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Check Out Debra Smith’s Story

Today we’d like to introduce you to Debra Smith.

Debra Smith

Hi, Debra; we appreciate you taking the time to share your story with us today. Where does your story begin?
My presence in the wine industry is a fluke. The year 2009 marked a purely unplanned change in career paths from my two passions, writing and clinical research, ideally suited to my Asperger’s diagnosis and quiet, analytical nature. I had moved “up North” from Raleigh, North Carolina, to work as a clinical research associate, a position that didn’t come to fruition. The tiny liquor store by my house on the outskirts of Annapolis, Maryland, was hiring part-time cashiers, and the two gritty middle-aged women business owners who had hired me informed me that I would go to wine school on their dime. You do not argue with women who embody dockers in every sense of the word.

Thus began my passion for wine and food pairing and a long, unplanned career in retail operations management. With a perfect score on my viniculture exam, a WSET 2 diploma in hand, and a successful stint in business development at the world’s largest clinical research organization behind me, I spent a decade overseeing day-to-day operations for another Annapolis business, a $6M family-owned start-up in the alcohol beverage industry. I was the only wine professional on staff, and for the first 8 years, wine sales accounted for 50% of our business.

Conservatively, I made well over 40,000 wine recommendations in my decade there. Much of my time was spent stocking the store, helping customers choose wine, spirits, and craft beer for events for up to 300 people, memorizing a portfolio of over 7,000 wines, and assisting both local and international wine and bourbon collectors in curating their private collections, bottle by bottle. We added local craft beers to our portfolio in year eight and expanded our beer cooler to accommodate them. We would get new craft beers weekly, so I made a tasting chart and learned about the product. The highlight of my week was returning to work after having been off for two days and associating with one of our store owners about the new product. We would walk around the store and discuss the latest inventory, and having that rapport with my business owner meant everything to me. When you can get others on board to discuss the product, it generates excitement. And as we all know, excitement leads to more sales!

Often, I would assist a customer with wine choices, excitedly discussing the nuances and pairing opportunities. Other customers would line up, listen, and follow me around the store in single file to purchase the wines I was discussing. I joked that I was the Pied Piper of Annapolis. Over time, the urge to do something with my growing passion for curating private collections and educating others prevailed, so in 2017, I picked out a name for a wine and food pairing business and applied for a Federal EIN while navigating potential possibilities for a viable business in the stringent Maryland alcohol market.

One day, I had a chance to meet with a neighbor-turned-friend in Annapolis who is a designer for the National Gallery of Art in Washington, DC. While walking our senior dogs, who do not care for other dogs, it was discovered in passing that they seemed to tolerate one another pretty well. We found this delightful and stayed in touch. I mentioned my business idea in time, and she talked about her upcoming 10-day trip to Italy. You need to be more precise about whether you think she invited me to accompany her on the trip. Instead, she proffered that if I would keep an eye on Henry while she was overseas, she would design my business logo and business cards and set up my social media accounts. I agreed, and the rest is history. With my new professional business presence, customers and residents took notice. I was asked to host corporate wine pairing events and recommend wines for elite corporate business dinners for companies such as Jaguar Land Rover North America and Lennar Corporation.

In 2021, after working twice as hard for a year and a half during COVID and needing a change in pace, I notified my longtime employer. I moved with my beloved rescue dog to coastal North Carolina to live on the water, be near family, and focus more on developing my work-from-home wine business idea. By then, I had already performed extensive research and test marketing for my business’s subscription boxes and local delivery. I had also met two local sisters who started a woman-owned gourmet wine, cheese, and chocolate shop that was about to open, and I was offered a part-time position as a wine specialist. Naturally transitioning into a team leadership role, I helped to establish a workflow, researched equipment technical issues, managed inventory and invoicing, educated staff, and worked closely with the business owner to understand how best to support her artistic vision for the new space.

Sometimes, life has other plans, no matter how thoughtfully we prepare ourselves to live well. Through a personal misfortune, my life changed almost overnight. I bade the work sisters a tearful farewell, and in April of 2022, I texted a friend of 35 years that I was on my way to her home in Charleston. I arrived the next afternoon with my 14-year-old Italian Greyhound rescue, Bristol Blue, buckled in the front passenger seat of my Subaru.

Shortly after my arrival, I was offered a position to train as a wine buyer for a large, local beverage corporation. After two shifts, I told the General Manager I felt the company culture could have been a better fit. I then interviewed for a management position at a failing urban winery in downtown Charleston and was offered a position on the spot during my Zoom interview. After discovering early on why the business was not viable, including the ongoing lack of retail product and quality wine issues, and relaying my findings to the C-suite and not receiving the support required for critical improvements during my six-month General Management tenure, I left that position in December of 2022 to accept another challenge; to work in operations management at a Fortune 500 company that was seeking turnaround expertise for one of their worst performing stores in the Charleston market. Within 5 months under my leadership, customer satisfaction rates rose approximately 60%. My simple recommendation for a staffing change to increase cash flow, deter theft, transform customer experience, and improve vendor and employee satisfaction was reviewed and implemented at this location. This was a remarkable feat, as my idea was wildly unpopular, and I was told by upper management that it would never happen. I measure success at work by seeing the outcome–happier customers, vendors, and employees–. I am thrilled to have been a part of the team that voiced a need for change and a steward for improvement at a mammoth company.

Earlier in February, I interviewed for a wine industry management position in the Charleston area, and a couple of hours later, a company officer called to extend an offer of employment, which I accepted. I look forward to the challenge. The best thing about this experience will be working with other like-minded individuals who are focused on the needs of the customer and knowledgeable about the product. I am especially delighted that the company owner is passionate about business development and wine. In the meantime, every spring since 2018, I get a phone call from my best client, an octogenarian in Annapolis, who wants wine and food pairing recommendations for her in-home annual bridge club event. As her wine consultant, I shall happily continue to provide my expertise free of charge.

Can you talk to us about the challenges and lessons you’ve learned? Looking back, has it been easy or smooth in retrospect?
As a woman with Asperger’s in a male-dominated industry, the road has not always been smooth. Because my challenges are with verbal communication, I have to work more than twice as hard to fit in at work and in social settings. The flip side of being less verbal is that my peers regard me as a great listener. People feel comfortable sharing information with me. As a leader, I have also found that males are historically less interested in what I have to say. So not only do I have the unfortunate challenge of reading the room, forming words, and then speaking those words, but I have also had to learn how to communicate with each individual to get my point across. Working in retail has allowed me to learn and discern social cues and become more comfortable with conversation. I can and will talk about wine, spirits, and craft beer all day. Fortunately, I studied auto mechanics for two years in high school. I worked diligently in my father’s construction business, paint and body shop, automotive garage, and welding shop for ten years in my youth, so I learned the value of hard work and dedication to one’s craft at an early age. This personal experience has helped tremendously in my ability to face life’s frequent challenges valiantly. Therefore, although working in a male-dominated industry is challenging, I prefer it for various reasons. My closest and most comfortable relationships are with men, who tend to be engineers and car enthusiasts. One of my best friends from high school is always stoked when I want to talk about cars, engine rebuilds, and modifications.

Thanks. What else should our readers know about your work and what you’re currently focused on?
I specialize in pairing wine with food; writing is my lifelong passion. I do enjoy creating social media content for my wine reviews and pairings. I also enjoy writing about life in the South and am a published author. I plan to publish at least two books someday. What sets me apart from others in the wine industry is my ability to listen to customers describe what they like and don’t like in a wine. My brain immediately begins sorting and sifting through information. This is how I build client wine profiles in my head—the same works for pairing wines with food. The results are immediate, and I cannot explain how I arrived at the results so quickly.

Another thing that sets me apart is my dogged work ethic. It is always exciting to meet others who are so immersed in details and who enjoy how those tiny parts fit together to form the big picture. I can concentrate for hours on business operations and planning. I can see the pitfalls of an idea, and sometimes, the warnings I give are labeled as “negative” when that is not the case. When you meet someone who says, “Be aware that this [negative reaction] may or will occur if you do this,” thank your lucky stars because you are being guided by someone highly analytical. Let us check out the problems because I can promise you that we only want you to win. We are motivated by winning and building successful teams. I am most proud of being strong and resilient due to working alongside my father, a man of few words, who showed me the value of hard work and perseverance.

Do you have recommendations for books, apps, blogs, etc?
For years, I have leaned on Dale Carnegie’s wisdom in the form of “How to Win Friends and Influence People.” I especially enjoy language puzzles, Legos, 3D puzzles, and building model engines. I follow the principle of Buddhism, which indicates that we should go through life without causing harm to others. I repeatedly read and listen to classic literature to escape reality and soothe my soul.

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Image Credits
Rio Denaro, Debra Smith

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