Exploring Life & Business with Stephanie Webster of The Rhined & Oakley Wines

Today we’d like to introduce you to Stephanie Webster

Hi Stephanie, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
I was the kid who never really knew what they wanted to be when they grew up. I always loved science, so I majored in Microbiology & Chemistry in undergrad—without a clear plan for what came next. During Micro Lab, we experimented with fermentation, making wine, yogurt, and cheese. The yogurt and cheese turned out great; the wine… not so much (turns out Welch’s grape juice isn’t ideal for winemaking!). But that experience sparked something in me—I became fascinated with the biology and chemistry of milk and started making yogurt at home, fermenting it next to the heater in my apartment.

At the same time, my curiosity about wine deepened. I wrote my senior thesis on native fermentation, essentially exploring “natural wine” before I even knew what it was. By the time I graduated, I still wasn’t sure what I wanted to do, but I was getting pretty good at homemade yogurt!

I went to grad school on a fellowship and eventually became a high school Biology teacher, but it didn’t take long to realize that the job wasn’t sustainable for me. I was coming home mentally and emotionally drained, often passing out on the couch by 8 PM—sometimes even talking in my sleep before it got dark.

Meanwhile, I had always worked in restaurants since I was 16, and by the time I finished grad school, I was working in fine dining with serious wine programs. I was excited to leave hospitality behind for a “real 9-5 job,” but when I finally did, I realized something: the food and hospitality industry energized me. I was happy after work, I had energy, and I was excited—a stark contrast to how I felt as a teacher.

That realization led me to combine my love of cheese, wine, and hospitality and open The Rhined in 2017. A year later, I purchased Oakley Wines, and I’ve been living my dream ever since. The past eight years have been a fun, wild, and rewarding ride, and along the way, I’ve discovered another passion beyond cheese and wine—business and entrepreneurship.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Definitely not a smooth road. Owning a small business is a rollercoaster—some days, when everything feels like it’s going wrong, I question everything, including what I’m doing with my life. And then there are days when I have a few wins, and I feel on top of the world. I’m sure it’s taking years off my life, but at the same time, how lucky am I to wake up every day and do what I love? Even on the worst days, I wouldn’t trade it for anything.

The Rhined opened in 2017. In 2018, I purchased Oakley Wines, which, at the time, was a failing business. Just as we were hitting our stride at Oakley Wines, the pandemic hit in early 2020, stopping all of our momentum. We had to close for several months, so we focused on The Rhined – building an online store, launching delivery, and doing all the “pivot-y” things that became necessary for survival during that time.

When we eventually reopened Oakley Wines, the closure turned out to be a blessing in disguise—I was able to relaunch the business on my own terms, rather than maintaining the previous owner’s vision.

Over the years, there have been so many ups and downs. At one point, we were so cash-poor that I had to take out a loan just to stay open. Fortunately, we worked through those struggles, and I was able to pay it back fairly quickly. And now—knock on wood—we finally seem to have our sh*t together. Of course, anything can change at any moment, so I almost hesitate to say that out loud, but right now, we’re in a good place. A lot of things are changing in the industry right now – another challenge. I’m hoping we can hang on to the “being in a good place” thing.

Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
At The Rhined and Oakley Wines, we believe that great cheese and wine start on the farm. We focus on working with small, family-run producers—farmers, cheesemakers, and winemakers who prioritize soil health, biodiversity, and low-intervention practices. Whether it’s a lively vineyard buzzing with birds and bees or a cheesemaker tending to their pasture and happy herd, the commitment to quality starts long before these products arrive in our shop.

The Rhined
Located at Cincinnati’s historic Findlay Market, The Rhined is a cut-to-order cheese and wine shop with a café-style atmosphere. Guests can enjoy a glass of wine and cheese plate in our cozy shop, or take home a freshly cut wedge from our curated case along with a bottle of wine and all the accouterment to pair!

Our catering offerings range from custom wedding spreads to office boxed lunches to cheese & charcuterie boards for gatherings of friends. Right next door, our private event space, Bloom Room by The Rhined, is available for celebrations, tastings and special events.

We also love educating and inspiring our guests through our “Get Cultured” classes where we explore Cheese Board Building, Cheese & Wine Pairing, and even deep dive into the technical aspects of cheese! Simply put, “cheese, wine, fun” are what we do best!

Oakley Wines
Oakley Wines is more than just a wine bar and bottle shop – its a welcoming space for our guests to explore great wine and share seasonally-inspired food. We keep things approachable and playful – because at the end of the day, it’s just wine and food – delicious, not pretentious.

We offer wine flights, tasting events, Raclette Night (in the colder months) and so much more – we love keeping our calendar exciting and fun. We also host offsite, private wine tastings and offer a private event space, The Cellar, perfect for toasting to life’s big and small milestones.

Make a reservation and bring your favorite people for a great time.

What sets us apart-
Our producers trust us to care for their product and find a great home for them. We take that responsibility seriously, – meticulously tending to our cheese case, telling the stories of our winemakers, and honoring the artisans behind these incredible products. We are deeply passionate about what we do, and we love sharing that passion with our guests and community.

What I’m most proud of-
I am proud of our organic growth, our commitment to quality, and our high level of service. But what I’m most proud of is our team. Their dedication to our guests, our community, and our mission and vision is what makes The Rhined & Oakley Wines truly special. Last year, we took a huge step toward breaking industry molds and changing industry culture by implementing a profit-sharing program with our team. The profit sharing program is in alignment with one of our guiding principles: “Our business is sustainable. If we do well, our staff does well too. We continue to grow.”

This is more than a business to me – it’s about changing lives through good food and good wine. Not just the lives of our guests, but the lives of our team. I’m excited for what’s ahead and hopeful that we can continue to push boundaries, uplift our industry, and create something truly lasting.

Above all, we believe in great food, great wine, and great people—and we’d love to share that with you.

We’d love to hear about how you think about risk taking?
I’m a risk-taker. I think you kind of have to be as an entrepreneur. When I opened The Rhined, I had no background in business, just a deep love for cheese, wine, and hospitality. A lot of people tried to talk me out of it including my parents and my teacher coworkers. I used all of our savings and took a line of equity out of our home to make it happen. I did the same again a year later to purchase Oakley Wines, which at the time was a failing business. Taking on a struggling business while still growing The Rhined was a huge risk, but I believed in what we could become.

I’ve taken out a loan just to stay open when we were cash-poor, I’ve also let our bank account slim down to stress-inducing levels to avoid taking out a loan, knowing (or at least really hoping) we’d find a way to pull through.

I’m more of a “say yes and figure it out” kind of person rather than a “figure it out and decide if we can” type. I don’t know -maybe I’m a little nuts, But I do think my “say yes” strategy and betting on myself and my team has paid off, even it has meant extra hours, tight margins, and getting by by the skin of our teeth at times.

Calculated (and maybe sometimes not-so-calculated) risk has been the key to our growth. I’ve learned that not being afraid to fail – and knowing that I can sleep at night if I’ve done everything in my power to make it work – makes all the difference.

Contact Info:

• Website: www.therhined.com | www.oakleywines.com
• Instagram: @therhined | @oakleywines | @bloomroomotr