Nestled in the South Loop of Chicago, Printers Row Wine Shop — a natural wine bar and boutique — brings a world of flavor to the neighborhood. Tanya Gentile and her late husband Flavio Vincent Gentile opened the shop in 2004, drawing from their experiences waiting tables during which they became wine connoisseurs by proxy. But the shop is more than just a place to find new, rare bottles; it’s the kind of neighborhood hub where you can have a drink at the bar while you shop, take in the summer sunshine at the outdoor patio, or even catch live music or a poetry reading. Patrons who want to bring some of the magic home can also sign up for their wine club and receive a monthly shipment of curated wines.
We sat down with Printers Row Wine Shop’s owner, Gentile, to get the inside scoop on how she built and now operates a successful multihypenate business that the locals cherish. She also shares why she decided to switch to Square and how it helped streamline business operations using SquarePayroll, Point of Sale (POS), and more.
Unlocking multiple revenue streams from a single business
According to our 2024 Future of Multihyphenate report, 40% of restaurateurs reported that 21% or more of their revenue comes from products or services outside of their core offerings. Printers Row Wine Shop is right on track with this diversified growth strategy.
Gentile started the shop strictly as a retail space selling affordable wines, craft beers, fine spirits, and snacks. She soon recognized that her community wanted more ways to engage with her shop. “We did a lot of tastings back in the day, and the space just really begged for our customers to want to stay and enjoy their wine at our establishment,” she said. “So right before COVID, we put in the actual bar and got the licenses for on-premise [alcohol], and here we are today.”
With multiple ways for customers to connect with the shop, Gentile needed a technology solution that would help her manage those new revenue opportunities without the challenges that come with managing a multifaceted business. Printers Row Wine Shop landed on using Square for Retail and Square for Restaurants together in order to take payments, manage inventory, and connect the front and back of the house. Employees also use the Square insights to inform the business strategy. For example, when to reorder inventory to avoid missing out on sales or how to generate more foot traffic on otherwise slow business days.
Square has streamlined most revenue sources, and we can see the report numbers for all of them combined or just locking in on one. It provides us with a simple way to analyze data and understand which revenue source is the most profitable.”
Tanya Gentile → Owner of Printers Row Wine Shop
Using loyalty programs to manage cash flow and keep customers coming back
Like most businesses, Printers Row Wine Shop has busy and slow days. Gentile wanted to find a creative way to keep her sales volume steady throughout the week and reward loyal customers. “We wanted to pick our slowest day and incentivize customers to come in on that day,” she said. “So with our loyalty program, you get a point for every dollar you spend. When you get 500 points, you get $15 to spend in the store. Monday was our slowest day, so we offer double points then.” Customers took note, and now the shop has seen an uptick in foot traffic on an otherwise slow day.
Gentile runs her points program through Square Loyalty, which integrates seamlessly with the rest of the business. Customers can sign up on the spot while they check out, whether that’s in-person or online through the website. Then the points start stacking up purchase after purchase.
People love [Square Loyalty]. People are always checking their points. It comes up on the POS screen and they get texts to their phones. The loyalty program through Square is fantastic.”
Reaching a wider audience with an online presence
Printers Row Wine Shop is constantly innovating, whether that’s with in-store events or organized wine trips to France. Gentile’s online store is her hub for information so customers from all over can keep up with the latest.
Knowing this was a valued experience for her customers, Gentile was looking to establish a branded online presence without having to invest in an expensive website developer. Using Square Online to launch the business’ website she’s been able to increase the shop’s discoverability, manage the wine club, and keep her community informed on upcoming events.
Growth isn’t stopping anytime soon for Gentile and Printers Row Wine Shop. She has plans to grow its wine club, to continue her in-store event series, and to keep curating a specialized retail experience. Printers Row has weathered some challenging storms and come out on the other side with an even stronger community at its side, eager to take part in whatever ventures the shop explores next.
