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There was a time when loyalty meant a punch card tucked in your wallet. You buy nine coffees and get your tenth free. It was simple, transactional, and entirely forgettable. But for today’s most forward-thinking hospitality and retail brands, loyalty has evolved into something deeper. While the freebies are great, loyalty is also about being known and remembered.
For businesses like Bluestone Lane, The Epicurean Trader, and Roaming Goat, loyalty isn’t defined by transactions or points. It’s built through moments of recognition, small gestures of care, and a genuine sense of belonging. And while the relationships feel personal, the operations behind them scale thanks to integrated loyalty technology.
At a recent Square Spring Releases event, the founders of these brands joined Square leaders for a live conversation about how they’re rethinking loyalty in an age of digital orders, busy staff, and rising customer expectations. Here are the biggest takeaways from that conversation — and how your business can turn everyday transactions into lasting relationships.
Loyalty begins with recognition
For Nick Stone, founder of Bluestone Lane, loyalty doesn’t begin with a purchase. It starts well before that, with something much more foundational: human connection.
“We are a human connection company,” Stone said. “We don’t talk about being a coffee company or a coffee brand. We’re very much about building communities and really being an antidote to this loneliness epidemic.” That idea of community has guided Bluestone Lane’s growth from a single café in New York to over 60 locations nationwide. Their goal isn’t to serve as many cups of coffee as possible. It’s to create a space that makes people feel seen.
Stone believes that recognition is a powerful act of hospitality. “And the example of that is knowing your name, or your face, or your order,” he explained.
That [human] recognition is so incredibly powerful. Right now in society, people are feeling more disconnected and lonely. So if you can double down on that, I really think that is the most powerful retention tool.”
Nick Stone → Founder of Bluestone Lane
That’s where technology plays a supporting role. Using Square tools, Bluestone Lane’s team can see past transactions and preferences, which helps them deliver those small, meaningful touches that make a guest feel remembered. “If tech enables my team to spend more time engaging and still have a really convenient, frictionless experience, I think it’s just going to enhance your proposition.”
Rather than automate for the sake of speed, Stone sees tools like Square as a way to deepen the brand’s promise. “Hospitality is built around making people feel good,” he said. “I’ve never been a big believer in being product led… brands that focus on making people feel good and part of something bigger are going to win.”
A paid loyalty model can drive deeper connection
At The Epicurean Trader, loyalty doesn’t follow a one-size-fits-all playbook. Matt Pond and his team have experimented with multiple approaches, some familiar, others more ambitious.
“We’ve actually done two loyalty programs,” Pond said. “One is kind of more a classic café loyalty program. You give your phone number, we have the ability to market to you, and in return, you get a free coffee every hundred dollars you spend.” The model is simple and effective, especially for casual customers who want a quick reward for their repeat visits.
Their second program adds a premium layer, and was designed for regulars who wanted a little more and were willing to pay for it. “We launched a separate program more on the market side, which is a paid loyalty program where you pay $20 a month or $200 a year. You get additional bonuses like discounts on everyday purchases, access to discounts at local restaurants, and discounted rides at gyms.” That extra layer gave customers a way to engage more intentionally.
What surprised them most was how eager people were to join. “We’ve found it’s actually quite inspiring how many people want to support The Epicurean Trader and purchase a paid membership program,” he said. “They’re rewarding us by actually committing to us and spending money with us on a weekly basis.”
Square’s integrated tools made the process smooth on the backend. With Square Loyalty and Square Marketing, the team can run both programs across all their stores, tracking rewards and sending targeted messages from a single platform, without losing the human touch. It’s clear from the response that people want more than just discounts. They want connection, recognition, and a reason to keep coming back.
Handwritten hospitality meets digital ordering
At Roaming Goat, a Mediterranean restaurant and wine bar in San Francisco, there’s no formal loyalty program in place. But that hasn’t stopped the team from building strong customer relationships through thoughtful, personal gestures — many of which start with data.
Founder Jacob Paronyan explained that even digital orders come with opportunities to connect. “Our digital customers take out orders from time to time,” he said. “Because often they’re within a mile and a half radius of us, we’ll randomly send something and write on the item, like, ‘We don’t think you’ve tried this dish yet. Here’s a complimentary dish from us.'”
This kind of handwritten hospitality is backed by Square’s order history tools, which allow the team to recognize returning guests even when they aren’t dining in. That visibility into customer behavior gives them the chance to surprise someone with a free item or acknowledge a repeat visit in a way that feels spontaneous and generous.
He’s also experimenting with marketing tools like email and text campaigns to stay connected without overwhelming guests. “We’re still kind of distilling what makes the most sense,” he said. “Because we don’t want it to feel artificial.”
Making loyalty omnichannel creates more touchpoints to connect
For many businesses, loyalty starts at the register. For The Epicurean Trader, it extends well beyond the storefront. Pond and his team use a mix of physical and digital tools to keep the connection going, no matter where the customer shops.
The Epicurean Trader manages three digital storefronts through Square Online, and their team uses geographic data to bring online customers into local stores. “If somebody purchases online, we have AI that would say, look, the address is in San Francisco,” said Pond. “We automatically print out a postcard that says, come in one of the stores. Here’s a discount. Come in, enjoy the in-store experience.”
That same logic works in reverse. When a shopper visits one of their five brick-and-mortar locations, the staff encourages them to explore the broader product selection available online. “If somebody comes into a physical store and purchases an item, we’re always trying to incentivize them to say, look, there’s only so many products we can fit in a 2,000 square foot store, but online we have this universe that’s larger.”
This back-and-forth between channels gives customers more ways to engage, while also helping the business learn more about individual preferences. It also supports a consistent experience, whether someone is buying a bottle of wine in person or restocking their pantry online.
Stone echoed the same omnichannel view, the idea of loyalty flowing across platforms. “People who subscribe to coffee being delivered at home are generally the same local that comes into the café every day,” he said. “I think there’s a huge opportunity to leverage partnerships and unique experiences to drive more personalization and loyalty.”
AI and individualized loyalty are changing the game
As technology evolves, so do customer expectations. For these brands, the next phase of loyalty is less about blanket offers and more about tailored experiences that feel specific to each guest.
“There’s too many loyalty programs, too many offerings that are generic,” said Nick Stone. What excites him is the potential for artificial intelligence to help businesses offer smarter, more personalized rewards.
“I think it’s just going to be so exciting in this new personalization frontier with AI, about having unique gamification and rewards.””
Nick Stone → Founder of Bluestone Lane
Stone imagines a future where every guest has their own version of loyalty, based on their habits, preferences, and behavior. “How do we get that cohort to visit two other Bluestones over the next month? What can we do to incentivize them?” he asked. “Because then I think they’ll even get more bought into the brand and more loyal.”
This kind of behavior-based targeting allows businesses to shape customer journeys in a way that feels natural rather than forced. Instead of offering the same punch-card reward to everyone, they can deliver something that speaks directly to the way each person interacts with the brand.
Building loyalty that lasts
Bluestone Lane, The Epicurean Trader, and Roaming Goat show that loyalty isn’t something you sell, it’s a relationship you build. It lives in handwritten notes, targeted messages, and membership programs people are proud to join. Real loyalty takes time, and it’s rooted in recognition and trust.
With Square, these businesses are able to deliver personalized experiences at scale without adding complexity behind the scenes. The tools stay in the background, making it easier for teams to focus on what matters: creating moments that feel genuine.
As Stone put it, “Retention is the most important thing.” And the most powerful retention tools aren’t points or perks. They’re the things people remember — a thoughtful gesture or a sense of belonging.
