenue models that didn't rely solely on donations.
But here's the hard truth: when I left, the store couldn't sustain itself.
Within months, it was gone. Not because it wasn't profitable. Not because the mission had changed. But because the systems I'd built—the infrastructure that made it all possible—couldn't operate without someone who understood them.
The tools were still running. The automations were still firing. But without an operator who knew why each piece existed, how they connected, and how to make decisions based on their outputs, the system couldn't sustain the operation.
Why This Story Matters
I'm not telling you this story to brag about what worked or to lament what failed. I'm telling you this story because the lessons I learned building that store—about systems, operations, community building, and sustainable growth—are more relevant today than they were in 2012.
Whether you're running a nonprofit that needs sustainable revenue, building a mission-driven business, or just trying to create something people actually want to buy and represent, the principles are the same:
Build products you'd actually wear yourself. Authenticity resonates. If you don't believe in what you're selling, your customers won't either.
Turn customers into community. Commerce isn't just about transactions. It's about creating something people are proud to be part of and excited to share.
Build systems that multiply your effectiveness. You can't do everything yourself, but you can build infrastructure that lets one person accomplish what should require a team.
Focus your energy on what matters most. Automate the routine so you have time for the creative, strategic, and human work that actually builds your brand.
Document everything. Systems only work if they can outlive your direct involvement. Knowledge transfer isn't optional—it's essential for sustainability.
This book is about all of those principles. How to build ecommerce operations that scale without burning out. How to create products people love and want to represent. How to use technology to multiply your effectiveness without losing the human touch. How to build something sustainable that doesn't depend entirely on you being in the loop every day.
What You'll Learn
In the chapters ahead, I'll show you exactly how I built and ran the Stupid Cancer store. Not as a blueprint to copy exactly—your business will be different—but as a framework for thinking about operations, systems, and sustainable growth.
You'll learn how to set quality standards and choose platforms that make you look legitimate from day one, even when you're still figuring things out.
You'll learn how to build a communication architecture that turns customer conversations into community relationships.
You'll learn how to stay connected to your business in real-time without being chained to your desk.
You'll learn how to automate the routine work so you have time and energy for the creative work that actually builds your brand.
You'll learn how to assemble an ecosystem of tools that functions like a team, handling tactical execution while you focus on strategic decisions.
And you'll learn from my mistakes—the things I wish I'd done differently, the processes I should have documented, the knowledge I should have transferred before leaving.
A Note on Tools and Timing
The story I'm about to tell you happened between 2012 and 2016. Some of the specific tools I used still exist. Others have been acquired, evolved, or replaced by better alternatives.
But here's the truth: the tools change, but the principles don't.
The principle of staying connected to your community in real-time is still valid, even if the specific platform has changed. The principle of automating routine work to free time for creative work is still critical, even if you're using different tools. The principle of building systems that work when you're not working—that's timeless.
Throughout this book, when I mention a specific tool, I'll explain what it did for me and what modern equivalents exist today. Because this isn't about replicating my exact tech stack from 2013. It's about understanding the thinking behind tool selection and system design.
You're going to make different choices than I did. You should. Your business is different. Your constraints are different. Your opportunities are different.
But the operator mindset? That's universal.
Let's Build Something
What started with a $20 t-shirt became a $215,000 operation that funded programs, built community, and proved that mission-driven commerce could work.
It also taught me that building something successful and building something sustainable are two different challenges. I got the first part right. I didn't fully get the second part right. This book is about both.
I'm excited to share what I learned with you. Not just the systems and tools, but the joy of building something people love. The satisfaction of creating products you're proud of. The thrill of watching customers become advocates. The creative challenge of turning constraints into advantages.
Let's build something people want to wear, buy, and represent. Let's turn your brand into community. Let's create commerce that strengthens rather than extracts.
Let's get to work.