Chapter 2: Every Conversation Is an Opportunity

The success of your business depends on two kinds of transactions: financial and conversational.

Most ecommerce operators obsess over the financial transactions. They optimize checkout flows, test pricing strategies, and monitor conversion rates. This makes sense. Revenue is easy to measure, and it's obviously critical to survival.

But conversational transactions are where the magic happens. Every customer question, suggestion, story, or complaint is an opportunity. An opportunity to deepen the relationship. An opportunity to learn what your community wants next. An opportunity to turn a buyer into an advocate who tells everyone they know about your brand.

The difference is that conversational transactions will happen whether you plan for them or not. Customers will find ways to reach you. They'll email, call, message on social media, leave reviews. The question isn't whether these conversations will happen. The question is whether you'll treat them as interruptions to manage, or as invitations to build something better together.

I learned this lesson through one of my favorite customer interactions at the Stupid Cancer store.

A woman named Jessica emailed us about a month after placing her first order. She'd bought a "Stupid Cancer" t-shirt and posted a photo of herself wearing it on Instagram. Within days, three of her friends had asked where they could get one. But here's the thing: they were all plus-size women, and we only carried up to XL at the time.

"I love this shirt," Jessica wrote, "and I know at least a dozen people who would buy it if you made it in their size. Have you thought about extended sizing?"

We hadn't. But we should have.

Within two weeks, I'd talked to our printer about expanding the size range. Within a month, we were carrying up to 3XL. And Jessica? She didn't just buy more shirts for herself. She organized a group order for eight friends, posted about it constantly, and became one of our most vocal advocates. She didn't just buy products. She became part of the community that shaped what we created.

That's the power of treating conversations as opportunities instead of obligations.

Every Channel Is an Invitation

Here's what most people get wrong about customer communication: they think of it as customer service. Something you have to provide. A cost center. A necessary evil.

But customer communication isn't a burden to bear. It's an invitation your community extends to you. They're saying: "I care enough about your brand to reach out. I have something to tell you. I want to be heard."

Your job isn't to minimize these conversations or handle them "efficiently." Your job is to show up for them. To listen. To respond in ways that strengthen the connection and show that their voice matters.

When I started mapping out how the Stupid Cancer store would communicate with customers, I identified five distinct channels: email, phone, live chat, social media, and physical mail. Each one gave our community a different way to reach us. Each one revealed different kinds of insights.

Email was where people shared their stories. Phone was where passionate supporters placed big orders and asked detailed questions. Live chat was where browsers became buyers. Social media was where community happened publicly. And physical mail? That's where people sent handwritten notes that made me tear up.

Each channel wasn't just a door into customer service. It was a window into what our community cared about.

Email: Where Stories Live

Email was where people told us their cancer stories. Not always, and not everyone. But often enough that checking the inbox became one of the most meaningful parts of running the store.

Someone would order a shirt, and in the "order notes" field they'd write something like: "My sister was just diagnosed. I'm buying this for her because I don't know what else to do, and I want her to know she's not alone."

Or they'd email weeks after receiving their order to tell us they'd worn the shirt to a doctor's appointment and another patient had stopped them in the waiting room to ask about it. "We talked for twenty minutes," they'd write. "She'd been feeling so isolated. The shirt gave us something to connect over."

These weren't customer service inquiries. These were invitations into people's lives. And they shaped how we thought about everything.

Early on, I made the mistake of treating email like a task to complete. Someone would send a question, I'd answer it as quickly as possible, and move on. Efficient, but soulless.

Then I started noticing something: the emails where I took time to actually engage—to ask a follow-up question, to share a related story, to connect them with a resource—those were the emails that turned one-time buyers into repeat customers and vocal advocates.

When Jessica emailed about extended sizing, I didn't just say "Thanks for the feedback." I asked her about her experience, what sizes her friends needed, what other products they wished existed. That conversation shaped our product roadmap for the next six months.

To handle email without losing the human touch, I set up role-based addresses: store@stupidcancer.org for general inquiries, support@stupidcancer.org for order questions, and returns@stupidcancer.org for returns. But I also integrated everything into Zendesk, which let me see the full conversation history with each customer and respond with context instead of treating every email like it existed in isolation.

The goal wasn't efficiency for its own sake. The goal was having the infrastructure to engage meaningfully at scale.

Phone: The Superfans

Phone orders made up less than one percent of total transactions, but those customers became some of our most passionate advocates.

The people who picked up the phone to call us weren't just buying shirts. They wanted to talk. They wanted to tell us about their diagnosis, their treatment, their frustration with how the world talks about cancer. They wanted to know our story. They wanted to feel connected to something bigger than a transaction.

I used Grasshopper, a virtual phone system that gave us a professional toll-free number but rang to my cell phone. The system cost less than $30 per month and made us look significantly more established than we were. But more importantly, it created space for the kinds of conversations that don't happen over email.

I remember a call from a guy named Marcus who wanted to order shirts for his entire kickball team. His girlfriend had been diagnosed with leukemia, and the team wanted to show support. What started as a bulk order inquiry turned into a thirty-minute conversation about his experience, what he wished people understood about being a caregiver, and how helpless he felt.

He placed a $400 order. But more importantly, he became an ambassador. He told everyone he knew about Stupid Cancer. He posted photos of the team wearing the shirts. He organized a fundraiser for us. And he emailed me a year later to let me know his girlfriend was in remission.

That relationship started with a phone call. It never would have developed the same way over email.

For years, companies have been trying to eliminate phone support because email is cheaper and more scalable. But eliminating phone support means eliminating the conversations that create your most devoted community members. Some interactions need to happen voice-to-voice. Some relationships need that level of connection to take root.

Live Chat: The Conversion Catalyst

Live chat is where hesitation turns into action.

I experimented with Lexity's live chat feature, which let me see who was browsing the store in real-time. I could see which products someone was viewing, how long they'd been on the site, and whether they'd added anything to their cart. If someone seemed stuck, I could proactively reach out.

The technology was impressive. But what made it powerful wasn't the efficiency—it was the human moment.

Someone would be looking at a hoodie, and I'd send a message: "Hey! I'm Kenny, I run this store. Let me know if you have any questions about sizing or anything else."

Most of the time, they'd respond. And most of the time, their question was simple: "Is this true to size?" or "When will this ship?" But occasionally, the conversation would go deeper.

"I want to buy this for my friend who's going through chemo. Do you think she'd like it?"

And I'd respond: "Tell me about her. What's her personality like?"

And we'd have a real conversation about who this person was, what they were going through, and what kind of message this gift would send. Sometimes I'd recommend a different product. Sometimes I'd suggest adding a handwritten note. Sometimes I'd just say, "That's really thoughtful. She's lucky to have you."

Live chat could have been robotic. It could have been all about converting browsers into buyers as efficiently as possible. But treating it like a chance to actually connect with people—that's what made it work.

The catch with live chat is that it only works if you can staff it properly. If someone clicks the chat button and gets no response, you've made things worse, not better. So I set the chat widget to only appear during specific hours when I knew someone would be monitoring it. Outside those hours, it would hide, and customers would be directed to email instead.

Better to be honest about availability than to promise something you can't deliver.

Social Media: Where Community Happens in Public

Social media was different from every other channel because it was public. When someone posted on our Facebook page or tweeted at us, everyone saw it. And how we responded showed the entire community who we were.

This public nature changed everything. It wasn't just about solving one person's problem. It was about demonstrating our values to everyone watching.

I integrated our social media channels into Zendesk so that Facebook messages and Twitter mentions would create tickets just like emails did. This meant nothing could slip through the cracks. But more importantly, it meant I could see the full relationship with each customer—their order history, previous interactions, everything—so I could respond with context instead of generic scripts.

Someone would post: "Just got my Stupid Cancer shirt and I LOVE IT." And instead of a generic "Thanks!" I'd respond with something personal: "So glad you love it! I saw you ordered the black one—it's one of my favorites too. Thanks for being part of the community."

Or someone would complain: "Ordered a shirt two weeks ago and it still hasn't shipped." And instead of getting defensive, I'd look up their order, figure out what happened, and respond publicly: "You're absolutely right to be frustrated. There was a delay with our printer. Your order shipped yesterday and you should have it by Friday. I'm sending you a discount code for your next order to make up for the wait."

Handling complaints publicly, with transparency and accountability, didn't hurt our reputation. It strengthened it. People watching could see that we owned our mistakes and made them right.

But social media wasn't just for customer service. It was where we tested ideas.

When we were thinking about creating a new design, I'd post a mockup and ask: "Would you wear this?" The response told us whether to move forward. When we were deciding between two colorways, I'd post both options and let the community vote. When we were considering a new product category entirely, I'd start a conversation: "We're thinking about making hoodies. Thoughts?"

The community didn't just buy what we created. They helped us decide what to create in the first place.

Physical Mail: The Handwritten Notes

People still send physical mail. Not often, but when they do, it's usually the most meaningful communication you'll receive.

The most common scenario: someone would return a product with a handwritten note explaining why. Sometimes it was simple: "Too small, please refund." But sometimes it was more: "This was a gift for my mom, but she passed away before I could give it to her. I can't keep it. I hope you understand."

Those notes required more than a refund. They required humanity.

I'd process the refund immediately, but I'd also write back. A handwritten note of my own. "I'm so sorry for your loss. Thank you for sharing that with me. Sending you strength."

Did it take more time? Yes. Did it matter? Absolutely.

I also received physical mail that wasn't about returns. People would send thank-you notes. They'd send photos of themselves wearing our products at cancer walks, survivor celebrations, memorial services. They'd send drawings, poems, and stories.

I kept every single one. They reminded me why the store existed. They reminded me that this wasn't just about selling shirts. It was about creating symbols of solidarity that helped people feel less alone.

To make the return process smoother for customers, I created a returns page on the website with a printable return form. Customers could fill it out, include it with their return, and I'd have all the information I needed. I also included return instructions with every shipment—a small printed card explaining the process.

But the system existed to make things easier, not to replace human connection. When someone sent a handwritten note, I responded with one. Because some moments require more than efficiency.

Proactive Communication: Showing You Care

Every channel can be approached reactively (waiting for customers to reach out) or proactively (reaching out first to strengthen the relationship).

Automated order confirmation emails are the most basic form of proactive communication. The customer places an order, and immediately they know it went through. They don't have to wonder. They don't have to email asking.

But proactive communication can go much further.

On Bigcommerce, I enabled shipping notifications, so customers would get an email the moment their order shipped, with tracking information included. They didn't have to check in to see if their package was on the way. We told them.

I also set up automated email sequences for specific scenarios:

●  ​If someone abandoned their cart, they'd get a reminder email 24 hours later: "Did you forget something? Your cart is waiting."

●  ​If someone made their first purchase, they'd get a welcome email explaining our mission and how their purchase supported it.

●  ​If someone hadn't ordered in six months, they'd get a "we miss you" email with a discount code.

These automated touchpoints weren't about sales alone. They were about maintaining connection. They were about showing that we noticed, we cared, and we wanted to stay in touch.

But the best proactive communication wasn't automated at all. It was personal.

When someone posted on Instagram wearing our shirt, I'd comment: "Love seeing this! Thanks for being part of the community." When someone mentioned us in a tweet, I'd reply. When someone sent a particularly moving email, I'd follow up weeks later to ask how they were doing.

These moments took more time than automation. But they created the relationships that automation alone never could.

Building Relationships, Not Just Managing Messages

The difference between customer service and community relationship building is the difference between handling inquiries efficiently and treating every conversation as a chance to deepen connection.

Community relationship building means every channel has clear ownership and response expectations, but also space for humanity. It means nothing falls through the cracks because every inquiry gets logged and tracked, but also that people feel heard, not processed. It means customers can choose how to reach you based on their preferences, and each interaction strengthens their relationship with your brand.

It means you've thought through what happens when volume spikes, when someone's off sick, when an inquiry comes in outside business hours. But you've also thought through what happens when someone shares their cancer story with you, or asks if you can help them organize a fundraiser, or tells you they wore your shirt to chemo and it made them feel brave.

Building this took time. I didn't implement everything at once. I started with email, got that working, then added phone, then integrated social media, then refined the process for returns. But each piece I added made the system more robust—and made the community stronger.

Eventually, customer communication stopped being something I had to find time for. It became one of my favorite parts of running the store. Because these conversations told me what was working, what needed to change, and what to build next. They reminded me why the store mattered. And they turned customers into advocates who spread the word more effectively than any marketing campaign ever could.

Your communication architecture won't look exactly like mine. You might not need phone support. You might need live chat during different hours. You might get more volume through Instagram than Facebook.

But the principles are universal: make it easy for your community to reach you, respond in ways that strengthen connection, track everything so nothing gets lost, and always look for opportunities to learn from the conversations happening around you.

Conversational transactions build relationships. Relationships create advocates. And advocates build your business in ways that paid advertising never could.

It's a joyful cycle, and it starts with treating every conversation as the opportunity it is.